Chatham, MA

Travel Guide

Chatham showing a house and boating
Chatham showing a house and boating
Chatham showing a windmill, wildflowers and general coastal views
Chatham which includes a house and a beach as well as a small group of people
Chatham which includes boating

Eid al-Fitr Sale

Members save up to 40% on hotels. Plan this year’s big trip and save.
Chatham Bars Inn

Chatham Bars Inn

5 out of 5
297 Shore Rd Chatham MA
The price is AED 1,337 per night from Mar 4 to Mar 5
AED 1,337
per night
Mar 4 - Mar 5
Book a stay at this luxury resort in Chatham. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the property condition ...
Chatham Bars Inn
Chatham Wayside Inn

Chatham Wayside Inn

4 out of 5
512 Main St Chatham MA
The price is AED 403 per night from Mar 1 to Mar 2
AED 403
per night
Mar 1 - Mar 2
Book a stay at this golf hotel in Chatham. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our ...
9.2/10 Wonderful! (635 reviews)
Friendly staff, clean and spacious room, convenience of having a restaurant on site, and convenience of walking to all the stores and restaurants.

Reviewed on 16 February 2026

Chatham Wayside Inn
Surfside Inn Chatham

Surfside Inn Chatham

2.5 out of 5
25 Holway St Chatham MA
Book a stay at this beach B&B in Chatham. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Chatham Lighthouse and Chatham Windmill are ...
8/10 Very Good! (159 reviews)
This is a beautiful property very centrally located. I highly recommend the surfside inn.

Reviewed on 15 October 2025

Surfside Inn Chatham
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Downtown Chatham Luxury 9 BR Home with Heated Pool.  Pets welcome!

Downtown Chatham Luxury 9 BR Home with Heated Pool. Pets welcome!

Chatham MA
Book a stay at this family-friendly vacation home in Chatham. Enjoy free WiFi, private pools, and a garden. Popular attractions Mayo House and Chatham Windmill ...
10/10 Exceptional! (40 reviews)
We’ve stayed here 3 times and always love it. Kitchen is very well-stocked, beds are comfortable and you cannot beat the location. Owner is very responsive if there are issues.

Reviewed on 17 December 2025

Downtown Chatham Luxury 9 BR Home with Heated Pool. Pets welcome!
Quaint & Cozy Downtown Chatham Home, Walk to Town and Beaches

Quaint & Cozy Downtown Chatham Home, Walk to Town and Beaches

Chatham MA
Stay at this vacation home in Chatham. Enjoy a garden, laundry facilities, and balconies or patios. Popular attractions Chatham Windmill and Mayo House are located ...
10/10 Exceptional! (117 reviews)
From the communications with the host before the stay to the stay itself to check out, this was an amazing trip. We stayed here in the winter and the house was warm and cozy. The house is equipped with all a family needs for a restful and enjoyable stay- comfy beds, lots of games, etc. The power ...

Reviewed on 1 January 2026

Quaint & Cozy Downtown Chatham Home, Walk to Town and Beaches
5 BR - Beautiful Property-Chatham in-Town & Oyster Beach Inlet

5 BR - Beautiful Property-Chatham in-Town & Oyster Beach Inlet

Chatham MA
Stay at this vacation home in Chatham. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Veterans Field and Chatham Drama Guild are located ...
9.8/10 Exceptional! (76 reviews)
The kitchen was fully stocked and had many extras. There was an extra refrigerator. The bedrooms were perfect and the downstairs shower was really nice. Unfortunately, the weather didn't cooperate for us to use the backyard and fire pit, but we enjoyed mornings on the front deck.

Reviewed on 16 October 2025

5 BR - Beautiful Property-Chatham in-Town & Oyster Beach Inlet
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Popular places to visit

Reviews of Chatham

4.7
Top Destination
5 - Excellent
74
5 - Excellent 73%
4 - Good
26
4 - Good 26%
3 - Okay
1
3 - Okay 1%
2 - Disappointing
0
2 - Disappointing 0%
1 - Terrible
0
1 - Terrible 0%

5/5 - Excellent

Verified traveler

Enjoying the quaint quiet atmosphere.

4/5 - Good

Verified traveler

Very beautiful place

4/5 - Good

Meghan

The National Seashore offers beautiful and interesting habitats to explore and is an easy drive away for an afternoon or day trip. The Chatham grocery store carries standard items. If you're a foodie or want organic or allergen-free items, bring them

5/5 - Excellent

Verified traveler

Perfect location for both local restaurants and shopping plus all of the Cape Cod opportunities.

3/5 - Okay

Bob

Not a lot going on during semi off season, especially on a Sunday and Monday. Maybe weekends are a little more lively.

5/5 - Excellent

Verified traveler

Great little town