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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Go beyond your typical stay in Chatham

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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.

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

1. Chatham Bars Inn

Chatham

Yousuf Hussain

฿13,169

฿15,072 total

includes taxes & fees

3 Nov - 4 Nov

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

A living room with wicker furniture, a fireplace, and a staircase.

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

An outdoor seating area with tables and chairs, a sign for 'Wild Goose Tavern', and large windows.

2. Chatham Wayside Inn

Chatham

Ashley

฿6,032

฿8,369 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 circular wooden structure with illuminated edges in a garden setting.

3. Pleasant Bay Village Resort

Chatham

sheila

฿8,105

฿9,276 total

includes taxes & fees

12 Oct - 13 Oct

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

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

An outdoor patio with a fire feature, wicker furniture, and hanging flower baskets.

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

4. Old Harbor Inn

Chatham

Adélaïde

฿11,872

฿13,587 total

includes taxes & fees

15 Oct - 16 Oct

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

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

A modern bedroom with a wooden wardrobe, a white robe hanging on the door, and a bed with a wooden frame.

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

5. Greyfinch Chatham Inn

Chatham

Jacob

฿5,391

฿7,399 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.

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

A bedroom with a bed, a nightstand, a lamp, a window with curtains, a hat, and a magazine on the bed.

6. Chatham Seafarer Inn

Chatham

Ian

฿6,512

฿7,453 total

includes taxes & fees

7 Oct - 8 Oct

A covered porch with wicker furniture and a red cushion, a brick pathway, and a grassy area with a sign in the background.

A dining area with a round table and white chairs, a staircase, and a blue accent wall.

A red two-story house with a covered porch, white trim, and multiple windows.

A beach with people sunbathing and swimming, a rocky shoreline, and houses in the background.

7. Surfside Inn Chatham

Chatham

Jenee

฿7,915

฿9,059 total

includes taxes & fees

7 Oct - 8 Oct

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

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

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

A white bicycle with brown tires parked outside a building with a wooden exterior.

8. Chatham Tides

South Chatham

Craig

฿6,517

฿7,459 total

includes taxes & fees

1 Nov - 2 Nov

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

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

A bedroom with a bed, a table, two chairs, a lamp, and a window with curtains.

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

9. Handkerchief Shoals Inn

South Harwich

Matthew

฿4,501

฿5,152 total

includes taxes & fees

7 Oct - 8 Oct

A hotel room with a large bed, teal walls, and a wooden headboard. There are two bedside tables with lamps and small plants.

A hotel room with two beds, a view of the outdoors, and a balcony.

A traditional fireplace with a clock above it, surrounded by various decorative items and a modern refrigerator.

A kitchen with a brick stove, a white countertop, and a sign labeled "POOL TOWELS".

10. Olde Tavern Motel And Inn

Orleans

Rosalie

฿3,334

฿3,816 total

includes taxes & fees

7 Oct - 8 Oct

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

A building with a red door, black shutters, and hanging flower baskets.

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

A sandy beach with gentle waves and a clear sky.

11. Eagle Wing Inn - Cape Cod

Eastham

Andrea

฿4,446

฿5,088 total

includes taxes & fees

7 Oct - 8 Oct

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

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

A beach with clear water, a sandy shore, and houses in the background.

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

12. Kingfisher Harwich Port

Harwich Port

Marc

฿7,706

฿8,820 total

includes taxes & fees

8 Oct - 9 Oct

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

A hotel reception area with a blue wall, a reception desk, a large window, and a welcome mat.

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

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

13. Rodeway Inn Orleans - Cape Cod

Orleans

Aldrick

฿3,507

฿4,013 total

includes taxes & fees

13 Oct - 14 Oct

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 brick building with a white picket fence, a lawn, and a sign for Skaket Beach Motel.

14. Skaket Beach Motel

Orleans

Wayne

฿4,363

฿4,993 total

includes taxes & fees

13 Oct - 14 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 large swimming pool with a fountain, surrounded by lounge chairs and umbrellas, set against a stone building with multiple windows and a balcony.

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

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

15. Winstead Inn

Harwich

Karen

฿8,809

฿10,082 total

includes taxes & fees

7 Oct - 8 Oct

A reception desk with a marble top, a wooden panel base, a desk lamp, a potted plant, and a wicker chair with a cushion.

A miniature golf course with two holes, a small pond, and a wooden bridge.

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

Outdoor wooden chairs and tables arranged in rows, likely for an outdoor seating area.

16. Holiday Hill Inn & Suites

Dennis Port

David

฿3,658

฿4,187 total

includes taxes & fees

7 Oct - 8 Oct

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

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

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

A modern interior with a wooden floor, a blue and white patterned wall, a large painting, and a bar area with a blue marble backsplash.

17. Pelham on Earle

West Harwich

Colleen

฿6,343

฿7,840 total

includes taxes & fees

27 Oct - 28 Oct

A window with a view of the beach and ocean.

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

A coastal property with a large grassy area, a parking lot, and buildings with a simple architectural style.

A table set for two with a green vase of flowers and three glasses, overlooking a body of water.

18. Nauset Beach Inn

East Orleans

Peter

฿7,901

฿9,630 total

includes taxes & fees

1 Nov - 2 Nov

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

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

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

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

19. The Villages at Ocean Edge

Brewster

Myunghee

฿4,269

฿6,428 total

includes taxes & fees

1 Nov - 2 Nov

A spacious living room with a large abstract painting, two chandeliers, and a coffee machine.

A dining area with a Monopoly board game, patterned chairs, and a large map on the wall.

A spacious hotel lobby with a reception desk, a dining area with chairs, and a patterned rug on the floor.

A building with a flag, a sign, and a pathway lined with flowers.

20. Brewster Green Resort

Brewster

Margaret

฿7,219

฿8,262 total

includes taxes & fees

13 Oct - 14 Oct

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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 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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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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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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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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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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Mayo House

8.0/10 (3 reviews)

Learn about the local history of Chatham with a stop at Mayo House. Wander the area's beautiful beaches or simply enjoy one of 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

Cape Sands Inn

8/10 Good

"Comfortable room. Great view. The adjoining room door did not lock."

Sunbird Cape Cod Resort

10/10 Excellent

"Excellent stay. Very clean. Great staff. Convenient to everything. Would definitely stay again."

Holiday Hill Inn & Suites

10/10 Excellent

"The staff was great and the kids loved the amenities"

Red Jacket Beach Resort

8/10 Good

"We enjoy our stay. Staff was friendly, plenty of parking- the beach with chairs, lounges and games was easily accessible. The pool area was very nice."

Uncommoner Hotel by Reverie Boutique Collection

10/10 Excellent

"Loved the hotel and can’t speak more highly of the staff. Only disappointment was the restaurant and grounds were closed our second night due to a private function. Our first night was rained out so giving up our last night to a private party was unfortunate. Maybe in the future they will open some part of the property for hotel guests to enjoy while accommodating a private party."

Riviera Beach Resort

10/10 Excellent

"Great property and excellent location!"

Hyannis Travel Inn

10/10 Excellent

"The staff were friendly and helpful. Great location. I would definitely stay again!"

Greyfinch Chatham Inn

10/10 Excellent

"Perfect location. Straight up honesty, it’s not a resort or a newly appointed hotel, but the location is perfect for walking in to town and the rooms are clean and quiet. Compared to other Cape hotels, this is unbeatable for price, quality and location."

Chatham Seafarer Inn

8/10 Good

"Our room was beautiful and very clean! A little odd there was not any staff on site outside the hours of 3 pm - 8 pm but we do not stay at many small hotels so maybe this is normal. They did give us a phone number to call."

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