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

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Check prices for these dates

In two weeks
25 Sept - 27 Sept
In two months
6 Nov - 8 Nov
In three months
4 Dec - 6 Dec
In four months
1 Jan - 3 Jan

Our top choices for Chatham cottages

Exterior

1. 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, (8 reviews)
"Lock didn’t work"
United States
Claudine
The price is €720
includes taxes & fees
30 Sept - 1 Oct
Town Center-Full Reno 2026-Steps To Shops & Eateries-Walk To Lighthouse Beach
House (3 Bedrooms) | Front of property

2. 6 Mi to Beach: Home w/ Deck in Brewster!

6 Mi to Beach: Home w/ Deck in Brewster!
3.0 star property
Brewster
The price is €593
includes taxes & fees
20 Sept - 21 Sept
6 Mi to Beach: Home w/ Deck in Brewster!
Beach

3. Stay in a TINY HOUSE!★0.4mi to Beach★Village★Restaurants★Pet Friendly ★ 2 bikes!

Stay in a TINY HOUSE!★0.4mi to Beach★Village★Restaurants★Pet Friendly ★ 2 bikes!
Dennis
9.8 out of 10, Exceptional, (121 reviews)
"Great little cottage close and convenient to everything."
United States
Shelby V.
The price is €265
includes taxes & fees
24 Sept - 25 Sept
Stay in a TINY HOUSE!★0.4mi to Beach★Village★Restaurants★Pet Friendly ★ 2 bikes!
Exterior

4. Harwich Hideaway with King Beds Pet Friendly!

Harwich Hideaway with King Beds Pet Friendly!
Harwich
8.8 out of 10, Excellent, (5 reviews)
"Dog friendly property!"
United States
Colleen O.
The price is €401
includes taxes & fees
30 Sept - 1 Oct
Harwich Hideaway with King Beds Pet Friendly!
Terrace/patio

5. On Town Cove with salt water access! Kayaks and paddle board available for use!

On Town Cove with salt water access! Kayaks and paddle board available for use!
Eastham
9.8 out of 10, Exceptional, (65 reviews)
"Clean, great location. "
United States
Peter G.
The price is €401
includes taxes & fees
20 Sept - 21 Sept
On Town Cove with salt water access! Kayaks and paddle board available for use!
Property grounds

6. Captain's Quarters by Nauset Beach

Captain's Quarters by Nauset Beach
East Orleans
10.0 out of 10, Exceptional, (12 reviews)
"Three women stayed in this cottage, it was completely fabulous, very clean, pretty cottagy feel, nice location, quiet & peaceful!mBeds were comfortable, kitchen was well organized and functional. The size was perfect, nice comfortable living room. Really overall a wonderful accommodation! We will definitely come back! Hopefully soon!"
United States
Peggy R.
The price is €522
includes taxes & fees
13 Sept - 14 Sept
Captain's Quarters by Nauset Beach
Terrace/patio

7. Seaside Escape-Art-filled 2 Bd on Town Cove

Seaside Escape-Art-filled 2 Bd on Town Cove
EASTHAM
7.4 out of 10, Good, (3 reviews)
"The cottage was very well decorated, maintained and well stocked. Loved the location with a view of the cove.My kids loved the loft"
United States
Myriam A.
Seaside Escape-Art-filled 2 Bd on Town Cove
Exterior

8. 🐚The Bay Cottage on Thumpertown Beach

🐚The Bay Cottage on Thumpertown Beach
Eastham
9.8 out of 10, Exceptional, (13 reviews)
"My group and I had another wonderful stay at the Bay Cottage! The space is sparkling clean when we arrived and the location cannot be beat. Tara is also very responsive and attentive which makes for an even better stay!"
United States
Sophia I.
The price is €343
includes taxes & fees
23 Sept - 24 Sept
🐚The Bay Cottage on Thumpertown Beach
Exterior

9. Driftwood Cottages - Crab

Driftwood Cottages - Crab
Eastham
8.8 out of 10, Excellent, (3 reviews)
"This is a cute little cottage within 10 minutes walk to a bay beach. Property was very clean. Hosts were easy to contact and responded quickly. It’s a good value for the money and we would definitely consider staying here again especially for the prime location. Pet friendly was also a huge plus!"
United States
Megan T.
The price is €721
includes taxes & fees
16 Sept - 17 Sept
Driftwood Cottages - Crab
Property grounds

