Chatham is the most charming location on the Cape. Sorry the remainder of the Cape is a close runner-up. I personally like the Elbow, which of off the beaten path. In the off-season the charm just increases three fold. No crowds, easy discounted reservations, the shops and eateries that remain open are rightfully worth your attention. The Chatham Wayside Inn, situated smack dab in the heart of "downtown" on Main Street couldn't be more convenient. Her rooms are well appointed nicely maintained. I felt like I was staying in the Capes version of Hogwart's Academy with stairs leading up, down, and around to various levels. The hallways adorned with local art and historic memorabilia. We enjoyed a Friday to Sunday stay. Friday night you could hear a pin drop. Saturday, well, we had a neighboring roomie that must have had a long evening at the Squire Tavern. Stumbling and bumbling into the Inn, door slamming, up the stairs, down the hall into his/her/their room, another slam. No regard for others at 12:30 am. Aside from this, we thoroughly enjoyed our stay, including a continental breakfast each morning. The Wild Goose Tavern is part of the premise. Quiet as well, but each night diners filled the windows over looking Main Street and Kate Gould Park. read more

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This place is horrible ! Zero ambience and the least helpful front desk and staff I have ever experienced . Save your money because the room smelled like mildew and the breakfast was gross . read more

Dinner? Delicious! ...Ambiance? Even better! A great place to meet friends...dining room is spacious, tables aren't crammed together. In the summer, lunch on the front porch is delightful! You won't be disappointed! read more

Am surprised this inn is rated so average although may be totally different in the summer. Stayed for weekend, located right on Main Street so walkable to shops and restaurants. Quaint old inn feel, sure little beat up but overall nice. Front desk welcoming and helpful. Nice fireplace in the lobby area. Restaurant attached is nice but wish it stayed open a little longer on weekend. Parking was decent. Overall we had a very nice stay read more

Service was below average. At breakfast there was actually no trash near the coffee station so no way to throw out the stirrer sticks or napkins and when I inquired with the front desk they seemed interrupted and seemed bothered to help. Also, not a friendly check-in or check-out -- not necessarily bad just not friendly/nice. Room was ok/fine. Good convenient location. Cold night and no one turned on the fireplace in the lobby. read more

Chatham Wayside Inn - Fireplace not lit on a cold damp night outside ? - Hotels Near Me - Chatham, Massachusetts

Staff was so sweet! We loved the breakfast and the coziness of the inn. We felt very comfortable. Rooms could be a little more upgraded. read more

Chatham Wayside Inn - Back side to enter to reception - Hotels Near Me - Chatham, Massachusetts

Stayed here several times. Used to be great. Terrible now. If you stay there and want food to your room good luck! I waited at the bar to order take out to bring to the room and waited forever! Ended up walking up the street to another hotel for dinner. Also, the room they put us in was above the kitchen and all we heard was noise all night. Sounded like a bowling alley! Definitely done staying here! read more

Do yourself a favor and eat/stay somewhere else. Management & staff are horrible and really do not care. Check your credit card statements and receipts!!! Twice. read more

Here in February on business during a bitter cold snap. This Inn should have been warm and cozy, but wasn't. Checked in around 5 pm. The reception lobby was drafty and very bare - no upholstery or curtains or carpet. We then went to our room and found the thermostat set at 60 degrees which was uncomfortably cold, and was only just inching towards 65 when we left for dinner two hours later. The room was small and clean, renovated fairly recently. But the synthetic fill pillows are terribly lumpy and the towels are no longer soft and fluffy. Breakfast was another disappointment, also cold, in a chilly room as devoid of textiles as the lobby. Overall it was not a comfortable stay and not a good value for the price. read more

Don't bother filling out their survey, they will not respond. You will get the automatic response that says they will address you concerns, but they won't. Room 217 is directly above the dumpsters which are emptied around 7am on Saturday and Sunday. read more

Have stayed in Chatham many times, never here. The front desk staff were not nearly as welcoming as one should expect at an Inn of this character, same when we checked out. You charge a facilities fee for.........what??? A closed restaurant? A minimal fitness center that doesn't 'open' until 8??? While the restaurant is closed, efforts can and SHOULD be made to provide a much better standard of food and beverages. You have a bar but 'noone around that can serve???' Come on. If you aren't interested in having business than close while the renovations are ongoing. That's kind of the overall feeling. Great location and the room was nice. But that's about it. I would not stay again. read more

