Chatham Holiday Rentals, Massachusetts: Private House Rentals

A boat on a calm river, a large house with a red roof, and dense greenery in the background.

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Our top choices for Chatham hotels

A pathway leading to a beach with boats in the background and a building with a tower.

An aerial view of a beach with rows of sunbeds and umbrellas, a pier extending into the water, and a small building near the beach.

A resort pool with multiple sun loungers and umbrellas, surrounded by beach views and boats.

1. Chatham Bars Inn

Chatham

Sylvia

10.003.675 ₫

11.449.206 ₫ total

includes taxes & fees

5 Nov - 6 Nov

A large house with a patio area featuring outdoor furniture and a well-lit garden.

A sandy beach path with a wooden fence leading to the ocean, under a partly cloudy sky.

A garden with a pergola structure, a pathway, and a seating area.

A restaurant with long communal tables and booths, large windows, and a view of buildings outside.

2. Chatham Wayside Inn

Chatham

Ashley

4.396.405 ₫

6.156.001 ₫ total

includes taxes & fees

2 Nov - 3 Nov

A sandy beach path with wooden fencing, leading to the ocean.

A two-story house with a covered porch, a well-maintained garden, and a driveway.

A sign for The Old Harbor Inn with a number 22 on the building.

A hotel room with a bed, a nightstand, a mirror, a shower area, and a lamp.

3. Old Harbor Inn

Chatham

Adélaïde

10.204.001 ₫

11.678.515 ₫ total

includes taxes & fees

1 Nov - 2 Nov

A swimming pool with blue water, surrounded by lounge chairs and a waterfall feature.

A covered porch with a lattice design, a stone pathway, and a view of a garden.

A house surrounded by dense trees and a gravel path leading to the front door.

A bedroom with a large bed, two side tables with lamps, a wooden nightstand, a wooden dresser, and a large window with a view of greenery.

4. Pleasant Bay Village Resort

Chatham

sheila

6.241.809 ₫

7.143.751 ₫ total

includes taxes & fees

25 Oct - 26 Oct

A white house with a grey roof, surrounded by a well-maintained lawn and flowering bushes.

A modern kitchen with white cabinetry, a wooden island with two barstools, and a decorative wall art piece.

A covered porch with white columns and a pathway leading to a door.

Four sun loungers aligned along a poolside with a tiled floor.

5. Greyfinch Chatham Inn

Chatham

Jacob

4.363.580 ₫

5.940.445 ₫ total

includes taxes & fees

1 Nov - 2 Nov

A house with a brick exterior, white exterior walls, and a front porch with white chairs.

A beach with a fallen tree, clear blue water, and a forested shoreline.

An outdoor patio with white metal chairs and a table, surrounded by blooming pink trees.

A white desk with a woven hat, a vase with white flowers, and two glasses of white wine.

6. Chatham Seafarer Inn

Chatham

Suzanne

6.018.758 ₫

6.888.217 ₫ total

includes taxes & fees

25 Oct - 26 Oct

A coastal scene with a large group of seals resting on the shore.

A coastal view with a beach, boats, and a house with a lawn and lamp post.

A set of outdoor brick steps leading to a building with a white balcony.

A house with a grassy yard and a view of the water.

7. The Hawthorne

Chatham

Richard

8.500.749 ₫

9.728.951 ₫ total

includes taxes & fees

25 Oct - 26 Oct

A balcony with wicker furniture, a table with a vase and wine glass, and a view of the sea.

A sunlit room with a view of the sea, featuring a sofa, a round table, and a chair.

A dining area with tables set for two, overlooking a body of water with a sailboat.

A room with a view of the sea, featuring a sofa, two chairs, a small table with a vase and a bottle, and a patterned carpet.

8. Wequassett Resort and Golf Club

Harwich

Uk Jin

9.201.482 ₫

11.268.278 ₫ total

includes taxes & fees

8 Nov - 9 Nov

A room with a bed, two wicker chairs, a small table, a coffee maker, and a view of the sea through a window.

A room with a large window overlooking the sea, a white desk, and nautical-themed decor.

A modern kitchen with white cabinets, a built-in oven, and a view of the ocean through large windows.

A beachfront property with a wooden deck, a sign labeled "SHOWER," and surfboards stored outside.

