Windham Vacations from $530

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The Latest Windham vacation packages

Price found within the past 48 hours. Click for updated prices.
Bentley House Bed and Breakfast

Bentley House Bed and Breakfast

2 out of 5
Price was $616, price is now $530 per person
$530
per person
Jul 30 - Aug 2
found 9 hours ago
Roundtrip flight included
Atlanta (ATL) to Rutland (RUT)
No reviews
The Quechee Inn at Marshland Farm

The Quechee Inn at Marshland Farm

3 out of 5
Price was $768, price is now $610 per person
$610
per person
Jul 6 - Jul 10
found 22 hours ago
Roundtrip flight included
New York (NYC) to Rutland (RUT)
9/10 Wonderful! (1,000 reviews)
Some maintenance issues But plenty of character

Reviewed on May 15, 2026

Lake Bomoseen Lodge

Lake Bomoseen Lodge

3.5 out of 5
Price was $926, price is now $740 per person
$740
per person
Jun 26 - Jun 29
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Rutland (RUT)
9.4/10 Exceptional! (926 reviews)
Originally booked for a room upon check in we were upgraded to the pine lodge where we stayed for 3 nights would highly recommend.

Reviewed on May 20, 2026

Chateau Rooms

Chateau Rooms

4.5 out of 5
Price was $1,151, price is now $941 per person
$941
per person
Jul 17 - Jul 19
found 8 hours ago
Roundtrip flight included
New York (NYC) to Rutland (RUT)
9.2/10 Wonderful! (66 reviews)
Such a beautiful time, So clean, and cozy. Such a beautiful, peaceful, and romantic place. Very enchanting, and the owner is so kind, and caring. Def cant wait to go back again.

Reviewed on Jan 4, 2026

Emrose Luxury Cabins

Emrose Luxury Cabins

2 out of 5
Price was $803, price is now $710 per person
$710
per person
Jul 30 - Aug 2
found 9 hours ago
Roundtrip flight included
Atlanta (ATL) to Rutland (RUT)
9/10 Wonderful! (93 reviews)
Will definitely be back!!

Reviewed on Apr 5, 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! (57 reviews)
"We had the best time at this beautiful house. Very clean and perfect for a large group"

Reviewed on Feb 22, 2026

Get rates
Luxury Two-Home Vermont Retreat Near Ski Resorts – Pool, Hot Tub & Sauna
Hampton Inn Brattleboro

Hampton Inn Brattleboro

2.5 out of 5
1378 Putney Road Brattleboro VT
Fully refundableReserve now, pay when you stay
$122 nightly
The price is $134 total per night from Jun 7 to Jun 8
$134 total
Jun 7 - Jun 8
Total with taxes and fees
8.2/10 Very Good! (978 reviews)
"Staff were amazing !!! The continental breakfast turbed out like a meeting ground for all the travellers. Everyone was so friendly."

Reviewed on May 19, 2026

Hampton Inn Brattleboro
Kimpton Taconic Hotel by IHG

Kimpton Taconic Hotel by IHG

4 out of 5
3835 Main St. Manchester VT
Fully refundable
$193 nightly
The price is $212 total per night from May 25 to May 26
$212 total
May 25 - May 26
Total with taxes and fees
9.4/10 Exceptional! (841 reviews)
"We always love this property!!"

Reviewed on May 4, 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.

Find the Best Windham Vacation Packages

Windham Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Rutland Southern Vermont Regional Airport (RUT)
Max Temp Winter
25ºF
Max Temp Summer
75ºF

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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 $530 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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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.