Deals on vacations and trips to Windham

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Windham flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
Fairmont Copley Plaza, Boston

Fairmont Copley Plaza, Boston

4.5 out of 5
Back Bay
Save 100% on your flight
Price was $683, price is now $456 per person
$456
per person
Dec 1 - Dec 3
found 23 hours ago
Roundtrip flight included
Baltimore (BWI) to Boston (BOS)
This hotel features a restaurant, a gym, and a bar/lounge. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. There's a rooftop terrace on site, and laundry facilities and concierge services are also offered.
Boston Lodge and Suites

Boston Lodge and Suites

4 out of 5
Dorchester
Price was $1,035, price is now $618 per person
$618
per person
Dec 3 - Dec 6
found 1 day ago
Roundtrip non-stop flight included
Memphis (MEM) 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 $1,029, price is now $636 per person
$636
per person
Jan 2 - Jan 4
found 2 hours ago
Roundtrip flight included
Baltimore (BWI) 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.
Four Seasons Hotel Boston

Four Seasons Hotel Boston

5 out of 5
Bay Village
Save 100% on your flight
Price was $1,893, price is now $1,261 per person
$1,261
per person
Dec 24 - Dec 27
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Boston (BOS)
This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, laundry service, and valet parking. There's a 24-hour gym on site, and laundry facilities and concierge services are also offered.
D. Hotel Suites & Spa

D. Hotel Suites & Spa

3 out of 5
Price was $799, price is now $546 per person
$546
per person
Dec 22 - Dec 28
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Boston (BOS)
A full-service spa, 2 restaurants, and an indoor pool are all featured at this smoke-free hotel. Enjoy the gym and free buffet breakfast each morning. You'll appreciate the hot tub, bar/lounge, and laundry facilities.

Top Windham hotels deals

Hilton Garden Inn Tewksbury Andover

Hilton Garden Inn Tewksbury Andover

3 out of 5
4 Highwood Drive Tewksbury MA
Free Cancellation
Reserve now, pay when you stay
$85 nightly
The price is $95 total per night
$95 total
Nov 5 - Nov 6
Total with taxes and fees
This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the 24-hour gym and perks like free self parking.
Methuen Inn and Conference Center

Methuen Inn and Conference Center

2.5 out of 5
159 Pelham Street Methuen MA
Free Cancellation
$103 nightly
The price is $115 total per night
$115 total
Oct 25 - Oct 26
Total with taxes and fees
A restaurant and a bar/lounge are featured at this hotel. Guests will appreciate free perks like free self parking and WiFi in public areas. A business center, luggage storage, and laundry facilities are also on offer.
Park View Inn - Salem

Park View Inn - Salem

2 out of 5
109 S Broadway Salem NH
Free Cancellation
Reserve now, pay when you stay
$82 nightly
The price is $89 total per night
$89 total
Nov 15 - Nov 16
Total with taxes and fees
This motel doesn't skimp on freebies - guests receive free WiFi and free self parking. The front desk is staffed around-the-clock and laundry facilities are on offer.
Parking included
Free WiFi
Holiday Inn Express Chelmsford by IHG

Holiday Inn Express Chelmsford by IHG

2.5 out of 5
8 Independence Drive Chelmsford MA
Free Cancellation
$101 nightly
The price is $113 total per night
$113 total
Nov 22 - Nov 23
Total with taxes and fees
This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Guests will appreciate freebies like full breakfast and free self parking.
Pool
Breakfast included
Courtyard by Marriott Boston Billerica/Bedford

Courtyard by Marriott Boston Billerica/Bedford

3 out of 5
270 Concord Rd Billerica MA
Free Cancellation
Reserve now, pay when you stay
$81 nightly
The price is $91 total per night
$91 total
Nov 22 - Nov 23
Total with taxes and fees
This hotel features an indoor pool, a 24-hour gym, and a restaurant. Traveling on business? Take advantage of the 5 conference rooms, free WiFi in public areas, and express check-out. Free self parking, a coffee shop, and a grocery/convenience store are also offered.
DoubleTree by Hilton Boston - Andover

DoubleTree by Hilton Boston - Andover

4 out of 5
123 Old River Rd Andover MA
Free Cancellation
Reserve now, pay when you stay
$122 nightly
The price is $137 total per night
$137 total
Nov 6 - Nov 7
Total with taxes and fees
The hotel's indoor pool, gym, and 2 bars/lounges are among the featured amenities. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. A hot tub, a restaurant, and a 24-hour front desk are also provided.
Pool
Hot Tub
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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.

Stay near popular Windham attractions

Windham Town Beach

Why not spend a lazy afternoon at Windham Town Beach during your trip to Windham?
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Frequently asked questions

How much are vacation packages to Windham?
Vacation packages, which include hotels and flights in Windham, start at just $456. Turn your travel fantasies into reality and secure your vacation with Travelocity today.
Where can I get the best vacation package deals for Windham?
Travelocity will be able to help you find a great Windham package deal. With no less than 400 air carriers and 1,000,000 properties across the world, you're bound to be able to craft the perfect itinerary.
Why should I purchase my Windham vacation package via Travelocity?
The three S's — savings, support and a stress-free booking — are just the tip of the iceberg. Enjoy a fulfilling travel experience knowing you have access to 24/7 customer support. With the Travelocity Price Match Guarantee, you can rest easy knowing you're getting the best deal available.
Will I save money on my Windham car rental if I book it with my hotel or flight?
Absolutely — bundle your hotel, flight and car into a Windham vacation package and you can save a handsome sum. With so many places to explore in and around Windham, that rental car will come in handy. Once you've buckled yourself in, crank up the tunes and make your way to Fenway Park, a famous attraction approximately 35 mi from Windham.
Which airport is best for Windham?
You have two options for flying into Windham, starting with Logan Intl. Airport (BOS). It's situated 35 mi from the city center, while Manchester-Boston Regional Airport (MHT) is 11 mi away from central Windham.
What is there to do in Windham?
Windham is teeming with places to explore, including Windham Country Club and Windham Town Beach. These renowned attractions top most people's itineraries.
Where should I stay when visiting Windham?
If you're looking for somewhere to lay your head, have a look at the Canobie Lake 3 bedroom Year Round Waterfront Home - Newly Renovated. It's the top pick for many visitors.

Photos of local treasures

Browse Windham vacation photos for more inspiration

A lake surrounded by trees with autumn foliage.