Deals on vacations and trips to Winchester
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Winchester flight + hotel vacation packages
Price found within the past 48 hours. Click for updated prices.
Mountain Lodge at Okemo
Clock Tower Base Area
Price was $942, price is now $823 per person
$823
per person
Dec 11 - Dec 14
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) 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.
The Shire Woodstock
Price was $1,533, price is now $1,130 per person
$1,130
per person
Dec 11 - Dec 14
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) 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.
Solitude Village at Okemo
Clock Tower Base Area
Price was $1,135, price is now $988 per person
$988
per person
Dec 11 - Dec 14
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) 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.
Winterplace at Okemo
Clock Tower Base Area
Price was $1,133, price is now $987 per person
$987
per person
Dec 11 - Dec 14
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) 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
Price was $1,041, price is now $916 per person
$916
per person
Dec 11 - Dec 14
found 1 day ago
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.
Top Winchester hotels deals
The Colonial Hotel
625 Betty Spring Road, Gardner, MA
Free Cancellation
Reserve now, pay when you stay
$160 nightly
The price is $179 total per night
$179 total
Oct 2 - Oct 3
Total with taxes and fees
This hotel features a restaurant, an indoor pool, and a bar/lounge. 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
Keene Elm City Hotel, an Ascend Collection Hotel
175 Key Rd, Keene, NH
Free Cancellation
Reserve now, pay when you stay
$125 nightly
The price is $136 total per night
$136 total
Oct 5 - Oct 6
Total with taxes and fees
This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Guests will appreciate freebies like buffet breakfast and free self parking.
Pool
Breakfast included
Hampton Inn Brattleboro
1378 Putney Road, Brattleboro, VT
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.
Pool
Hot Tub
Colonial Motel And Spa
889 Putney Rd, Brattleboro, VT
Free Cancellation
Reserve now, pay when you stay
$140 nightly
The price is $154 total per night
$154 total
Sep 30 - Oct 1
Total with taxes and fees
This smoke-free motel features a full-service spa, 2 indoor pools, and a restaurant. Business travelers can take advantage of the free WiFi in public areas. Enjoy the gym and perks like free self parking.
Pool
Hot Tub
The Putney Inn
57 Putney Landing Rd, Putney, VT
Free Cancellation
Reserve now, pay when you stay
$94 nightly
The price is $103 total per night
$103 total
Oct 26 - Oct 27
Total with taxes and fees
Free self parking is available and the motel's front desk is staffed around-the-clock. Guests will appreciate free perks like continental breakfast and WiFi in public areas. A picnic area is also provided.
Breakfast included
Pet friendly
Best Western Plus Keene Hotel
401 Winchester St, Keene, NH
Free Cancellation
Reserve now, pay when you stay
$149 nightly
The price is $162 total per night
$162 total
Sep 30 - Oct 1
Total with taxes and fees
This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the 24-hour gym and free perks like buffet 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
New England Sweetwater Farm & Distillery
You can take time to visit New England Sweetwater Farm & Distillery during your travels to Winchester. While you're in the area, stroll along the lakeside.
Richmond Wildlife Manangement Area
Explore the great outdoors at Richmond Wildlife Manangement Area, a lovely green space in Richmond.
Winchester Speedpark
You can take time to visit Winchester Speedpark during your travels to Winchester. While you're in the area, stroll along the lakeside.
Frequently asked questions
Photos of local treasures
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