Windham Vacations from $320

Book a Hotel + Flight or Car together to unlock savings

Photo by Andres Loango

  • Plan, book, travel with confidence

  • Better together

    Save up to $1,045 when you book a flight and hotel together*

  • Find the right fit

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

  • 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.

The Latest Windham vacation packages

Price found within the past 48 hours. Click for updated prices.
Embassy Suites Boston Logan Airport

Embassy Suites Boston Logan Airport

3.5 out of 5
East Boston
Price was $456, price is now $320 per person
$320
per person
Jan 8 - Jan 11
found 21 hours ago
Roundtrip flight included
Dallas (DFW) to Boston (BOS)
8.8/10 Excellent! (2,117 reviews)
Room was great. Wish I stayed longer. Airport was close by, shuttle at 4am was really nice!

Reviewed on Nov 2, 2025

The Whitney Hotel

The Whitney Hotel

4 out of 5
Beacon Hill
Save 100% on your flight
Price was $944, price is now $552 per person
$552
per person
Jan 8 - Jan 11
found 21 hours ago
Roundtrip flight included
Dallas (DFW) to Boston (BOS)
9.6/10 Exceptional! (475 reviews)
Love to the room, it was perfect for what we needed. Excellent service and excellent location. We will definitely stay here again.

Reviewed on Oct 13, 2025

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Save 100% on your flight
Price was $997, price is now $604 per person
$604
per person
Jan 8 - Jan 11
found 21 hours ago
Roundtrip flight included
Dallas (DFW) to Boston (BOS)
9.8/10 Exceptional! (1,019 reviews)
Excellent hotel, great location, staff fantastic

Reviewed on Oct 31, 2025

The McKernan Inn

The McKernan Inn

3 out of 5
Save 100% on your flight
Price was $518, price is now $342 per person
$342
per person
Jan 22 - Jan 25
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Boston (BOS)
9.2/10 Wonderful! (69 reviews)
Picturesque and quiet location! Laundry facilities! Staff was more than accommodating and a lovely ocean view with a delicious breakfast made for a memorable stay!

Reviewed on Oct 21, 2025

The Bostonian Boston

The Bostonian Boston

4 out of 5
Government Center
Price was $544, price is now $385 per person
$385
per person
Jan 8 - Jan 11
found 21 hours ago
Roundtrip flight included
Dallas (DFW) to Boston (BOS)
8.4/10 Very Good! (1,952 reviews)
Average hotel for the price that takes full advantage of their hotel location.

Reviewed on Nov 2, 2025

Don't see what you're looking for?
See all available trips from Columbus to Windham
View all trips

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
$114 nightly
The price is $124 total per night from Nov 24 to Nov 25
$124 total
Nov 24 - Nov 25
Total with taxes and fees
9/10 Wonderful! (1,041 reviews)
Nice rooms, friendly staff

Reviewed on Oct 29, 2025

DoubleTree by Hilton Manchester Downtown
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
$89 nightly
The price is $99 total per night from Nov 23 to Nov 24
$99 total
Nov 23 - Nov 24
Total with taxes and fees
8.8/10 Excellent! (807 reviews)
I thought the staff was amazing. Especially Ursella and jose. She def went outbof her way to help me. She was very knowledgeable about the hotel. Very personal yet professional and i watched her with other guests and she was amazing.. jose temebered my name he helped her a new room. They both were ...

Reviewed on Oct 26, 2025

Hilton Garden Inn Tewksbury Andover
Methuen Inn and Conference Center

Methuen Inn and Conference Center

2.5 out of 5
159 Pelham Street, Methuen, MA
Fully refundable
$97 nightly
The price is $108 total per night from Nov 3 to Nov 4
$108 total
Nov 3 - Nov 4
Total with taxes and fees
6.2/10 (1,071 reviews)
Great water pressure and lovely bath towels made for an enjoyable shower after a long drive. Room was clean and bed had a mattress topper to improve sleep.

Reviewed on Oct 26, 2025

Methuen Inn and Conference Center
See all 452 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.

Find the Best Windham Vacation Packages

Windham Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Manchester-Boston Regional Airport (MHT)
Population
13,100
Top Sights
Canobie Lake Park, Windham Town Beach and New Hampshire Aviation Historical Society

More vacations you might like

All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Frequently asked questions

How much does a Windham vacation package cost?
You'll find cheap prices from $320 on Expedia for your Windham escape. However, a range of factors like the length of stay, hotel choice and season will influence how much your vacation to Windham costs.
What are the cheapest months to go to Windham?
You can typically find reduced prices and better availability in October, November and December. Explore our cheap Windham vacation packages and you could get some great off-season discounts.
How many days is enough for Windham?
Generally, a handful of days is enough to see the major sights during your Windham vacation. However, if you prefer to have time to kick back or go on day tours, think about extending your trip.
Is it worth booking a vacation package to Windham?
During your Windham vacation, you can look forward to experiencing some top-notch fishing and cycling. Leave enough room in your schedule to discover major sights like Windham Country Club and Windham Town Beach.
How to find the best Windham package deals?
Start your search for a Windham package deal by entering your preferred travel dates and destination under our "Packages" tab. Then select some filters, like "Popular locations" and "Amenities," to fine-tune the results to your exact needs. You can also sort by "Package discount" and discover offers that come with big savings. If you don't find the perfect Windham package deal straight away, simply play around with your dates and search again. Bear in mind that deals are only available for a limited time, so book early and get your Windham escape off to a flying start.
Is it cheaper to book a Windham vacation as a package?
You can enjoy significant savings on your next Windham break by booking a customized vacation package. Click on the "Package" heading, then enter your destination and travel dates to see some great hotel prices and airfares. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a car rental and you may land a better deal.
When to book a vacation package to Windham?
If you've got your Windham travel dates confirmed, book as early as you can to score some unbeatable deals. With Expedia, you can generally reserve some flights up to a year in advance. Prefer spur-of-the-moment adventures? Our last-minute deals are great for jetting off on a whim.
Does Expedia offer Book Now, Pay Later Windham vacation packages?
If you're like us, you love jet-setting around the world but don't love the big price tag that can sometimes come with it. That's why we offer Book Now, Pay Later vacations. With the help of online lender Affirm, you can spread the cost of your Windham trip over 3, 6 or 12 months. There are also no late payment fees or hidden costs, so you can snap up cheap vacation packages with payment plans as soon as you spot them.

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.