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.
Hampton Inn Brattleboro
Price was $596, price is now $572 per person
$572
per person
May 1 - May 4
found 1 day ago
Roundtrip non-stop flight included
Madison (MSN) to Springfield (VSF)
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. Enjoy the hot tub and perks like free self parking.
Jackson Gore Village, A Vail Resorts Property
Jackson Gore Base Area
Price was $715, price is now $614 per person
$614
per person
May 1 - May 4
found 1 day ago
Roundtrip non-stop flight included
Madison (MSN) 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.
Latchis Hotel
Price was $630, price is now $593 per person
$593
per person
May 1 - May 4
found 1 day ago
Roundtrip non-stop flight included
Madison (MSN) 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.
Holiday Inn Express Hotel & Suites Brattleboro by IHG
Price was $743, price is now $700 per person
$700
per person
May 1 - May 4
found 1 day ago
Roundtrip non-stop flight included
Madison (MSN) to Springfield (VSF)
This hotel features an indoor pool and a 24-hour gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Guests will appreciate freebies like on-the-go breakfast and free self parking.
Grand Summit Resort, A Vail Resorts Property
Price was $834, price is now $735 per person
$735
per person
May 15 - May 17
found 13 hours ago
Roundtrip non-stop flight included
San Francisco (SFO) 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.
Top Windsor hotels deals
Killington Mountain Lodge, Tapestry Collection by Hilton
2617 Killington Rd Killington VT
Free Cancellation
Reserve now, pay when you stay
$147 nightly
The price is $161 total per night
$161 total
Apr 5 - Apr 6
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
White River Inn and Suites
91 Ballardvale Drive White River Junction VT
Free Cancellation
Reserve now, pay when you stay
$121 nightly
The price is $133 total per night
$133 total
Mar 22 - Mar 23
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 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
$139 nightly
The price is $151 total per night
$151 total
Mar 22 - Mar 23
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
Align Inn Vermont
5817 Woodstock Rd Quechee VT
Free Cancellation
Reserve now, pay when you stay
$116 nightly
The price is $128 total per night
$128 total
Mar 25 - Mar 26
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
Pointe at Castle Hill Resort
2940 State Route 103 Cavendish VT
$135 nightly
The price is $146 total per night
$146 total
Mar 24 - Mar 25
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.
Pool
Hot Tub
Woodstock Inn & Resort
Fourteen The Green Woodstock VT
$349 nightly
The price is $384 total per night
$384 total
Mar 22 - Mar 23
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
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
Paradise Park
Explore the great outdoors at Paradise Park, a lovely green space in Windsor. Wander the riverfront in this quaint area.
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.
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.
Frequently asked questions
Photos of local treasures
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