Hotels in Chatham Windmill, MA: Compare 10+ Sites & Save

AirbnbBooking.comVrboExpediaKayakTripadvisorHotels.comAgoda.com
  1. VBOR
  2. Hotels
  3.  USA

  4.  Massachusetts
  5.  Chatham
  6.  Chatham Windmill

Refine your search

Price per night

Amenity Filter

Rating

20 Best Hotels in Chatham Windmill (Starting from $109)

Chatham Wayside Inn
Chatham Wayside Inn
Hotel
Chatham, MA, USA
0.4k from Chatham Windmill center

Cheap, Accommodations, Pools, Parking, 4-star, Lodgings, Places to stay, Family, Accessible hotels

8.8

Fabulous

157 reviews

$544
Average price / night
Check Availability
Greyfinch Chatham Inn
Greyfinch Chatham Inn
Hotel
Chatham, MA, USA
0.8k from Chatham Windmill center

Accommodations, Pools, Parking, 4-star, Lodgings, Places to stay, Family, Accessible hotels

8.6

Fabulous

63 reviews

$575
Average price / night
Check Availability
Surfside Inn Chatham
Surfside Inn Chatham
Hotel
Chatham, MA, USA
0.8k from Chatham Windmill center

B&bs, Accommodations, Parking, Inns, Lodgings, Beach, Places to stay, Family

8.1

Very Good

81 reviews

$334
Average price / night
Check Availability
Chatham Seafarer Inn
Chatham Seafarer Inn
Hotel
2079 Main St, Chatham, MA, 02633, United States
4.2k from Chatham Windmill center

AC, Barbecue, Extra Bed, Free Parking, Heater, Housekeeping, Internet, No Smoking, Outdoor Space

9.0

Fabulous

319 reviews

$235
Average price / night
Check Availability
The Hawthorne
The Hawthorne
Hotel
Chatham Windmill, Chatham, Massachusetts, USA
0.9k from Chatham Windmill center

Cheap, Accommodations, Motels, Parking, 4-star, Lodgings, Beach, Places to stay, Family

8.8

Fabulous

100 reviews

$4035
Average price / night
Check Availability
Pleasant Bay Village Resort
Pleasant Bay Village Resort
Hotel
1191 Orleans Road, Chatham, MA, 02633, United States
4.5k from Chatham Windmill center

AC, Babysitting, Breakfast Available, Business Services, Free Parking, Hot Tub, Housekeeping, Internet, Laundry

9.6

Exceptional

304 reviews

$245
Average price / night
Check Availability
Queen Anne Inn
Queen Anne Inn
Hotel
Chatham, MA, USA
1.1k from Chatham Windmill center

Cheap, Accommodations, Pools, Parking, Romantic, Boutique, 4-star, Lodgings, Jacuzzis

8.6

Fabulous

78 reviews

$427
Average price / night
Check Availability
Chatham Tides
Chatham Tides
Hotel
394 Pleasant St, South Chatham, MA, 02659, United States
6.2k from Chatham Windmill center

AC, Barbecue, Business Services, Free Parking, Heater, Housekeeping, Internet, Microwave, No Smoking

9.4

Superb

677 reviews

$204
Average price / night
Check Availability
Captain's House Inn
Captain's House Inn
Hotel
Chatham, MA, USA
1.7k from Chatham Windmill center

B&bs, Luxury, Accommodations, Parking, Inns, 4-star, Lodgings, Jacuzzis, Places to stay

9.1

Superb

269 reviews

$569
Average price / night
Check Availability
The Chatham Motel
The Chatham Motel
Hotel
Chatham, MA, USA
2.6k from Chatham Windmill center

Cheap, Accommodations, Pools, Motels, Parking, 3-star, Lodgings, Places to stay, Family

8.6

Fabulous

84 reviews

$2514
Average price / night
Check Availability
Handkerchief Shoals Inn
Handkerchief Shoals Inn
Hotel
Chatham Windmill, Chatham, Massachusetts, USA
7.3k from Chatham Windmill center

View, Hot Tub, Breakfast, Internet, Air Conditioner, Sports/Activities, Security/Safety

8.2

Very Good

75 reviews

$2463
Average price / night
Check Availability
Harwichport Resort Club
Harwichport Resort Club
Hotel
Harwich Port, MA, USA
9.6k from Chatham Windmill center

Cheap, Accommodations, Pools, Parking, 4-star, Lodgings, Places to stay

8.4

Very Good

22 reviews

$109
Average price / night
Check Availability
Kingfisher Harwich Port
Kingfisher Harwich Port
Hotel
Chatham Windmill, Chatham, Massachusetts, USA
9.6k from Chatham Windmill center

View, Child Friendly, Internet, Air Conditioner, Smoking, Parking, Ocean View

4.0

Review score

1 reviews

$3175
Average price / night
Check Availability
Winstead Beach Resort
Winstead Beach Resort
Hotel
Chatham Windmill, Chatham, Massachusetts, USA
9.6k from Chatham Windmill center

B&bs, Cheap, Accommodations, Parking, Inns, Lodgings, Beach, Places to stay, Family

9.2

Superb

52 reviews

$5662
Average price / night
Check Availability
The Winstead Inn
The Winstead Inn
Hotel
Chatham Windmill, Chatham, Massachusetts, USA
9.6k from Chatham Windmill center

B&bs, Cheap, Accommodations, Pools, Parking, Inns, 4-star, Lodgings, Beach

8.7

Fabulous

70 reviews

$5957
Average price / night
Check Availability

Pro Tip:
VacationByOwnerRentals aggregates the best inventory from leading travel sites, including Booking.com, Agoda.com, Expedia.com, Vrbo.com, and Airbnb.com. Use our Advanced Filters to compare verified homes, villas, cabins, condos, cottages, vacation rentals, hotels, and eco-friendly stays. Our goal is to help you find the absolute best Hotels in Chatham Windmill.

Chatham Windmill Hotels on the Map

Frequently Asked Questions

You can explore 20 verified hotels in Chatham Windmill. These include a range of options from luxury resorts and boutique hotels to budget-friendly accommodations suitable for different travel styles.

Hotel prices in Chatham Windmill vary depending on the season, location, and property type. Rates typically start from around $109 per night, with higher prices for premium hotels, central locations, or peak travel dates.

Most hotels in Chatham Windmill include amenities such as Guest Services, View, and Internet. Additional features like breakfast, parking, or resort facilities may vary by property, so it’s helpful to review the details before booking.

You can identify top-rated hotels in Chatham Windmill by sorting listings based on guest ratings and reviews. Looking at recent feedback, overall scores, and review volume can help you find properties that consistently deliver a high-quality experience.

For popular travel periods or busy locations, booking 30 to 60 days in advance is generally recommended to secure preferred options. During quieter periods, you may find more flexibility and availability closer to your travel dates.

Yes, some hotels in Chatham Windmill welcome pets. Currently, 1 listings allow pets, although policies may vary. It’s a good idea to review any pet-related rules before booking.

Many hotels in Chatham Windmill offer flexible or refundable booking options. Checking the cancellation policy before confirming your reservation can help you choose a rate that suits your travel plans.