Windham Vacation Packages

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Top Windham Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Lake Bomoseen Lodge

Lake Bomoseen Lodge

3.5 out of 5
Price was CA $782, price is now CA $697 per person
CA $697
per person
Nov 7 - Nov 11
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Rutland (RUT)
9.4/10 Exceptional! (809 reviews)
Room was clean and comfortable with lovely back deck overlooking the lake.

Reviewed on Aug. 12, 2025

North Star Lodge and Resort

North Star Lodge and Resort

2 out of 5
Price was CA $2,290, price is now CA $1,971 per person
CA $1,971
per person
Oct 8 - Oct 13
found 14 hours ago
Roundtrip non-stop flight included
Ottawa (YOW) 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 Vermont Inn

The Vermont Inn

3 out of 5
Price was CA $1,806, price is now CA $1,640 per person
CA $1,640
per person
Oct 8 - Oct 13
found 14 hours ago
Roundtrip non-stop flight included
Ottawa (YOW) to Rutland (RUT)
9.2/10 Wonderful! (407 reviews)
Was a wonderful little bed and breakfast. Will stay here again.

Reviewed on Jul. 23, 2025

Emrose Luxury Cabins

Emrose Luxury Cabins

2 out of 5
Price was CA $1,762, price is now CA $1,606 per person
CA $1,606
per person
Oct 8 - Oct 13
found 14 hours ago
Roundtrip non-stop flight included
Ottawa (YOW) to Rutland (RUT)
9/10 Wonderful! (39 reviews)
We were able to have our amall dog with us.

Reviewed on Jul. 20, 2025

Days Inn by Wyndham Rutland/Killington Area

Days Inn by Wyndham Rutland/Killington Area

2.5 out of 5
Price was CA $1,569, price is now CA $1,440 per person
CA $1,440
per person
Oct 10 - Oct 14
found 18 hours ago
Roundtrip flight included
Saskatoon (YXE) to Rutland (RUT)
6.4/10 (1,004 reviews)
Clean and comfortable. Good value for what you get. Would stay again.

Reviewed on Aug. 18, 2025

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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! (50 reviews)
"We have family reunions every two years and we all agreed that this was the best one! The house was perfect for over 20 people, Grandparents, parents and grandchildren.The house was VERY well stocked with everything you could need or want. And the owners were extremely responsive and helpful with ..."

Reviewed on Aug. 13, 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 $184 per night from Sep 1 to Sep 2
CA $184
CA $277 total
Sep 1 - Sep 2
includes taxes & fees
7.2/10 Good! (511 reviews)
"Nice facilities"

Reviewed on Aug. 11, 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 $194 per night from Aug 21 to Aug 22
CA $194
CA $214 total
Aug 21 - Aug 22
includes taxes & fees
6.6/10 (1,006 reviews)
"Staff was helpful. Quiet area"

Reviewed on Aug. 17, 2025

Colonial Motel And Spa
See all 2,523 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
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Frequently asked questions

How much does a Windham vacation package cost?
You'll find cheap prices from CA $697 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.