Chatham, MA Cottages from SAR 562

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Our top choices for Chatham cottages

A patio with two striped lounge chairs, a small round table, and two blue glass candle holders.

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

EASTHAM

Myriam A.

SAR 1,803 total

includes taxes & fees

16 Nov - 17 Nov

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

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

Harwich

david r.

SAR 2,100 total

includes taxes & fees

16 Nov - 17 Nov

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

3. 🦀Waterfront at The Velvet Crab~Amazing Sunsets

Eastham

Emily A.

SAR 1,506 total

includes taxes & fees

16 Nov - 17 Nov

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

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

Dennis

Holleigh B.

SAR 1,995 total

includes taxes & fees

19 Nov - 20 Nov

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

5. Cozy, vacation home in a charming duplex cottage

Yarmouth

Sarah B.

SAR 1,306 total

includes taxes & fees

1 Dec - 2 Dec

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

6. Cottage Getaway walk to beach

Eastham

SAR 46,064 total

includes taxes & fees

21 Nov - 22 Nov

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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

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

Chatham Bars Inn

Chatham

10/10 Excellent

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...

Marc

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

Chatham Tides

South Chatham

10/10 Excellent

joanna

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

Wequassett Resort and Golf Club

Harwich

10/10 Excellent

ruby12376

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

Candleberry Inn on Cape Cod

Brewster

10/10 Excellent

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...

Maria&Mike

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

A Beach Breeze Inn

West Harwich

10/10 Excellent

Lois

Skaket Beach Motel

Orleans

10/10 Excellent

Dolores

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

Charm on Main by Ocean Edge

Sea Pines

10/10 Excellent

Laura

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

Nauset Beach Inn

East Orleans

10/10 Excellent

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...

RICHARD

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

An English Garden Bed & Breakfast

Dennis Port

10/10 Excellent

Frank

A porch with white chairs and a planter with flowers.

The Captain Farris House B&B

Bass River

10/10 Excellent

Couldn't ask for more. The staff were extremely friendly and generous. The room was beautiful -- not overly luxurious, but full of character and with an extremely comfortable bed. One fixture on the bathroom sink was broken, and the TV was on the small side, but I would hardly call these complaints given how nice the overall experience was. And to top it off, the breakfast was amazing -- both the quality of the food and the service. We would definitely stay at the Captain Farris again.

Matt

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

Brewster by the Sea Inn

West Brewster

10/10 Excellent

Tony and Rachel

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

The Escape Inn

Bass River

10/10 Excellent

Steven

Hyannis Travel Inn

Hyannis

10/10 Excellent

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...

Luis

A two-story motel with a red and white facade, a driveway, and a sign for the Rodeway Inn.

Rodeway Inn Orleans - Cape Cod

Orleans

10/10 Excellent

This is a basic motel, but our rooms were newly painted, new floor in the bathroom, enough plugs by the bed, with a refrigerator and small microwave. The beds, sheets, pillows were comfortable. Big negative was the small, scratchy towels, but you can't have it all. The room was very clean. It is convenient to most Cape locations and activities. We did not use the pool but it appeared well-maintained. The motel was a VERY fair price for the Cape on Memorial Day weekend. I would definitely...

Alexandra

A two-story white building with green shutters, a sign indicating it is a Village Inn, and a well-maintained lawn.

The Village Inn Cape Cod

Yarmouth Port

10/10 Excellent

Anonymous traveler

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

Pelham House Resort

Dennis Port

10/10 Excellent

Anonymous traveler

Frequently Asked Questions

How much do cottages in Chatham cost?

Cottages in Chatham range between SAR 562 and SAR 37,527 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.

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.

Search Cottages in Chatham

Change your mind

Treat yourself

Be picky

Find vacation rentals that suit your style

Check prices for these dates

Our top choices for Chatham cottages

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

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

3. 🦀Waterfront at The Velvet Crab~Amazing Sunsets

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

5. Cozy, vacation home in a charming duplex cottage

6. Cottage Getaway walk to beach

Learn more about Chatham

Top reviews in Chatham

Chatham Bars Inn

10/10 Excellent

Frequently Asked Questions

How much do cottages in Chatham cost?

What are the best cottages in Chatham?

How many cottages are there in Chatham?

Why book your cottage in Chatham with Expedia?

How can I find cheap cottages in Chatham?