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.
COHO Inn & Motor Lodge

COHO Inn & Motor Lodge

2 out of 5
Price was $914, price is now $829 per person
$829
per person
Feb 8 - Feb 13
found 1 day ago
Roundtrip non-stop flight included
Austin (AUS) 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.
Chalet 239

Chalet 239

2 out of 5
Price was $1,068, price is now $911 per person
$911
per person
Feb 8 - Feb 13
found 1 day ago
Roundtrip non-stop flight included
Austin (AUS) 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.
Mount Snow Grand Summit Resort

Mount Snow Grand Summit Resort

3 out of 5
Price was $1,694, price is now $1,487 per person
$1,487
per person
Feb 8 - Feb 13
found 1 day ago
Roundtrip non-stop flight included
Austin (AUS) 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.
Mountaineer Inn

Mountaineer Inn

2 out of 5
Price was $1,002, price is now $888 per person
$888
per person
Feb 8 - Feb 13
found 1 day ago
Roundtrip non-stop flight included
Austin (AUS) to Springfield (VSF)
A seasonal outdoor pool is featured at this motel, along with free self parking. WiFi in public areas is free. A terrace, a garden, and express check-in are also on offer.
Deerfield Valley Inn

Deerfield Valley Inn

3 out of 5
Price was $940, price is now $861 per person
$861
per person
Feb 8 - Feb 13
found 1 day ago
Roundtrip non-stop flight included
Austin (AUS) 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 garden, a lobby fireplace, and express check-in 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 17 - Dec 18
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
$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 24 - Nov 25
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
$94 nightly
The price is $103 total per night
$103 total
Nov 19 - Nov 20
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
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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.

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?
$829 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