Exclusive Chatham Windmill Vacation Deals

Chatham Windmill vacation package deals

Price found within the past 48 hours. Click for updated prices.
Sea Crest Beach Resort

Sea Crest Beach Resort

3.5 out of 5
Save 100% on your flight
Price was $1,329, price is now $942 per person
$942
per person
Jul 17 - Jul 20
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Boston (BOS)
A private beach, 2 restaurants, and an indoor pool are all featured at this smoke-free hotel. Enjoy beachfront dining and relax with sun loungers and beach umbrellas. There's fun for all ages with a children's pool and an arcade/game room, and families will appreciate the picnic area.
Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Save 100% on your flight
Price was $2,165, price is now $1,369 per person
$1,369
per person
Jul 23 - Jul 26
found 1 day ago
Roundtrip flight included
Dallas (DAL) to Boston (BOS)
A marina, a 24-hour gym, and a restaurant are all featured at this luxury hotel. Families will appreciate the onsite laundry facilities, kid-friendly dining, and babysitting. Enjoy the indoor pool and perks like free WiFi.
Nantucket Inn

Nantucket Inn

3.5 out of 5
Price was $3,163, price is now $2,022 per person
$2,022
per person
Jul 22 - Jul 28
found 6 hours ago
Roundtrip non-stop flight included
Denver (DEN) to Boston (BOS)
2 outdoor tennis courts, 2 hot tubs, and an indoor pool are all featured at this smoke-free resort. Traveling on business? Take advantage of the business center, free WiFi in public areas, and free airport shuttle. Enjoy a meal from the restaurant and perks like free self parking and a free beach shuttle.
By the Sea Guests Bed & Breakfast & Suites

By the Sea Guests Bed & Breakfast & Suites

3.5 out of 5
Price was $1,959, price is now $1,253 per person
$1,253
per person
Jul 22 - Jul 28
found 6 hours ago
Roundtrip non-stop flight included
Denver (DEN) to Boston (BOS)
This guesthouse doesn't skimp on freebies - guests receive free WiFi and free self parking. A terrace, a garden, and a lobby fireplace are also on offer.
Summer House Hotel

Summer House Hotel

2 out of 5
Price was $3,351, price is now $2,326 per person
$2,326
per person
Jul 22 - Jul 28
found 6 hours ago
Roundtrip non-stop flight included
Denver (DEN) to Boston (BOS)
This hotel features a private beach and 2 restaurants. Unwind with a drink at one of the 2 bars/lounges and enjoy free perks like continental breakfast and WiFi in public areas. Enjoy the seasonal outdoor pool and unwind at the beach bar and poolside bar.
The Inn at Hastings Park, Relais & Chateaux - Boston

The Inn at Hastings Park, Relais & Chateaux - Boston

4 out of 5
Save 100% on your flight
Price was $1,514, price is now $1,078 per person
$1,078
per person
Jun 23 - Jun 26
found 5 hours ago
Roundtrip flight included
Tampa (TPA) to Boston (BOS)
A restaurant and a bar/lounge are featured at this hotel. A terrace, limo/town car service, and a snack bar/deli are also on offer.

Frequently asked questions

How much are vacation packages to Chatham Windmill?
Grab an express ticket to an awesome deal with Travelocity's $942 Chatham Windmill vacation package. Not only can you save a tidy sum on your hotel and return flights, you can also add on a few interesting local activities or even a rental car.
Where can I get the best vacation package deals for Chatham Windmill?
Landing an amazing package deal to Chatham Windmill is a cinch with Travelocity. With around 400 airlines and 1,000,000 properties all over the world, the choice is yours when it comes to picking your flights and hotels.
Why should I purchase my Chatham Windmill vacation bundle with Travelocity?
With exceptional service, 24/7 customer support and some of the most incredible getaways money can buy, you'll never wander alone. And if you happen to find a better price, we'll match it. That's our Price Match Guarantee.

Top Chatham Windmill hotel deals

Chatham Bars Inn

Chatham Bars Inn

5 out of 5
297 Shore Rd Chatham MA
$476 nightly
The price is $545 total per night
$545 total
May 20 - May 21
Total with taxes and fees
A private beach, a full-service spa, and 3 outdoor tennis courts are all featured at this luxury resort. Relax with beach cabanas and sun loungers, and cool off with a drink at the beachside bar. Enjoy the gym and perks like free valet parking and a free beach shuttle.
Chatham Wayside Inn

Chatham Wayside Inn

4 out of 5
512 Main St Chatham MA
$294 nightly
The price is $337 total per night
$337 total
May 20 - May 21
Total with taxes and fees
This hotel features a restaurant, a gym, and a bar/lounge. Enjoy the seasonal outdoor pool and free perks like continental breakfast and free self parking. A business center, free WiFi in public areas, and a terrace are also on offer.
Quaint & Cozy Downtown Chatham Home, Walk to Town and Beaches

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

Chatham MA
$494 nightly
The price is $565 total per night
$565 total
May 18 - May 19
Total with taxes and fees
This vacation home features a garden, laundry facilities, and barbecue grills.
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.