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.
Deerfield Valley Inn

Deerfield Valley Inn

2 out of 5
Price was $874, price is now $708 per person
$708
per person
Oct 14 - Oct 19
found 14 hours ago
Roundtrip non-stop flight included
Denver (DEN) to Springfield (VSF)
This bed & breakfast features free WiFi in public areas, barbecue grills, and free self parking. A free bus station shuttle is offered as well. A 24-hour business center, a garden, and a lobby fireplace are also on offer.
Stone Hearth Inn and Eatery

Stone Hearth Inn and Eatery

3 out of 5
Price was $1,319, price is now $1,010 per person
$1,010
per person
Oct 14 - Oct 19
found 14 hours ago
Roundtrip non-stop flight included
Denver (DEN) to Springfield (VSF)
This bed & breakfast features free self parking and free WiFi in public areas. Enjoy the free buffet breakfast each morning. A garden is also provided.
Winterplace at Okemo, A Vail Resorts Property

Winterplace at Okemo, A Vail Resorts Property

4 out of 5
Clock Tower Base Area
Price was $1,166, price is now $968 per person
$968
per person
Oct 14 - Oct 19
found 14 hours ago
Roundtrip non-stop flight included
Denver (DEN) to Springfield (VSF)
Ski-in/ski-out access and an indoor pool are featured at this smoke-free aparthotel. Enjoy the gym and perks like free self parking and free WiFi. Enjoy the hot tub and conveniences like express check-out and laundry facilities.
Mount Snow Lodging by Vail Resorts

Mount Snow Lodging by Vail Resorts

3 out of 5
Price was $1,037, price is now $866 per person
$866
per person
Oct 14 - Oct 19
found 14 hours ago
Roundtrip non-stop flight included
Denver (DEN) to Springfield (VSF)
Solitude Village at Okemo by Vail Resorts

Solitude Village at Okemo by Vail Resorts

4 out of 5
Clock Tower Base Area
Price was $1,035, price is now $868 per person
$868
per person
Oct 14 - Oct 19
found 14 hours ago
Roundtrip non-stop flight included
Denver (DEN) to Springfield (VSF)
This smoke-free aparthotel's ski-in/ski-out access and 2 hot tubs are some of the highlights. Enjoy the gym and perks like free self parking and free WiFi. A sauna is also provided.

Top Winchester hotels deals

2 private mountain RV pads for rent. Full hook ups

2 private mountain RV pads for rent. Full hook ups

Winchester NH
$75 nightly
The price is $81 total per night
$81 total
Sep 3 - Sep 4
Total with taxes and fees
A garden is available at this campground.
Pet friendly
Free WiFi
Latchis Hotel

Latchis Hotel

2.5 out of 5
50 Main Street Brattleboro VT
Free Cancellation
Reserve now, pay when you stay
$135 nightly
The price is $149 total per night
$149 total
Sep 3 - Sep 4
Total with taxes and fees
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.
Pet friendly
Parking included
Colonial Motel

Colonial Motel

3 out of 5
889 Putney Rd Brattleboro VT
Free Cancellation
Reserve now, pay when you stay
$84 nightly
The price is $93 total per night
$93 total
Sep 3 - Sep 4
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 garden, a grocery/convenience store, and a lobby fireplace are also on offer.
Breakfast included
Pet friendly
The Colonial Hotel

The Colonial Hotel

3 out of 5
625 Betty Spring Road Gardner MA
$170 nightly
The price is $190 total per night
$190 total
Sep 7 - Sep 8
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

Keene Elm City Hotel, an Ascend Collection Hotel

2.5 out of 5
175 Key Rd Keene NH
Free Cancellation
Reserve now, pay when you stay
$141 nightly
The price is $153 total per night
$153 total
Sep 3 - Sep 4
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

Hampton Inn Brattleboro

2.5 out of 5
1378 Putney Road Brattleboro VT
Free Cancellation
Reserve now, pay when you stay
$114 nightly
The price is $125 total per night
$125 total
Sep 8 - Sep 9
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
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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.

Stay near popular Winchester attractions

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.
See properties

Frequently asked questions

How much are vacation packages to Winchester?
$708 is all you need to spend for a wonderful vacation in Winchester. Bundle your flights and hotel into a vacation package with Travelocity and see the savings start to add up. With prices this good, it's never been more tempting to travel.
How long should my Winchester vacation be?
Many visitors like to spend around 3 nights in Winchester. But what works for them mightn't work for you. Whether you prefer to stay for a few days or a few weeks, you'll enjoy discovering all the amazing things that this destination has to offer.
Where can I get the best vacation package deals for Winchester?
Travelocity has endless ways to score a sensational Winchester package deal. Select from 400 partner airlines and 1,000,000 properties all over the globe and craft a travel itinerary that fits your style. With this amount of choice at your fingertips, it's easy to plan your next big adventure.
Why should I purchase my Winchester vacation bundle via Travelocity?
From our 24/7 support to our range of exhilarating destinations, we're dedicated to fulfilling your vacation dreams. All you'll have to do is to click and book — our Price Match Guarantee will make sure you get the cheapest price.
Will I save money on my Winchester car rental if I book it with a hotel or flight?
With a Winchester vacation package, you can combine your hotel, flight and car bookings and save a whole lot. If you're eager to uncover the best of this exciting area, why not make tracks to Fenway Park? This popular attraction is 70 mi from Winchester. With your own set of wheels, you'll be there in a flash.
Which airport is best for Winchester?
Bradley Intl. Airport (BDL) (60 mi away from the downtown area), Manchester-Boston Regional Airport (MHT) (50 mi away from central Winchester) and Lebanon Municipal Airport (LEB) (60 mi away from central Winchester) are the best options for Winchester.
Where should I stay when visiting Winchester?
Many people opt to check in to the Story Book Lake Front Chateau with Private Beach!. It's a terrific base for your Winchester getaway.

Photos of local treasures

Browse Winchester vacation photos for more inspiration

A snow-covered town with a river running through it, surrounded by mountains and trees.
A snow-covered bridge over a river with a red roof, surrounded by trees and buildings.
A wooden pedestrian bridge with a lattice roof structure.
A covered bridge with a sign reading "Ashuelot Covered Bridge 1864" and a warning about the fine for riding or driving over it.