10. Castaway Cottage on the bay~Dog Friendly Too!

Castaway Cottage on the bay~Dog Friendly Too!
Eastham
9.8 out of 10, Exceptional, (19 reviews)
"Cottage was quaint. The location was amazing - very peaceful and quiet. Our favorite place to sit was in the two swinging chairs overlooking the bay. The sunsets were absolutely amazing. We really enjoyed our stay and hope to be back."
United States
Patty M.
The price is €450
includes taxes & fees
24 Sept - 25 Sept
Castaway Cottage on the bay~Dog Friendly Too!
Terrace/patio

11. The Breeze on Minister's Pond

The Breeze on Minister's Pond
Eastham
10.0 out of 10, Exceptional, (26 reviews)
"The Breeze is the cutest, warmest, comfiest home. We thoroughly enjoyed our stay and will definitely book again!"
United States
MelanieC
The price is €428
includes taxes & fees
17 Sept - 18 Sept
The Breeze on Minister's Pond
Exterior

12. Charming 2-bedroom cottage in fabulous Harwich with WiFi, AC

Charming 2-bedroom cottage in fabulous Harwich with WiFi, AC
Harwich
9.0 out of 10, Wonderful, (6 reviews)
"would stay here again"
United States
david r.
The price is €442
includes taxes & fees
5 Oct - 6 Oct
Charming 2-bedroom cottage in fabulous Harwich with WiFi, AC
Beach

13. Edgewood on Campground Beach/Steps to the Sand

Edgewood on Campground Beach/Steps to the Sand
Eastham
10.0 out of 10, Exceptional, (10 reviews)
"Cozy cottage right by the beach. Great area not for to restaurants and beaches. Would definitely stay again!"
United States
Melinda W.
The price is €420
includes taxes & fees
28 Sept - 29 Sept
Edgewood on Campground Beach/Steps to the Sand
Property grounds

14. Pondside/Kayak/Firepit/Dog Friendly~Willow Haven

Pondside/Kayak/Firepit/Dog Friendly~Willow Haven
Eastham
9.8 out of 10, Exceptional, (6 reviews)
"Great hideaway location on the Cape. Well equipped rental."
United Kingdom
Richard F.
The price is €348
includes taxes & fees
5 Oct - 6 Oct
Pondside/Kayak/Firepit/Dog Friendly~Willow Haven
Terrace/patio

15. Pond View~ Abuts conservation and walking trails. There is fishing at the pond

Pond View~ Abuts conservation and walking trails. There is fishing at the pond
Dennis
10.0 out of 10, Exceptional, (138 reviews)
"Everything was perfect just like every other time we stayed! Louise makes you feel like you are home away from home...everything one needs is available. Thank you again for the memories!!"
United States
Kimberly C.
The price is €232
includes taxes & fees
14 Sept - 15 Sept
Pond View~ Abuts conservation and walking trails. There is fishing at the pond
Exterior

16. 🌊The Ocean Cottage on Thumpertown Beach

🌊The Ocean Cottage on Thumpertown Beach
Eastham
9.6 out of 10, Exceptional, (12 reviews)
"We absolutely loved the place and the location right near Thumpertown Beach was perfect!"
United States
Jeff P.
The price is €345
includes taxes & fees
6 Oct - 7 Oct
🌊The Ocean Cottage on Thumpertown Beach
Exterior

17. Charming West Yarmouth Cottage- Minutes to Beaches, Dining & Family Fun

Charming West Yarmouth Cottage- Minutes to Beaches, Dining & Family Fun
Yarmouth
9.4 out of 10, Exceptional, (9 reviews)
"Area was quiet and place was clean! Solid location"
United States
Nicholas
The price is €417
includes taxes & fees
14 Sept - 15 Sept
Charming West Yarmouth Cottage- Minutes to Beaches, Dining & Family Fun
Terrace/patio

