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.
The Shire Woodstock
Price was $553, price is now $433 per person
$433
per person
Nov 22 - Nov 25
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) 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.
The Covered Bridge Inn
Save 100% on your flight
Price was $771, price is now $556 per person
$556
per person
Dec 9 - Dec 16
found 12 hours ago
Roundtrip flight included
New York (JFK) to Springfield (VSF)
This hotel features free self parking and free WiFi in public areas. Enjoy the free continental breakfast each morning.
Latchis Hotel
Save 100% on your flight
Price was $725, price is now $543 per person
$543
per person
Dec 9 - Dec 16
found 12 hours ago
Roundtrip flight included
New York (JFK) 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.
Hampton Inn Brattleboro
Save 100% on your flight
Price was $599, price is now $478 per person
$478
per person
Dec 9 - Dec 16
found 12 hours ago
Roundtrip flight included
New York (JFK) 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.
Mountaineer Inn
Price was $536, price is now $434 per person
$434
per person
Nov 7 - Nov 10
found 13 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Springfield (VSF)
A seasonal outdoor pool is featured at this motel, along with free self parking. WiFi in public areas is free. A terrace, a garden, and express check-in are also on offer.
Top Windsor hotels deals
White River Inn and Suites
91 Ballardvale Drive, White River Junction, VT
Free Cancellation
Reserve now, pay when you stay
$99 nightly
The price is $109 total per night
$109 total
Nov 2 - Nov 3
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
$174 nightly
The price is $189 total per night
$189 total
Nov 5 - Nov 6
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
The Shire Woodstock
46 Pleasant St., Woodstock, VT
Free Cancellation
Reserve now, pay when you stay
$158 nightly
The price is $174 total per night
$174 total
Nov 2 - Nov 3
Total with 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
Woodstock Inn & Resort
Fourteen The Green, Woodstock, VT
$449 nightly
The price is $494 total per night
$494 total
Nov 2 - Nov 3
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
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
$71 nightly
The price is $79 total per night
$79 total
Oct 19 - Oct 20
Total with 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 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
Oct 19 - Oct 20
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
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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