Dishonest thieves. I was double billed for a stay. I was charged when I made the reservation and when I checked out. My credit card statement confirms it. They refuse to even listen. I sent them copies of both charges showing the charges on different dates with different transaction numbers for the exact same amount. Their "Area Director of Operations" Jennifer Simmons even said in an email that "we are not disputing your two charges", but refuses to do the right thing and give me back my $746.46............. read more

Excellent central Chatham location downtown with ample private parking lot. On-site restaurant. Full breakfast included. Fitness center and pool. Friendly staff but unable to answer most questions. Need training in customer service, not accommodating or customer focused (management's job.) No bellman or help offered to carry bags up a flight of stairs. Overpriced for the level of service. read more

Good location in the center of town. Restaurant food terrible, cold and plain.Continental breakfast opened late. People just decided to walk in because nobody was there to open officially. They basically had meager rations. Quiche thing that was cold. No bagels or English muffins. Coffee not marked. Yet, they had cream cheese and bread slices? Something I think was fish which was dry and looked like it was ready for the trash. Just terrible.for the rate, criminal! Too bad because staff friendly. read more

I am a big fan of the Chatham Wayside Inn, I've stayed here twice, and both have been fantastic. The rooms are nice and traditional while also being updated and clean. The staff at the Inn are amiable and accommodating. There is also a great restaurant in the main part of it which is very good for lunch and dinner. There is also a lovely outdoor pool, although it is a bit small, you cannot beat the location being right downtown Chatham. This hotel is pricey. I've gone a few times earlier in the season when the price is not as high, but if you expect to go peak season, you're most likely going to spend upwards of 600 per night. read more

We have been guests of the Wayside inn for 25 years. This is a lovely inn managed by a team of people who should not be in contact with the public. The Inn manager Jennifer has been with the inn for a number of years...we return each year despite here terrible manner in handling guest services. This is a small inn and you will encounter Jennifer at the front desk on a daily basis. While making our reservation online 2 weeks ago, I discovered within hours that I had typed in the wrong dates online....I immediately contacted the inn by phone and told them of my error. Within 2 hours. I was assured it was fine and the person I spoke with made the correction. She did not send me an email with the correction - huge error on my part for not insisting on the email. Upon our arrival we discovered we had been charged for the previous night - the correction had never been made - we were told in person by Jennifer after much discussion that they would go ahead and alter the reservation and change the date for our stay. Her assistant standing next to her made the adjustment and I signed the guest check in document. 5 days later the bill is on my credit card and the conversation never happened according to Jennifer. Please take it up with your credit card company "I refuse to credit you the night you didn't stay...I have no memory of our conversation." I am currently waiting to view the document I signed which has the hand written adjustment on it. We will never stay at this Inn again. read more

Stayed last August, left early due to the pending hurricane, but found the staff to be very helpful had gotten in late due to traffic, the restaurant had just closed. The manager said he would ask a few of the staff to stay and they did so we could eat. As things were during Covid, most places closed early so we were especially thankful. Room was clean, shopping is right out your door close to some of the beaches. In house restaurant is also convenient. Would recommend it to anyone, likely to go back. read more

Location is unbeatable. You could not be in a better spot for downtown Chatham. Put in the middle of the downtown Chatham, you are a stone throw from all the best restaurants, bars, shopping, and galleries. The pictures that are on the Wayside Inn website do not do this stay any justice. We were blown away at how beautiful the Inn was as well as how much nicer our room was than we expected. Cleanliness: Throughout our whole stay we felt the whole premises was extremely clean. Especially during the pandemic, we felt very comfortable with the cleanliness of the entire Inn as well as our room. Staff: The front desk is extremely helpful and accommodating. The restaurant that is apart of the Inn had exemplary service. We plan on rebooking next year as we were so impressed. read more

