Location: EASTHAM
Guest rating: 7.4/10 (Good, 3 reviews)
Price: $419 nightly, $479 total, Nov 15 - Nov 16, Total with taxes and fees, for Our top choices for Chatham cottages
Review: The cottage was very well decorated, maintained and well stocked. Loved the location with a view of the cove.My kids loved the loft, by Myriam A.

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

A single-story house with a front porch, a small front yard, and a flagpole with an American flag.

Location: Harwich
Guest rating: 9/10 (Wonderful, 6 reviews)
Price: $485 nightly, $555 total, Nov 15 - Nov 16, Total with taxes and fees, for Our top choices for Chatham cottages
Review: would stay here again, by david r.

3. 🦀Waterfront at The Velvet Crab~Amazing Sunsets

An outdoor patio with a table and chairs, a covered grill, and a view of a lake.

Location: Eastham
Guest rating: 9.8/10 (Exceptional, 30 reviews)
Price: $352 nightly, $403 total, Nov 15 - Nov 16, Total with taxes and fees, for Our top choices for Chatham cottages
Review: 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., by Emily A.

4. Cape Cod Beach Cottage, only 5 minute walk to Glendon beach & local restaurants

A house with a white picket fence, a well-maintained lawn, and a clear blue sky.

Location: Dennis
Guest rating: 9.6/10 (Exceptional, 92 reviews)
Price: $465 nightly, $532 total, Nov 19 - Nov 20, Total with taxes and fees, for Our top choices for Chatham cottages
Review: We had a great stay! We loved how close it was to the beach and that we could bring our dog. We also really appreciated the outdoor shower and extra room with tv for space., by Holleigh B.

5. Cozy, vacation home in a charming duplex cottage

A house with a front porch, a small garden, and a mailbox.

Location: Yarmouth
Guest rating: 9.6/10 (Exceptional, 10 reviews)
Price: $304 nightly, $348 total, Dec 1 - Dec 2, Total with taxes and fees, for Our top choices for Chatham cottages
Review: Amazingly clean, comfortable and a great location. We didn’t want to leave!, by Sarah B.

6. Cottage Getaway walk to beach

A wooden cabin with a snow-covered roof and a small porch area.

Location: Eastham
Price: $10,749 nightly, $12,302 total, Nov 21 - Nov 22, Total with taxes and fees, for Our top choices for Chatham cottages

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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Learn more about Chatham

Stroll the historic Main Street lined with boutiques, then head to Lighthouse Beach for seal-spotting at low tide. Seafood shacks serve the freshest catch, while the Chatham Bandstand hosts free summer concerts that locals never miss.

See all hotels in Chatham

A lighthouse with a house nearby, under a starry night sky with visible Milky Way.

Top reviews in Chatham

Chatham Tides

A deck with a view of the ocean, a blue umbrella, and a white chair.

Location: South Chatham
Review: Winter or summer, this is our favorite spot to vacation- we love the peaceful, serene atmosphere of the town and Chatham Tides. Main St. has a cute, unique, little stores if shopping is what you enjoy. Property is well kept, ocean view room provides precisely the view that we love to wake up to. Staff is always helpful and accommodating, without being overbearing. Can't wait to return!, by joanna, January 3, 2025, rated 10/10 Excellent

Chatham Bars Inn

A deck with white Adirondack chairs and a small round table, overlooking a beach and ocean.

Location: Chatham
Review: Highly recommend Chatham Bars Inn! Stay in the cottages along the water and start each day with a view of the sunrise, fishing boats, and harbor seals. Walk to the pool, beach, and the buffet breakfast. Walk to Main Street in town for even more restaurants, ice cream and candy shops, and great browsing in stores you can only find on the Cape. Staff was excellent and very professional. Everyone - check-in staff, pool and beach staff, restaurant staff, kids camp staff, were extremely..., by Marc, August 27, 2016, rated 10/10 Excellent

Wequassett Resort and Golf Club

A large two-story house with a balcony, a stone pathway, and a view of a lake.

Location: Harwich
Review: Great hotel at the Cape. Staff was very detailed and provided personalized service. Hotel facilities were top notch. I especially loved the decor. On site restaurant was pricey but had amazing food., by ruby12376, October 19, 2015, rated 10/10 Excellent

Charm on Main by Ocean Edge

A two-story house with a covered porch, a brick pathway leading to the entrance, and a well-maintained lawn.

Location: Sea Pines
Review: Everything was prefect from check in to check out. Jillian and staff are top notch! We loved the breakfast daily, beautiful property that is meticulously kept and location in the cape is excellent! We will be back and thank you for a wonderful stay!!!, by Laura, October 24, 2026, rated 10/10 Excellent

A Beach Breeze Inn

A flagpole with an American flag, a circular flower bed with pink and white flowers, and white Adirondack chairs.

