Windham Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Top Windham Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Harvest Barn Inn
CA $1,147
per person
Oct 12 - Oct 15
found 19 hours ago
Roundtrip flight included
Detroit (DTT) to Rutland (RUT)
9.8/10 Exceptional! (270 reviews)
We had a great stay at Harvest Barn Inn ! We enjoyed superb breakfasts created by Blessing! They are friendly and respectful hosts and the front porch view was beautiful! Parking is plentiful ! It was quiet at night and the couple was responsive by text!
Reviewed on Aug 16, 2026
Ready to book your vacation to Windham?
Windham Hotel Deals
Luxury Two-Home Vermont Retreat Near Ski Resorts – Pool, Hot Tub & Sauna
Windham VT
10/10 Exceptional! (63 reviews)
"We had the absolute best time at Suki’s property. Even better than the photos, the pool, house, seclusion, outdoor dining area, all of it was perfect for our golf trip and the best summer weekend. More beds than we could count, the home was clean and very comfortable. Highly recommend!"
Reviewed on Jul 29, 2026
Kimpton Taconic Hotel by IHG
3835 Main St. Manchester VT
Fully refundable
CA $302
CA $390 total
Sep 9 - Sep 10
includes taxes & fees
9.4/10 Exceptional! (862 reviews)
"A few unexpected extra charges for property fees"
Reviewed on Aug 17, 2026
The Equinox Golf Resort & Spa
3567 Main Street Route 7A Manchester VT
Fully refundableReserve now, pay when you stay
CA $221
CA $319 total
Sep 7 - Sep 8
includes taxes & fees
7.4/10 Good! (659 reviews)
"We loved this hotel, really nice amenities, great rooms. I wish we had planned less activities and spent more time at the hotel. If you want to stay in the hotel, plan to spend a day in the hotel. Breakfast ends at 11 and bar closes at around 10 depending on crowd."
Reviewed on Aug 16, 2026
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.
Frequently asked questions
How much does a Windham vacation package cost?
You'll find cheap prices from CA $1,147 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?
- Pick your dates: The things you want to do in Windham and your favourite season can help you decide when to go.
- 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.
- 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.
- 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.
