Windham Vacations from $614

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The Latest Windham vacation packages

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

The Vermont Inn

3 out of 5
Price was $717, price is now $614 per person
$614
per person
Dec 4 - Dec 7
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Rutland (RUT)
9.2/10 Wonderful! (408 reviews)
Was a wonderful little bed and breakfast. Will stay here again.

Reviewed on Jul 23, 2025

The Mountain Inn at Killington

The Mountain Inn at Killington

2.5 out of 5
Price was $1,082, price is now $927 per person
$927
per person
Dec 4 - Dec 7
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Rutland (RUT)
9.2/10 Wonderful! (880 reviews)
Great location, amenities, food, and view.

Reviewed on Sep 14, 2025

North Star Lodge and Resort

North Star Lodge and Resort

2 out of 5
Price was $824, price is now $707 per person
$707
per person
Dec 4 - Dec 7
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Rutland (RUT)
8.6/10 Excellent! (1,000 reviews)
It was really quiet. We liked our room. We stayed here for the Spartan Races weekend and they even put up some posters and chatted about the event with us. I love when local business gets implicated.

Reviewed on Sep 13, 2025

Killington Mountain Lodge, Tapestry Collection by Hilton

Killington Mountain Lodge, Tapestry Collection by Hilton

3.5 out of 5
Price was $761, price is now $664 per person
$664
per person
Dec 4 - Dec 7
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Rutland (RUT)
7.4/10 Good! (1,004 reviews)
Sheets were stained staff was slow and food took way to long. 45 minutes for a grilled cheeze

Reviewed on Sep 14, 2025

Ski in & out Spruce Glen Townhomes on Great Eastern Trail

Ski in & out Spruce Glen Townhomes on Great Eastern Trail

3 out of 5
Price was $994, price is now $883 per person
$883
per person
Dec 4 - Dec 7
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Rutland (RUT)
9/10 Wonderful! (47 reviews)
We booked a non-smoking room. Showed up and the place ABSOLUTELY reaked of smoke. The smell was caked into everything including bedding. It was like they were smoking 10 packs plus a day and didn’t leave. Lamps and cabinets were broken as well. Cleaners also showed up at 6am blasting music, which was well before the 11am check out of the property. owners of the property did communicate well and that was much appreciated. However after this stay we are still feeling sub par out this place.

Reviewed on Aug 4, 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! (52 reviews)
"We had a wonderful stay at this beautiful Vermont property. The home was exceptionally clean upon arrival, which was much appreciated and made us feel comfortable right away. Any requests or questions we had were addressed promptly by the host, who was always pleasant and accommodating. The peaceful ..."

Reviewed on Aug 18, 2025

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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
$196 nightly
The price is $216 total per night from Sep 17 to Sep 18
$216 total
Sep 17 - Sep 18
Total with taxes and fees
7.2/10 Good! (529 reviews)
"The hotel prominently promotes walking trails in and near on their property. While they provide maps no staff could explain how to access. The maps were very confusing. We set out and could not find a trail head. We finally used Google Maps and found that the nearest access was a few blocks away ..."

Reviewed on Sep 14, 2025

The Equinox Golf Resort & Spa
Hampton Inn Brattleboro

Hampton Inn Brattleboro

2.5 out of 5
1378 Putney Road, Brattleboro, VT
$135 nightly
The price is $149 total per night from Sep 29 to Sep 30
$149 total
Sep 29 - Sep 30
Total with taxes and fees
8/10 Very Good! (884 reviews)
AOK
"Staff was very friendly and professional. Bed was very comfortable! Breakfast was good!"

Reviewed on Sep 16, 2025

Hampton Inn Brattleboro
See all 2,545 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 can pick up a vacation package to this destination from $614 on Expedia. However, how much your vacation to Windham costs will depend on factors like your hotel choice, length of stay and season.
What are the cheapest months to go to Windham?
You're likely to find lower rates and greater availability in March, April and October. Browse our cheap Windham vacation packages and you could get some excellent off-season deals.
How many days is enough for Windham?
Typically, a handful of days is enough to check out the major sights during your Windham vacation. However, if you'd like to have time to relax or go on day tours, consider extending your trip.
How to find the best Windham package deals?
Finding a cheap Windham package deal is a breeze with Expedia. After you've entered your destination and travel dates under our "Packages" tab, set your budget, add a couple of filters and browse what's available. You can personalize your search by "Popular locations," "Property type," "Guest rating" and more. Sort the results by "Price: low to high" to view the most economical Windham package deals. Want a simple trick to score the biggest savings? Have some flexibility with your departure dates and consider going away on a weekday, when prices are often lower.
Is it cheaper to book a Windham vacation as a package?
An Expedia vacation package could land you significant savings when compared to arranging hotels and flights separately. Better still, you can personalize your Windham getaway to fit your exact needs. Pick your preferred flight time, select the hotel type and add a rental car. Explore our bundles to see how much you can save.
When to book a vacation package to Windham?
If you're considering a spontaneous Windham trip, check out our last-minute deals that can be booked up to one week before you take off. Prefer not to wait until the last minute? You can score sensational deals on your hotels and flights by booking ahead.
Does Expedia offer Book Now, Pay Later Windham vacation packages?
Your Windham break is meant to be an escape from your daily routine, not a source of money-related stress. So to allow you a little more flexibility, we've joined up with online lender Affirm to bring you our Book Now, Pay Later vacations. Choose one of our vacation packages with payment plans and spread the total cost over 3, 6 or 12 months. Plus, there aren't any hidden costs or late payment fees to worry about.

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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.