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.
The Covered Bridge Inn

The Covered Bridge Inn

2.5 out of 5
Price was $882, price is now $761 per person
$761
per person
Dec 24 - Dec 28
found 16 hours ago
Roundtrip flight included
El Paso (ELP) to Springfield (VSF)
This hotel features free self parking and free WiFi in public areas. Enjoy the free continental breakfast each morning.
Mount Snow Grand Summit Resort

Mount Snow Grand Summit Resort

3 out of 5
Price was $1,688, price is now $1,592 per person
$1,592
per person
Dec 26 - Dec 30
found 4 hours ago
Roundtrip non-stop flight included
Kansas City (MCI) to Springfield (VSF)
Ski-in/ski-out access, a full-service spa, and 2 hot tubs are all featured at this smoke-free resort. Enjoy a meal from the restaurant and freebies like WiFi in public areas and an area shuttle. You'll appreciate the outdoor pool, bar/lounge, and laundry facilities.
Sinclair Inn Bed and Breakfast

Sinclair Inn Bed and Breakfast

4 out of 5
Price was $1,186, price is now $1,139 per person
$1,139
per person
Dec 29 - Jan 3
found 1 day ago
Roundtrip non-stop flight included
Nashville (BNA) 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.
COHO Inn & Motor Lodge

COHO Inn & Motor Lodge

2 out of 5
Price was $929, price is now $808 per person
$808
per person
Dec 24 - Dec 28
found 16 hours ago
Roundtrip flight included
El Paso (ELP) to Springfield (VSF)
A bar/lounge and a terrace are featured at this motel, along with free self parking. Guests will appreciate free perks like continental breakfast and WiFi in public areas. A garden, a snack bar/deli, and a lobby fireplace are also on offer.

Top Winchester hotels deals

The Colonial Hotel

The Colonial Hotel

3 out of 5
625 Betty Spring Road Gardner MA
Free Cancellation
Reserve now, pay when you stay
$158 nightly
The price is $177 total per night
$177 total
Dec 1 - Dec 2
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

Hampton Inn Brattleboro

2.5 out of 5
1378 Putney Road Brattleboro VT
Free Cancellation
Reserve now, pay when you stay
$91 nightly
The price is $100 total per night
$100 total
Dec 7 - Dec 8
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
Hampton Inn & Suites Greenfield

Hampton Inn & Suites Greenfield

2.5 out of 5
184 Shelburne Rd Greenfield MA
Free Cancellation
Reserve now, pay when you stay
$183 nightly
The price is $205 total per night
$205 total
Nov 25 - Nov 26
Total with taxes and fees
This hotel doesn't skimp on freebies - guests receive free buffet breakfast, free WiFi, and free self parking. Traveling for business? Take advantage of the 24-hour business center, express check-in, and conference space. Enjoy the gym and conveniences like a 24-hour front desk and laundry facilities.
Breakfast included
Pet friendly
Comfort Inn & Suites Brattleboro I-91

Comfort Inn & Suites Brattleboro I-91

2.5 out of 5
1186 Putney Road Brattleboro VT
Free Cancellation
Reserve now, pay when you stay
$110 nightly
The price is $121 total per night
$121 total
Dec 7 - Dec 8
Total with taxes and fees
This hotel features an indoor pool, a gym, and a restaurant. 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 Covered Bridge Inn

The Covered Bridge Inn

2.5 out of 5
1043 Putney Road Brattleboro VT
Free Cancellation
Reserve now, pay when you stay
$74 nightly
The price is $81 total per night
$81 total
Nov 20 - Nov 21
Total with taxes and fees
This hotel features free self parking and free WiFi in public areas. Enjoy the free continental breakfast each morning.
Breakfast included
Parking included
The Putney Inn

The Putney Inn

2.5 out of 5
57 Putney Landing Rd Putney VT
Free Cancellation
Reserve now, pay when you stay
$80 nightly
The price is $89 total per night
$89 total
Dec 18 - Dec 19
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
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.

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.

New England Sweetwater Farm & Distillery

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.

Winchester Speedpark

Bennett Gorge

You can take time to visit Bennett Gorge during your travels to Richmond.

Bennett Gorge

Frequently asked questions

How much are vacation packages to Winchester?
$761 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

Photo by Donny Campos
Photo by Donny Campos