Went here for rehearsal dinner. The wait staff was very nice and accommodating. My aunt has a severe food allergy and they made sure to cater to her every need, It's always nice when the staff is knowledgeable. We were in a private room with our own private bartender, We even had access to their patio which had tables and created a great atmosphere to mingle with other guests. For dinner I had the stuffed chicken, it was stuffed with cranberry stuffing and sausage. It was very tasty. The other option was Seared scallops which my whole table raved about. If in the Cape Cod area and need a place to hold a banquet I would recommend the Chatham Wayside Inn. Bravo folks. Can't really comment on the hotel but will say it is in the heart of Chatham. Also with in walking distance to many shops and a couple of restaurants. read more

Was able to book a room right off the street where the front desk person allowed me to see the room first before going threw and i got to see what I was getting. i was NOT disappointed with the three choice i was shown. i was a bit surprised that the rooms where all different. the staff was very friendly and well knowledge with the area and events happening . i sat by the fire and relaxed for hours. there was a family playing cards and a large mint bowl that seemed like people from every where came to get . we where able to book a table at the goose as in guest and had a quick bite to eat each morning of our stay with the breakfast provided. the only thing i think that truly mattered was the cleanliness of the entire place so clean and taken care of. will definitely rave to friend and family about this place. read more

Absolutely decadent place to stay with spacious rooms decorated tastefully Cape Cod. The inn sits in the center of the action smack in the middle of picturesque downtown Chatham. It is an inn that has been modernized and the junior suites on the main inn third floor are heaven with huge rooms with a small deck overlooking the park and in a quiet location. The lobby is quaint and includes the Wild Goose tavern restaurant which is an upscale establishment downstairs. The staff is friendly and welcoming and the prices well, let's just say it's Chatham, the fancy part of the Cape and you better bring your wallet. Highly recommend this spot if you want a luxury resort feel in the best town on Cape Cod. read more

We stayed here last weekend and started the weekend off with a bad taste in my mouth to begin with. My boyfriend booked us a junior king suite (room 208 I believe) for my birthday weekend, however when I found out my sister would be in town from across the country for just the weekend we wanted to change our dates. The hotel would not allow us to move our reservation one week (mind you, it is off season and they were dead.) The hotel has a 21 day policy to change or cancel reservations and we called 20 days prior. This left me livid! We were told because we called 20 days prior to our reservation and not 21 days prior we would have to speak with the manager, who was on vacation. We called 6 times, and she was NEVER available to speak with us not did she return our numerous calls until two days prior to our trip when she told us she would not let us change the dates of our trip. This was crazy to me, to not be able to speak with a manager for WEEKS, and for the hotel to not work with us at all is just bad business. Also, at the time of booking they charge the entire amount of the hotel, so instead of losing the $700 we had paid for a two nights stay, I didn't get to see my sister. When we arrived we were greeted by a really sweet and welcoming front desk woman who got us all set. Our room was beautiful and clean, but so tiny. We ate dinner both nights in the restaurant, which was great. All the waitstaff was wonderful and accommodating to my gluten allergy. There was a young guy named Max who took really great care of us, and the bartender was friendly and made good drinks. At some points there were really unfriendly people working the front desk, and I found the manager useless, but for the most part the staff was great. The hotel has a wonderful location, and is really beautiful but feels slightly overpriced. Again, their lack of customer service in respect to allowing us to change the date of our visit by just a few days was absolutely ludicrous to me! Had it not been for that I probably would have given an extra star. read more

Chatham Wayside Inn - Hotels Near Me - Chatham, Massachusetts

A really, really nice and upscale Inn located in the heart of Chatham. Stayed at the Wayside Inn for a couple of nights in early June, and thoroughly enjoyed our visit. This inn is located right on Main Street, conveniently located to a variety of shops and restaurants. Rooms, which are IMMACULATE are situated to the back of the building and are exceptionally quiet. Ample/private parking. Very friendly staff. Inn even provided a complimentary Continental breakfast (bagels, cereal, pastries, yogurt, etc.) which was a nice value-add. Wild Goose tavern is a great option for lunch/dinner, and offers an extensive menu. You can definitely tell that the management takes pride in the Wayside Inn, as it reflects in every aspect of our stay. I would certainly consider staying at the Wayside Inn again. read more

