⭐ Top 10 Hotels Near Chatham Windmill for 2026

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Our top choices for Chatham Windmill hotels

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

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

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

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

1. Chatham Bars Inn

1.1 km from Chatham Windmill

Yousuf Hussain

S$572

includes taxes & fees

3 Nov - 4 Nov

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.

2. Greyfinch Chatham Inn

1.5 km from Chatham Windmill

Jacob

S$282

includes taxes & fees

5 Nov - 6 Nov

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.

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

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

3. Chatham Wayside Inn

0.5 km from Chatham Windmill

Ashley

S$318

includes taxes & fees

1 Nov - 2 Nov

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

A bedroom with a large bed, two wall-mounted picture frames, a window with a view, and a wicker chair.

A wooden boardwalk leading to a covered area with a view of the sunset over the ocean.

A spacious indoor dining area with multiple tables and wicker chairs, large windows with decorative plates, and an exit sign.

4. Charm on Main by Ocean Edge

13.2 km from Chatham Windmill

Kathleen

S$214

includes taxes & fees

6 Oct - 7 Oct

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

A nighttime pool area with lounge chairs and a lifebuoy.

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.

5. The Escape Inn

19.5 km from Chatham Windmill

Toby

S$124

includes taxes & fees

1 Nov - 2 Nov

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

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

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

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.

6. Pleasant Bay Village Resort

4.5 km from Chatham Windmill

sheila

S$325

includes taxes & fees

18 Oct - 19 Oct

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

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

7. Chatham Seafarer Inn

4.2 km from Chatham Windmill

Ian

S$284

includes taxes & fees

14 Oct - 15 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 kitchen with a white island, a fireplace, and a surfboard decoration.

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

8. Eagle Wing Inn - Cape Cod

14.8 km from Chatham Windmill

Andrea

S$193

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

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.

9. Chatham Tides

6.2 km from Chatham Windmill

Craig

S$283

includes taxes & fees

1 Nov - 2 Nov

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

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

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

A covered patio with a round table and four chairs.

10. Skaket Beach Motel

12 km from Chatham Windmill

Wayne

S$160

includes taxes & fees

12 Oct - 13 Oct

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 playground with two blue slides and a climbing structure.

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

11. Brewster Green Resort

12 km from Chatham Windmill

Margaret

S$280

includes taxes & fees

21 Oct - 22 Oct

A hotel room with a large bed, a small table with chairs, a green armchair, a dresser, and a balcony with a view of trees.

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

A row of white, two-story buildings with a white fence in front, likely a motel or small hotel.

12. Blue Rock Resort

18.3 km from Chatham Windmill

Daisy

S$140

includes taxes & fees

7 Oct - 8 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.

13. Wequassett Resort and Golf Club

6 km from Chatham Windmill

Angela

S$633

includes taxes & fees

18 Oct - 19 Oct

A room with nautical-themed decor, including a map, anchor-patterned rug, and a view of the sea through the window.

A blue outdoor seating area with picnic tables and umbrellas, surrounded by a wooden fence and trees.

A hotel room with a bed, two nightstands, a chair, a fireplace, and wall art.

A Beach Breeze Inn sign with a lighthouse graphic, a vacancy sign, and a building with a brick flower bed in front.

14. A Beach Breeze Inn

12.4 km from Chatham Windmill

Debra

S$189

includes taxes & fees

12 Oct - 13 Oct

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

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.

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

15. Rodeway Inn Orleans - Cape Cod

13.2 km from Chatham Windmill

Aldrick

S$153

includes taxes & fees

7 Oct - 8 Oct

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

16. Pelham on Earle

11.7 km from Chatham Windmill

Colleen

S$299

includes taxes & fees

29 Oct - 30 Oct

A two-story house with a porch, a star decoration, and outdoor seating.

A dining area with a wooden table and chairs, large windows with a view of greenery, and a vase with flowers on the table.

A house with a blue door and a number '187' on the front.

A spacious living room with large windows, a patterned rug, and two sofas.

17. Sea Meadow Inn

14.9 km from Chatham Windmill

Joanne

S$355

includes taxes & fees

8 Oct - 9 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 spacious living room with a wooden ceiling, large windows, a dining area with a table set for four, and a sofa with cushions.

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

18. Whalewalk Inn and Spa

14.2 km from Chatham Windmill

Purav

S$322

includes taxes & fees

13 Oct - 14 Oct

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

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

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

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

19. Kingfisher Harwich Port

9.6 km from Chatham Windmill

Marc

S$336

includes taxes & fees

6 Oct - 7 Oct

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

Three children playing in shallow water on a beach.

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

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

20. The Villages at Ocean Edge

13 km from Chatham Windmill

Myunghee

S$244

includes taxes & fees

1 Nov - 2 Nov

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Compare popular hotels close to Chatham Windmill

Property	Property class	Guest rating
Chatham Bars Inn	9.2 Wonderful 868 reviews	View
Greyfinch Chatham Inn	8.8 Excellent 288 reviews	View
Chatham Wayside Inn	9.2 Wonderful 744 reviews	View
Charm on Main by Ocean Edge	9.6 Exceptional 47 reviews	View
The Escape Inn	9.4 Exceptional 794 reviews	View

Top Chatham Windmill Hotel Reviews

The Hawthorne

8/10 Good

"Beautiful spot with wonderful views of Chatham Bars without the crazy experience of Chatham Bars Inn"

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."

Old Harbor Inn

10/10 Excellent

"This is a lovely inn with very friendly owners and staff. The snacks and baked goods were an added plus. Breakfast was delicious, and we enjoyed our conversations with the owner.The inn is very convenient to the downtown area of Chatham,as well. We will definitely stay here again while on the Cape."

Surfside Inn Chatham

10/10 Excellent

"In the hallway to our room was a step which was very hard to see and my wife tripped on it and almost fell because of it - it should be marked with a paint line and written notice of its presence! You might consider having juice available for breakfast - orange or apple or both. Overall a pleasant place to stay!"

The Chatham Motel

8/10 Good

"The beds were comfortable and the room had a coffee maker, fridge and microwave. Very convenient to restaurants and Chatham downtown area."

Other attractions near Chatham Windmill

A lighthouse with an American flag, a white building with a red roof, and a 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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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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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 seaside 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 154 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 154 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 Railroad Museum and Chatham Shark Center. 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

Change your mind

Treat yourself

Be picky

Check prices for these dates

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Our top choices for Chatham Windmill hotels

1. Chatham Bars Inn

2. Greyfinch Chatham Inn

3. Chatham Wayside Inn

4. Charm on Main by Ocean Edge

5. The Escape Inn

6. Pleasant Bay Village Resort

7. Chatham Seafarer Inn

8. Eagle Wing Inn - Cape Cod

9. Chatham Tides

10. Skaket Beach Motel

11. Brewster Green Resort

12. Blue Rock Resort

13. Wequassett Resort and Golf Club

14. A Beach Breeze Inn

15. Rodeway Inn Orleans - Cape Cod

16. Pelham on Earle

17. Sea Meadow Inn

18. Whalewalk Inn and Spa

19. Kingfisher Harwich Port

20. The Villages at Ocean Edge

Compare popular hotels close to Chatham Windmill

Top Chatham Windmill Hotel Reviews

The Hawthorne

Greyfinch Chatham Inn

Old Harbor Inn

Surfside Inn Chatham

The Chatham Motel

Other attractions near Chatham Windmill

Chatham Lighthouse

Veterans Field

Chatham Lighthouse Beach

Chase Park

Mayo House

Atwood House Museum

Chatham Seaside Links

Chatham Railroad Museum

Frequently asked questions