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.
Jackson Gore Village
Jackson Gore Base Area
per person
Jun 9 - Jun 13
just found
Roundtrip non-stop flight included
Dallas (DFW) to Springfield (VSF)
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.
Winterplace at Okemo
Clock Tower Base Area
per person
Jul 3 - Jul 7
found 22 hours ago
Roundtrip non-stop flight included
Miami (MIA) to Springfield (VSF)
Ski-in/ski-out access and an indoor pool are featured at this smoke-free aparthotel. Enjoy the hot tub and perks like free self parking and free WiFi. Express check-out, laundry facilities, and barbecue grills are also on offer.
Solitude Village at Okemo
Clock Tower Base Area
per person
Jul 3 - Jul 7
found 22 hours ago
Roundtrip non-stop flight included
Miami (MIA) to Springfield (VSF)
Ski-in/ski-out access and an outdoor pool are featured at this smoke-free aparthotel. Enjoy the indoor pool and perks like free self parking and free WiFi. A gym, a hot tub, and a sauna are also on offer.
Top Windsor hotels deals
Fat Sheep Farm & Cabins
122 Best Rd, Windsor, VT
The price is $222 per night
$222
includes taxes & fees
$204 per night
May 4 - May 5
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
The price is $134 per night
$134
includes taxes & fees
$122 per night
May 7 - May 8
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
The price is $132 per night
$132
includes taxes & fees
$120 per night
May 5 - May 6
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
The price is $373 per night
$373
includes taxes & fees
$339 per night
May 26 - May 27
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
The price is $165 per night
$165
includes taxes & fees
$152 per night
May 22 - May 23
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
The price is $172 per night
$172
includes taxes & fees
$156 per night
May 12 - May 13
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
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