Windham Vacations from $809

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The Latest Windham vacation packages

Price found within the past 48 hours. Click for updated prices.
Days Inn by Wyndham Rutland/Killington Area

Days Inn by Wyndham Rutland/Killington Area

2.5 out of 5
Price was $929, price is now $809 per person
$809
per person
Jul 16 - Jul 21
found 1 day ago
Roundtrip flight included
New York (NYC) to Rutland (RUT)
6.6/10 (1,001 reviews)
Could be cleaners in the room. Found hair all over the bathroom.

Reviewed on Jun 9, 2026

Lake Bomoseen Lodge

Lake Bomoseen Lodge

3.5 out of 5
Price was $1,103, price is now $967 per person
$967
per person
Jul 16 - Jul 21
found 1 day ago
Roundtrip flight included
New York (NYC) to Rutland (RUT)
9.4/10 Exceptional! (936 reviews)
We stayed lake front and the view was amazing!! Loved watching the sunset and the fire pit was a huge plus, as were the lounge chairs. Plenty of fresh towels, but they do need to sweep under the beds. Water pressure was ok. Over all, a great stay and I would definitely return!

Reviewed on Jun 6, 2026

HIGHLANDS CASTLE overlooking Lake George.. plus 2 other Castles!

HIGHLANDS CASTLE overlooking Lake George.. plus 2 other Castles!

3 out of 5
Save 100% on your flight
Price was $3,947, price is now $3,517 per person
$3,517
per person
Jul 20 - Jul 25
found 1 day ago
Roundtrip flight included
New York (NYC) to Rutland (RUT)
9.8/10 Exceptional! (17 reviews)
We loved our visit here. John and Yvonne were wonderful. The space was clean, quiet, and truly magical. The views were second to none and the castle and other buildings are truly worth experiencing. We loved learning about the history of this place and we will certainly be back.

Reviewed on Jan 18, 2026

Best Western Inn & Suites Rutland-Killington

Best Western Inn & Suites Rutland-Killington

2.5 out of 5
Price was $960, price is now $876 per person
$876
per person
Jul 24 - Jul 28
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Rutland (RUT)
8.8/10 Excellent! (1,001 reviews)
Room was ok and the breakfast was ok. Nowhere handy for dinner. Ok for an overnight stop on route. Would find somewhere different next time.

Reviewed on Jun 10, 2026

Mountain Green Resort

Mountain Green Resort

4 out of 5
Price was $1,220, price is now $1,124 per person
$1,124
per person
Jul 24 - Jul 28
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Rutland (RUT)
4/10 (2 reviews)
Clean room, elevator broken and not enough bathroom towels.

Reviewed on Dec 28, 2025

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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! (59 reviews)
"House was amazing"

Reviewed on Jun 7, 2026

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Luxury Two-Home Vermont Retreat Near Ski Resorts – Pool, Hot Tub & Sauna
Kimpton Taconic Hotel by IHG

Kimpton Taconic Hotel by IHG

4 out of 5
3835 Main St. Manchester VT
Fully refundable
$208 nightly
The price is $229 total per night from Jun 16 to Jun 17
$229 total
Jun 16 - Jun 17
Total with taxes and fees
9.4/10 Exceptional! (849 reviews)
"I can’t say enough about the Frontenac. The staff was sincerely friendly and went out of their way to help us with whatever we needed. We left the Fairmont Frontenac to head back to Connecticut. When we got back, my sister realized she left her Kindle in her room. We called to see if it had been ..."

Reviewed on Jun 11, 2026

Kimpton Taconic Hotel by IHG
Hampton Inn Brattleboro

Hampton Inn Brattleboro

2.5 out of 5
1378 Putney Road Brattleboro VT
Fully refundableReserve now, pay when you stay
$119 nightly
The price is $131 total per night from Jul 2 to Jul 3
$131 total
Jul 2 - Jul 3
Total with taxes and fees
8.2/10 Very Good! (990 reviews)
"We had a reat stay. Hotel was vey clean and staff was. Very helpful"

Reviewed on Jun 1, 2026

Hampton Inn Brattleboro
See all 2,638 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 $809 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.