Chatham Chatham Windmill Hotels: 2026 Limited-Time Hotel Deals @Expedia

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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.

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

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

Pamela

HK$3,456

HK$3,955 total

includes taxes & fees

20 Sept - 21 Sept

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.

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

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

jacquelyn

HK$2,346

HK$3,026 total

includes taxes & fees

16 Sept - 17 Sept

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

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

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.

3. Greyfinch Chatham Inn

1.5 km from Chatham Windmill

Sara

HK$1,464

HK$1,963 total

includes taxes & fees

2 Sept - 3 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 staircase with a wooden finish, a white wall with a teal accent, and a modern light fixture.

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

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

4. Surfside Inn Chatham

0.8 km from Chatham Windmill

Jenee

HK$1,842

HK$2,108 total

includes taxes & fees

1 Oct - 2 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".

5. Olde Tavern Motel And Inn

12.3 km from Chatham Windmill

Rosalie

HK$854

HK$978 total

includes taxes & fees

2 Sept - 3 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 circular wooden structure with illuminated edges in a garden setting.

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

6. Pleasant Bay Village Resort

4.5 km from Chatham Windmill

Allison

HK$1,893

HK$2,167 total

includes taxes & fees

27 Sept - 28 Sept

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.

7. Charm on Main by Ocean Edge

13.2 km from Chatham Windmill

Kathleen

HK$1,393

HK$1,594 total

includes taxes & fees

2 Sept - 3 Sept

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

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

8. Sea Meadow Inn

14.9 km from Chatham Windmill

Joanne

HK$2,328

HK$2,704 total

includes taxes & fees

1 Oct - 2 Oct

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

A modern living room with a large blue sectional sofa, a woven coffee table, and a large window offering a view of the street.

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.

9. Dennis Port Surf Club (Boutique Hotel)

14.8 km from Chatham Windmill

Jose Alejandro

HK$916

HK$1,048 total

includes taxes & fees

2 Sept - 3 Sept

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 breakfast buffet with pastries, a lamp, and storage containers on a wooden table.

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

10. Skaket Beach Motel

12 km from Chatham Windmill

Jason

HK$1,097

HK$1,256 total

includes taxes & fees

15 Sept - 16 Sept

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

A compact kitchen with a dining area, a bed, and a small living space.

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.

11. Doryman Motel

14.6 km from Chatham Windmill

Leslie

HK$1,133

HK$1,296 total

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

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.

12. Chatham Tides

6.2 km from Chatham Windmill

Melissa

HK$2,370

HK$2,713 total

includes taxes & fees

1 Oct - 2 Oct

A beach with a sunset, calm water, and rocks.

A large, two-story house with a well-maintained lawn and a prominent tree in front.

A dining area with wicker furniture, wooden tables, and large windows with views of trees.

A bar area with a wooden barrel, glasses, candles, and a martini glass.

13. The Old Manse Inn

14 km from Chatham Windmill

Shannon

HK$2,446

HK$2,799 total

includes taxes & fees

7 Sept - 8 Sept

A house with a brick exterior, white exterior walls, and a front porch with white chairs.

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

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

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

14. Chatham Seafarer Inn

4.2 km from Chatham Windmill

Nicholas

HK$1,656

HK$1,896 total

includes taxes & fees

17 Sept - 18 Sept

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 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.

15. Wequassett Resort and Golf Club

6 km from Chatham Windmill

Lisa

HK$5,295

HK$6,484 total

includes taxes & fees

29 Sept - 30 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 deck with outdoor furniture, a large umbrella, and a view of a garden with flowers and a tree.

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

16. The Villa Callo Inn

13.6 km from Chatham Windmill

Shawn

HK$2,639

HK$3,468 total

includes taxes & fees

2 Sept - 3 Sept

A dining area with a long table set for a meal, surrounded by chairs.

A small house with a porch, a red umbrella, and a table with chairs.

A white two-story house with a sloped roof, a porch, and a sign indicating it is a Tern Inn.

A landscaped garden with a gravel path, flowering plants, and a fenced area with a pool.

17. The Tern Inn Bed & Breakfast and Cottages

12.5 km from Chatham Windmill

Donald

HK$1,384

HK$1,585 total

includes taxes & fees

22 Sept - 23 Sept

A beach with clear blue water, a sandy shore, and rocky outcrops.

A Kingfisher Oceanside building with a white picket fence, picnic tables, and solar panels on the roof.

A building with a sign reading "Kingfisher Oceanside 15".

