Windham Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

Photo by Andres Loango

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to CA $1,096 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

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

    Rest easy

    Plan, book, and manage your trip all in one place

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.
Lakeside Inn

Lakeside Inn

2 out of 5
per person
Oct 10 - Oct 14
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
7.4/10 Good! (2,199 reviews)
Staff was very friendly and room was clean. Bathroom was very outdated but clean

Reviewed on Aug. 4, 2025

Four Seasons Hotel Boston

Four Seasons Hotel Boston

5 out of 5
Bay Village
per person
Sep 6 - Sep 9
found 1 day ago
Roundtrip flight included
Toronto (YTZ) to Boston (BOS)
9.4/10 Exceptional! (435 reviews)
Not my favorite Four Seasons. I requested that they remove any alcohol from my room and they didn’t accommodate that simple request. They seemed hurried. B-

Reviewed on Jun. 22, 2025

Club Quarters Hotel Faneuil Hall, Boston

Club Quarters Hotel Faneuil Hall, Boston

4 out of 5
Downtown Boston
per person
Oct 10 - Oct 14
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9/10 Wonderful! (2,696 reviews)
Great food next door at Elephant and Castle . The potato and leek casserole was excellent. The elevator is small and the rooms are very close together. It gets loud if you have noisy neighbors.

Reviewed on Aug. 5, 2025

Staypineapple, A Delightful Hotel, South End

Staypineapple, A Delightful Hotel, South End

3 out of 5
South End
per person
Oct 10 - Oct 14
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
8.8/10 Excellent! (968 reviews)
Worked out really well from 3 days in Boston

Reviewed on Aug. 6, 2025

The Langham, Boston

The Langham, Boston

5 out of 5
Downtown Boston
per person
Oct 24 - Oct 27
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Boston (BOS)
9.6/10 Exceptional! (1,016 reviews)
Very convenient boutique hotel

Reviewed on Aug. 5, 2025

Ready to book your vacation to Windham?

 

Choose your dates

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! (1,013 reviews)
"."

Reviewed on Aug. 5, 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 $151 per night from Aug 10 to Aug 11
CA $151
CA $164 total
Aug 10 - Aug 11
includes taxes & fees
8.8/10 Excellent! (853 reviews)
"Very nice and new and clean! Great pool!"

Reviewed on Aug. 5, 2025

Even Hotels Manchester Airport by IHG
Seabrook Inn

Seabrook Inn

2.5 out of 5
9 Stard Rd, Seabrook, NH
Fully refundableReserve now, pay when you stay
The price is CA $136 per night from Sep 1 to Sep 2
CA $136
CA $148 total
Sep 1 - Sep 2
includes taxes & fees
6.4/10 (1,005 reviews)
clean room
"One night stay, clean room, ez check in and out"

Reviewed on Jul. 28, 2025

Seabrook Inn
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 $674 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.