The Best Hotels Closest to Chatham Windmill in Chatham - 2026 Updated Prices

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Our top choices for Chatham Windmill hotels

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

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.

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

1. Old Harbor Inn

0.5 mi from Chatham Windmill

Adélaïde

£305

includes taxes & fees

15 Oct - 16 Oct

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".

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.

2. Chatham Bars Inn

0.7 mi from Chatham Windmill

Yousuf Hussain

£360

includes taxes & fees

25 Oct - 26 Oct

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

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.

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

3. Chatham Wayside Inn

0.3 mi from Chatham Windmill

Ashley

£188

includes taxes & fees

29 Oct - 30 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 white house with a grey roof, surrounded by a well-maintained lawn and flowering bushes.

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

4. Greyfinch Chatham Inn

0.9 mi from Chatham Windmill

Sara

£174

includes taxes & fees

18 Oct - 19 Oct

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

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

5. Candleberry Inn on Cape Cod

8.7 mi from Chatham Windmill

Susan

£234

includes taxes & fees

29 Sept - 30 Sept

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

6. Whalewalk Inn and Spa

8.8 mi from Chatham Windmill

Purav

£256

includes taxes & fees

4 Oct - 5 Oct

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

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

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

A sandy beach with gentle waves and a clear sky.

7. Eagle Wing Inn - Cape Cod

9.2 mi from Chatham Windmill

Andrea

£103

includes taxes & fees

4 Oct - 5 Oct

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 circular wooden structure with illuminated edges in a garden setting.

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

8. Pleasant Bay Village Resort

2.8 mi from Chatham Windmill

sheila

£190

includes taxes & fees

11 Oct - 12 Oct

A two-story house with a porch, surrounded by well-maintained gardens and trees.

A porch with white chairs and a planter with flowers.

A bedroom with a four-poster bed, a television on a wooden cabinet, a plant, and a tray with glasses and a bottle.

A dining area with a checkered floor, white tables, and chairs. There are bookshelves with books and decorative items.

9. The Captain Farris House B&B

11.8 mi from Chatham Windmill

Ruth Ann

£144

includes taxes & fees

4 Oct - 5 Oct

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.

10. Brewster by the Sea Inn

9.8 mi from Chatham Windmill

Grace

£289

includes taxes & fees

7 Oct - 8 Oct

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

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

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

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

11. Charm on Main by Ocean Edge

8.2 mi from Chatham Windmill

Kathleen

£159

includes taxes & fees

5 Oct - 6 Oct

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

7.7 mi from Chatham Windmill

Debra

£111

includes taxes & fees

12 Oct - 13 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 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.

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

13. Chatham Tides

3.9 mi from Chatham Windmill

Craig

£194

includes taxes & fees

28 Oct - 29 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 traditional fireplace with a clock above it, surrounded by various decorative items and a modern refrigerator.

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

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

14. Olde Tavern Motel And Inn

7.6 mi from Chatham Windmill

Rosalie

£86

includes taxes & fees

1 Oct - 2 Oct

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

A fenced backyard with artificial grass, two Adirondack chairs, and a wooden fence.

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

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

15. Doryman Motel

9.1 mi from Chatham Windmill

Nicole

£112

includes taxes & fees

9 Oct - 10 Oct

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

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

16. Dennis Port Surf Club (Boutique Hotel)

9.2 mi from Chatham Windmill

effie

£73

includes taxes & fees

30 Sept - 1 Oct

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 two-story white house with black shutters, a front door with a number 1421, and a well-maintained lawn.

17. Sesuit Harbor House

11.7 mi from Chatham Windmill

Natasha

£215

includes taxes & fees

1 Oct - 2 Oct

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 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.

18. The Villa Callo Inn

8.5 mi from Chatham Windmill

Shawn

£361

includes taxes & fees

4 Oct - 5 Oct

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

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.

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

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

19. Wequassett Resort and Golf Club

3.7 mi from Chatham Windmill

Angela

£374

includes taxes & fees

26 Oct - 27 Oct

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 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.

20. The Escape Inn

12.1 mi from Chatham Windmill

Toby

£81

includes taxes & fees

1 Oct - 2 Oct

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Compare popular hotels close to Chatham Windmill

Property	Property class	Guest rating
Old Harbor Inn	9.6 Exceptional 171 reviews	View
Chatham Bars Inn	9.2 Wonderful 866 reviews	View
Chatham Wayside Inn	9.2 Wonderful 738 reviews	View
Greyfinch Chatham Inn	8.8 Excellent 287 reviews	View
Candleberry Inn on Cape Cod	10.0 Exceptional 149 reviews	View

Top Chatham Windmill Hotel Reviews

Chatham Village - Adorable Studio Apartment in Antique Home

10/10 Excellent

"Really great place to stay. Clean. Beautiful. Walking distance to town. Lovely neighborhood. ZERO complaints."

