Stayed here this past weekend, and its in a prime location on Circuit Ave. It's walkable to pretty much everything. I liked that you can store your belongings before check in, and they offer a fully stacked back patio with snacks, coffee, and drinks. The room was very spacious, well stocked and clean. Also, the staff I interacted with were all very friendly too. I would definitely recommend and stay here again! read more

The rooms are beautiful. Everything is so comfortable from the beds to the couch even to the chairs outside. The Solarium is very nice its like being at home in my sunroom. My other favorite parts are the beach room hot tub/outdoor shower.But the best part about this beautiful inn is the staff! read more

Stayed here for one night while visiting a friend, and it was the best!! Kevin and John were so sweet and accommodating, willing to help with anything we asked. There are also a ton of free amenities (hot tub, snack/coffee bar, beach chairs, cornhole, etc). The room was super clean and spacious for even one night. Would love to stay here again if I'm ever in the area. Can't thank the staff enough for their kindness! read more

I stayed at the Dockside Inn for 3 nights. I really enjoyed my stay here - the room was very cute and very clean, and the hotel was quiet. The Dockside Inn also has a little breakfast room stocked with breakfast food, snacks, coffee and other drinks. It also has some great restaurants and a cute downtown area within walking distance. One day when we returned from a day out, we were greeted with freshly baked chocolate chip cookies! I will definitely return to the Dockside Inn for my next visit to the area. read more

Awesome deal! This Inn is super reasonably priced for what you get. The rooms and spotless and have comfortable beds. Most rooms look out to the ocean and it is located right in the heart of Oak Bluffs. Steps from all the restaurants and bars. We will definitely be back! read more

Dockside Inn - Rainy day... but looks directly out to the ocean! - Hotels Near Me - Oak Bluffs, Massachusetts

John was fantastic and super helpful! Beautiful and clean space. Not only was the customer service remarkable but everyone was above and beyond friendly. I highly recommend! read more

While trying to decide where to go for our 7th wedding anniversary, we happened upon The Dockside Inn. We've wanted to go to Martha's Vineyard but didn't want to go during the busiest time of the year. After MUCH research, we settled on Oak Bluffs and The Dockside Inn. Before making my reservation, I called and spoke to John (I believe he is the owner). From the first conversation with him, I knew I picked the right place. When we arrived, we were greeted by Lianne. She is a beautiful and friendly young woman who makes you feel right at home. Her warm smile and cheery attitude are just as nice as the decor. After not even 5 minutes, we were off to a short tour and then to our room. Here is the breakdown: Room: We stayed in Room 29. It has a VERY comfortable queen bed. The room was SPOTLESS and had an amazing view of the harbor across the street. It also had a small fridge and amenities like soap, shampoo and conditioner. There is a tv but we didn't watch it much. There is also a nice area downstairs that offers complimentary coffee, tea, hot chocolate, granola bars, fresh fruit, ice cream, Popsicles, yogurt and pastries. VERY nice touch! No, there is no breakfast or food served there but that is NOT a big deal because of what they offer and because you are within walking distance to many restaurants. Location: We took the ferry and left our car in Woods Hole. The area is truly walkable. We loved walking around and seeing all of the shops and restaurants (some not open for the season yet but when we come back in September, they will be). Food: We ate at the Lookout Tavern and Linda Jeans. The food was good at both places. We had a photo shoot to commemorate our anniversary and first time in MV. Our last shots were in the lobby of The Dockside Inn and Lianne bought out a bottle of champagne for us! So thoughtful! John also came out and wished us well. He even commented that we had an amazing sunset just as I requested (when I made the reservation). Remembering your customers and providing such outstanding customer service is what makes this 5 stars in my book! The clean room, great location and complimentary goodies exceed well over 5 stars. I can't say enough about this place! I can't wait to go back and my husband feels the same way. Thank you for a fantastic anniversary!! read more

