Windham Vacation Packages

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Top Windham Vacation Deals

Price found within the past 48 hours. Click for updated prices.
The Putney Inn

The Putney Inn

2.5 out of 5
per person
Nov 5 - Nov 9
found 6 hours ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Rutland (RUT)
8.4/10 Very Good! (1,000 reviews)
Always a pleasure. Have stayed several times & no complaints. The staff are amazing, friendly, & helpful

Reviewed on Aug. 8, 2025

North Star Lodge and Resort

North Star Lodge and Resort

2 out of 5
per person
Nov 5 - Nov 9
found 6 hours ago
Roundtrip flight included
Winnipeg (YWG) to Rutland (RUT)
8.6/10 Excellent! (1,000 reviews)
For the price it's not to bad, slightly dated interior in need of a facelift, but would go back based on the price.

Reviewed on Aug. 10, 2025

The Engel House

The Engel House

3 out of 5
per person
Nov 5 - Nov 9
found 6 hours ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Rutland (RUT)
9.4/10 Exceptional! (13 reviews)
A very quaint property. The room was comfortable and clean.

Reviewed on May 27, 2025

Align Inn Vermont

Align Inn Vermont

2.5 out of 5
per person
Nov 5 - Nov 9
found 6 hours ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Rutland (RUT)
9.2/10 Wonderful! (1,012 reviews)
Sweet place. Clean and very nice people that work there.

Reviewed on Aug. 11, 2025

Killington Mountain Lodge, Tapestry Collection by Hilton

Killington Mountain Lodge, Tapestry Collection by Hilton

3.5 out of 5
per person
Nov 5 - Nov 9
found 6 hours ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Rutland (RUT)
7.4/10 Good! (1,000 reviews)
Views were spectacular

Reviewed on Jul. 16, 2025

Ready to book your vacation to Windham?

 

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Windham Hotel Deals

Escape in Rural Vermont! 2 Homes SaunaPool, Hot Tub, Game House Mountain Views.

Escape in Rural Vermont! 2 Homes SaunaPool, Hot Tub, Game House Mountain Views.

Windham
9.8/10 Exceptional! (49 reviews)
"We had a fabulous multi-generational stay here this summer. The house is clean and beautiful and the kids, teens and adults had so many things to keep them entertained - the sauna, hot tub, pool and outdoor shower were fabulous. The game room with pool, ping pong, darts and foosball kept us all entertained ..."

Reviewed on Aug. 3, 2025

Get rates
Escape in Rural Vermont! 2 Homes SaunaPool, Hot Tub, Game House Mountain Views.
The Equinox Golf Resort & Spa

The Equinox Golf Resort & Spa

4.5 out of 5
3567 Main Street Route 7A, Manchester, VT
Fully refundableReserve now, pay when you stay
The price is CA $170 per night from Sep 1 to Sep 2
CA $170
CA $261 total
Sep 1 - Sep 2
includes taxes & fees
7.2/10 Good! (508 reviews)
"Beautiful hotel in Manchester with gorgeous mountain views and large property. Our room had a comfortable bed but bathroom shower curtain needed to be replaced. Hotels.com had outdoor pool listed as an amenity but there was only an indoor pool. The resort fee was $45 a person and pickle ball was ..."

Reviewed on Aug. 9, 2025

The Equinox Golf Resort & Spa
Colonial Motel And Spa

Colonial Motel And Spa

3 out of 5
889 Putney Rd, Brattleboro, VT
Fully refundableReserve now, pay when you stay
The price is CA $193 per night from Aug 13 to Aug 14
CA $193
CA $212 total
Aug 13 - Aug 14
includes taxes & fees
6.6/10 (1,000 reviews)
"The room I was given was quite impressive in size. Plenty accommodating for me and my dog. The a/c worked well, fridge was plenty cold, bed was comfortable and clean, the grounds surrounding the buildings is very nice for traveling with a dog. The front desk help was gracious and accommodating. That ..."

Reviewed on Aug. 9, 2025

Colonial Motel And Spa
See all 2,532 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.
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Frequently asked questions

How much does a Windham vacation package cost?
You'll find cheap prices from CA $1,169 on Expedia for your Windham break. However, a range of factors like your choice of hotel, the season and length of stay will influence how much your vacation to Windham costs.
What are the cheapest months to go to Windham?
The off-season is the best time to head to Windham if you're hoping to keep costs down. Another tip for scoring cheap Windham vacation packages? Try to avoid visiting during public holidays and any major events.
How many days is enough for Windham?
The ideal length for your Windham vacation depends on what you'd like to see. Usually, a few days to a week will give you time to tick off all the major sights and discover some hidden treasures along the way.
How to find the best Windham package deals?
Begin your search for a Windham package deal by entering your preferred trip dates and destination under our "Packages" tab. Then select a few filters, like "Property type" and "Amenities," to tailor the results to your exact style. You can also sort by "Package discount" and discover offers that come with unbeatable savings. If you don't find the perfect Windham package deal right away, just switch up your dates and search again. Remember that deals are only available for a limited time, so book early and get your Windham adventure off to a flying start.
Is it cheaper to book a Windham vacation as a package?
Expedia vacation packages are designed to give you more bang for your buck. Bundle your car rental, flight and hotel into one great-value price and enjoy significant savings. You'll typically get a better deal than booking each component individually. And you'll still have the freedom to create a tailored Windham vacation by choosing your preferred accommodation type, airline and car class.
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 take off. Prefer not to wait until the last minute? You can score awesome deals on your hotels and flights by booking well in advance.
How to plan a trip to Windham?

  1. Pick your dates: The things you want to do in Windham and your favourite season can help you decide when to go.
  2. Plan your budget wisely: In addition to the cost of your accommodations, you should consider other expenses. These include transportation, food and flights. Also, put aside some extra funds for unexpected costs that may come up during your trip to Windham.
  3. Set the duration of your trip: Start by making a list of all the attractions and activities you'd like to experience in Windham. Then, estimate how long you'll need for each, along with any travel time.
  4. Combine your hotel and flights: Epic destination, check. Length of stay, check. Now all that's left is to choose a Windham vacation package that brings all your bookings together.

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