Windham Vacation Packages

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Top Windham Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Pointe at Castle Hill Resort

Pointe at Castle Hill Resort

3.5 out of 5
Price was CA $1,186, price is now CA $1,048 per person
CA $1,048
per person
Aug 18 - Aug 25
found 14 hours ago
Roundtrip flight included
Montreal (YUL) to Rutland (RUT)
8.8/10 Excellent! (1,000 reviews)
Everything was great

Reviewed on Jun 30, 2026

Align Inn Vermont

Align Inn Vermont

2.5 out of 5
Price was CA $1,434, price is now CA $1,193 per person
CA $1,193
per person
Aug 18 - Aug 25
found 14 hours ago
Roundtrip flight included
Montreal (YUL) to Rutland (RUT)
9.4/10 Exceptional! (1,226 reviews)
Room was quite clean. I did eat breakfast because I was having breakfast elsewhere

Reviewed on Jul 10, 2026

Castle Hill Resort And Spa

Castle Hill Resort And Spa

3.5 out of 5
Price was CA $2,140, price is now CA $1,827 per person
CA $1,827
per person
Aug 18 - Aug 25
found 14 hours ago
Roundtrip flight included
Montreal (YUL) to Rutland (RUT)
9/10 Wonderful! (118 reviews)

My Place Hotel-Randolph VT

My Place Hotel-Randolph VT

2 out of 5
Price was CA $1,425, price is now CA $1,272 per person
CA $1,272
per person
Sep 15 - Sep 19
found 18 hours ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Rutland (RUT)
9.4/10 Exceptional! (476 reviews)
This place is wonderful. Super clean. Bathroom shower/tub was so shiny. Beds clean and comfortable. Loved the full fridge with the built-in ice maker. We really enjoyed that. It was nice to have a stovetop too and the toaster. The sink even had a garbage disposal. They have frozen dinners for sale if you forget to bring your own and they sell ice cream as the fridge has the freezer. We will definitely stay there again. Best place and very reasonably priced too. My only issue was the super big/thick pillows. Luckily I did bring my own. Over all it is a really terrific place to stay. Staff was friendly and helpful. Very, very clean. I highly recommend this place.

Reviewed on Jul 4, 2026

Lake Bomoseen Lodge

Lake Bomoseen Lodge

3.5 out of 5
Price was CA $1,586, price is now CA $1,449 per person
CA $1,449
per person
Aug 9 - Aug 13
found 10 hours ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Rutland (RUT)
9.4/10 Exceptional! (947 reviews)
We stayed at the Maple Cottage and enjoyed the beautiful view of the lake. My family and pup had a great stay, and the staff was very helpful. We’d be happy to come back!

Reviewed on Jul 7, 2026

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Windham Hotel Deals

Luxury Two-Home Vermont Retreat Near Ski Resorts – Pool, Hot Tub & Sauna

Luxury Two-Home Vermont Retreat Near Ski Resorts – Pool, Hot Tub & Sauna

Windham VT
10/10 Exceptional! (61 reviews)
"We had an excellent stay with 6 families and 10 kids. The cabin was wonderful and the hosts were amazing!"

Reviewed on Jun 30, 2026

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Luxury Two-Home Vermont Retreat Near Ski Resorts – Pool, Hot Tub & Sauna
Grand Summit Resort, A Vail Resorts Property

Grand Summit Resort, A Vail Resorts Property

3 out of 5
89 Grand Summit Way West Dover VT
Fully refundable
The price is CA $217 per night from Jul 13 to Jul 14
CA $217
CA $260 total
Jul 13 - Jul 14
includes taxes & fees
8.6/10 Excellent! (289 reviews)
"ac had to be turned back on every few hours. fridge broke three times and maintenance needed to bring new ones. pool and hot tub was closed even tho i specifically bought this booking because expedia said it was available. fire pit was nice and they had a great fourth of july celebration"

Reviewed on Jul 5, 2026

Grand Summit Resort, A Vail Resorts Property
Kimpton Taconic Hotel by IHG

Kimpton Taconic Hotel by IHG

4 out of 5
3835 Main St. Manchester VT
Fully refundable
The price is CA $336 per night from Jul 27 to Jul 28
CA $336
CA $429 total
Jul 27 - Jul 28
includes taxes & fees
9.4/10 Exceptional! (854 reviews)
"The hotel was beautiful very tranquil. Lots to see and do. The staff were friendly and attentive to the guests. The food in the restaurant was amazing. The staff there were also friendly. It was so peaceful in the mountains and the hotel grounds were beautiful."

Reviewed on Jun 29, 2026

Kimpton Taconic Hotel by IHG
See all 2,643 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 $1,048 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.

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