Windham Vacation Packages
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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.
Meco Hotel - Hostel
West End
Price was CA $3,037, price is now CA $1,566 per person
CA $1,566
per person
Jul 23 - Jul 28
found 24 hours ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
8.6/10 Excellent! (406 reviews)
1st time, felt safe. Towels were available. Bring your own lock. 1 block from train station. And good food and stores nearby
Reviewed on May 15, 2026
By the Sea Guests Bed & Breakfast & Suites
Price was CA $1,665, price is now CA $1,057 per person
CA $1,057
per person
Jul 30 - Aug 3
found 3 hours ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.2/10 Wonderful! (185 reviews)
Our room had an wonderful Ocean View. The room was excellent and meals were awesome. Staff were very helpful. We will be going back next year!
Reviewed on Sep 20, 2025
Windham Hotel Deals
DoubleTree by Hilton Boston - Andover
123 Old River Rd Andover MA
Fully refundableReserve now, pay when you stay
The price is CA $168 per night from May 24 to May 25
CA $168
CA $188 total
May 24 - May 25
includes taxes & fees
8.4/10 Very Good! (1,007 reviews)
No breakfast somes with the room that is extra so it was not an option
Reviewed on May 17, 2026
La Quinta Inn & Suites by Wyndham Boston-Andover
131 River Rd Andover MA
Fully refundableReserve now, pay when you stay
The price is CA $160 per night from May 25 to May 26
CA $160
CA $178 total
May 25 - May 26
includes taxes & fees
8.2/10 Very Good! (2,071 reviews)
Used condoms found in room. Staff was apologetic.
Reviewed on May 17, 2026
Courtyard by Marriott Boston Billerica/Bedford
270 Concord Rd Billerica MA
Fully refundableReserve now, pay when you stay
The price is CA $162 per night from May 24 to May 25
CA $162
CA $181 total
May 24 - May 25
includes taxes & fees
9/10 Wonderful! (1,007 reviews)
Had a great experience at the Courtyard Boston Billerica/Bedford. The staff was incredibly friendly and accommodating from the moment we arrived. They were kind enough to offer us an early check-in, which was amazing and very appreciated. Ironically, we ended up getting stuck at the rental car counter ...
Reviewed on May 17, 2026
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.
Explore a world of travel with Expedia
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