Recently stayed for a impromptu weekend away. The hotel is right in down town and you can easily walk to restaurants and shopping. Our room was very nice with up to date furnishings. The bathroom was huge and we truly loved the updates!! (Even inspired an update to our master bath) The only complaint to mention is the mattress was an older style spring mattress and wasn't all that comfortable, and there was a stain on the carpet that was a little funky to look at. Otherwise the hotel staff was friendly and accommodating and we had a great stay! The Wild Goose restaurant attached to the hotel was fabulous. Bobby the bartender was outstanding both night's and was so funny and helpful!! The food and drinks we had were very good. Defenitly stop in! read more

Make sure you get familiar with the cancellation policy specially in the off season ( Winter months) Chatham Bars inn and oceans Edge Mansion in Brewster are more reasonable with the cancellation policy and cost to stay at either are also very reasonable Wild Goose restaurant in the hotel very nice however staff was puzzled as to why no one was staying in the hotel having a negative effect on there business ( Squire , across the street was packed) read more

We often stay here at Christmas time and I have never found the staff to be anything but helpful and professional so I am not sure why some other folks had such bad experiences. The breakfast had plenty of fresh fruit and baked goods. My only advice to management would be as follows. We stayed in room 210 in the main part of the hotel (not one of the out buildings). The room was very large but lacked a desk. Most people would like a place to sit down and use the phone or a computer and how much could a desk cost? Please get one. One other piece of advice in terms of the bathroom. There is no place to place your personal items in the bathroom. Spend a few dollars and put up a shelf on the wall. There is plenty of wall space to install it. read more

I am completely heartbroken writing this review. Let me preface this by saying that my sister is getting married in Chatham and has a large room block set up with this hotel for future dates. My family is helping them bring in thousands of dollars. Up until this point they had been nothing but kind and easy to deal with. I made a reservation with this venue because I wanted to check out the area and get some wedding things done with my sister while they are in the off season. We thought it would be quiet and we were excited to go and spend some time there. She has stayed here multiple times but this was going to be my first. Due to the sudden and unexpected death of a family member, we found out were going to be unable to check into our room on the scheduled day because the funeral was that morning. I called the hotel and asked them what our options were in terms of pushing the reservation a day, canceling, or rescheduling - anything at all to help ease the already stressful situation that we were in. THEY DID NOTHING. I tried explaining that we were going through a terrible time, and that the funeral was the day of check in...could they please make an exception, that we would rally and come up the following day, so we wouldn't lose all of our money...THEY DID NOTHING. Not only could they do nothing, but the woman on the phone was so cold and unaccommodating that I embarrassingly began to cry on the phone. I can't even get mad because I am honestly just so disheartened and disappointed at the lack of empathy and decency demonstrated by this hotel. We have pulled our reservation for the weekend of the wedding (luckily it is more than within their 3 week cancellation period) and we expect others from our family to do the same in the days to come. My sister even went as far as to update her wedding website and remove the hotel so she and her future husband are not associated with them. DO NOT BOOK WITH THIS HOTEL. There are so many other beautiful places to stay in the area where they won't take advantage of you. read more

Awfully pricey but of course it is the Cape in July so tourists are fair game. That said, the Inn has terrific rooms with small enclosed porches attached to many of the rooms. Great place to sit with your coffee first thing in the morning before the rest of the world wakes up. Service in the dinning room for breakfast is friendly and efficient. The inn is located right in town so after a few drinks at the Squire, you simply have to navigate one street crossing and you are back in your room. Nice place but remember to bring the wallet. Chatham ain't cheap. PS AC is terrible not good on a humid night. read more

I was hanging out with a few friends at the Chatham Squire one Friday afternoon and mysteriously found myself in a position where it would have been unwise to drive miles home. It was a very foggy murky evening and I stopped in the Chatham Wayside Inn to totally expecting them not to have any available rooms. I walked in and was greeted by a very friendly gentleman at the front desk. He stated that they were pretty much booked through the weekend but he'd check because there was a couple flying in and they were delayed somewhere. To my surprise he found a room for me but it was not cheap. Since it was late in the evening he gave me a discounted rate which basically took a third off the room price so I jumped on it. The room he gave me was fantastic. The room was facing the park in the rear of the Inn and had a pretty good view as far as I could tell. The fog was amazing that evening. Based on my other reviews you can tell that I am pretty picky and this room was not a disappointment. The Chatham Wayside is a nice Inn and should be considered if you decide to overnight in downtown Chatham especially after falling victim to those pesky ice cubes. read more

