Chatham Windmill Vacation Deals: Chatham Windmill, Chatham Vacations

Chatham Windmill vacation package deals

Price found within the past 48 hours. Click for updated prices.

D. Hotel Suites & Spa

$368

per person

Sep 25 - Sep 28

found 1 day ago

Roundtrip flight included

Raleigh (RDU) to Boston (BOS)

A full-service spa, 2 restaurants, and an indoor pool are all featured at this smoke-free hotel. You'll appreciate the gym, bar/lounge, and laundry facilities.

Boston Lodge and Suites

Dorchester

Save 100% on your flight

$404

per person

Nov 2 - Nov 4

found 1 day ago

Roundtrip non-stop flight included

Dallas (DFW) to Boston (BOS)

Free WiFi in public areas, a terrace, and a garden are available at this hotel. Families will appreciate the playground, onsite laundry facilities, and in-room childcare. A hair salon, a picnic area, and express check-out are also on offer.

Apartments in Salem

Save 100% on your flight

$1,335

per person

Oct 28 - Oct 31

found 1 day ago

Roundtrip flight included

Dallas (DFW) to Boston (BOS)

Free WiFi in public areas, express check-in, and express check-out are available at this apartment. Luggage storage is also provided.

Raffles Boston

Back Bay

Save 100% on your flight

$1,552

per person

Oct 10 - Oct 13

found 1 day ago

Roundtrip flight included

Dallas (DFW) to Boston (BOS)

A full-service spa, 3 restaurants, and an indoor pool are all featured at this luxury hotel. Traveling on business? Take advantage of the free WiFi in public areas, laundry service, and valet parking. You'll appreciate the 24-hour gym, bar/lounge, and rooftop terrace.

Mandarin Oriental, Boston

Back Bay

Save 100% on your flight

$1,712

per person

Oct 9 - Oct 12

found 22 hours ago

Roundtrip flight included

Philadelphia (PHL) to Boston (BOS)

A full-service spa, a gym, and a restaurant are all featured at this luxury hotel. Traveling on business? Take advantage of the business center, express check-in, and valet parking. You'll appreciate the sauna, bar/lounge, and limo/town car service.

The Cove At Salem

Save 100% on your flight

$607

per person

Nov 3 - Nov 7

found 2 hours ago

Roundtrip non-stop flight included

Dallas (DFW) to Boston (BOS)

This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. A communal living room and barbecue grills are also provided.

Frequently asked questions

How much are vacation packages to Chatham Windmill?

Grab an express ticket to an awesome deal with Travelocity's $368 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 Wayside Inn

512 Main St, Chatham, MA

$334 nightly

$382 total

Sep 1 - Sep 2

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.

Pool

Breakfast included

Chatham Bars Inn

297 Shore Rd, Chatham, MA

$558 nightly

$638 total

Sep 22 - Sep 23

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.

On private beach

Pool

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

$565 nightly

$647 total

Sep 7 - Sep 8

Total with taxes and fees

This vacation home features a garden, laundry facilities, and barbecue grills.

Kitchen

Washer

Don't see what you're looking for?

See all available properties in Chatham Windmill

View all properties

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.