⭐ Top 10 Hotels Near Chatham Windmill for 2026

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Our top choices for Chatham Windmill hotels

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

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

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

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

1. Old Harbor Inn

0.8 km from Chatham Windmill

Kazuho

S$726

includes taxes & fees

22 Aug - 23 Aug

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

A hotel entrance with a sign reading "Chatham Bars Inn Cape Cod".

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

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

2. Chatham Bars Inn

1.1 km from Chatham Windmill

Yousuf Hussain

S$841

includes taxes & fees

14 Sept - 15 Sept

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.

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

3. Chatham Wayside Inn

0.5 km from Chatham Windmill

jacquelyn

S$574

includes taxes & fees

26 Aug - 27 Aug

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

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

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

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

4. Greyfinch Chatham Inn

1.5 km from Chatham Windmill

Tatyana

S$373

includes taxes & fees

1 Sept - 2 Sept

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

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

A staircase with a wooden finish, a white wall with a teal accent, and a modern light fixture.

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

5. Surfside Inn Chatham

0.8 km from Chatham Windmill

Jenee

S$364

includes taxes & fees

8 Sept - 9 Sept

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

A spacious living room with a wooden ceiling, large windows, a dining area with a table set for four, and a sofa with cushions.

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.

6. Whalewalk Inn and Spa

14.2 km from Chatham Windmill

Mounia

S$392

includes taxes & fees

27 Aug - 28 Aug

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

A neatly made bed with white bedding, two bedside tables with lamps, and a book on the bed.

A table set outdoors with a glass of iced tea, a glass of lemonade, and a bowl of fruit salad.

A living room with two armchairs, a sofa, a fireplace, and a window with curtains.

7. Candleberry Inn on Cape Cod

14 km from Chatham Windmill

Christopher

S$579

includes taxes & fees

23 Aug - 24 Aug

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

8. Eagle Wing Inn - Cape Cod

14.8 km from Chatham Windmill

Paul

S$260

includes taxes & fees

1 Sept - 2 Sept

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

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.

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

A circular wooden structure with illuminated edges in a garden setting.

9. Pleasant Bay Village Resort

4.5 km from Chatham Windmill

Allison

S$422

includes taxes & fees

7 Sept - 8 Sept

A pathway flanked by vibrant flowers and greenery, leading to a house with large windows.

A living room with a sofa, a chair, a television, and a hallway leading to another room.

A traditional house with a garden pathway leading to the entrance, surrounded by lush greenery and a white picket fence.

A bedroom with a large bed, a chair, a nightstand, and a window with curtains.

10. The Villa Callo Inn

13.6 km from Chatham Windmill

Shawn

S$623

includes taxes & fees

22 Aug - 23 Aug

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

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

A dining area with round tables and chairs, floral centerpieces, and decorative wall signs.

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

11. Olde Tavern Motel And Inn

12.3 km from Chatham Windmill

Rosalie

S$196

includes taxes & fees

2 Sept - 3 Sept

A backyard with a fire pit, outdoor seating, string lights, and a hammock.

A modern living room with a blue sofa, a coffee table, a large window, and a surfboard decoration.

A pool area with lounge chairs, a hot tub, and string lights.

A room with arcade games, a TV, a large window, and a plant.

12. Dennis Port Surf Club (Boutique Hotel)

14.8 km from Chatham Windmill

Jose Alejandro

S$234

includes taxes & fees

13 Sept - 14 Sept

A wooden staircase leading to a beach with a clear view of the ocean.

A swimming pool with lounge chairs and a building with a curved roof.

A motel with a covered porch, a brick wall, and yellow flowers.

13. Doryman Motel

14.6 km from Chatham Windmill

Leslie

S$247

includes taxes & fees

20 Sept - 21 Sept

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

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

14. Chatham Tides

6.2 km from Chatham Windmill

Jing

S$523

includes taxes & fees

7 Sept - 8 Sept

A hotel with a white facade, a covered outdoor seating area with white chairs and tables, and a view of the sunset.

A spacious dining area with white chairs and a marble table, a staircase, and a TV in the background.

A two-story building with a white picket fence, a 'No Lifeguard on Duty' sign, and a 'Shallow Water No Diving' warning sign.

A sign for the Escape Inn Hotel with the address 1237.

15. The Escape Inn

19.5 km from Chatham Windmill

Denise

S$199

includes taxes & fees

1 Sept - 2 Sept

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 pool area with lounge chairs and a fire pit, surrounded by stone walls and potted plants.

16. Wequassett Resort and Golf Club

6 km from Chatham Windmill

Lisa

S$1,054

includes taxes & fees

7 Sept - 8 Sept

Two people seated on red chairs at a stone fire pit with a house in the background.

A double room with two beds, a small table with a lamp, a refrigerator, and a window with curtains.

Two people riding bicycles on a sidewalk with a house in the background.

A cozy living room with a striped sofa, a small white table, and a round side table with flowers.

17. Sesuit Harbor House

18.9 km from Chatham Windmill

Matthew

S$478

includes taxes & fees

9 Sept - 10 Sept

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

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

18. Nauset Beach Inn

12.5 km from Chatham Windmill

Peter

S$654

includes taxes & fees

15 Sept - 16 Sept

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

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

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

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.

19. Pelham on Earle

11.7 km from Chatham Windmill

Julie

S$367

includes taxes & fees

10 Sept - 11 Sept

A hot tub with a tiled edge and a metal ladder, surrounded by a carpeted floor and wooden walls.

A patio area with white lounge chairs, a building with large windows, and a clear blue sky.

