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 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

Our top choices for Chatham cottages

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
$642 nightly
The price is $735
Sep 30 - Oct 1
Total with taxes and fees
Town Center-Full Reno 2026-Steps To Shops & Eateries-Walk To Lighthouse Beach
A house with a porch decorated with Christmas lights and wreaths.

2. Newly Refreshed Upscale Cottage/Pvt 2 KING BR Ensuite /1 Mile to Hardings Beach

Newly Refreshed Upscale Cottage/Pvt 2 KING BR Ensuite /1 Mile to Hardings Beach
Chatham
10.0 out of 10, Exceptional, (20 reviews)
"Everything exceeded expectations"
United States
Marc S.
$1,041 nightly
The price is $1,192
Oct 3 - Oct 4
Total with taxes and fees
Newly Refreshed Upscale Cottage/Pvt 2 KING BR Ensuite /1 Mile to Hardings Beach
A house surrounded by trees with a clear path leading to the front door.

3. 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.
$426 nightly
The price is $488
Sep 30 - Oct 1
Total with taxes and fees
Harwich Hideaway with King Beds Pet Friendly!
A wooden deck with white railings, wicker chairs, and a blue umbrella.

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.
$360 nightly
The price is $412
Oct 20 - Oct 21
Total with taxes and fees
On Town Cove with salt water access! Kayaks and paddle board available for use!
A metal showerhead attached to a house's exterior wall, with water flowing down a blue gutter.

5. 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.
$462 nightly
The price is $529
Oct 4 - Oct 5
Total with taxes and fees
Captain's Quarters by Nauset Beach
A patio with two striped lounge chairs, a small round table, and two blue glass candle holders.

6. 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.
$433 nightly
The price is $495
Oct 1 - Oct 2
Total with taxes and fees
Seaside Escape-Art-filled 2 Bd on Town Cove
A two-story house with a front porch, a small attached garage, and a gravel driveway.

7. 🌊The Ocean Cottage on Thumpertown Beach

🌊The Ocean Cottage on Thumpertown Beach
Eastham
9.4 out of 10, Exceptional, (13 reviews)
"We absolutely loved the place and the location right near Thumpertown Beach was perfect!"
United States
Jeff P.
$324 nightly
The price is $371
Sep 29 - Sep 30
Total with taxes and fees
🌊The Ocean Cottage on Thumpertown Beach
A beach with a wooden boardwalk and a rocky foreground.

8. 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.
$398 nightly
The price is $456
Sep 29 - Sep 30
Total with taxes and fees
Edgewood on Campground Beach/Steps to the Sand
A single-story house with a gabled roof, a front porch, and a small front yard.

9. 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.
$407 nightly
The price is $466
Oct 27 - Oct 28
Total with taxes and fees
Charming 2-bedroom cottage in fabulous Harwich with WiFi, AC
A single-story mobile home with a porch, a small deck, and a gravel driveway.

10. Driftwood Cottages - 65A - Whale

Driftwood Cottages - 65A - Whale
Eastham
$685 nightly
The price is $783
Sep 28 - Sep 29
Total with taxes and fees
Driftwood Cottages - 65A - Whale
An outdoor patio with wicker furniture, a round table, and a view of trees and water.

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
$340 nightly
The price is $389
Oct 19 - Oct 20
Total with taxes and fees
The Breeze on Minister's Pond
An outdoor patio with a table and chairs, a covered grill, and a view of a lake.

12. 🦀Waterfront at The Velvet Crab~Amazing Sunsets

🦀Waterfront at The Velvet Crab~Amazing Sunsets
Eastham
9.8 out of 10, Exceptional, (26 reviews)
"Perfect size home for a family of 4, welcoming and cozy! Having -All towels and linens and shampoo, body wash and conditioner all included made for a much easier stay! Highly recommend."
United States
Emily A.
$358 nightly
The price is $410
Oct 19 - Oct 20
Total with taxes and fees
🦀Waterfront at The Velvet Crab~Amazing Sunsets
A wooden deck with a view of a lake, surrounded by trees.

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

Pondside/Kayak/Firepit/Dog Friendly~Willow Haven
Eastham
9.8 out of 10, Exceptional, (7 reviews)
"Great hideaway location on the Cape. Well equipped rental."
United Kingdom
Richard F.
$311 nightly
The price is $356
Oct 19 - Oct 20
Total with taxes and fees
Pondside/Kayak/Firepit/Dog Friendly~Willow Haven
Two wicker swing chairs facing a sunset over the ocean.

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

Castaway Cottage on the bay~Dog Friendly Too!
Eastham
9.6 out of 10, Exceptional, (20 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.
$477 nightly
The price is $546
Oct 3 - Oct 4
Total with taxes and fees
Castaway Cottage on the bay~Dog Friendly Too!
A single-story house with a brown exterior and white trim, featuring a front door, multiple windows, and a small porch area.

15. 🐚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.
$324 nightly
The price is $371
Oct 4 - Oct 5
Total with taxes and fees
🐚The Bay Cottage on Thumpertown Beach
A wooden deck with two Adirondack chairs, a small table, and a covered porch area overlooking a grassy yard with a wooden fence and a small shed in the background.

16. 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, (141 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.
$245 nightly
The price is $280
Oct 15 - Oct 16
Total with taxes and fees
Pond View~ Abuts conservation and walking trails. There is fishing at the pond
A wooden deck with a barbecue grill, outdoor furniture, and a book titled "The Barbecue Bible".

17. The Mod Pod~2 bd/2.5 bth/dog/games/steps to beach

The Mod Pod~2 bd/2.5 bth/dog/games/steps to beach
Wellfleet
6.0 out of 10, (1 review)
$461 nightly
The price is $528
Sep 29 - Sep 30
Total with taxes and fees
The Mod Pod~2 bd/2.5 bth/dog/games/steps to beach
A house with a front porch, a small garden, and a mailbox.

18. Cozy, vacation home in a charming duplex cottage

Cozy, vacation home in a charming duplex cottage
Yarmouth
9.6 out of 10, Exceptional, (9 reviews)
"Cozy small home perfect for a girls weekend! Close proximity to the ferries and several good restaurants close by!"
United States
Sue N.
$361 nightly
The price is $413
Sep 28 - Sep 29
Total with taxes and fees
Cozy, vacation home in a charming duplex cottage
A single-story mobile home with a front porch, a small deck, and a wooden fence.

19. 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.
$695 nightly
The price is $795
Sep 28 - Sep 29
Total with taxes and fees
Driftwood Cottages - Crab
A house with a deck, a flag, and a garage.

20. 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
$365 nightly
The price is $418
Sep 28 - Sep 29
Total with taxes and fees
Charming West Yarmouth Cottage- Minutes to Beaches, Dining & Family Fun
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

Cape Sands Inn

Cape Sands Inn

8/10 Good
"Staff was pleasant"
Kathleen 3-night trip
Posted 9 hours ago
Cape Sands Inn

Find out more about Chatham

Chatham Cottages information

Number of reviews
368
Accommodation
471 Cottages
Lowest Price
$280
Highest Price
$1,192

Frequently asked questions

How much do cottages in Chatham cost?
Cottages in Chatham range between $280 and $1,192 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 471 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 traveler favorite. 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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