See all

I really appreciated that the room was recently renovated and modern, but when I walked in, there was a strong moldy smell. I'm not sure if the carpet got wet, but the stench was more pronounced in the bed area than the bathroom. When I alerted the front desk, the attendant Lysoled and Febreezed the room-- not quite the fix I was looking for or expecting. The inn is conveniently located near the ferry and Circuit Avenue, and the snack room is a nice amenity. But avoid selecting any rooms on the first floor near the courtyard. One night, a very loud group was outside my room until 11 pm ("quiet" time starts at 10 p.m.) Neither the virtual concierge Loomis or the on-call staffer responded to calls or texts to ask the group to quiet down. When I informed the attendant the following morning, she was very nonchalant and unhelpful, a total bummer. I will likely look elsewhere for my next MV trip. read more

Just got back from a 2-night stay here for the summer solstice weekend. I picked the Dockside based on unanimous positive feedback from my friends and Yelp reviews. I had a great time and would return if staying in Oak Bluffs again. The only reason for the 4-star review is simply because of the price. I understand it's the Vineyard and pretty much a haven for the 1%, but $300/night for a tiny room gets a 1-star deduction for value. Perhaps they used a wide angle lens taking pictures of it on the website, because it looked much bigger. I'm not sure how the other reviewer scored a $99/night room, but you're welcome to visit their website and see for yourself (they are probably sold out for the rest of the summer anyways). The location is unreal. You can walk to the Oak Bluffs ferry and you're right by Nancy's which is where you'll wanna spend most of your day drinking and eating. There's a cafe across the street for your espresso fix, and Jim's Package Store is right there for all your libation needs. You're a block away from Giordano's Take Out for late night pizza and seafood. Don't forget to go to Back Door Donuts - just follow the smell. Fresh donuts at 1am is the best thing for your waistline since the Paleo diet. You're also walking distance to the beach and I believe the hotel provides towels and chairs. You can also ask for a parking permit if you brought your car. As the other reviews mentioned, there is a room with coffee and pastries in the morning, bottled water, and ice cream that is free for all guests. The parking situation is a dirt road behind the hotel with 4 parking spaces; although with some creative parking I saw 7 cars back there including my own. I had plans in Vineyard Haven and Edgartown so I paid the $150 for the car ferry. I'm just not a bus/taxi kinda guy. The room itself was $259/night, and came to $600 for 2 nights after taxes. It was VERY small, not much bigger than the bed itself. The bathroom was as big as the room (I think it was handicap accessible) and had a closet with mini fridge in it. The room was very clean and modern. The free WiFi was very fast. The staff was amazing. Melissa called me the day of my arrival since I was running late just to make sure I was okay. She also gave me some tips on places to check out. I spoke to the manager, John, back in January and he was super helpful and friendly as well. I have already recommended The Dockside to a couple of friends in real life who have since booked reservations. If you are planning on primarily staying around Oak Bluffs, you won't need a car. I'd recommend taking the Island Queen ferry out of Falmouth as the parking situation is better than Steamship Authority. Also, make sure you have the Google Map app on your iPhone. The GPS in my 3-series didn't have the towns of Oak Bluffs, Vineyard Haven, or Tisbury so I relied on my phone for most of the trip. There are a lot of confusing 1-way streets, so study the Google Map street view if you get a free minute. Will save you from making a 9-mile detour like I did :) read more

Great hospitality and nice clean room. My wife and I took advantage of the hot tub, which we had to ourselves! Can't beat the location either! A short walk from the ferry and right in the middle of shops and food. A++ place to stay on the island and will definitely return. read more

This is THE hotel to stay in when you are itching to get to the Vineyard. Close to everything. It's itn the heart of Oak Bluffs. You can walk all over town. Just go! read more

If you are not a BALLER and have a house already... this is a great alternative. I booked because I read reviews on Yelp, Trip Advisor, etc. I figured out before i got there that they had just renovated the place. I am pretty sure we were in the first 10 people that have stayed in our room. The rooms are very well decorated, VERY clean, and perfect amount of space. The renovations really make this place TOP NOTCH. There is FREE WiFi, and they let you borrow towels, umbrellas, and beach chairs. How cool is that??? They do not have a pool - but they have a hot tub. They also have a cool service where you can text a number where someone will answer your questions - it's a virtual concierge. It's not a computer, but a real person. Great location - easy to walk to Oak Bluffs and from the Ferry. read more

