Deals on vacations and trips to Windsor
Save when you book Windsor package deals
Windsor flight + hotel vacation packages
Price found within the past 48 hours. Click for updated prices.
Grand Summit Resort, A Vail Resorts Property
Price was $704, price is now $658 per person
$658
per person
Jun 26 - Jun 29
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Springfield (VSF)
Ski-in/ski-out access, a full-service spa, and 2 hot tubs are all featured at this smoke-free resort. Enjoy a meal from the restaurant and freebies like WiFi in public areas and an area shuttle. You'll appreciate the outdoor pool, bar/lounge, and laundry facilities.
Latchis Hotel
Price was $914, price is now $754 per person
$754
per person
Jun 26 - Jun 29
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) 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.
The Shire Woodstock
Price was $978, price is now $807 per person
$807
per person
Jun 26 - Jun 29
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Springfield (VSF)
This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. A garden and a picnic area are also provided.
Jackson Gore Village, A Vail Resorts Property
Jackson Gore Base Area
Price was $768, price is now $679 per person
$679
per person
Jun 26 - Jun 29
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Springfield (VSF)
Ski-in/ski-out access, 2 restaurants, and 3 hot tubs are all featured at this smoke-free hotel. 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.
Top Windsor hotels deals
Fireside Inn & Suites West Lebanon
25 Airport Road West Lebanon NH
Free Cancellation
Reserve now, pay when you stay
$144 nightly
The price is $157 total per night
$157 total
May 31 - Jun 1
Total with 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
Killington Mountain Lodge, Tapestry Collection by Hilton
2617 Killington Rd Killington VT
Free Cancellation
Reserve now, pay when you stay
$130 nightly
The price is $143 total per night
$143 total
May 25 - May 26
Total with taxes and fees
This hotel features a 24-hour gym and a hot tub. Traveling on business? Take advantage of the 2 conference rooms, along with free WiFi in public areas. Self parking, a terrace, and a lobby fireplace are also offered.
Hot Tub
Pet friendly
Align Inn Vermont
5817 Woodstock Rd Quechee VT
Free Cancellation
Reserve now, pay when you stay
$113 nightly
The price is $124 total per night
$124 total
May 21 - May 22
Total with 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
Woodstock Inn & Resort
Fourteen The Green Woodstock VT
$359 nightly
The price is $395 total per night
$395 total
May 25 - May 26
Total with 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
Hampton Inn White River Junction
104 Ballardvale Dr White River Junction VT
Free Cancellation
Reserve now, pay when you stay
$129 nightly
The price is $142 total per night
$142 total
May 31 - Jun 1
Total with 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 business center and free internet in public areas. There's a gym on site, and a 24-hour front desk and a terrace are also provided.
Pool
Breakfast included
The Mountain Inn at Killington
47 Old Mill Rd Killington VT
Free Cancellation
Reserve now, pay when you stay
$156 nightly
The price is $172 total per night
$172 total
May 21 - May 22
Total with 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
Brownsville Trail
You can take time to visit Brownsville Trail during your travels to Windsor. Discover the mountain views in this family-friendly area, or seek out the ski slopes.
Paradise Park
4/5(4 reviews)
Explore the great outdoors at Paradise Park, a lovely green space in Windsor. Wander the riverfront in this quaint area.
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.
Frequently asked questions
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