Location: West Harwich
Review: My sister and I did a few day trip to the Cape and once again stayed here. It is clean and comfortable and I always sleep well! Pam is lovely and accommodating and the queen of muffins. Not fancy, shmancy...but has everything you need/want for a motel and very comfortable. This was our second trip and stay and we will be visiting Pam again!, by Lois, June 23, 2018, rated 10/10 Excellent

Skaket Beach Motel

Location: Orleans
Review: I had booked for two nights but when I arrived the booking was for one night the room was very nice and updated but not close to a beach not close to transportation on a very busy highway, by Dolores, May 18, 2024, rated 10/10 Excellent

Candleberry Inn on Cape Cod

A two-story house with a symmetrical facade, a central entrance, and a flag.

Location: Brewster
Review: Great place to stay! My husband and I were a little worried about vacationing during the pandemic. But, we were put at ease when we read about the policies the innkeepers (Marco and Angelo) put in place during COVID-19, and the overall cleanliness of the inn and our room. The gourmet breakfast and afternoon treats were delicious! It's one of the things we look forward each day. The amenities were great! Since a lot of the restaurants are already fully booked, we're fortunate to have our own..., by Maria&Mike, September 12, 2020, rated 10/10 Excellent

The Escape Inn

A two-story motel with a balcony on the second floor, a covered outdoor seating area, and a parking lot.

Location: Bass River
Review: We stayed for 3 nights. We visited Cape Cod National Seashore on our arrival day. The next day we took a roundtrip ferry ride to Nantucket. The day after, a round-trip ferry ride to Martha's vineyard. Breakfast was included. We had a room on the 2nd floor which was nice and quiet., by Steven, October 14, 2015, rated 10/10 Excellent

The Villages at Ocean Edge

A patio with two Adirondack chairs and a small table, overlooking a grassy yard and trees.

Location: Brewster
Review: I had a great overall experience staying at The Villages at Ocean Edge! The check in process was easy and the staff was able to accommodate my check-in early request. I would book another stay in the future and I would definitely recommend this place to others., by Amanda, March 19, 2024, rated 10/10 Excellent

An English Garden Bed & Breakfast

A two-story house with a balcony, a chimney, and a garden with a white archway.

Location: Dennis Port
Review: Very nice, cute house. We had a small balcony which was nice to sit outside. Breakfast was freshly made an delicious. The location is very good to reach different spots around cape cod! Perfect stay. Definitely recommend!, by Frank, September 16, 2024, rated 10/10 Excellent

Hyannis Travel Inn

Location: Hyannis
Review: The location is everything as it is 1 street over from main street. The room was a nice size with 2 double beds and was clean with a large private balcony overlooking the street. The room had a mini fridge, a TV with limited cable, a telephone, great air conditioning and lighting. The bathroom was small with a very small and low toilet, low water pressure and a very small shower head, but the water temperature was good. Also limited counter space. The beds were very uncomfortable , uneven And..., by Luis, June 21, 2024, rated 10/10 Excellent

Love Farms Lodge

A covered balcony with a white railing, grey siding, and a glass door leading to the interior.

Location: West Dennis
Review: Beautiful property, nice sized room and amenities. Owners were super nice and accommodating., by Anonymous traveler, July 17, 2021, rated 10/10 Excellent

Brewster by the Sea Inn

A two-story building with a sign reading "The Orchard House."

Location: West Brewster
Review: Elizabeth and the entire staff were so pleasant and accomodating. Suite was newly done. Great location on the "quiet" side of the Cape within minutes of everything. Thoroughly enjoyed our stay., by Tony and Rachel, August 8, 2016, rated 10/10 Excellent

Pelham House Resort

A modern two-story house with a large balcony, a well-maintained lawn, and a view of the water at sunset.

Location: Dennis Port
Review: What a wonderful night we had at Pelham House! The rooms were spacious and extremely clean, the view from the room was gorgeous, and the staff were all so kind and helpful! We will definitely be coming back!, by Anonymous traveler, June 16, 2019, rated 10/10 Excellent

Nauset Beach Inn

An aerial view of a coastal property with a large lawn, several buildings, and a beach in the background.

Location: East Orleans
Review: The Nauset Beach Inn at Orleans is a special gem. The accommodations were clean and well kept. The view from our living room picture window was amazing, especial the early morning sunrises. Glorious! Not to be missed. We enjoyed the large firepit afternoons and evenings. The fireplace was a nice touch. Location was convenient for the many places to eat and visit. The owner was friendly and helpful. One suggestion for our cabin #4 is that it needs a shelf for toiletries in the bathroom. There..., by RICHARD, October 11, 2026, rated 10/10 Excellent

Ocean Club on Smuggler's Beach

A beachside patio with lounge chairs and umbrellas, overlooking the ocean.

Location: Bass River
Review: Enjoyed the enclosed patio with Lounge chairs. Plexiglass kept the wind out whilst we enjoyed the sun, by Darlene, June 1, 2024, rated 10/10 Excellent

Blue Lobster Inn

Location: Bass River
Review: The room was exceptionally clean. The staff went above the call of duty to help me while I was there., by Crystal, November 7, 2026, rated 10/10 Excellent

Frequently Asked Questions

How much do cottages in Chatham cost?

Cottages in Chatham range between $347 and $12,302 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 9.6. 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 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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