My fiancé and I came to visit the island off season and stayed here, mostly because of the inexpensive rates but also due to the location. It is located right in Oaks bluff walking distance to all the stuff you want to see and right next to the ocean. Our room want an ocean view but we had access to a little deck area which was lovely for enjoying a cocktail during sunset. The room was clean and elegantly decorated. The staff was also great and recommended a yummy dinner spot and bus line tips to get to other parts if the island. There was a mini fridge in the room and ice machine around the corner. We would definatley stay here again and highly reccomend to anyone visiting MV! read more

Dockside Inn - What a lovely place to stay! - Hotels Near Me - Oak Bluffs, Massachusetts

Great location, close to everything in Oaks Bluffs: the ferry, the restaurants (where Obama picked up his fried seafood, for example) and shops. The Innkeeper was friendly and very accommodating to try and make our lives easier given our baby in tow. Just don't judge her rough and salty exterior and you'll do fine! Decor? The place looks like a giant effing doily. I guess that's what Victorian is all about. The girls liked it. There is a nice garden to sit in for your breakfast. Parking is scarce but we actually never were without a spot. Only downside was stained carpeting. And somewhat cramped rooms. If you have a lot of cash, which you probably do if you're planning to vacation on the Vineyard, go ahead and dock this one star for these facts. But I'd have no reservations making this our MV home base in the future....like in 10 years when the prices are 3x again more expensive! Oh, by the way, this IS one of the more affordable places to stay on the island and, as such, is a good value. read more

My boyfriend and I recently stayed at the Dockside Inn during our first visit to Martha's Vineyard. I would definitely recommend it! We arrived on a Friday afternoon and were greeted with a glass of champagne. The lobby area is small, but very clean and modern. In the back they have a lovely courtyard with a jacuzzi. There is a separate closed-in porch that has waters, yogurts, popsicles, coffee, pastries, and much more. It is all complimentary, making our breakfast easy and delicious! The room was clean and recently renovated with a beautiful view of the harbor. It is incredibly convenient from being able to walk there from the ferry, across the street from great restaurants and bars, and a very short walk to cute shops. The location cannot be beat! Overall, it was a great choice for Oak Bluffs! read more

This was the perfect place to stay on my recent trip to Martha's Vineyard. I was impressed with Dockside Inn from the moment I made my reservation 6+ months ago. When I got the confirmation email there was a note in there that was written by an actual human being. It was so unexpected and awesome. So, this place is cute as a button. (Did I just type that?) I scored a room overlooking the harbor and it was so freaking nice. I was in love with the porch - I had chairs, a table, and a bench right outside my door. One evening I was super sunburned and didn't want to go out, so I just sat outside with a book, watched the sunset, and drank wine. Perfection doesn't even begin to describe it. I mean...seriously. It's what vacation dreams are made of. Besides the perfect location, view, and porch action, they also hook you up. There is a little storage room with anything you could possibly need for the beach. Chairs? Check. Towels? Check. Umbrellas? Check. (Clearly I should have actually used an umbrella - see also: super sunburn). They even had things for collecting seashells and other random stuff. And their stuff isn't crappy, either - my beach chair was actually really nice. They also have this little room in the courtyard with SNACKS! Bottled water for days, a whole chest of ice cream and popsicles, popcorn, and on and on. It was a fun treat. I also noticed board games in the luggage room, so if you come with kiddos - take note. The rooms are updated with modern decor, the bed was comfy, and there is a small fridge as well. I wish the bathroom update matched the room update - it wasn't terrible, but they are about a decade apart decor wise. But hey, it's a mom and pop place and everything was still fine and in working order - what more do you need? The room also had a binder full of MV tips, suggestions, and other various things. I especially liked suggestion #1. :) The staff I encountered were all super nice. The location is perfect. I could seriously go on and on, but I was very happy with my decision to stay at the Dockside Inn and I'd stay here again without question if I ever make it back to this neck of the woods. read more

I recently spent one night here for my boyfriend's birthday and we were very happy. The Inn is located just a short walk from the ferry, which is very convenient when you have large bags. The lobby is modern and clean, and the girls checking us in were very friendly. The staff showed us around the inn which included a kitchen stocked with TONS of complementary items! Ice cream, water bottles, snacks, beer, wine etc. There were also coolers, chairs and towels for the beach and an outdoor shower and hot tub. Our room had huge windows with an amazing view of the harbor. Right across the street are great restaurants to grab dinner and drinks with even more amazing views. Overall a great place to spend a couple of nights on the vineyard. read more

