Windham Vacation Packages

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    Better together

    Save up to CA $1,096 when you book a flight and hotel together*
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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.
Sea Mist Resort

Sea Mist Resort

3 out of 5
per person
Sep 3 - Sep 7
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Boston (BOS)
8.8/10 Excellent! (127 reviews)
Great resort with suites, very cosy with great amenities, close to excellent beach and shopping.

Reviewed on Aug. 2, 2025

Studio Allston Hotel

Studio Allston Hotel

3.5 out of 5
Brighton
per person
Sep 17 - Sep 22
found 24 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Boston (BOS)
8.6/10 Excellent! (1,033 reviews)
Great stay. Nice location. Parking was very convenient with quite reasonable price. We also enjoyed the pool table and pingpong table in the lobby.

Reviewed on Jul. 29, 2025

The Westin Boston Seaport District

The Westin Boston Seaport District

4 out of 5
Seaport District
per person
Oct 2 - Oct 5
found 3 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Boston (BOS)
9/10 Wonderful! (1,996 reviews)
Very nice, clean and great location

Reviewed on Aug. 2, 2025

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
per person
Sep 28 - Sep 30
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.8/10 Exceptional! (1,001 reviews)
Favorite hotel in Boston amazing pool and gym

Reviewed on Aug. 2, 2025

The Langham, Boston

The Langham, Boston

5 out of 5
Downtown Boston
per person
Sep 4 - Sep 7
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Boston (BOS)
9.6/10 Exceptional! (1,016 reviews)
I had an amazing stay over the 4th of July, the bubbly left in my room was a great treat! Nothing but luxuries throughout my stay and i will be returning!!

Reviewed on Jul. 28, 2025

Ready to book your vacation to Windham?

 

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Windham Hotel Deals

DoubleTree by Hilton Manchester Downtown

DoubleTree by Hilton Manchester Downtown

4 out of 5
700 Elm St., Manchester, NH
Fully refundableReserve now, pay when you stay
The price is CA $147 per night from Aug 10 to Aug 11
CA $147
CA $159 total
Aug 10 - Aug 11
includes taxes & fees
8.8/10 Excellent! (1,005 reviews)
"Although I was only there for 1 night I I availed myself of the snack/drinks area in the lobby & the bar. Staff were knowledgeable & friendly. I will definitely go again."

Reviewed on Jul. 30, 2025

DoubleTree by Hilton Manchester Downtown
Even Hotels Manchester Airport by IHG

Even Hotels Manchester Airport by IHG

3.5 out of 5
55 John E. Devine Drive, Manchester, NH
Fully refundableReserve now, pay when you stay
The price is CA $135 per night from Aug 10 to Aug 11
CA $135
CA $147 total
Aug 10 - Aug 11
includes taxes & fees
8.8/10 Excellent! (841 reviews)
"Hotel was very clean, front desk staff very helpful, busy area around hotel would definitely stay again"

Reviewed on Jul. 28, 2025

Even Hotels Manchester Airport by IHG
La Quinta Inn & Suites by Wyndham Boston-Andover

La Quinta Inn & Suites by Wyndham Boston-Andover

3 out of 5
131 River Rd, Andover, MA
Fully refundableReserve now, pay when you stay
The price is CA $162 per night from Aug 14 to Aug 15
CA $162
CA $181 total
Aug 14 - Aug 15
includes taxes & fees
8/10 Very Good! (1,815 reviews)
"Cimfortable bed, good shower, clean."

Reviewed on Jul. 31, 2025

La Quinta Inn & Suites by Wyndham Boston-Andover
See all 422 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
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Frequently asked questions

How much does a Windham vacation package cost?
Offering excellent value package deals from CA $933 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.

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