9. Chatham Tides

South Chatham

Chad

4.163.791 ₫

4.765.458 ₫ total

includes taxes & fees

15 Nov - 16 Nov

A blue door labeled "Office" with a small window and a mailbox.

A reception area with a counter, a blue door labeled "Office," and a wall-mounted shelf with various items.

An outdoor patio with round tables and chairs, picnic tables, and umbrellas.

A sign for Handkerchief Shoals Inn with a well-maintained garden in the foreground.

10. Handkerchief Shoals Inn

South Harwich

Matthew

4.605.757 ₫

5.271.292 ₫ total

includes taxes & fees

25 Oct - 26 Oct

A two-story residential building with a well-maintained lawn, a wooden fence, and a patio area with outdoor furniture.

A modern bathroom with a glass shower enclosure, a white sink, and a towel rack.

A cozy living room with a fireplace, striped sofa, wooden flooring, and exposed beams.

A staircase with wooden steps and a white wall. There is a white sofa with a geometric pillow in the living area.

11. Kingfisher Harwich Port

Harwich Port

Marc

6.249.046 ₫

7.152.105 ₫ total

includes taxes & fees

24 Oct - 25 Oct

A balcony with a view of a beach, a table with a vase of flowers, and a chair.

Two blue Adirondack chairs facing a sunset over a beach with a fence and vegetation in the foreground.

A room with large windows overlooking a beach, a table with a bottle and glasses, and a chair.

A spacious living room with a large window, a ceiling fan, and a glass coffee table with flowers.

12. Winstead Beach Resort

Harwich Port

William

6.564.884 ₫

7.513.691 ₫ total

includes taxes & fees

24 Oct - 25 Oct

A gazebo with a red roof and white trim, surrounded by a well-maintained lawn and a large tree with pink flowers.

A sandy beach with gentle waves and a clear sky.

A modern kitchen with stainless steel appliances, wooden cabinets, and a marble countertop.

A kitchen with a white island, a fireplace, and a surfboard decoration.

13. Eagle Wing Inn - Cape Cod

Eastham

Timothy

4.461.885 ₫

5.106.466 ₫ total

includes taxes & fees

24 Oct - 25 Oct

A two-story house with a front porch, a mailbox, and a well-maintained garden.

A hotel room with a bed, a bench, a desk, a microwave, and a television.

A swimming pool with lounge chairs and a covered seating area.

A covered porch with white Adirondack chairs, a trash can, and a door marked with the number 9.

14. Pelham on Earle

West Harwich

Colleen

4.884.894 ₫

6.037.884 ₫ total

includes taxes & fees

26 Oct - 27 Oct

A garden area with a welcome sign, outdoor seating, and a blue umbrella.

A swimming pool with lounge chairs and umbrellas, surrounded by greenery and a building.

A dining area with multiple tables and chairs, some with flower centerpieces.

A hotel room with a large bed, two bedside tables, a wall-mounted painting, and a patterned carpet.

15. Rodeway Inn Orleans - Cape Cod

Orleans

Aldrick

2.847.971 ₫

3.259.503 ₫ total

includes taxes & fees

26 Oct - 27 Oct

A park with green grass, trees, and a clear blue sky.

A two-story house with a porch, surrounded by lush greenery and flowering bushes.

A spa area with a hot tub and a swimming pool, surrounded by large windows and potted plants.

A staircase with ornate brass handrails and a mirror.

16. Whalewalk Inn and Spa

Eastham

Purav

6.687.653 ₫

7.654.020 ₫ total

includes taxes & fees

27 Oct - 28 Oct

A large, red-roofed building with a stone facade, surrounded by well-maintained gardens and a cobblestone driveway.

An outdoor patio with tables and chairs, umbrellas, and a bar area.

A rooftop bar with outdoor seating and a view of the water.

An outdoor bar area with multiple screens displaying sports, surrounded by patrons.

17. The Mansion at Ocean Edge

Brewster

Pamela

4.734.987 ₫

6.898.359 ₫ total

includes taxes & fees

22 Nov - 23 Nov

A hotel room with two beds, a desk with a television, a red chair, and a window with green curtains.

A compact living space with a dining area, kitchenette, and a television.

A covered patio with a round table and four chairs.

A breakfast buffet with pastries, a lamp, and storage containers on a wooden table.