We came here for our honeymoon, and it will be hard to stay anywhere else after the experience here! It is conveniently located two blocks from the Steamship Authority Ferry. When we got in, the first thing we were struck by were the signs everywhere about a water ban. It meant we couldn't/shouldn't drink the tap water. Apparently it happens sometimes, and affects all businesses at the same time. We didn't know that! We thought we were staying at some dump! The girls behind the desk were really helpful. They let us know the ban didn't affect us anyway, since they have bottled water all the time. With the room, you get full access to their kitchen full of cold water in the fridge, ice cream, chips/snacks, K-cup coffee, just about anything you'll need getting around the island. Also, you got an ice machine, ice chests (we just took one to the room to keep wine and such on ice), the jacuzzi, and outdoor shower. Let's not forget that the girls put cookies out in the afternoon! Oh man, I know they were just regular old packaged, self-bake cookies, but they get some good ones. Point is, this place will hook you up while staying there. As for the room, we got a great one facing the bluff. Also had a few chairs and a coffee table outside, which I put to good use in the mornings just to hang out. Nice and clean, and air conditioned for those sticky, humid days. Also right across the street from the package store! Made for a really relaxing stay! We would definitely stay here again. read more

We did not stay here however we did do the tour of the island with Troy and it was AWESOME! Great way to get an overview of the island and learn a lot of about the history and culture. Troy was very informative and gave many tips about what to do during our time here. I am definitely going to recommend this to anyone that comes to Martha's Vineyard, this is a must do! read more

Super clean Convenient location Unbelievably friendly staff We loved Loomis, the virtual concierge. We stayed in room 20 - it had an extra set of windows overlooking the harbor. Even though this is very close to the main strip, the streets were very quiet. It was amazing to be able to sleep with the windows open (a luxury we rarely get, living in NYC)! Overall, I would definitely recommend this place to others. read more

Very central, right where it needs to be. Super friendly staff and owner. Nice solarium with free snacks. Very clean rooms, all you need. The TV could be bigger, I think it was only 24". Not disappointed- very pleased read more

Dockside Inn - This is the room. Small but clean and comfy. - Hotels Near Me - Oak Bluffs, Massachusetts

Room is nice, service is a bit iffy. No parking they have 4 spots if your lucky, and they won't help with directing to a parking location, and all parking in the area is until 8 pm. absurd for a whole island dedicated to tourism. read more

Great location and beautiful views. This was our first time staying here and have to say we will be back again. It's a short walk from the OB harbor with walking distance to all OB has to offer. The amenities are above par for the island and the second floor harbor rooms have wonderful views. A wonderful place to relax at night with a drink and watch the boats in the harbor read more

Another phenomenal stay on MV and at Dockside Inn. Everything about the Inn is just right! Our room was charming, very clean and so very comfortable. Perfect spot to start your day straight through to when you lay your head down to sleep. The staff is incredible. The solarium is stocked with coffee and snacks. This is a feature you would be hard pressed to find anywhere else on the island. The Beach room has all the gear you could need for a great day at the beach. Beach towels, chairs , games, ice, etc. All this is included in your room fee. Also Dockside Beach is a few short step up the road. Book it. You will not regret it. read more

Nice but overpriced. We stayed for 4 days in early August. The price was $300/rm. We stayed here b/c they allowed dogs. Good location. The rooms were tidy but not worth $300. Breakfast was also disappointing (Stale bagels from Costco). They do had a nice hot tub. We did have a problem with the bill which was irritating too. Overall, not worth the money. It's of other nicer hotels in town. read more

We had a wonderful stay at Dockside. You would think our favorite part of this inn would be the close proximity to the ocean, the convenient downtown location near everything, the HOT TUB or OUTDOOR SHOWER, or the gracious and personable host John.. or even the amazing family time we were able to share there. But nope. Our favorite part of this inn was the snack room.. While trying to remember all the crap to pack for a family of 4, there was no room in our brains for remembering to pack snacks. Dockside had us covered. When returning from the hot tub, it really was a special treat to grab a pop tart on the way back to our room. It meant the world to a couple of tired parents, who happened to have been on a very strict diet prior to the vacation, to enjoy such treats. Dockside does a lot of things right, but the little details is what makes it an outstanding place to stay. Thanks for thinking of everything.. We'll be back!! read more