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

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

20. Brewster Green Resort

12 km from Chatham Windmill

Jim

S$339

includes taxes & fees

15 Sept - 16 Sept

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Compare popular hotels close to Chatham Windmill

Property	Property class	Guest rating
Old Harbor Inn	9.6 Exceptional 166 reviews	View
Chatham Bars Inn	9.2 Wonderful 857 reviews	View
Chatham Wayside Inn	9.2 Wonderful 721 reviews	View
Greyfinch Chatham Inn	8.8 Excellent 279 reviews	View
Surfside Inn Chatham	8.2 Very good 169 reviews	View

Top Chatham Windmill Hotel Reviews

Surfside Inn Chatham

8/10 Good

"Room was exactly what we expected."

Queen Anne Inn

8/10 Good

"The staff was very helpful for suggesting places to eat and visit"

Chatham Wayside Inn

8/10 Good

"Great location, close to the famous Squire and the restaurant (Wild Goose Tavern) on-site was terrific and made the experience a positive one. Elena makes an awesome martini, and Bobby was a friendly welcoming personality. Ben was awesome during dinner. Hotel staff should take lessons from the restaurants customer service training. Front Desk team is as cold as Elena’s martinis. Never a greet or smile unless we initiated. Not very welcoming. Room was fine. Bathroom not fine. Never stood in a tub that creaked before. Cheap bath fitter tub/shower, hospital room bathroom feel. Bed was comfy. Small pool which served its purpose for a quick refreshing dip. Wound consider a return but definitely wound explore other options as well."

Greyfinch Chatham Inn

10/10 Excellent

"The property was nice and clean. Ideal for a short stay for our family. The staff was very friendly and responsive."

The Chatham Motel

10/10 Excellent

"Its very clean and the staff is nice. Its quiet place and the parking is by your front door i like that its easy to unload and load your stuff. I will definetly going back too stay again.."

Other attractions near Chatham Windmill

A lighthouse with a glass enclosure and metal railing, set against a partly cloudy sky.

Chatham Lighthouse

9.4/10 (173 reviews)

Learn about the local history of Chatham when you take a trip to Chatham Lighthouse. Wander through the beautiful beaches and seaside in this trendy area.

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A baseball game at night with players on the field and a house in the background.

Veterans Field

9.6/10 (9 reviews)

Catch an event at Veterans Field during your trip to Chatham. Wander the beautiful beaches and seaside in the area.

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Chase Park

You can take time to visit Chase Park during your travels to Chatham. Wander the beautiful beaches in this trendy area.

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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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Atwood House Museum

6.0/10 (1 review)

You can spend an afternoon browsing the exhibits at Atwood House Museum in Chatham. Stroll along the beautiful beaches in this trendy area or visit its seafood restaurants.

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Chatham Seaside Links

9.2/10 (20 reviews)

Enjoy a round of golf in Chatham at Chatham Seaside Links. Wander the area's beautiful beaches or simply enjoy one of its seafood restaurants.

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Chatham Railroad Museum

8.8/10 (3 reviews)

You can spend an afternoon browsing the exhibits at Chatham Railroad Museum in Chatham. Stroll along the area's beautiful beaches or simply savour its seafood restaurants.

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Frequently asked questions

What's the area like around Chatham Windmill?

Chatham Windmill is located in a trendy area of Chatham known for its top seafood restaurants and sporting events. If you're looking for a convenient place to stay, take a look at the 153 hotels and other accommodation options you'll find within a mile.

What's the best place to stay near Chatham Windmill?

Adjacent to Chatham Windmill, Chatham Wayside Inn is one of the top choices for your stay based on our traveller data, and this hotel offers free breakfast and a restaurant. Other good options within a short distance include Chatham Bars Inn and Queen Anne Inn.

How many hotels are there close to Chatham Windmill?

Expedia has 153 hotels and other accommodation options within a mile from Chatham Windmill.

If I need to cancel the hotel reservation for my stay near Chatham Windmill, will I receive a refund?

Yes! You'll find that most hotel room reservations are fully refundable if cancelled before the accommodation's cancellation deadline, which is usually within 24-48 hours of your check-in date. If your reservation is non-refundable, you may still be able to cancel and get a refund within 24 hours of your booking. Enter your dates, click on "Search", then use the filter option "fully refundable" to review the best deals near Chatham Windmill.

What can I see and do near Chatham Windmill?

You'll want to browse the collections at Atwood House Museum, Chatham Shark Center and Chatham Railroad Museum. Some landmarks that you won't want to miss include Chatham Lighthouse, Chatham Lighthouse Beach and Mayo House. Dip your toes in the water at Hardings Beach, Ridgevale Beach and Red River Beach.

Hotels near Chatham Windmill

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Treat yourself

Be picky

Check prices for these dates

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Our top choices for Chatham Windmill hotels

1. Old Harbor Inn

2. Chatham Bars Inn

3. Chatham Wayside Inn

4. Greyfinch Chatham Inn

5. Surfside Inn Chatham

6. Whalewalk Inn and Spa

7. Candleberry Inn on Cape Cod

8. Eagle Wing Inn - Cape Cod

9. Pleasant Bay Village Resort

10. The Villa Callo Inn

11. Olde Tavern Motel And Inn

12. Dennis Port Surf Club (Boutique Hotel)

13. Doryman Motel

14. Chatham Tides

15. The Escape Inn

16. Wequassett Resort and Golf Club

17. Sesuit Harbor House

18. Nauset Beach Inn

19. Pelham on Earle

20. Brewster Green Resort

Compare popular hotels close to Chatham Windmill

Top Chatham Windmill Hotel Reviews

Surfside Inn Chatham

Queen Anne Inn

Chatham Wayside Inn

Greyfinch Chatham Inn

The Chatham Motel

Other attractions near Chatham Windmill

Chatham Lighthouse

Veterans Field

Chase Park

Mayo House

Atwood House Museum

Chatham Seaside Links

Chatham Railroad Museum

Frequently asked questions