Some good some room for improvement. First the good. The blackened fish tacos were tasty and well prepared and filling. I especially enjoyed the fried jalapeño peppers that served as an accent in each of the two tacos. Now where improvement can be made. The menu said heirloom tomato mozzarella and basil salad. The plate showed up with cherry tomatoes and basil that looked like it had been in the freezer overnight. Not a fair exchange at $10.50 a plate. Go and expect the average, you will not be disappointed. read more

We stayed here for a night over Labor Day weekend 2017. It was very nice, very charming and in the perfect location- but definitely not worth the outrageous price (it was over $500/a night that weekend). The hotel was incredibly quaint (had a New England, Gilmore girls vibe) and the staff was very sweet. Like other reviews have mentioned, the building was older without a ton of insulation in the walls, so if you decide to stay here, make sure you request to be on the end (away from the ice machine and hallway traffic). Be careful of their crazy policies and charges (a 'resort fee' is added to the already overpriced nightly charge, and you must pay for your entire stay upon booking and cannot cancel within 21 days). Overall, it's very nice, just can't justify the rates. There are other nice places to stay within driving distance of Chatham that are much more reasonable. read more

Very nice bed and breakfast and in a great location. The rooms are small and pricy but it is the cape. Very clean and the front desk staff was excellent and helpful. Why only a 3 star?? For the price a full breakfast should be offered, and the staff that works the breakfast buffet where young and rude. The girl waitress had no patients when an older gentleman asked for more coffee. The pool is small but will work if it is not crowded. Overall I would stay here again though. read more

We have stayed at the Wayside twice since April 2019 and both times have left us with a sour note. The staff at the front desk never smiles when spoken to directly or when they make eye contact with you throughout your stay. This is not just something I observed. In the lobby a group next to me was speaking of the same thing! read more

Very nice hotel with a perfect location. However, seemingly unfair billing left a bad taste in my mouth. Booked a room for "Up to 5" online for $240. After checking out, they added $65 because we had four people. Apparently the $240 rate is for two people?? A room is a room. And nowhere, when I booked online, did it ask me "how many people, because the rates are different". NOT COOL. I guess by being the best located hotel in Chatham, they can be a bully and make up any rules they want. read more

Bad problem with noise from floors above you. Breakfast barely begins at 7:30, so customers leave and just goes down the street for coffee and breakfast. Thus, the "free breakfast" is utterly worthless, too late, and the food is recycled all week long. Front desk workers NEVER smile. For the price, the experience is extremely UNDERWHELMING. read more

Very rude staff at front desk. Charged the FULL amount as a deposit without mentioning that the deposit would be the full amount for the 2 nights. Plus, when calling to ask for explanation, the lady at the front desk said she had no time to talk to me as she has other stuff to do and that she is sure that I didn't understand when I booked first. This is the last time I book there. Also 75USD cancellation fees.... read more

Have never stayed at the hotel, but have eaten at the restaurant a few times. In the heart of Chatham, which is nice, but the service can be very slow. The food is so-so. They're famous for their clam chowder (and rightfully so) and offer a pretty diverse seafood-oriented menu. There are some better places in Chatham--namely, Christian's across the street. read more

Had lunch with friends. Service was excellent. Bowl of of clam chowder was top notch. Wife had a bowl of mussels, nicely spiced. Great location -can dine inside or out. read more

Amazing local stripe bass !! Outdoor dinning amazing ! Right on Main Street Chatham! Heaters on point great wine selection how can u go wrong . I highly recommend! read more

Bring your check book and ear plugs to this noisy, over-priced Inn. We paid $450 per night for a room with no amenities. We had asked for a room on the 2nd level since we are quiet seniors. We were assured that there would be no problem with our request. Instead, we were put on the ground floor with a very noisy family above us. We spent 3 nights with very little sleep. They had small children running back and forth until 1 a.m. Needless to say, we will not be returning to this Inn. read more