Deals on vacations and trips to Windsor
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Windsor flight + hotel vacation packages
Price found within the past 48 hours. Click for updated prices.
Latchis Hotel
per person
Jul 3 - Jul 8
found 1 day ago
Roundtrip flight included
Tampa (TPA) to Springfield (VSF)
A restaurant and a bar/lounge are featured at this hotel. Guests will appreciate free perks like free self parking and WiFi in public areas. Free parking and luggage storage are also offered on site.
Mount Snow Grand Summit Resort
per person
Jul 3 - Jul 8
found 1 day ago
Roundtrip flight included
Tampa (TPA) to Springfield (VSF)
This smoke-free resort features ski-in/ski-out access, a full-service spa, and a restaurant. Enjoy the outdoor pool and perks like free valet parking and a free area shuttle. You'll appreciate the gym, bar/lounge, and laundry facilities.
Top Windsor hotels deals
Fat Sheep Farm & Cabins
122 Best Rd, Windsor, VT
$204 nightly
The price is $222 total per night
$222 total
May 12 - May 13
Total includes taxes and fees
This farm stay doesn't skimp on freebies - guests receive free WiFi and free self parking. If you want to take your pet along, this pet-friendly property offers everything you'll need for your pet including food and water bowls. A terrace, a garden, and a picnic area are also on offer.
Pet friendly
Parking included
Killington Mountain Lodge, Tapestry Collection by Hilton
2617 Killington Rd, Killington, VT
Free Cancellation
Reserve now, pay when you stay
$122 nightly
The price is $134 total per night
$134 total
May 14 - May 15
Total includes taxes and fees
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.
Hot Tub
Pet friendly
Align Inn Vermont
5817 Woodstock Rd, Quechee, VT
Free Cancellation
Reserve now, pay when you stay
$120 nightly
The price is $132 total per night
$132 total
May 11 - May 12
Total includes taxes and fees
This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Guests will appreciate freebies like continental breakfast and free self parking.
Pool
Breakfast included
Woodstock Inn & Resort
Fourteen The Green, Woodstock, VT
$349 nightly
The price is $384 total per night
$384 total
May 26 - May 27
Total includes taxes and fees
This luxury resort features a golf course, a full-service spa, and 4 restaurants. Enjoy the 2 indoor tennis courts and perks like free valet parking and free WiFi. Relax with a drink at one of the 2 bars/lounges and enjoy the 2 hot tubs and indoor pool.
Pool
Hot Tub
Hilton Garden Inn Hanover Lebanon
35 Labombard Rd, Lebanon, NH
Free Cancellation
Reserve now, pay when you stay
$152 nightly
The price is $165 total per night
$165 total
May 26 - May 27
Total includes taxes and fees
This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the gym and perks like free self parking.
Pool
Pet friendly
The Mountain Inn at Killington
47 Old Mill Rd, Killington, VT
Free Cancellation
Reserve now, pay when you stay
$153 nightly
The price is $168 total per night
$168 total
May 18 - May 19
Total includes taxes and fees
This hotel features a restaurant, an outdoor pool, and a bar/lounge. Enjoy the free ski shuttle and onsite ski storage. Enjoy the gym and free perks like continental breakfast and free self parking.
Pool
Breakfast included
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.
Popular places to visit
Harpoon Brewery
4.5/5(5 reviews)
You can take time to visit Harpoon Brewery during your travels to Windsor. Wander the forest or discover the area's mountain views.
American Precision Museum
You can spend time exploring the galleries in American Precision Museum in Windsor. Wander the riverfront in this quaint area.
Mt Ascutney Hospital and Health Center: Primary Care - Windsor
Though Mt Ascutney Hospital and Health Center: Primary Care - Windsor might be what brings you to town, perhaps you'll have a chance to explore more of Windsor while you are here.
Photos of local treasures
Browse Windsor vacation photos for more inspiration
