The Best Hotels Closest to Chatham Windmill in Chatham 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 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.

1. Old Harbor Inn

0.8 km from Chatham Windmill

Adélaïde

NT$11,206

NT$12,825 total

includes taxes & fees

Oct 15 - Oct 16

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 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.

2. Chatham Wayside Inn

0.5 km from Chatham Windmill

Ashley

NT$5,694

NT$7,899 total

includes taxes & fees

Nov 1 - Nov 2

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.

3. Chatham Bars Inn

1.1 km from Chatham Windmill

Yousuf Hussain

NT$12,430

NT$14,226 total

includes taxes & fees

Nov 3 - Nov 4

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 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.

4. Greyfinch Chatham Inn

1.5 km from Chatham Windmill

Jacob

NT$5,107

NT$7,010 total

includes taxes & fees

Nov 1 - Nov 2

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

A dining table with a plate of food, a mug, and a bowl of berries.

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

5. Sea Meadow Inn

14.9 km from Chatham Windmill

Joanne

NT$7,967

NT$9,255 total

includes taxes & fees

Oct 21 - Oct 22

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

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

A hotel room with a bed, nightstand, lamp, microwave, coffee maker, and a tray with snacks and a vase of flowers.

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

6. Candleberry Inn on Cape Cod

14 km from Chatham Windmill

Susan

NT$10,171

NT$11,641 total

includes taxes & fees

Nov 1 - Nov 2

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

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

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

A staircase with ornate brass handrails and a mirror.

7. Whalewalk Inn and Spa

14.2 km from Chatham Windmill

Purav

NT$8,226

NT$9,415 total

includes taxes & fees

Oct 13 - Oct 14

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 sandy beach with gentle waves and a clear sky.

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

8. Eagle Wing Inn - Cape Cod

14.8 km from Chatham Windmill

Andrea

NT$4,419

NT$5,057 total

includes taxes & fees

Oct 18 - Oct 19

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

9. Pleasant Bay Village Resort

4.5 km from Chatham Windmill

sheila

NT$7,678

NT$8,787 total

includes taxes & fees

Oct 12 - Oct 13

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

A pool area with lounge chairs and umbrellas, surrounded by trees.

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

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

10. Charm on Main by Ocean Edge

13.2 km from Chatham Windmill

Kathleen

NT$5,734

NT$6,563 total

includes taxes & fees

Oct 22 - Oct 23

A table set with plates, glasses, a mug, and a blue hydrangea.

A swimming pool with a fountain, surrounded by greenery and a gazebo.

A bedroom with a fireplace, two armchairs, a bed, and a view of the outdoors.

A garden with a white pergola, various plants, and a large tree.

11. Brewster by the Sea Inn

15.8 km from Chatham Windmill

Grace

NT$9,693

NT$11,094 total

includes taxes & fees

Nov 4 - Nov 5

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

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.

A clear blue swimming pool with a metal ladder, surrounded by lounge chairs and an American flag.

12. A Beach Breeze Inn

12.4 km from Chatham Windmill

Debra

NT$4,101

NT$4,694 total

includes taxes & fees

Oct 12 - Oct 13

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.

13. Chatham Tides

6.2 km from Chatham Windmill

Craig

NT$5,682

NT$6,503 total

includes taxes & fees

Nov 8 - Nov 9

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

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.

A deck with outdoor furniture, a large umbrella, and a view of a garden with flowers and a tree.

14. The Villa Callo Inn

13.6 km from Chatham Windmill

Shawn

NT$13,352

NT$17,101 total

includes taxes & fees

Oct 9 - Oct 10

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

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.

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

15. Wequassett Resort and Golf Club

6 km from Chatham Windmill

Angela

NT$12,866

NT$15,756 total

includes taxes & fees

Oct 26 - Oct 27

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

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.

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

16. Sesuit Harbor House

18.9 km from Chatham Windmill

Natasha

NT$8,515

NT$9,746 total

includes taxes & fees

Oct 11 - Oct 12

A window with a view of the beach and ocean.

