Exclusive Chatham Windmill Vacation Deals

Chatham Windmill vacation package deals

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

Coachman Inn

2.5 out of 5
Save 100% on your flight
Price was $282, price is now $180 per person
$180
per person
Feb 12 - Feb 17
found 7 hours ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
This hotel doesn't skimp on freebies - guests receive free continental breakfast, free WiFi, and free self parking. Business travelers can take advantage of the 24-hour business center. Enjoy the seasonal outdoor pool and conveniences like a picnic area and free newspapers.
Boston Lodge and Suites

Boston Lodge and Suites

4 out of 5
Dorchester
Price was $838, price is now $314 per person
$314
per person
Jan 23 - Jan 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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.
Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Price was $2,954, price is now $1,415 per person
$1,415
per person
Mar 8 - Mar 14
found 15 hours ago
Roundtrip non-stop flight included
San Juan (SJU) 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.
citizenM Boston Back Bay

citizenM Boston Back Bay

4 out of 5
Fenway–Kenmore
Save 100% on your flight
Price was $600, price is now $380 per person
$380
per person
Feb 24 - Feb 28
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) to Boston (BOS)
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. WiFi in public areas is free. A coffee shop, a communal living room, and express check-in are also on offer.
The Whitney Hotel

The Whitney Hotel

4 out of 5
Beacon Hill
Save 100% on your flight
Price was $513, price is now $337 per person
$337
per person
Jan 27 - Jan 29
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. WiFi in public areas is free. Valet parking, a garden, and a lobby fireplace are also offered.
Comfort Inn & Suites Logan International Airport

Comfort Inn & Suites Logan International Airport

2.5 out of 5
Save 100% on your flight
Price was $446, price is now $294 per person
$294
per person
Feb 24 - Feb 28
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) to Boston (BOS)
This hotel features an indoor pool, a gym, and a restaurant. Relax with a drink at the bar/lounge and enjoy perks like free buffet breakfast and a free airport shuttle. Self parking, a 24-hour business center, and free WiFi in public areas are also offered.

Frequently asked questions

How much are vacation packages to Chatham Windmill?
Grab an express ticket to an awesome deal with Travelocity's $180 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
$273 nightly
The price is $312 total per night
$312 total
Dec 23 - Dec 24
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
Free Cancellation
Reserve now, pay when you stay
$169 nightly
The price is $194 total per night
$194 total
Jan 5 - Jan 6, 2026
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.
Downtown Chatham Luxury 9 BR Home with Heated Pool. Pets welcome!

Downtown Chatham Luxury 9 BR Home with Heated Pool. Pets welcome!

Chatham MA
This vacation home features an outdoor pool and a hot tub. There's fun for all ages with a playground and an arcade/game room, and barbecue grills are available on site. A garden and laundry facilities are also provided.
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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.