Windham Vacations from $404

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The Latest Windham vacation packages

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

The Putney Inn

2.5 out of 5
Price was $508, price is now $404 per person
$404
per person
Sep 29 - Oct 3
found 11 hours ago
Roundtrip flight included
Fort Lauderdale (FLL) to Rutland (RUT)
8.4/10 Very Good! (1,005 reviews)
My stay here was perfect for what I was looking for, just a one night stay in the area. The property is dated but the accommodations are clean and the surrounding area is extremely quiet and secluded, but the parking lot is well lit and safe. I would stay here again if I needed a short term accommodation.

Reviewed on Aug 22, 2025

North Star Lodge and Resort

North Star Lodge and Resort

2 out of 5
Price was $1,622, price is now $1,274 per person
$1,274
per person
Sep 30 - Oct 6
found 17 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Rutland (RUT)
8.6/10 Excellent! (1,006 reviews)
Every person here was extremely polite and welcoming.They were a very welcoming group.Room was clean. It is disappointing the breakfast area and the bar are closed in the summer.I understand why the bar is closed, since less people stay in the summer, but they could provide a little more then coffee, even just donuts.

Reviewed on Aug 22, 2025

Days Inn by Wyndham Rutland/Killington Area

Days Inn by Wyndham Rutland/Killington Area

2.5 out of 5
Price was $555, price is now $444 per person
$444
per person
Sep 29 - Oct 3
found 11 hours ago
Roundtrip flight included
Fort Lauderdale (FLL) to Rutland (RUT)
6.4/10 (1,005 reviews)
Clean and comfortable. Good value for what you get. Would stay again.

Reviewed on Aug 18, 2025

The Vermont Inn

The Vermont Inn

3 out of 5
Price was $1,124, price is now $939 per person
$939
per person
Sep 30 - Oct 6
found 17 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Rutland (RUT)
9.2/10 Wonderful! (407 reviews)
Was a wonderful little bed and breakfast. Will stay here again.

Reviewed on Jul 23, 2025

Lake Bomoseen Lodge

Lake Bomoseen Lodge

3.5 out of 5
Price was $639, price is now $537 per person
$537
per person
Sep 29 - Oct 3
found 11 hours ago
Roundtrip flight included
Fort Lauderdale (FLL) to Rutland (RUT)
9.4/10 Exceptional! (814 reviews)
Room was clean and comfortable with lovely back deck overlooking the lake.

Reviewed on Aug 12, 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! (51 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
$170 nightly
The price is $187 total per night from Aug 26 to Aug 27
$187 total
Aug 26 - Aug 27
Total with taxes and fees
7.2/10 Good! (514 reviews)
"Classic colonial inn. Beautiful property in a nice area with good amenities. Golf course is nice. Scenic and challenging design."

Reviewed on Aug 20, 2025

The Equinox Golf Resort & Spa
Colonial Motel And Spa

Colonial Motel And Spa

3 out of 5
889 Putney Rd, Brattleboro, VT
Fully refundableReserve now, pay when you stay
$126 nightly
The price is $139 total per night from Aug 25 to Aug 26
$139 total
Aug 25 - Aug 26
Total with taxes and fees
6.6/10 (1,003 reviews)
"Appears to house a lot of homeless."

Reviewed on Aug 22, 2025

Colonial Motel And Spa
See all 2,523 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 $404 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.