18. Kingfisher Oceanside

14.8 km from Chatham Windmill

David

HK$1,430

HK$1,636 total

includes taxes & fees

7 Sept - 8 Sept

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

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

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

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

19. Brewster Green Resort

12 km from Chatham Windmill

Jim

HK$1,717

HK$1,965 total

includes taxes & fees

24 Sept - 25 Sept

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

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

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

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

20. Kingfisher Harwich Port

9.6 km from Chatham Windmill

Marc

HK$1,800

HK$2,060 total

includes taxes & fees

7 Sept - 8 Sept

View all properties

Compare popular hotels close to Chatham Windmill

Property	Property class	Guest rating
Old Harbor Inn	9.6 Exceptional 168 reviews	View
Chatham Wayside Inn	9.2 Wonderful 723 reviews	View
Greyfinch Chatham Inn	8.8 Excellent 280 reviews	View
Surfside Inn Chatham	8.2 Very good 170 reviews	View
Olde Tavern Motel And Inn	9.4 Exceptional 286 reviews	View

Top Chatham Windmill Hotel Reviews

Queen Anne Inn

8/10 Good

"7/10 — Charming property with room for improvement We stayed for two nights this past weekend and overall had a pleasant stay. We were in the back cottage, and the room itself was totally fine. I especially liked the hardwood floors, and we had no major concerns with the room during our stay. The bathroom could use some updating, but everything was functional. The main building has a cute, eclectic New England feel, with some really charming sitting areas and common spaces. There’s definitely a lot of character to the property, and with a few updates and a little more attention to the grounds, I think it could be a really lovely place. One area that stood out was the upkeep of the outdoor spaces. There were tables and chairs with quite a few fallen leaves sitting on them throughout the weekend, which made the outdoor areas feel a bit less inviting than they could have been. A little more regular maintenance would make a noticeable difference. The front desk receptionist was wonderful. She was very friendly and checked in with us a couple of times throughout the weekend to make sure everything was going well and that we didn’t need anything, which we really appreciated. Overall, we had a good stay and everything went smoothly. The property has a lot of charm and potential, and I think some updates to the bathrooms and a bit more attention to the outdoor grounds could really elevate the experience."

Cozy Cape near Chatham Center

10/10 Excellent

"The house was perfect and in a great location, and the host was very kind and responsive! Would definitely stay again!"

Private Beach, Water Views, Incredible Location!

10/10 Excellent

"We stayed here for 6 nights with 2 of our adult children. The house was beautiful in an exceptionally quiet, peaceful setting with panoramic views and a wrap around deck. The house was comfortable and pristine with a beautiful kitchen that was very well stocked with everything you’d need for cooking in and very nice bathrooms with great showers! Chatham is centrally located for quick trips to many public beaches. We visited Chatham beaches, Nauset beach and Corporation Beach. We were able to watch seals from the private beach one night."

Waterfront Chatham Village, Short Walk to Town & Lighthouse Beach

10/10 Excellent

"Lovely location, well equipped home, great selection of toys for kids"

Old Harbor Inn

10/10 Excellent

"The owner was so nice and knowledgeable. He made us feel like home."

Chatham Village: Lovely 1-Bedroom Apartment in Antique Home

10/10 Excellent

"First time to the Cape- Loved the location and ease of getting a copy of coffee with a short walk to town. Everything was clean and quiet. Thank you for such a great place to stay."

Greyfinch Chatham Inn

10/10 Excellent

"Clean room and great location"

Walk to Chatham Main St., boutiques, restaurants, galleries, and nightlife!

10/10 Excellent

"Beautiful property is great location! Very comfortable, quiet and centrally located. Susan was an excellent host!"

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

8/10 Good

"Great house, location was great also. Great yard for children to play. The biggest complaints are the master bedroom upstairs had a huge claw foot tub for shower, not suitable for seniors. The downstairs master bedroom had a ridiculous high bed impossible even for young couple to climb in with step. The lighting in the house was inadequate. We received a text reminding us to not have flood lights on after 10pm and be off the top deck by then which was no problem because we were always in way before then. Paul was very professional and recommended a great rental for sheets and bicycles."

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 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.

Chatham Chatham Windmill Hotels

Change your mind

Treat yourself

Be picky

Check prices for these dates

Filter by

Star rating

Guest rating

Our top choices for Chatham Windmill hotels

1. Old Harbor Inn

2. Chatham Wayside Inn

3. Greyfinch Chatham Inn

4. Surfside Inn Chatham

5. Olde Tavern Motel And Inn

6. Pleasant Bay Village Resort

7. Charm on Main by Ocean Edge

8. Sea Meadow Inn

9. Dennis Port Surf Club (Boutique Hotel)

10. Skaket Beach Motel

11. Doryman Motel

12. Chatham Tides

13. The Old Manse Inn

14. Chatham Seafarer Inn

15. Wequassett Resort and Golf Club

16. The Villa Callo Inn

17. The Tern Inn Bed & Breakfast and Cottages

18. Kingfisher Oceanside

19. Brewster Green Resort

20. Kingfisher Harwich Port

Compare popular hotels close to Chatham Windmill

Top Chatham Windmill Hotel Reviews

Queen Anne Inn

Cozy Cape near Chatham Center

Private Beach, Water Views, Incredible Location!

Waterfront Chatham Village, Short Walk to Town & Lighthouse Beach

Old Harbor Inn

Chatham Village: Lovely 1-Bedroom Apartment in Antique Home

Greyfinch Chatham Inn

Walk to Chatham Main St., boutiques, restaurants, galleries, and nightlife!

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

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