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

A room with a large window, a television, a dresser, and a chair.

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

17. Nauset Beach Inn

12.5 km from Chatham Windmill

Peter

NT$7,458

NT$9,090 total

includes taxes & fees

Nov 1 - Nov 2

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

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

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

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

18. The Escape Inn

19.5 km from Chatham Windmill

Toby

NT$2,696

NT$3,085 total

includes taxes & fees

Nov 1 - Nov 2

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

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

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.

19. Brewster Green Resort

12 km from Chatham Windmill

Margaret

NT$9,127

NT$10,446 total

includes taxes & fees

Oct 13 - Oct 14

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 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.

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

20. Winstead Inn

9.6 km from Chatham Windmill

Karen

NT$8,345

NT$9,551 total

includes taxes & fees

Oct 13 - Oct 14

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Compare popular hotels close to Chatham Windmill

Property	Property class	Guest rating
Old Harbor Inn	9.6 Exceptional 172 reviews	View
Chatham Wayside Inn	9.2 Wonderful 745 reviews	View
Chatham Bars Inn	9.2 Wonderful 869 reviews	View
Greyfinch Chatham Inn	8.8 Excellent 288 reviews	View
Sea Meadow Inn	10.0 Exceptional 27 reviews	View

Top Chatham Windmill Hotel Reviews

The Chatham Motel

10/10 Excellent

"Excellent"

Captain's House Inn

10/10 Excellent

"This is a beautiful b&b in beautiful Chatham. We had a lovely clean room with a comfortable queen bed, fireplace and jacuzzi tub. Homemade breakfast every morning was wonderful and a tea service in the afternoon. 20 minute walk to Main St. We thoroughly enjoyed our 3 night stay !"

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!"

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 spend time at Chatham Lighthouse. Wander 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 vacation is part of your travel plans, Chatham Lighthouse Beach might be the perfect place to seek out 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 when you take a trip to 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 studying the exhibits at Atwood House Museum during your travels in Chatham. Stroll along the beautiful beaches in this trendy area, or check out 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 during your travels in Chatham. Stroll along the area's seaside, or simply savor 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, check out the 154 hotels and other accommodations 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 traveler 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 will I find close to Chatham Windmill?

Expedia has 154 hotels and other accommodations 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! The majority of hotel bookings are fully refundable if cancelled prior to the accommodation's cancellation deadline, which is usually within 24-48 hours of your check-in date. If you booked a non-refundable reservation, it might still be possible to cancel it and get a refund within 24 hours of your booking. Put your dates in and click on "Search", then use the filter option "fully refundable" to review top deals close to Chatham Windmill.

Where can I learn more about changing or cancelling my trip in the area near Chatham Windmill?

To access more information about picking new dates or cancelling your stay near Chatham Windmill, click here.

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.

Find hotels near Chatham Windmill, Chatham from NT$3,085

Change your mind

Treat yourself

Be picky

Check prices for these dates

Filter by

Star rating

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Our top choices for Chatham Windmill hotels

1. Old Harbor Inn

2. Chatham Wayside Inn

3. Chatham Bars Inn

4. Greyfinch Chatham Inn

5. Sea Meadow Inn

6. Candleberry Inn on Cape Cod

7. Whalewalk Inn and Spa

8. Eagle Wing Inn - Cape Cod

9. Pleasant Bay Village Resort

10. Charm on Main by Ocean Edge

11. Brewster by the Sea Inn

12. A Beach Breeze Inn

13. Chatham Tides

14. The Villa Callo Inn

15. Wequassett Resort and Golf Club

16. Sesuit Harbor House

17. Nauset Beach Inn

18. The Escape Inn

19. Brewster Green Resort

20. Winstead Inn

Compare popular hotels close to Chatham Windmill

Top Chatham Windmill Hotel Reviews

The Chatham Motel

Captain's House Inn

The Hawthorne

Greyfinch Chatham Inn

Old Harbor Inn

Surfside Inn Chatham

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

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