A boat on a calm river, a large house with a red roof, and dense greenery in the background.

Chatham Chalets

Check prices for these dates

In two weeks
Sep 18 - Sep 20
In two months
Oct 30 - Nov 1
In three months
Nov 27 - Nov 29
In four months
Dec 25 - Dec 27
No exact matches found, but these alternatives could be just right

Recommended hotels in Chatham

A white house with a grey roof, surrounded by a well-maintained lawn and flowering bushes.

1. Greyfinch Chatham Inn

Greyfinch Chatham Inn
3.0 star property
Chatham
8.8 out of 10, Excellent, (280 reviews)
"Clean room and great location"
United Kingdom
Sara
$210 nightly
The price is $240
Oct 1 - Oct 2
Total with taxes and fees
Greyfinch Chatham Inn
A house with a brick exterior, white exterior walls, and a front porch with white chairs.

2. Chatham Seafarer Inn

Chatham Seafarer Inn
3.5 star property
Chatham
9.0 out of 10, Wonderful, (338 reviews)
"Excellent!"
United States
Nicholas
$194 nightly
The price is $222
Sep 22 - Sep 23
Total with taxes and fees
Chatham Seafarer Inn
A house surrounded by dense trees and a gravel path leading to the front door.

3. Pleasant Bay Village Resort

Pleasant Bay Village Resort
3.0 star property
Chatham
9.6 out of 10, Exceptional, (328 reviews)
"Loved our recent stay ! This hotel Is so private and nice! My tweens loved the pool and feeding the koi fish everyday! Loved easy access of ordering poolside lunch and just a quick drive to Main Street for shopping. What a gem of a hotel-we will def be back! Thank you for such a great staff! Staff was so polite and helpful"
United States
Allison
$213 nightly
The price is $243
Sep 22 - Sep 23
Total with taxes and fees
Pleasant Bay Village Resort
A covered porch with wicker furniture, a table with a bottle and glasses, and a painting on the wall.

4. Chatham Wayside Inn

Chatham Wayside Inn
4.0 star property
Chatham
9.2 out of 10, Wonderful, (725 reviews)
"Nice location and cute hotel! The staff was great, and the restaurant was really good!"
United States
Nicole Ann
$397 nightly
The price is $454
Sep 29 - Sep 30
Total with taxes and fees
Chatham Wayside Inn
A red two-story house with a covered porch, white trim, and multiple windows.

5. Surfside Inn Chatham

Surfside Inn Chatham
2.5 star property
Chatham
8.2 out of 10, Very Good, (171 reviews)
"Very nice clean property"
United States
Jenee
$235 nightly
The price is $269
Oct 1 - Oct 2
Total with taxes and fees
Surfside Inn Chatham
A building with a blue roof, a white steeple, and a flagpole with an American flag.

6. The Chatham Motel

The Chatham Motel
2.0 star property
Chatham
9.2 out of 10, Wonderful, (637 reviews)
"My mom and I had a wonderful time staying at the Chatham Motel for our girls get away weekend. It was so nice and clean. The hotel manager Jennifer was so nice and helpful getting us checked in and to our room. I definitely will be coming back next year and highly recommend. The motel is super close to beaches and downtown Chatham."
United States
Meghan
$281 nightly
The price is $321
Sep 7 - Sep 8
Total with taxes and fees
The Chatham Motel
A two-story house with a covered porch, a well-maintained garden, and a driveway.

7. Old Harbor Inn

Old Harbor Inn
3.5 star property
Chatham
9.6 out of 10, Exceptional, (168 reviews)
"The owner was so nice and knowledgeable. He made us feel like home."
United States
Pamela
$441 nightly
The price is $505
Sep 20 - Sep 21
Total with taxes and fees
Old Harbor Inn
A resort pool with multiple sun loungers and umbrellas, surrounded by beach views and boats.

8. Chatham Bars Inn

Chatham Bars Inn
5.0 star property
Chatham
9.2 out of 10, Wonderful, (859 reviews)
"Amazing hospitality, food and location!"
United States
Yousuf Hussain
$578 nightly
The price is $662
Sep 24 - Sep 25
Total with taxes and fees
Chatham Bars Inn
A two-story house with a porch, white chairs, and a small table.

9. Seaside condo with patio, beach access, loft, board games, gas grill, & firepit

Seaside condo with patio, beach access, loft, board games, gas grill, & firepit
Chatham
10.0 out of 10, Exceptional, (1 review)
"Lovely spot on the water!"
United States
Elizabeth T.
$435 nightly
The price is $498
Sep 9 - Sep 10
Total with taxes and fees
Seaside condo with patio, beach access, loft, board games, gas grill, & firepit
A single-story house with a grey roof, white trim, and a pink door.

10. Quaint Chatham home w/beautiful backyard & furnished multi-level deck, dogs OK

Quaint Chatham home w/beautiful backyard & furnished multi-level deck, dogs OK
Chatham
9.6 out of 10, Exceptional, (105 reviews)
"Our second year in a row staying here. Cute house and great location! "
United States
Erin M.
$521 nightly
The price is $596
Sep 29 - Sep 30
Total with taxes and fees
Quaint Chatham home w/beautiful backyard & furnished multi-level deck, dogs OK
A two-story house with a covered front porch, a chimney, and a small garden area with steps leading to the entrance.