Water View-Walk town/beach, pets considered, Linen Option

10/10 Excellent

"The house was beautiful, comfortable, convenient, clean, and well-supplied. It was in a great area. Since we happened to be there during a Nor’easter, it was also comforting to know that the house had a generator - even though we never lost power. Paul, the owner, was very easy to communicate with and answered all my questions quickly. Highly recommend!"

5 BR - Beautiful Property-Chatham in-Town & Oyster Beach Inlet

10/10 Excellent

"The house is in a great location and has plenty of room for a group."

Seaside condo with patio, beach access, loft, board games, gas grill, & firepit

10/10 Excellent

"The location right at the beach was ideal and we were willing to pay this price for two nights, even in the off-season, but I would not stay longer. Our only real issue was with the television which we were not able to get to work because all the apps seemed to need updating and we didn't feel like spending the time. We got a prompt response when we messaged to find out what services were available, and would have signed in on our own accounts (which I don't think we should have to do when we spend that much to stay somewhere), but we just didn't want to watch tv badly enough to go through the updating of the apps."

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!"

Quaint & Cozy Downtown Chatham Home, Walk to Town and Beaches

10/10 Excellent

"Charming and close to town"

Chatham Wayside Inn

10/10 Excellent

"Loved the Inn and will definitely stay there again in the future. Perfect location...just steps to the shops and eateries on Main Street. Our standard king room was lovely and spacious. The mattress and bedding was extremely comfortable and had everything we needed. The gym and pool looked beautiful but unfortunately we didn't have a chance to use them. Dinner our first night at the tavern on the property was excellent. The seafood pot pie was absolutely! The only slight downside for us was that the continental breakfast was a bit lacking. Considering the price of the rooms, I think the Inn could do a little better. However, this would not keep us from staying here again. A great experience overall."

Greyfinch Chatham Inn

10/10 Excellent

"This place is so cute! When we first pulled up we were unsure because it looks like an old roadside motel. But it’s quickly apparent that it’s been beautifully updated with fresh paint and hanging plants. The driveway and parking lot are spotless as are the rooms. The decor in the rooms is updated and coastal. The staff was lovely. I would absolutely stay here again!"

Waterfront Chatham Village, Short Walk to Town & Lighthouse Beach

10/10 Excellent

"This property was perfect for our small relaxed bachelorette weekend! The back yard views and patio are to die for and the house is perfect for hosting small and larger groups. They have everything you need from beach towels to serving dishes and cookware. Its walking distance to the main street with shops and restaurants. It was a perfect weekend for us girls! The only thing we wish there was on the property was a small firepit to enjoy that outdoor patio through the evening. Linda and Keith were very easy to communicate with and provided great suggestions around the area. Definitely would recommend!"

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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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 156 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 156 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.

Search Hotels Near Chatham Windmill, Chatham

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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 Bars Inn

3. Chatham Wayside Inn

4. Greyfinch Chatham Inn

5. Candleberry Inn on Cape Cod

6. Whalewalk Inn and Spa

7. Eagle Wing Inn - Cape Cod

8. Pleasant Bay Village Resort

9. The Captain Farris House B&B

10. Brewster by the Sea Inn

11. Charm on Main by Ocean Edge

12. A Beach Breeze Inn

13. Chatham Tides

14. Olde Tavern Motel And Inn

15. Doryman Motel

16. Dennis Port Surf Club (Boutique Hotel)

17. Sesuit Harbor House

18. The Villa Callo Inn

19. Wequassett Resort and Golf Club

20. The Escape Inn

Compare popular hotels close to Chatham Windmill

Top Chatham Windmill Hotel Reviews

Chatham Village - Adorable Studio Apartment in Antique Home

Water View-Walk town/beach, pets considered, Linen Option

5 BR - Beautiful Property-Chatham in-Town & Oyster Beach Inlet

Seaside condo with patio, beach access, loft, board games, gas grill, & firepit

Surfside Inn Chatham

Quaint & Cozy Downtown Chatham Home, Walk to Town and Beaches

Chatham Wayside Inn

Greyfinch Chatham Inn

Waterfront Chatham Village, Short Walk to Town & Lighthouse Beach

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