18. Windswept on Campground Beach

Windswept on Campground Beach
Eastham
9.4 out of 10, Exceptional, (3 reviews)
"So nice to be steps from the beach for morning walks and sunset catching . A great location on the Cape. Glad to have the grill to enjoy our fresh caught striped bass Capt Joe (ReelEz) put us on . The charm of a historic cottage made for comfortable family time. Thank you !"
United States
Lars S.
The price is €607
includes taxes & fees
28 Sept - 29 Sept
Windswept on Campground Beach
Exterior

19. Driftwood Cottages - 65A - Whale

Driftwood Cottages - 65A - Whale
Eastham
The price is €711
includes taxes & fees
16 Sept - 17 Sept
Driftwood Cottages - 65A - Whale
Exterior

20. Pet Friendly Cape Cod Cottage Near Beaches w/ AC + Electric Vehicle Charging

Pet Friendly Cape Cod Cottage Near Beaches w/ AC + Electric Vehicle Charging
Bass River
10.0 out of 10, Exceptional, (10 reviews)
"The cottage was cozy and renovated in an excellent location with lots to do nearby. Nina made things easy and convenient for an all around outstanding stay. "
United States
Nathan S.
The price is €576
includes taxes & fees
27 Sept - 28 Sept
Pet Friendly Cape Cod Cottage Near Beaches w/ AC + Electric Vehicle Charging
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.
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Top Chatham Hotel Reviews

Greyfinch Chatham Inn

Greyfinch Chatham Inn

8/10 Good
"The property was absolutely charming and the room was spacious and adorable. Great parking and beautiful pool/fire pit area. Bicycles were available for riding around Chatham. We did find a bug in the bathroom which was a little disappointing. Overall, the stay was great and the bed was super comfortable."
Julie 1-night trip
Posted 4 hours ago
Greyfinch Chatham Inn

Find out more about Chatham

Chatham Cottages information

Number of reviews
450
Accommodation
490 Cottages
Lowest Price
€232
Highest Price
€721

Frequently asked questions

How much do cottages in Chatham cost?
Cottages in Chatham range between €232 and €721 per night. These stays offer a chance to reconnect with nature — at a price you can afford. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
What are the best cottages in Chatham?
There are multiple cottages in Chatham that have a total average guest review rating of 9.5. 16 Flakeyard Way - Four Bedroom House is a terrific place to relax and put your feet up between adventures. This 3.5-star cottage also offers a water view and WiFi. 10 Squanto Drive - One Bedroom House is another top pick with visitors to the area. It has a 3.5-star rating and amenities including WiFi and clothes washing facilities.
How many cottages are there in Chatham?
You can choose from 490 cottages in Chatham. No matter if you're holidaying with the family or planning a retreat with your buddies, Expedia can help you find the right place to get back to nature.
Are there any family-friendly cottages in Chatham?
Settle in at 16 Flakeyard Way - Four Bedroom House, a 3.5-star cottage not far from town. Amenities here include WiFi and a patio. Another family-friendly option where you can swap the urban jungle for fresh air and nature is 10 Squanto Drive - One Bedroom House. WiFi and a stovetop help make this 3.5-star cottage a traveller favourite. After checking in and chilling together in your comfortable new digs, it's time to head out and visit some of the local sights. Skaket Beach and Sea Street Beach are popular family-friendly attractions in Chatham.
Why book your cottage in Chatham with Expedia?
Expedia has some superb cottages in Chatham, so start planning for a memorable stay close to nature. If you need to stick to a budget, select how much you want to spend and your preferred property star rating. Or, use our filters to search for cottages with free WiFi or a pool. We'll help you find the right place whatever your trip looks like.
How can I find cheap cottages in Chatham?
Expedia can help you easily track down cheap cottages in Chatham. To discover your special stay in a couple of quick clicks, try out the filter tool to tailor your search results by amenities, star rating and budget.
What is there to do in Chatham near my cottage?
No matter your interests, Chatham has loads of things to keep you occupied. Chatham Fish Pier, Chatham Lighthouse and Atwood House Museum are on most visitors' to-do lists. Don't forget to check out Chatham Railroad Museum, Chatham Drama Guild and Monomoy National Wildlife Refuge either. With Expedia's hotel deals in Chatham, you'll be able to discover more fabulous attractions like these with the cash you save.