Windham Vacation Packages

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    Save up to CA $4,200 when you book a flight and hotel together*

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    With over 300,000 hotels worldwide, it's easy to create a perfect package

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Your Windham Vacation

The vibrant city of Windham is calling. Discover its highlights and hidden gems with a Windham vacation package that's customized to you. If your trip to Windham includes some sightseeing, check out renowned attractions like Canobie Lake Park, The Mall at Rockingham Park and Tuscan Village Salem. Your perfect Windham vacation is just clicks away. Browse hotels, airfares and more on Expedia for a getaway that's tailored just for you.

Top Windham Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Boston Lodge and Suites

Boston Lodge and Suites

4 out of 5
Dorchester
Price was CA $1,411, price is now CA $706 per person
CA $706
per person
Jan 29 - Feb 1
found 1 hour ago
Roundtrip flight included
Toronto (YYZ) to Boston (BOS)
8.4/10 Very good! (194 reviews)
The accommodation was great and spacious enough for a large group. There were five of us, and it was perfect for our needs. The apartment was clean, and everything we needed was provided, including towels, soap, dishwasher detergent, and more. We turned on the oven to make dinner, but we were unable to turn it off because the buttons weren’t working. We called for assistance and received a response very quickly, which made us feel supported and taken care of. Overall, we had a great stay! The apartment was lovely, and the location was excellent, especially for getting to Boston by public transportation.

Reviewed on Oct 17, 2026

The Newbury Boston

The Newbury Boston

5 out of 5
Back Bay
Save 100% on your flight
Price was CA $2,564, price is now CA $1,227 per person
CA $1,227
per person
Dec 24 - Dec 27
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Boston (BOS)
9.4/10 Exceptional! (744 reviews)

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Price was CA $2,098, price is now CA $1,136 per person
CA $1,136
per person
Jan 28 - Jan 31
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to Boston (BOS)
9.8/10 Exceptional! (1,004 reviews)

Four Seasons Hotel Boston

Four Seasons Hotel Boston

5 out of 5
Bay Village
Price was CA $2,406, price is now CA $1,579 per person
CA $1,579
per person
Jan 29 - Feb 1
found 24 hours ago
Roundtrip flight included
Toronto (YYZ) to Boston (BOS)
9.4/10 Exceptional! (491 reviews)

Raffles Boston

Raffles Boston

5 out of 5
Back Bay
Price was CA $2,383, price is now CA $1,635 per person
CA $1,635
per person
Jan 29 - Feb 1
found 6 hours ago
Roundtrip flight included
Toronto (YYZ) to Boston (BOS)
9.6/10 Exceptional! (343 reviews)

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Windham Hotel Deals

Methuen Inn and Conference Center

Methuen Inn and Conference Center

2.5 out of 5
159 Pelham Street Methuen MA
Fully refundable
The price is CA $107 per night from Dec 8 to Dec 9
CA $107
CA $119 total
Dec 8 - Dec 9
includes taxes & fees
Methuen Inn and Conference Center
Hilton Garden Inn Tewksbury Andover

Hilton Garden Inn Tewksbury Andover

3 out of 5
4 Highwood Drive Tewksbury MA
Fully refundableReserve now, pay when you stay
The price is CA $109 per night from Dec 4 to Dec 5
CA $109
CA $121 total
Dec 4 - Dec 5
includes taxes & fees
9/10 Wonderful! (1,627 reviews)
"The staffs are really nice."

Reviewed on Nov 7, 2026

Hilton Garden Inn Tewksbury Andover
Holiday Inn Express Chelmsford by IHG

Holiday Inn Express Chelmsford by IHG

2.5 out of 5
8 Independence Drive Chelmsford MA
Fully refundableReserve now, pay when you stay
The price is CA $127 per night from Dec 6 to Dec 7
CA $127
CA $142 total
Dec 6 - Dec 7
includes taxes & fees
8.8/10 Excellent! (1,248 reviews)
"It was very nice. They are dog friendly and we were able to bring our pup for $35 extra per night. Breakfast was included and it was good. They cleaned the room once we left for the day, new towels, made the beds."

Reviewed on Nov 6, 2026

Holiday Inn Express Chelmsford by IHG
See all 454 properties in Windham
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.
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Stay near popular Windham attractions

Windham Town Beach

Why not spend a lazy afternoon at Windham Town Beach during your trip to Windham?
See properties

Frequently asked questions

How much does a Windham vacation package cost?
Offering excellent value package deals from CA $706 on Expedia, you'll be thrilled with how little a vacation to Windham costs! Our packages make travel planning easier and your savings go further.
What are the cheapest months to go to Windham?
Plan your trip for the low or shoulder season and you're likely to find cheap Windham vacation packages. Keep in mind that school vacation periods and major events and festivals can impact prices, so do some research before booking.
How many days is enough for Windham?
With a well-planned itinerary, you can easily tick off the most popular Windham attractions in a few days. But if you prefer to discover hidden spots or take day trips, think about booking your Windham vacation for longer.
Is it worth booking a vacation package to Windham?
Whether you're planning to discover attractions like Windham Country Club and Windham Town Beach, or eager to experience its terrific fishing and cycling, a Windham vacation is sure to exceed your expectations. Book your getaway with Expedia and find out why Windham is such a good vacation destination.
How to find the best Windham package deals?
Use Expedia's filters to help you find some unbeatable Windham package deals. When you begin your search, just set your maximum budget and then order the results by "Price: low to high." If you're looking to save, plan your trip for midweek, or search for Windham package deals in the off-season. Switch up your travel dates and you may score even bigger discounts. As a rule of thumb, it's typically best to lock in your vacation package as early as possible.
Is it cheaper to book a Windham vacation as a package?
An Expedia vacation package could save you hundreds of dollars when compared to booking flights and accommodations individually. Better still, you can customize your Windham getaway to fit your exact style. Choose your preferred flight time, select the hotel type and add a rental car. Check out our great deals to see how much you can save.
When to book a vacation package to Windham?
If you're planning a spontaneous Windham adventure, browse our last-minute deals that can be booked up to a week before you go. Prefer not to wait until the last minute? You can land terrific deals on your hotels and flights by booking well in advance.
How to plan a trip to Windham?

  1. Pick the ideal time to travel: Your schedule, favourite season and the type of weather you enjoy can all impact your decision on when to go to Windham.
  2. Set a budget: Consider expenses like flights, meals and transportation when working out how much to save for your trip to Windham. Then, choose a property that fits your budget, whether that's a low-cost option or a lavish getaway.
  3. Decide your trip length: Consider how long you'd like to spend exploring Windham. Plan your days so you can get to all the attractions and activities you're interested in without rushing.
  4. Bundle your bookings: With your travel dates in place, you can combine your car rental, hotels, flights and more into a personalized Windham vacation package.

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.