Deals on vacations and trips to Windham

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Killington Mountain Lodge, Tapestry Collection by Hilton

Killington Mountain Lodge, Tapestry Collection by Hilton

3.5 out of 5
Price was $661, price is now $586 per person
$586
per person
Nov 6 - Nov 9
found 17 hours ago
Roundtrip non-stop flight included
Akron (CAK) to Rutland (RUT)
This hotel features a 24-hour gym and a hot tub. There's a free ski shuttle, and ski passes and ski storage are available on site. WiFi in public areas is free.
Ski in & out Spruce Glen Townhomes on Great Eastern Trail

Ski in & out Spruce Glen Townhomes on Great Eastern Trail

3 out of 5
Save 100% on your flight
Price was $2,894, price is now $2,374 per person
$2,374
per person
Dec 30 - Jan 3
found 10 hours ago
Roundtrip non-stop flight included
Fort Lauderdale (FLL) to Rutland (RUT)
This cabin doesn't skimp on freebies - guests receive free WiFi and free self parking. Enjoy ski-in/ski-out access and onsite ski storage. Enjoy the sauna and conveniences like express check-out and laundry facilities.
Beechwood Home in Mendon

Beechwood Home in Mendon

2 out of 5
Save 100% on your flight
Price was $3,784, price is now $3,127 per person
$3,127
per person
Dec 30 - Jan 3
found 10 hours ago
Roundtrip non-stop flight included
Fort Lauderdale (FLL) to Rutland (RUT)
This vacation home doesn't skimp on freebies - guests receive free WiFi and free self parking. Laundry facilities are provided for your convenience.
Sweet Life in Pittsfield

Sweet Life in Pittsfield

2 out of 5
Save 100% on your flight
Price was $3,050, price is now $2,549 per person
$2,549
per person
Dec 30 - Jan 3
found 10 hours ago
Roundtrip non-stop flight included
Fort Lauderdale (FLL) to Rutland (RUT)
This vacation home doesn't skimp on freebies - guests receive free WiFi and free self parking. A full-service spa is also provided.
The Engel House

The Engel House

3 out of 5
Price was $881, price is now $754 per person
$754
per person
Dec 30 - Jan 3
found 10 hours ago
Roundtrip non-stop flight included
Fort Lauderdale (FLL) to Rutland (RUT)
This bed & breakfast features free self parking and free WiFi in public areas. Enjoy the free buffet breakfast each morning. A lobby fireplace, a communal living room, and a library are also on offer.

Top Windham hotels 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.

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Ski-in/ski-out access and an outdoor pool are featured at this smoke-free vacation home. There's fun for all ages with a playground and an arcade/game room, and families will appreciate the onsite laundry facilities. Enjoy the hot tub and conveniences like a garden and concierge services.
The Equinox Golf Resort & Spa

The Equinox Golf Resort & Spa

4.5 out of 5
3567 Main Street Route 7A, Manchester, VT
Free Cancellation
Reserve now, pay when you stay
$172 nightly
The price is $189 total per night
$189 total
Nov 2 - Nov 3
Total with taxes and fees
This luxury hotel features a golf course, a full-service spa, and 4 restaurants. Enjoy the 3 outdoor tennis courts and get free self parking. Make the most of the indoor pool and 24-hour gym, and relax with drinks at one of the 2 bars/lounges.
Jackson Gore Village

Jackson Gore Village

3 out of 5
111 Jackson Gore Road, Ludlow, VT
$193 nightly
The price is $213 total per night
$213 total
Nov 6 - Nov 7
Total with taxes and fees
This smoke-free hotel features ski-in/ski-out access, a full-service spa, and 2 restaurants. There's a free ski shuttle, and ski lessons, ski passes and ski storage are available on site. Bring the family and enjoy the mini golf, playground, and arcade/game room.
Hampton Inn and Suites Manchester

Hampton Inn and Suites Manchester

2.5 out of 5
4519 Main St, Manchester Center, VT
$135 nightly
The price is $149 total per night
$149 total
Oct 26 - Oct 27
Total with taxes and fees
This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the hot tub and free perks like buffet breakfast and free self parking.
Pool
Hot Tub
The Covered Bridge Inn

The Covered Bridge Inn

2.5 out of 5
1043 Putney Road, Brattleboro, VT
Free Cancellation
Reserve now, pay when you stay
$126 nightly
The price is $139 total per night
$139 total
Oct 8 - Oct 9
Total with taxes and fees
This hotel features free self parking and free WiFi in public areas. Enjoy the free continental breakfast each morning.
Breakfast included
Parking included
Pointe at Castle Hill Resort

Pointe at Castle Hill Resort

3.5 out of 5
2940 State Route 103, Cavendish, VT
$134 nightly
The price is $145 total per night
$145 total
Nov 5 - Nov 6
Total with taxes and fees
A full-service spa, an indoor pool, and a restaurant are all featured at this smoke-free hotel. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the gym and perks like free self parking.
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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 are vacation packages to Windham?
Travelocity offers hotel and flight vacation packages starting as low as $586. With such great bargains, you'll be saying hello to Windham in no time.
Where can I get the best vacation package deals for Windham?
Landing an unbeatable package deal to Windham is a piece of cake with Travelocity. With around 400 partner airlines and 1,000,000 properties around the world, you're spoiled for choice when it comes to your hotels and flights.
Why should I book my Windham vacation bundle with Travelocity?
We've got a destination for every kind of traveler, exceptional service and round-the-clock customer support. In addition to that, we'll match any lower price you happen to find with our Price Match Guarantee.
Can I save on my Windham car rental if I combine it with my hotel or flight?
Combining your car, hotel and flight into a Windham vacation package is an excellent way to land the best deal. Plus, having your own rental car gives you the freedom to get to all those big sights you're hoping to check out. Sitting 100 mi away from Windham, Fenway Park is one place that should be on your must-do list. Buckle up and make a day trip of it.
Which airport is best for Windham?
One of the handiest options is Lebanon Municipal Airport (LEB), which you'll find 40 mi northeast of downtown Windham. Your other choice is Rutland Southern Vermont Regional Airport (RUT), 25 mi away from central Windham).
Where should I stay when visiting Windham?
If you're looking for a place to spend your nights, take a look at the Remote Cabin, Private Lake & 80 Acres, Mtn Views. It's the top pick for many travelers.

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