This location has been on my list for a long time to circle back and write a review. As a family of three we booked a room last minute for two nights and headed to MV. This location had a last minute cancelation so it worked out amazingly. When we arrived we were treated by friendly faces and given a tour to all the goodies and beach supplies. Loved that we didn't need to pack anything and loved the beach snacks. Great location and easy to get to the Inkwell. Expensive, but that is to be expected for MV. Don't expect anything extra special with the rooms. read more

Just returned from a 3 day 2 night trip to Martha's Vineyard-LOVED the Dockside. The renovations are amazing and the attention to details made the stay even easier and more relaxing. Beach chairs, towels and coolers are available to the guests-a few less things to carry over on the ferry. We stayed in Room #30 with 2 very comfortable pull out beds and a queen bed-we were fighting over the pullouts for the first time in our lives! Great location and great place to enjoy a few days on a beautiful island! read more

Hands down the best place ever ! Perfect location. Perfect staff. Stay in room 20 for the best view of the water. John.... you really are the Chief of Comfort! We had such a great time. We will be back next year for sure ! read more

Very classy place. Spent two weekends there this summer. (We stayed at Summercamp Hotel in town a few years ago and were not impressed.) Dockside staff is superb and the rooms are top shelf. They have a great location in town and also provide island tours. The owner went out of his way to find us a venue to watch the Mayweather fight since very few places had it available. The front desk staff know the island very well and plan out your daily schedule as needed. We went to four different awesome beaches (less touristy) and ate at great spots they recommended. The kids loved the hot tub and fully stocked free snack/coffee room in the yard. A family member had a health emergency while near the hotel and one of the staff members went out of his way to provide transportation to a hospital near by. The locals have done a great job in preserving the island. We only wished we could have stayed longer. (Obama knows the best spots to chill for sure :-) ) DO NOT ever go to Back Door Donuts in town. ( I came back 12 pounds heavier). read more

This place was fantastic! First off, rooms are super cheap for the island, starting at $99 for a very comfortable room. Secondly, it's right near the Oak Bluffs Steamship Authority, so it's a quick walk to and from the ferry. But the main thing is all the extra amenities this place includes with their room rate. You get access to their 24 hour e-concierge via text messaging called Loomis. We used it for pretty much everything, asking from what places to eat, where to go, how to get there, etc. If it's a really nice sunny day for you to enjoy the beach areas on the island or lay out in the sun, they have beach accessories you're able to borrow. Also, they have an area where there are complimentary snacks, such as ice cream sandwiches/pops, coffee/tea, popcorn, chips, fruit, and in the morning bagels/doughnuts. I'd recommend this place to anyone going to the island. read more

These folks make you feel right at home. Stayed here while cycling the Vineyard. They accommodated a large group of riders catering to us before and after our ride. A block away from the docks and nightlife. Would highly recommend this Inn. John Tiernan is "Chief of Comfort" and takes his job seriously! Thanks for a wonderful experience! read more

We were pretty disappointed by the Dockside after seeing so many positive Yelp and Tripadvisor reviews. Their website also does a good job deceiving you into thinking this is an upscale place. However, it looks like an old motel that got a fresh coat of paint and some new carpets. Our room smelled a bit musty, the TV was tiny, and there was no phone in the room. The biggest problem with the room was that our heating/AC unit smelled like a skunk. When I told the girl at the front desk about this I was told "Well, we do have skunks on the island." .... Great, now what are you going to do about it? It was like pulling teeth to get her to try to resolve the issue. A maintenance person did come out shortly thereafter and mostly solved the issue, but I couldn't believe the reaction of the girl on duty. To be fair, afterwards, she did leave a nice bottle of wine in our room apologizing. We were pretty psyched about their hot tub, but found it was pretty small and also the cover smelled very moldy. Also, their front desk closes at 10pm and the only method of contact after that is a text-message based concierge system. Ridiculous. One very important thing to note is that they do not have guaranteed parking, though their website leads you to believe they might. They only 6 or so parking spots for about 30 rooms. We had paid to take our car over on the ferry and when we found this out were pretty upset since if we wanted to keep our parking spot we basically couldn't take the car around much. There is overnight offstreet parking nearby, but you have to move your car by 8am. Lame. We'll be trying somewhere else next time. read more

