Deals on vacations and trips to Winchester
Save when you book Winchester package deals
Winchester flight + hotel vacation packages
Price found within the past 48 hours. Click for updated prices.
Sinclair Inn Bed and Breakfast
Price was $731, price is now $663 per person
$663
per person
Dec 4 - Dec 7
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Springfield (VSF)
This bed & breakfast doesn't skimp on freebies - guests receive free full breakfast and free WiFi. A garden and a picnic area are also provided.
Mount Snow Grand Summit Resort
Save 100% on your flight
Price was $972, price is now $744 per person
$744
per person
Oct 11 - Oct 18
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Springfield (VSF)
This smoke-free resort features ski-in/ski-out access, a full-service spa, and a restaurant. Enjoy the outdoor pool and perks like free valet parking and a free area shuttle. You'll appreciate the gym, bar/lounge, and laundry facilities.
Jackson Gore Village
Jackson Gore Base Area
Save 100% on your flight
Price was $901, price is now $715 per person
$715
per person
Oct 11 - Oct 18
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.
Winterplace at Okemo
Clock Tower Base Area
Price was $936, price is now $839 per person
$839
per person
Oct 14 - Oct 18
found 19 hours ago
Roundtrip 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.
Solitude Village at Okemo
Clock Tower Base Area
Price was $910, price is now $818 per person
$818
per person
Oct 14 - Oct 18
found 19 hours ago
Roundtrip 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.
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
Sep 11 - Sep 12
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
Hampton Inn Brattleboro
1378 Putney Road, Brattleboro, VT
$135 nightly
The price is $149 total per night
$149 total
Sep 17 - Sep 18
Total with taxes and fees
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
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
Sep 16 - Sep 17
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
The Putney Inn
57 Putney Landing Rd, Putney, VT
Free Cancellation
Reserve now, pay when you stay
$138 nightly
The price is $151 total per night
$151 total
Sep 17 - Sep 18
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
$139 nightly
The price is $151 total per night
$151 total
Sep 14 - Sep 15
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
Travelodge by Wyndham Brattleboro VT
1254 Putney Rd, Brattleboro, VT
Free Cancellation
Reserve now, pay when you stay
$80 nightly
The price is $88 total per night
$88 total
Sep 14 - Sep 15
Total with taxes and fees
This motel doesn't skimp on freebies - guests receive free WiFi and free self parking. Staff at the 24-hour front desk can provide around-the-clock assistance.
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
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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