11. Beautiful home near Jacknife Beach and bike trail

Beautiful home near Jacknife Beach and bike trail
Chatham
9.8 out of 10, Exceptional, (86 reviews)
"This is second time to stay here! We love the location and hospitality of the hosts! Great place!"
United States
Barbara P.
$589 nightly
The price is $674
Oct 1 - Oct 2
Total with taxes and fees
Beautiful home near Jacknife Beach and bike trail
A lighthouse with a cylindrical tower and a white building with a red roof.

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

Quaint & Cozy Downtown Chatham Home, Walk to Town and Beaches
Chatham
10.0 out of 10, Exceptional, (127 reviews)
"Our stay was wonderful!"
United States
Corinne J.
$583 nightly
The price is $667
Oct 4 - Oct 5
Total with taxes and fees
Quaint & Cozy Downtown Chatham Home, Walk to Town and Beaches
A two-story house with a sloped roof, a front porch, and a small deck.

13. Chatham Break! 3 BR, A/C, Outdoor Shower + Deck, Near Beaches, Large Quiet Yard

Chatham Break! 3 BR, A/C, Outdoor Shower + Deck, Near Beaches, Large Quiet Yard
Chatham
10.0 out of 10, Exceptional, (108 reviews)
"Great stay. House is in a great location and is well maintained. Bonnie was super helpful. "
United States
Will M.
$541 nightly
The price is $619
Sep 10 - Sep 11
Total with taxes and fees
Chatham Break! 3 BR, A/C, Outdoor Shower + Deck, Near Beaches, Large Quiet Yard

14. Town Center-Full Reno 2026-Steps To Shops & Eateries-Walk To Lighthouse Beach

Town Center-Full Reno 2026-Steps To Shops & Eateries-Walk To Lighthouse Beach
Chatham
9.8 out of 10, Exceptional, (7 reviews)
"Lock didn’t work"
United States
Claudine
$794 nightly
The price is $909
Sep 22 - Sep 23
Total with taxes and fees
Town Center-Full Reno 2026-Steps To Shops & Eateries-Walk To Lighthouse Beach
A two-story house with a covered patio, a grill, and a well-maintained lawn.

15. Spacious 4BR house in perfect Chatham with AC

Spacious 4BR house in perfect Chatham with AC
Chatham
$1,068 nightly
The price is $1,222
Sep 13 - Sep 14
Total with taxes and fees
Spacious 4BR house in perfect Chatham with AC
A two-story house with a covered porch and a stone staircase leading to the entrance.

16. Stunning Beach Retreat - Walk to Beach - Chatham Bars Inn - Town + Game Room

Stunning Beach Retreat - Walk to Beach - Chatham Bars Inn - Town + Game Room
Chatham
10.0 out of 10, Exceptional, (22 reviews)
"House was wonderful with plenty of room. Great outdoor spaces with a deck and patio. Very convenient location. Host responsive to our needs. Would definitely stay again. "
United States
Sally S.
$1,468 nightly
The price is $1,680
Oct 4 - Oct 5
Total with taxes and fees
Stunning Beach Retreat - Walk to Beach - Chatham Bars Inn - Town + Game Room
A deck with a view of the ocean, a blue umbrella, and a white chair.

17. Chatham Tides

Chatham Tides
2.5 star property
South Chatham
9.4 out of 10, Exceptional, (759 reviews)
"Beautiful property and great location!"
United States
Melissa
$297 nightly
The price is $340
Oct 1 - Oct 2
Total with taxes and fees
Chatham Tides
A motel with a central entrance, two outdoor seating areas with umbrellas, and a parking lot with visible cracks.

18. Olde Tavern Motel And Inn

Olde Tavern Motel And Inn
2.5 star property
Orleans
9.4 out of 10, Exceptional, (288 reviews)
"Nice breakfast, the staff was super nice !"
Canada
Rosalie
$108 nightly
The price is $124
Oct 4 - Oct 5
Total with taxes and fees
Olde Tavern Motel And Inn
A building with a sign reading "BUMPER CARS and Arcade" and a parking lot with chairs and tables outside.

19. Holiday Hill Inn & Suites

Holiday Hill Inn & Suites
2.0 star property
Dennis Port
8.4 out of 10, Very Good, (1,010 reviews)
"Great location and my daughters enjoyed the pool!"
United States
Elizabeth
$86 nightly
The price is $99
Oct 4 - Oct 5
Total with taxes and fees
Holiday Hill Inn & Suites
A brick building with a white picket fence, a lawn, and a sign for Skaket Beach Motel.

20. Skaket Beach Motel

Skaket Beach Motel
2.0 star property
Orleans
9.2 out of 10, Wonderful, (489 reviews)
"Check in was a breeze.. The room was impeccable. The beds were very comfortable and it was very quiet at night. Wonderful location to beaches, shops, and restaurants. Would definitely stay here again!"
United States
Jason
$135 nightly
The price is $155
Oct 4 - Oct 5
Total with taxes and fees
Skaket Beach Motel
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Chatham Hotel Reviews

Holiday Inn Express Hyannis Cape Cod by IHG

Holiday Inn Express Hyannis Cape Cod by IHG

10/10 Excellent
"Good stay"
James 1-night trip
Posted 1 hour ago
Holiday Inn Express Hyannis Cape Cod by IHG

Find out more about Chatham

Chatham Chalets information

Number of reviews
4,295
Accommodation
0 Chalets
Lowest Price
$99
Highest Price
$1,680

Explore a world of travel with Expedia