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

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Our top choices for Chatham Windmill hotels

A coastal scene with a large group of seals resting on the shore.

A coastal house with a view of the sea and beach.

A coastal view with a beach, boats, and a house with a lawn and lamp post.

A set of outdoor brick steps leading to a building with a white balcony.

1. The Hawthorne

0.9 km from Chatham Windmill

Richard

HK$2,581

HK$2,954 total

includes taxes & fees

27 Oct - 28 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 living room with wicker furniture, a fireplace, and a staircase.

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

2. Chatham Wayside Inn

0.5 km from Chatham Windmill

Ashley

HK$1,335

HK$1,869 total

includes taxes & fees

2 Nov - 3 Nov

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.

3. Chatham Bars Inn

1.1 km from Chatham Windmill

Linda

HK$3,035

HK$3,474 total

includes taxes & fees

12 Nov - 13 Nov

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 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.

4. Greyfinch Chatham Inn

1.5 km from Chatham Windmill

Jacob

HK$1,335

HK$1,815 total

includes taxes & fees

5 Nov - 6 Nov

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

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.

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

5. Candleberry Inn on Cape Cod

14 km from Chatham Windmill

Dvir

HK$2,378

HK$2,722 total

includes taxes & fees

29 Oct - 30 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 staircase with ornate brass handrails and a mirror.

6. Whalewalk Inn and Spa

14.2 km from Chatham Windmill

Purav

HK$2,030

HK$2,324 total

includes taxes & fees

28 Oct - 29 Oct

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

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

A two-story building with a sign reading "The Orchard House."

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

7. Brewster by the Sea Inn

15.8 km from Chatham Windmill

Grace

HK$2,385

HK$2,730 total

includes taxes & fees

14 Nov - 15 Nov

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

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

8. A Beach Breeze Inn

12.4 km from Chatham Windmill

Debra

HK$1,012

HK$1,159 total

includes taxes & fees

18 Oct - 19 Oct

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

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

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.

9. Charm on Main by Ocean Edge

13.2 km from Chatham Windmill

Kathleen

HK$1,699

HK$1,944 total

includes taxes & fees

18 Oct - 19 Oct

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

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.

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.

10. Pelham on Earle

11.7 km from Chatham Windmill

Colleen

HK$1,483

HK$1,833 total

includes taxes & fees

13 Nov - 14 Nov

A room with a bed, two wicker chairs, a small table, a coffee maker, and a view of the sea through a window.

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.

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

11. Chatham Tides

6.2 km from Chatham Windmill

Anthony

HK$1,264

HK$1,447 total

includes taxes & fees

10 Nov - 11 Nov

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

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

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.

12. Wequassett Resort and Golf Club

6 km from Chatham Windmill

Angela

HK$2,894

HK$3,544 total

includes taxes & fees

11 Nov - 12 Nov

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

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

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.

13. The Villa Callo Inn

13.6 km from Chatham Windmill

Shawn

HK$3,296

HK$4,221 total

includes taxes & fees

19 Oct - 20 Oct

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

A large, two-story house with a covered patio area, outdoor seating, and a stone waterfall feature.

A large swimming pool with a fountain, surrounded by lounge chairs and umbrellas, set against a stone building with multiple windows and a balcony.

14. Winstead Inn

9.6 km from Chatham Windmill

Karen

HK$1,766

HK$2,021 total

includes taxes & fees

27 Oct - 28 Oct

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.

15. Sesuit Harbor House

18.9 km from Chatham Windmill

Natasha

HK$2,365

HK$2,707 total

includes taxes & fees

18 Oct - 19 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 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.

16. The Escape Inn

19.5 km from Chatham Windmill

Toby

HK$705

HK$806 total

includes taxes & fees

1 Nov - 2 Nov

An outdoor patio with a stone table and metal chairs, surrounded by greenery and trees.

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

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

A covered patio with a round table and four chairs.

17. Skaket Beach Motel

12 km from Chatham Windmill

Wayne

HK$1,020

HK$1,168 total

includes taxes & fees

28 Oct - 29 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 white desk with a woven hat, a vase with white flowers, and two glasses of white wine.

