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.
Mountain Lodge at Okemo
Clock Tower Base Area
per person
Sep 24 - Sep 27
found 1 day ago
Roundtrip non-stop flight included
San Diego (SAN) to Springfield (VSF)
Ski-in/ski-out access and a restaurant are featured at this smoke-free hotel. Take advantage of ski lessons, ski rentals and ski passes on site, and enjoy downhill skiing. Families will appreciate the onsite laundry facilities and babysitting.
Winterplace at Okemo
Clock Tower Base Area
per person
Sep 24 - Sep 27
found 1 day ago
Roundtrip non-stop flight included
San Diego (SAN) 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.
Jackson Gore Village
Jackson Gore Base Area
per person
Sep 24 - Sep 27
found 1 day ago
Roundtrip non-stop flight included
San Diego (SAN) 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.
Solitude Village at Okemo
Clock Tower Base Area
per person
Sep 24 - Sep 27
found 1 day ago
Roundtrip non-stop flight included
San Diego (SAN) 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.
Lincoln Inn & Gallery
West Woodstock
per person
Sep 24 - Sep 27
found 1 day ago
Roundtrip non-stop flight included
San Diego (SAN) to Springfield (VSF)
This inn features free self parking and free WiFi in public areas. Enjoy the free self-serve breakfast each morning. A fireplace in the lobby and a picnic area are also provided.
Top Windsor hotels deals
White River Inn and Suites
91 Ballardvale Drive, White River Junction, VT
Free Cancellation
Reserve now, pay when you stay
$122 nightly
The price is $134 total per night
$134 total
Aug 24 - Aug 25
Total includes taxes and fees
This hotel doesn't skimp on freebies - guests receive free continental breakfast, free WiFi, and free self parking. Traveling on business? Take advantage of the 24-hour business center and free internet in public areas. There's an indoor pool on site, and a 24-hour front desk and a terrace are also provided.
Pool
Breakfast included
Fireside Inn & Suites West Lebanon
25 Airport Road, West Lebanon, NH
Free Cancellation
Reserve now, pay when you stay
$164 nightly
The price is $178 total per night
$178 total
Aug 17 - Aug 18
Total includes taxes and fees
This hotel features an indoor pool, a hot tub, and a restaurant. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the gym and perks like free self parking.
Pool
Hot Tub
Woodstock Inn & Resort
Fourteen The Green, Woodstock, VT
$449 nightly
The price is $494 total per night
$494 total
Sep 1 - Sep 2
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
Align Inn Vermont
5817 Woodstock Rd, Quechee, VT
Free Cancellation
Reserve now, pay when you stay
$132 nightly
The price is $145 total per night
$145 total
Aug 24 - Aug 25
Total includes taxes and fees
This hotel features an indoor pool and a gym. Business travelers can take advantage of the free WiFi in public areas. Guests will appreciate freebies like continental breakfast and free self parking.
Pool
Breakfast included
Super 8 by Wyndham White River Junction
442 North Hartland Rd, I-91 Exit 11 Rt 5 S 1/4 Mile, White River Junction, VT
Free Cancellation
Reserve now, pay when you stay
$84 nightly
The price is $93 total per night
$93 total
Aug 24 - Aug 25
Total includes taxes and fees
This motel doesn't skimp on freebies - guests receive free on-the-go breakfast, free WiFi, and free self parking. Traveling on business? Take advantage of the 24-hour business center and free internet in public areas. A terrace, a picnic area, and laundry facilities are also on offer.
Breakfast included
Pet friendly
The Shire Woodstock
46 Pleasant St., Woodstock, VT
Free Cancellation
Reserve now, pay when you stay
$199 nightly
The price is $219 total per night
$219 total
Aug 31 - Sep 1
Total includes taxes and fees
This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. A garden and a picnic area are also provided.
Pet friendly
Parking 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
You can take time to visit Harpoon Brewery during your travels to Windsor. Wander the forest or discover the area's mountain views.
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.
American Precision Museum
You can spend time exploring the galleries in American Precision Museum in Windsor. Wander the riverfront in this quaint area.
Frequently asked questions
Photos of local treasures
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