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
Oct 2 - Oct 4
In two months
Nov 13 - Nov 15
In three months
Dec 11 - Dec 13
In four months
Jan 8 - Jan 10

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 CA $500
CA $1,091 total
includes taxes & fees
Sep 22 - Sep 23
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 CA $200
CA $960 total
includes taxes & fees
Sep 20 - Sep 21
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.
Stay in a TINY HOUSE!★0.4mi to Beach★Village★Restaurants★Pet Friendly ★ 2 bikes!
Terrace/patio

4. 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, (66 reviews)
"Clean, great location. "
United States
Peter G.
The price is CA $219
CA $603 total
includes taxes & fees
Sep 20 - Sep 21
On Town Cove with salt water access! Kayaks and paddle board available for use!
Exterior

5. 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 CA $567
CA $775 total
includes taxes & fees
Sep 30 - Oct 1
Harwich Hideaway with King Beds Pet Friendly!
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)
"Cape Cod cottage close to the beach."
United States
Bill B.
The price is CA $291
CA $827 total
includes taxes & fees
Oct 4 - Oct 5
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.
The price is CA $262
CA $772 total
includes taxes & fees
Sep 21 - Sep 22
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 CA $206
CA $553 total
includes taxes & fees
Oct 5 - Oct 6
🐚The Bay Cottage on Thumpertown Beach
Exterior

9. Driftwood Cottages - 65A - Whale

Driftwood Cottages - 65A - Whale
Eastham
The price is CA $306
CA $1,164 total
includes taxes & fees
Sep 23 - Sep 24
Driftwood Cottages - 65A - Whale
Beach nearby

10. 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 CA $274
CA $677 total
includes taxes & fees
Sep 28 - Sep 29
Edgewood on Campground Beach/Steps to the Sand
Exterior

11. 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 CA $347
CA $726 total
includes taxes & fees
Oct 13 - Oct 14
Charming 2-bedroom cottage in fabulous Harwich with WiFi, AC
Property grounds

12. 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 CA $259
CA $615 total
includes taxes & fees
Sep 24 - Sep 25
Castaway Cottage on the bay~Dog Friendly Too!
Property grounds

13. 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 CA $212
CA $560 total
includes taxes & fees
Oct 5 - Oct 6
Pondside/Kayak/Firepit/Dog Friendly~Willow Haven
Terrace/patio

14. 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 CA $290
CA $843 total
includes taxes & fees
Sep 28 - Sep 29
Windswept on Campground Beach
Exterior

15. 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 CA $377
CA $844 total
includes taxes & fees
Sep 20 - Sep 21
Pet Friendly Cape Cod Cottage Near Beaches w/ AC + Electric Vehicle Charging
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 CA $206
CA $553 total
includes taxes & fees
Sep 28 - Sep 29
🌊The Ocean Cottage on Thumpertown Beach
Terrace/patio

17. 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, (140 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 CA $313
CA $406 total
includes taxes & fees
Oct 15 - Oct 16
Pond View~ Abuts conservation and walking trails. There is fishing at the pond
Exterior

18. 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 CA $277
CA $663 total
includes taxes & fees
Sep 21 - Sep 22
Charming West Yarmouth Cottage- Minutes to Beaches, Dining & Family Fun
Exterior

19. Cozy, vacation home in a charming duplex cottage

Cozy, vacation home in a charming duplex cottage
Yarmouth
9.6 out of 10, Exceptional, (8 reviews)
"Cozy small home perfect for a girls weekend! Close proximity to the ferries and several good restaurants close by!"
United States
Sue N.
The price is CA $306
CA $634 total
includes taxes & fees
Sep 20 - Sep 21
Cozy, vacation home in a charming duplex cottage
Exterior

20. 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 CA $318
CA $1,182 total
includes taxes & fees
Sep 20 - Sep 21
Driftwood Cottages - Crab
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

Hyannis Travel Inn

Hyannis Travel Inn

8/10 Good
"Was a lower end hotel. You eat breakfast in hot pool area. The staff was great."
Roger 3-night trip
Posted 2 hours ago
Hyannis Travel Inn

Find out more about Chatham

Chatham Cottages information

Number of reviews
435
Accommodation
472 Cottages
Lowest Price
CA $406
Highest Price
CA $1,182

Frequently asked questions

How much do cottages in Chatham cost?
Cottages in Chatham range between CA $406 and CA $1,182 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 472 cottages in Chatham. No matter if you're vacationing 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.

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