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Dockside Inn

4.5 (49 reviews)
Open 7:00 am - 10:00 pm

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Rainy day... but looks directly out to the ocean!
Tom C.

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!

The Dockside Inn
Loni A.

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!!

What a lovely place to stay!
Meg B.

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!

This is the room. Small but clean and comfy.

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Ask the Community - Dockside Inn

What is the best way to get to this Inn from Boston Airport?

The Dockside Inn is located on Marthas Vineyard. Marthas Vineyard is an island off of Cape Cod. Marthas Vineyard and Cape Cod are located in Massachusetts. When Leaving Boston Logan Airport, you can take a peter pan bus to Woodshole Ma. The Peter… Read more

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Review Highlights - Dockside Inn

It is located right in Oaks bluff walking distance to all the stuff you want to see and right next to the ocean.

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Kathleen's Kottage On Martha's Vineyard

Kathleen's Kottage On Martha's Vineyard

(2 reviews)

Kathleen and Frank made us immediately feel like family. The rooms were beautiful and immaculately…read morekept, the bed was really comfy; we stayed in the Mary so we had our own sitting area and bathroom in a separate structure! The deck and yard are a great place to relax and enjoy the gardens and birds, or eat a yummy breakfast made right in the kitchen. This was my first time on the Vineyard and I'm so happy I stared here for it, Kathleen and Frank helped us find the best places to eat and see the sights. Our family will return for sure!

We had been to the Vineyard for day trips but never overnight. We opted to try Kathleen's Kottage…read moreafter reading another reviewer say they couldn't imagine staying anywhere else. They are spot on. We initially booked 3 nights and thankfully our room was open for another so we added a 4th. We stayed in the Millie - on the 2nd floor of the main house - queen bed and an oversized bathroom with twin sinks and lovely tiled bench shower. Kathleen and Frank are amazing hosts - you'll instantly take to them as they are so cordial and easy to get along with. Both know the island so well and can offer many recommendations for recreation and dining. Kathleen has a number of relationships with island businesses and she uses them to your advantage. If you want to rent a car, Kathleen calls and negotiates the best possible rate for you and then arranges for the car to be delivered. Breakfast is always a treat with a daily hot entree such as Portuguese sweetbread french toast, Frittata, or eggs benny. Make sure she makes her ebelskivers - a Danish, filled mini-pancake. Deelish!! The Kottage is small - 3 rooms total - so book early ... and often!

Dockside Inn - hotels - Updated June 2026

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