We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.
We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.
All 9 Chatham hotels

The Chatham Wayside Inn

3.5 of 5 Hotel   |   512 Main Street, Chatham, MA 02633
Hotel amenities
The Chatham Wayside Inn
Best prices for your stay
Enter dates for best prices
Check In Check Out
Show Prices
Compare best prices from top travel sites
You added The Chatham Wayside Inn to your Saves list
Ranked #7 of 9 Hotels in Chatham
Certificate of Excellence 2014
A recent review
5 of 5 stars reviewed 4 weeks ago
Luisa S Boston, Massachusetts
Write a Review

173 reviews from our community

Traveler rating
See reviews for
Rating summary
  • Location
    4.5 of 5 stars
  • Sleep Quality
    4.5 of 5 stars
  • Rooms
    4 of 5 stars
  • Service
    4 of 5 stars
  • Value
    3.5 of 5 stars
  • Cleanliness
    4.5 of 5 stars
Traveler tips help you choose the right room.   Room tips (45)
Date | Rating
  • English first
  • French first
  • German first
  • Spanish first
  • Any
English first
  • All months
  • Mar-May only
  • Jun-Aug only
  • Sep-Nov only
  • Dec-Feb only
All months
Boston, Massachusetts
4 reviews 4 reviews
3 helpful votes 3 helpful votes
5 of 5 stars Reviewed 4 weeks ago

Our family spent the weekend during the Christmas Stroll. Great location, friendly service, good food! Located in the middle of downtown Chatham...park your car and you won't need it til you leave. A place great for any season!

Was this review helpful? Yes 1
Westwood, New Jersey
Top Contributor
57 reviews 57 reviews
10 hotel reviews
25 helpful votes 25 helpful votes
5 of 5 stars Reviewed December 15, 2014

When I come to Chatham I usually stay at the Bradford, the Wayside's sister inn. However, upon making my reservations for Christmas Stroll Weekend, I discovered that the Bradford was shutting down. They suggested the Wayside. I have stayed there once before when I was a child and from what I remember, it was lovely. And it still is! The... More 

Was this review helpful? Yes
Senior Contributor
39 reviews 39 reviews
20 hotel reviews
47 helpful votes 47 helpful votes
3 of 5 stars Reviewed December 14, 2014

There are a lots of things to like about the Wayside Inn, particularly it's location right on the main shopping street in Chatham. While the public spaces aren't particularly comfortable, our room was nice (large, bright, tasteful), staff was extremely helpful, and the breakfast was good. However, the undisclosed "facilities fee" negated a lot of that. So much for the... More 

Was this review helpful? Yes 2
Top Contributor
98 reviews 98 reviews
43 hotel reviews
47 helpful votes 47 helpful votes
5 of 5 stars Reviewed November 26, 2014

If you're looking for a small New England Inn then this doesn't really tick the box. It is a full blown hotel really but still very nice and in a great central location in town. We were staying in the main part of the property but there is a massive extension, bigger than the original, so if you're fussy about... More 

Was this review helpful? Yes 1
Maynard, Massachusetts
13 reviews 13 reviews
6 hotel reviews
6 helpful votes 6 helpful votes
4 of 5 stars Reviewed November 4, 2014

Walking into our 2nd floor room in the main building it smelled like clean fresh linens, the lights were on and a soft radio was playing. It was very welcoming. We had a door off to a small deck with two chairs and a table that over looked the property. The king size bed was very comfortable and the room... More 

Was this review helpful? Yes 1
Top Contributor
148 reviews 148 reviews
33 hotel reviews
101 helpful votes 101 helpful votes
5 of 5 stars Reviewed October 25, 2014

What you see in ALL the pictures is what we got. That cute white inn, we were street side, second floor, right corner unit, but odds are in high season you will not see it. I do not recall in my research seeing anywhere that the white inn part was added on to again and again, till now the cute... More 

Was this review helpful? Yes 4
New Orleans, Louisiana
Senior Contributor
23 reviews 23 reviews
23 hotel reviews
50 helpful votes 50 helpful votes
4 of 5 stars Reviewed October 21, 2014

We stayed at the Wayside Inn for a wedding we recently attended in Chatham. It was a perfect spot to explore the town of Chatham, particularly since we were preoccupied with wedding activities as opposed to solely relaxing and vacationing on the Cape. It was certainly more affordable than the Chatham Bars Inn, which is a resort atmosphere as opposed... More 

Was this review helpful? Yes 1
Chatham, Massachusetts
Top Contributor
60 reviews 60 reviews
11 hotel reviews
53 helpful votes 53 helpful votes
4 of 5 stars Reviewed October 6, 2014

We stayed at the Chatham Wayside Inn for two nights in one of their higher-end rooms overlooking the park. The room had a nice gas fireplace -- very cozy. The room was clean and comfortable enough, although the decor was rather outdated. The bed could really have been better: the mattress was fairly thin and was quite hard/stiff; the head... More 

Was this review helpful? Yes
Chapel Hill, North Carolina
Top Contributor
57 reviews 57 reviews
20 hotel reviews
42 helpful votes 42 helpful votes
4 of 5 stars Reviewed September 22, 2014

If one would stay in Chatham, and at the Wayside Inn, it is a great location for day trips to Martha's Vineyard, Nantucket, and Provincetown. The Inn itself, used by us on Tauck tour, was wonderful. Had the honeymoon suite, after 57 years of marriage, it was nice to be recognized. Our room, 214, was fantastic, except for the shower.... More 

Was this review helpful? Yes 1
Hummelstown, Pennsylvania
11 reviews 11 reviews
7 hotel reviews
5 helpful votes 5 helpful votes
5 of 5 stars Reviewed September 13, 2014

Room was beautiful, bright and clean. Inn is lovely and located on Main Street in downtown Chatham. Extra treat was our patio opened to the town gazebo and Friday night was the Chamber of Commerce's band night (colorfully uniformed forty-piece band). Would definitely stay here again!

Was this review helpful? Yes 1
Questions? Get answers from hotel staff and past guests. Ask a question
Owners: What's your side of the story?
Register now for free — and start getting automatic notification of new reviews, responding to traveler feedback, adding new photos to your listing and much more.
Manage your listing

Been to The Chatham Wayside Inn? Share your experiences!

Write a Review Add Photos & Videos

Additional Information about The Chatham Wayside Inn

Address: 512 Main Street, Chatham, MA 02633
Location: United States > Massachusetts > Cape Cod > Chatham
Price Range (Based on Average Rates): $$
Hotel Class:3.5 star — The Chatham Wayside Inn 3.5*
Number of rooms: 56
Reservation Options:
TripAdvisor is proud to partner with Orbitz, Expedia and Travelocity so you can book your The Chatham Wayside Inn reservations with confidence. We help millions of travelers each month to find the perfect hotel for both vacation and business trips, always with the best discounts and special offers.
Also Known As:
The Chatham Wayside Hotel Chatham
Chatham Wayside Inn
Hotel Style:
#8 Romantic Hotel in Chatham

33 photos of this hotel

Traveler photos: See what travelers like you saw

All traveler photos (22)
Room/suite (2)
Hotel & grounds (7)
Pool/beach area (1)
Other (12)

Management photos: Courtesy of the property manager

All management photos (11)
Hotel & grounds (1)
Other (10)
Hotels you might also like...
Check In Check Out
Price Your Stay