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.
Studio Allston Hotel

Studio Allston Hotel

3.5 out of 5
Brighton
per person
Jul. 10 - Jul. 14
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Boston (BOS)
8.6/10 Excellent! (1,006 reviews)
Well designed, clean and comfortable! Convenient location.

Reviewed on Apr. 30, 2025

The Inn at Hastings Park, Relais & Chateaux - Boston

The Inn at Hastings Park, Relais & Chateaux - Boston

4 out of 5
Save 100% on your flight
per person
Jul. 26 - Jul. 30
found 1 day ago
Roundtrip non-stop flight included
Halifax (YHZ) to Boston (BOS)
9.6/10 Exceptional! (234 reviews)
Beautiful accommodations and unique character

Reviewed on Nov. 6, 2024

The Cove At Salem

The Cove At Salem

3 out of 5
Save 100% on your flight
per person
Jul. 10 - Jul. 14
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Boston (BOS)
9.4/10 Exceptional! (459 reviews)
This was a cute cozy little suite! It was perfect for a small girls trip getaway! The only thing missing was a microwave in the room. It was nice to have access extra towels and blankets available without calling to have them brought. Staff was kind and friendly!

Reviewed on Apr. 24, 2025

The Beverly

The Beverly

3 out of 5
per person
Jul. 10 - Jul. 14
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Boston (BOS)
8.4/10 Very Good! (277 reviews)
Communication was fantastic.

Reviewed on Feb. 27, 2025

The Boston Hotel

The Boston Hotel

2 out of 5
Brighton
per person
Jul. 10 - Jul. 14
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Boston (BOS)
7.4/10 Good! (525 reviews)
I was charged 25 dollars for parking in the hotel parking lot ...wich felt like a trap considering i dont remember any notification about parking charges nor were there very many options for parking around the hotel because of congestion in that area...very disappointing...especially cause i wasnt aware and able to budget for that cost.

Reviewed on Apr. 27, 2025

Ready to book your vacation to Windham?

 

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Windham Hotel Deals

La Quinta Inn & Suites by Wyndham Salem NH
La Quinta Inn & Suites by Wyndham Salem NH
2.5 out of 5
8 Keewaydin Dr, Salem, NH
Fully refundableReserve now, pay when you stay
The price is CA $134 per night from May 4 to May 5
CA $134
CA $145 total
includes taxes & fees
May 4 - May 5
8/10 Very Good! (1,006 reviews)
"Will be staying here again on future trips"

Reviewed on Apr. 28, 2025

La Quinta Inn & Suites by Wyndham Salem NH
Park View Inn - Salem
Park View Inn - Salem
2 out of 5
109 S Broadway, Salem, NH
Fully refundableReserve now, pay when you stay
The price is CA $131 per night from May 5 to May 6
CA $131
CA $142 total
includes taxes & fees
May 5 - May 6
8.6/10 Excellent! (1,338 reviews)
"Always a winner."

Reviewed on Apr. 25, 2025

Park View Inn - Salem
La Quinta Inn & Suites by Wyndham Boston-Andover
La Quinta Inn & Suites by Wyndham Boston-Andover
2.5 out of 5
131 River Rd, Andover, MA
Fully refundableReserve now, pay when you stay
The price is CA $169 per night from May 4 to May 5
CA $169
CA $189 total
includes taxes & fees
May 4 - May 5
8/10 Very Good! (1,732 reviews)
"Crazy things almost had me give 2 stars, but it was clean and large so I gave 4. Here are my picks for things that could easily be fixed: -I had an ADA room, which was roomy and accommodating, however it was a tub with bars rather that a walk in shower but that was ok for us. The bigger issue was ..."

Reviewed on Apr. 26, 2025

La Quinta Inn & Suites by Wyndham Boston-Andover
See all 427 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 $983 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.