18. Skaket Beach Motel

Orleans

Wayne

3.359.980 ₫

3.845.497 ₫ total

includes taxes & fees

25 Oct - 26 Oct

A two-story house with a well-lit front porch, a staircase leading to the entrance, and a garden with various plants and flowers.

A cozy living room with a fireplace, a Christmas tree, and festive decorations.

A corner building with a curved roof, large windows, and a well-maintained garden with various plants and flowers.

A large swimming pool with a fountain, surrounded by lounge chairs and umbrellas, set against a stone building with multiple windows and a balcony.

19. Winstead Inn

Harwich

Karen

5.815.350 ₫

6.655.862 ₫ total

includes taxes & fees

26 Oct - 27 Oct

A modern kitchen with a large island, wooden cabinets, a white refrigerator, and pendant lighting.

A golf course with sand bunkers, trees, and a clear blue sky.

A restaurant with brick arches, wooden tables, and chairs. There is a bar area with bottles and a television screen.

An outdoor patio with tables and chairs, umbrellas, and a view of the ocean.

20. The Villages at Ocean Edge

Brewster

Myunghee

3.103.177 ₫

4.734.815 ₫ total

includes taxes & fees

8 Nov - 9 Nov

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Stay near popular Chatham attractions

A beach with people walking and standing on the sand, and the ocean in the background.

Chatham Lighthouse Beach

9.2/10 (46 reviews)

If a restful holiday is part of your travel plans, Chatham Lighthouse Beach might be the perfect place to visit during your trip to Chatham. Stroll along this trendy area's seaside or simply enjoy its seafood restaurants.

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A calm sea with several boats anchored near the shore.

Chatham Fish Pier

9.4/10 (107 reviews)

Watch local fishermen unload their daily catch while seals swim nearby at this authentic working waterfront. Savour fresh seafood from the on-site market while enjoying panoramic harbour views from the observation deck.

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A lighthouse with an American flag, a white building with a red roof, and a cloudy sky.

Chatham Lighthouse

9.4/10 (173 reviews)

This historic 1808 beacon stands sentinel over Cape Cod's treacherous waters, guiding mariners for generations. Join a free summer Wednesday tour to climb the 48-foot tower for panoramic Atlantic views.

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Chatham Windmill

9.2/10 (38 reviews)

This 1797 gristmill showcases Chatham's agricultural heritage with wooden gears and mechanisms. During summer "Corn Grinding Days," you can witness the historic mill transforming grain just as it did centuries ago.

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Ridgevale Beach

9.6/10 (21 reviews)

Why not spend a care-free afternoon at Ridgevale Beach during your travels in Chatham? Stroll along this trendy area's seaside or simply enjoy its seafood restaurants.

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Chatham Seaside Links

9.2/10 (20 reviews)

This historic nine-hole course challenges golfers with coastal winds and strategic play along the Atlantic. Enjoy the natural undulations and ocean views while navigating the traditional seaside links layout.

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Caleb Nickerson House

6.0/10 (1 review)

Step back in time at this preserved 1829 Cape-style house with three working fireplaces. Watch demonstrations of hearth cooking and colonial crafts while exploring the historic homestead's period rooms.

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Cockle Cove Beach

9.0/10 (28 reviews)

If a restful holiday is part of your travel plans, Cockle Cove Beach might be the perfect place to visit during your trip to Chatham. Stroll along this trendy area's seaside or simply enjoy its seafood restaurants.

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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 Chatham Hotel Reviews

Hyannis Travel Inn

8/10 Good

"We loved the two gentlemen who helped at the check in desk when we arrived - very knowledgeable and helpful!"

Bayside Resort Hotel

8/10 Good

"Staff very friendly"

Greyfinch Chatham Inn

10/10 Excellent

"Quaint smaller property. Room was spacious and bed very comfortable. Had a plug issue and was fixed immediately. Grounds are immaculate. Sat by the fire pit in back area near the pool. Great location a minute away from downtown Chatham."

Margaritaville Resort Cape Cod

8/10 Good

"Overall, the hotel and our room were lovely. There was a large event taking place during our stay, and a significant number of younger guests from the event were gathered throughout the public areas. While completely understandable, it did make it difficult for us to enjoy those spaces. Our only real disappointment was breakfast. We needed something quick and were directed to the to-go area, but waited more than 20 minutes for a simple breakfast sandwich. When it was made incorrectly, the interaction felt unnecessarily dismissive and we were made to feel as though the mistake was our fault. A little more customer-service-minded handling would have made a big difference. Aside from that experience, we had a lovely room and enjoyed our stay overall."