Location, location, location. You can walk off the ferry with your bags, and then walk to everything within Oak Bluffs. We stayed in the efficiency suite and it worked out well for us with our two-year-old. They provided a perfectly suitable Pack-n-Play. We were able to close the bedroom door and enjoy the rest of the night from the living area or the outside deck. Staff was friendly, rooms were clean, would be 5 stars if they would put some money into it. Needed new towels and bathroom fixtures, but then I'm guessing they could increase the rates. Wireless was free but spotty. They warned us of that because we were on the third floor farthest from the office. No pool was kind of a bummer, but the beach is close. They provided beach chairs for us, which was also nice. Had a great time and will be our first choice if we decide to stay in Oak Bluffs again. read more

I stayed here Memorial Day Weekend and I loved it. It was centrally located in Oak Bluffs near all the bars, restaurants, the ferry, etc. The owner was incredibly nice and greeted us when we got there 2 hours before check-in (had we got there on time we would have also been greeted with a glass of champs). Our room was already ready and had been upgraded! The room was clean (and I own a cleaning company so I'm pretty picky) and had so many nice extras. I am a pillar at 5 star hotels and my expectations can be high. Ladies, have you ever stayed somewhere that provides you with makeup remover packets? This may have been a small gesture (that saves their towels), but it meant so much and made me so happy. They have a room with beach equipment that you can take (and bring back) if you want to have a beach day. Coolers, towels, etc. Another room with all sorts of free snacks from 7am - 10pm. I loved this place and will definitely be staying there when in The Vineyard. read more

Can't say enough about John and the Dockside Inn. An unexpected visit from my family left us with a cramped house. I called the Dockside and they answered, boy did they answer!!! The Inn is clean, the rooms feel like home. Service is top notch and the view from the suite is absolutely breathtaking. No need to stay anywhere else. read more

The Dockside Inn is located in the heart of Oaks Bluff - just a block or two from both Ferry's. The small hotel is more like a B&B - 22 rooms and family owned and operated. The staff is extremely welcoming and helpful. The continental breakfast from 8-10 a.m. is lovely. There is a hot tub, back patio, game room and much more. There are 4 bike (or moped) rental shops next door and the town is 1 block away. The rooms are comfortable as are the beds. I recommend this for a relaxing weekend away! read more

I was looking forward to a fall weekend stay at dockside but hurricane winds from Joaquin shut down ferry service from Falmouth so I called dockside and they were very cold and unbending with their policy of 21 days advance notice. I understand this policy - especially in summer months - but there is no way they would resell my room because you couldn't get there from some ferries. They indicated woods hole ferry runs 365 days a year etc etc. Really - who wants to ride a ferry with such rough seas. Very disappointed in attitude/service. read more

Very happy I chose to stay at Dockside Inn during my last visit to Martha's Vineyard. My room was spotless, the bed was very comfortable with nice linens, the shower had excellent pressure (which is a huge plus in my book), and I appreciated the light blocking blinds on the windows. The staff was very friendly and helpful, and the free coffee bar is a great idea. I will definitely stay at the Dockside Inn again! read more

Stayed here a few weeks back for a girls weekend away and overall a great experience. I found that the staff was very friendly. They also have a room where you can go to get coffee, snacks, etc. which was great because all of the breakfast places around were mobbed. The also have a room where you can grab supplies for the beach which is really nice. The best part was Loomis - the virtual, text based concierge. Allegedly, he is an island local and you can text him 24X7 (not sure how this is possible) for tips about the island. So, I tried this out stating that me and my girlfriends wanted to find a place for drinks on a Saturday night where we could dance and not feel like cougars. Oak Bulffs seems to be a really young crowd for nightlife. Loomis did not disappoint. He recommended the MV Chowder Company, which I would have never thought of and was just perfect with DJ, good drinks, and laid back atmosphere. Wish we had more than a weekend there! read more