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

18. Chatham Seafarer Inn

4.2 km from Chatham Windmill

Ian

HK$1,828

HK$2,092 total

includes taxes & fees

19 Oct - 20 Oct

An outdoor seating area with a fire feature, a pool, and a view of the ocean.

A beach with a modern building, a staircase, and a rocky shoreline.

A spacious room with a large window overlooking the ocean, a stone fireplace, and a modern chandelier.

A pool area with lounge chairs and a table, overlooking the ocean.

19. Pelham House Resort

14.8 km from Chatham Windmill

sandra

HK$2,032

HK$2,559 total

includes taxes & fees

30 Oct - 31 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 sign for Blue Rock Golf Course surrounded by a variety of colorful flowers.

20. Blue Rock Resort

18.3 km from Chatham Windmill

Camille

HK$744

HK$860 total

includes taxes & fees

26 Oct - 27 Oct

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Compare popular hotels close to Chatham Windmill

Property	Property class	Guest rating
The Hawthorne	9.4 Exceptional 204 reviews	View
Chatham Wayside Inn	9.2 Wonderful 755 reviews	View
Chatham Bars Inn	9.2 Wonderful 871 reviews	View
Greyfinch Chatham Inn	8.8 Excellent 294 reviews	View
Candleberry Inn on Cape Cod	10.0 Exceptional 152 reviews	View

Top Chatham Windmill Hotel Reviews

Chatham Wayside Inn

10/10 Excellent

"Great location! Right in the heart of downtown Chatham. The restaurant was a bonus with standard Cape Cod cuisine and very yummy. They also provide bikes if you want to pedal around town. The breakfast included was a bit light, but there's a perfect Cafe next door. We'll definitely stay there again."

Greyfinch Chatham Inn

10/10 Excellent

"Clean room. Conveniently located. Friendly staff. Would say there again."

Chatham Bars Inn

10/10 Excellent

"We liked everything. The service was amazing and the resort is beautiful."

Old Harbor Inn

10/10 Excellent

"We thoroughly enjoyed or 25th anniversary weekend at the Old Harbor inn! The staff and owner’s were amazing. The inn was well maintained the atmosphere and amenities were on point. The room was super and clean. The breakfast was great. Thanks to all who made our stay very enjoyable! We will be recommending this inn to our friends."

Chatham Village - Adorable Studio Apartment in Antique Home

10/10 Excellent

"Very clean and comfortable apartment located conveniently to shopping and restaurants. Would highly recommend to couples!"

Walk to Downtown Chatham, Steps to Beach!

10/10 Excellent

"Great stay!"

Waterfront Chatham Village, Short Walk to Town & Lighthouse Beach

10/10 Excellent

"Spectacular views, perfect location. We had a great stay, was easy to stroll into town or the beach. It was hard to leave the back patio, with the beautiful view of Mill pond. Highly recommend. Communication was excellent from the owners."

The Hawthorne

8/10 Good

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

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!"

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.

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. The Hawthorne

2. Chatham Wayside Inn

3. Chatham Bars Inn

4. Greyfinch Chatham Inn

5. Candleberry Inn on Cape Cod

6. Whalewalk Inn and Spa

7. Brewster by the Sea Inn

8. A Beach Breeze Inn

9. Charm on Main by Ocean Edge

10. Pelham on Earle

11. Chatham Tides

12. Wequassett Resort and Golf Club

13. The Villa Callo Inn

14. Winstead Inn

15. Sesuit Harbor House

16. The Escape Inn

17. Skaket Beach Motel

18. Chatham Seafarer Inn

19. Pelham House Resort

20. Blue Rock Resort

Compare popular hotels close to Chatham Windmill

Top Chatham Windmill Hotel Reviews

Chatham Wayside Inn

Greyfinch Chatham Inn

Chatham Bars Inn

Old Harbor Inn

Chatham Village - Adorable Studio Apartment in Antique Home

Walk to Downtown Chatham, Steps to Beach!

Waterfront Chatham Village, Short Walk to Town & Lighthouse Beach

The Hawthorne

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

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