Riviera Beach Resort

10/10 Excellent

"Wonderful hotel, clean and right on the beach. Will stay they again!"

Hyannis Harbor Hotel

10/10 Excellent

"Great location, staff was extremely helpful"

Chatham Bars Inn

10/10 Excellent

"Amazing property and staff."

Sunbird Cape Cod Resort

10/10 Excellent

"Team members was excellent"

Cape Cod Family Resort and Parks

10/10 Excellent

"Excellent experience"

More cheap stays in Chatham

Cape Sands Inn

149 Main St - RT 28 West Yarmouth MA

1.746.673 ₫

1.998.930 ₫ total

25 Oct - 26 Oct

includes taxes & fees

Hyannis Travel Inn

18 North St Hyannis MA

2.558.754 ₫

2.928.352 ₫ total

25 Oct - 26 Oct

includes taxes & fees

9.6/10 Exceptional! (1,021 reviews)

Blue Dolphin Inn

5950 State Highway rt 6 n. Eastham MA

2.560.501 ₫

2.930.493 ₫ total

24 Oct - 25 Oct

includes taxes & fees

8/10 Very good! (1,000 reviews)

Holiday Inn Express Hyannis Cape Cod by IHG

1470 Iyannough Road Hyannis MA

2.765.522 ₫

3.165.141 ₫ total

22 Nov - 23 Nov

includes taxes & fees

Hyannis Plaza Hotel

662 Main Street Hyannis MA

2.713.055 ₫

3.363.551 ₫ total

27 Oct - 28 Oct

includes taxes & fees

7.2/10 Good! (1,001 reviews)

Courtyard Resort

125 North St Hyannis MA

3.359.980 ₫

3.845.626 ₫ total

25 Oct - 26 Oct

includes taxes & fees

8.6/10 Excellent! (160 reviews)

Hotels in Chatham with star rating

Frequently asked questions

What's the seasonal weather like in Chatham?

The hottest months are usually August and July, with an average temperature of 19°C, while the coldest months are February and January, with an average of 3°C. Average annual precipitation for Chatham is 1362 mm.

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Book Hotels in Chatham on Expedia.com

Find hotels in Chatham, MA from 1.998.930 ₫

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in Chatham

Check prices for these dates

Filter by

Star rating

Guest rating

Our top choices for Chatham hotels

1. Chatham Bars Inn

2. Chatham Wayside Inn

3. Old Harbor Inn

4. Pleasant Bay Village Resort

5. Greyfinch Chatham Inn

6. Chatham Seafarer Inn

7. The Hawthorne

8. Wequassett Resort and Golf Club

9. Chatham Tides

10. Handkerchief Shoals Inn

11. Kingfisher Harwich Port

12. Winstead Beach Resort

13. Eagle Wing Inn - Cape Cod

14. Pelham on Earle

15. Rodeway Inn Orleans - Cape Cod

16. Whalewalk Inn and Spa

17. The Mansion at Ocean Edge

18. Skaket Beach Motel

19. Winstead Inn

20. The Villages at Ocean Edge

Stay near popular Chatham attractions

Chatham Lighthouse Beach

Chatham Fish Pier

Chatham Lighthouse

Chatham Windmill

Ridgevale Beach

Chatham Seaside Links

Caleb Nickerson House

Cockle Cove Beach

Learn more about Chatham

Top Chatham Hotel Reviews

Hyannis Travel Inn

Bayside Resort Hotel

Greyfinch Chatham Inn

Margaritaville Resort Cape Cod

Riviera Beach Resort

Hyannis Harbor Hotel

Chatham Bars Inn

Sunbird Cape Cod Resort

Cape Cod Family Resort and Parks

More cheap stays in Chatham

Cape Sands Inn

Hyannis Travel Inn

Blue Dolphin Inn

Holiday Inn Express Hyannis Cape Cod by IHG

Hyannis Plaza Hotel

Courtyard Resort

Hotels in Chatham with star rating

Frequently asked questions

Explore a world of travel with Expedia

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