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In two weeks
Jan 9 - Jan 11
In two months
Feb 20 - Feb 22
In three months
Mar 20 - Mar 22
In four months
Apr 17 - Apr 19

Our top choices for Chatham cottages

Terrace/patio
Darling, secluded cottage with large yard - walk to Chatham & Lighthouse Beach

Cottage in Chatham

Darling, secluded cottage with large yard - walk to Chatham & Lighthouse Beach
9.6 out of 10, Exceptional, (30)
"CutePrivateGreat outdoor showe "
United States
Stephanie D.
$291 nightly
The price is $333
Jan 4 - Jan 5, 2026
Total with taxes and fees
Darling, secluded cottage with large yard - walk to Chatham & Lighthouse Beach
Outdoor dining
🦀Waterfront at The Velvet Crab~Amazing Sunsets

Cottage in Eastham

🦀Waterfront at The Velvet Crab~Amazing Sunsets
9.8 out of 10, Exceptional, (23)
"Everything was great, we really enjoyed our stay!"
United States
Anna T.
$373 nightly
The price is $427
Dec 29 - Dec 30
Total with taxes and fees
🦀Waterfront at The Velvet Crab~Amazing Sunsets
Exterior
Dennisport : Dog Friendly with a fenced in large yard. 1/2 mile from beach

Cottage in Dennis

Dennisport : Dog Friendly with a fenced in large yard. 1/2 mile from beach
9.6 out of 10, Exceptional, (177)
"Fenced in yard was perfect and close walk to both beach and restaurants."
United States
Mike Kayla B.
$306 nightly
The price is $350
Dec 26 - Dec 27
Total with taxes and fees
Dennisport : Dog Friendly with a fenced in large yard. 1/2 mile from beach
Terrace/patio
Beautiful cottage, fireplace, cozy Beach 1. 4 mile . Family relaxation fire pit!

Cottage in Harwich

Beautiful cottage, fireplace, cozy Beach 1. 4 mile . Family relaxation fire pit!
9.6 out of 10, Exceptional, (4)
"We had an amazing stay! The house was exactly what we were looking for when booking. The host was amazing and accommodating for our dates. Communication was easy and responsive. We look forward to booking again in the future. "
United States
Laura J.
$664 nightly
The price is $760
Dec 24 - Dec 25
Total with taxes and fees
Beautiful cottage, fireplace, cozy Beach 1. 4 mile . Family relaxation fire pit!
Exterior
Charming 2-bedroom cottage in fabulous Harwich with WiFi, AC

Cottage in Harwich

Charming 2-bedroom cottage in fabulous Harwich with WiFi, AC
8.6 out of 10, Excellent, (4)
"Great accommodation for what we needed."
United States
Judith F.
$401 nightly
The price is $459
Jan 6 - Jan 7, 2026
Total with taxes and fees
Charming 2-bedroom cottage in fabulous Harwich with WiFi, AC
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

Chatham Wayside Inn

Chatham Wayside Inn

10/10 Excellent
"Charming, cozy , clean! "
Erica 1-night trip
Posted 2 days ago
Chatham Wayside Inn

Find out more about Chatham

Chatham Cottages information

Number of reviews
215
Accommodation
443 Cottages
Lowest Price
$333
Highest Price
$760

Frequently asked questions

How much do cottages in Chatham cost?
Cottages in Chatham range between $333 and $760 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 9.4. 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 443 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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