Deals on vacations and trips to Winchester

Save when you book Winchester package deals

Choose two or more items and save on your trip:

Winchester flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
Sinclair Inn Bed and Breakfast

Sinclair Inn Bed and Breakfast

4 out of 5
Price was $603, price is now $532 per person
$532
per person
Sep 2 - Sep 5
found 1 day ago
Roundtrip flight included
Orlando (MCO) 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.
Vikings Villages Resort

Vikings Villages Resort

2 out of 5
Price was $872, price is now $725 per person
$725
per person
Oct 2 - Oct 4
found 1 day ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Springfield (VSF)
A rooftop terrace is featured at this hotel, along with free self parking. WiFi in public areas is free. A garden, a lobby fireplace, and a picnic area are also on offer.
Deerfield Valley Inn

Deerfield Valley Inn

2 out of 5
Price was $1,053, price is now $891 per person
$891
per person
Oct 8 - Oct 12
found 1 day ago
Roundtrip non-stop flight included
Houston (IAH) 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.
Chalet 239

Chalet 239

2 out of 5
Price was $1,106, price is now $957 per person
$957
per person
Oct 8 - Oct 12
found 1 day ago
Roundtrip non-stop flight included
Houston (IAH) to Springfield (VSF)
The motel doesn't skimp on freebies - guests receive free on-the-go breakfast and free self parking. A picnic area and a virtual front desk are also provided.
Latchis Hotel

Latchis Hotel

2.5 out of 5
Price was $824, price is now $718 per person
$718
per person
Oct 2 - Oct 4
found 1 day ago
Roundtrip non-stop flight included
Philadelphia (PHL) 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.

Top Winchester hotels deals

Peaceful and relaxing cottage steps from Forest Lake.

Peaceful and relaxing cottage steps from Forest Lake.

Winchester NH
Get rates
This vacation home features a garden, laundry facilities, and barbecue grills.
Kitchen
Washer
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
Jul 15 - Jul 16
Total with taxes and fees
A garden is available at this campground.
Pet friendly
Free WiFi
The Colonial Hotel

The Colonial Hotel

3 out of 5
625 Betty Spring Road Gardner MA
Free Cancellation
Reserve now, pay when you stay
$170 nightly
The price is $190 total per night
$190 total
Jul 19 - Jul 20
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
$119 nightly
The price is $129 total per night
$129 total
Jul 19 - Jul 20
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
Best Western Plus Keene Hotel

Best Western Plus Keene Hotel

3 out of 5
401 Winchester St Keene NH
Free Cancellation
Reserve now, pay when you stay
$119 nightly
The price is $129 total per night
$129 total
Jul 15 - Jul 16
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
Colonial Motel

Colonial Motel

3 out of 5
889 Putney Rd Brattleboro VT
Free Cancellation
Reserve now, pay when you stay
$77 nightly
The price is $84 total per night
$84 total
Aug 2 - Aug 3
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
Don't see what you're looking for?
See all available properties in Winchester
View all properties
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?
$532 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.