Windham Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

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  • Plan, book, travel with confidence

  • Better together

    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.
By the Sea Guests Bed & Breakfast & Suites

By the Sea Guests Bed & Breakfast & Suites

3.5 out of 5
Price was CA $1,105, price is now CA $772 per person
CA $772
per person
Sep 3 - Sep 6
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.4/10 Exceptional! (193 reviews)
Loved it here! Everyone was friendly and helpful.

Reviewed on Jul 1, 2026

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Price was CA $2,245, price is now CA $1,329 per person
CA $1,329
per person
Aug 7 - Aug 10
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.8/10 Exceptional! (1,002 reviews)
We were there for 5 days. It was impeccable. The location, service, ambiance everything was perfect! All small attentions that makes you feel comfortable. We took the water taxi from (and to) the airport directly to the hotel fastest way to get there. Easy to walk around and along the waterfront. Breakfast was excellent

Reviewed on Jun 15, 2026

Meco Hotel - Hostel

Meco Hotel - Hostel

2 out of 5
West End
Price was CA $1,698, price is now CA $1,134 per person
CA $1,134
per person
Aug 16 - Aug 19
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
8.6/10 Excellent! (467 reviews)
A beautiful, convenient, affordable place, especially for someone just in transit between airports.

Reviewed on Jun 30, 2026

The Langham, Boston

The Langham, Boston

5 out of 5
Downtown Boston
Price was CA $1,628, price is now CA $1,097 per person
CA $1,097
per person
Aug 7 - Aug 10
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.8/10 Exceptional! (1,000 reviews)
Wonderful service and spacious family room. No complaints!

Reviewed on Jun 28, 2026

Mountain View Grand Resort & Spa

Mountain View Grand Resort & Spa

4 out of 5
Price was CA $2,587, price is now CA $1,745 per person
CA $1,745
per person
Aug 4 - Aug 11
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Manchester (MHT)
8.8/10 Excellent! (1,004 reviews)
Gorgeous property, attentive staff, and very comfortable bed.

Reviewed on Jun 27, 2026

Ready to book your vacation to Windham?

 

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Windham Hotel Deals

Big Fish, Little Pond. Fire Pit Swimming, Hiking, Kayaking, and Fishing!

Big Fish, Little Pond. Fire Pit Swimming, Hiking, Kayaking, and Fishing!

Windham NH
9.2/10 Wonderful! (11 reviews)
Almost lake front
"We found the beds and living room with the AC comfortable. Enough room for two couples. We where one so plenty. What you would expect for an older lake front house."

Reviewed on Jul 6, 2025

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Big Fish, Little Pond. Fire Pit Swimming, Hiking, Kayaking, and Fishing!
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 $155 per night from Jul 19 to Jul 20
CA $155
CA $173 total
Jul 19 - Jul 20
includes taxes & fees
9/10 Wonderful! (1,120 reviews)
"Lots of parking. Great price. Super nice staff. Conveniently located."

Reviewed on Jul 1, 2026

Hilton Garden Inn Tewksbury Andover
La Quinta Inn & Suites by Wyndham Salem NH

La Quinta Inn & Suites by Wyndham Salem NH

3 out of 5
8 Keewaydin Dr Salem NH
Fully refundableReserve now, pay when you stay
The price is CA $142 per night from Jul 7 to Jul 8
CA $142
CA $154 total
Jul 7 - Jul 8
includes taxes & fees
8.4/10 Very good! (1,260 reviews)
"Es muy bueno el servicio"

Reviewed on Jun 30, 2026

La Quinta Inn & Suites by Wyndham Salem NH
See all 450 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.
All Inclusive Vacations
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Beach Vacations
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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 $772 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.