Book Exclusive Winchester Vacation Packages

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Winchester flight + hotel packages

Price found within the past 48 hours. Click for updated prices.
Best Western Springfield Hotel

Best Western Springfield Hotel

2.5 out of 5
Price was CA $1,244, price is now CA $1,111 per person
CA $1,111
per person
Dec 29 - Jan 2
found 1 day ago
Roundtrip non-stop flight included
Buffalo (BUF) to Springfield (VSF)
Stay at this hotel in Springfield. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions State Fish and Wildlife Management Area and Baltimore Covered Bridge are located nearby.
The Shire Woodstock

The Shire Woodstock

3 out of 5
Price was CA $1,757, price is now CA $1,425 per person
CA $1,425
per person
Jan 24 - Jan 31
found 6 hours ago
Roundtrip flight included
Toronto (YTO) to Springfield (VSF)
Stay at this hotel in Woodstock. Enjoy free WiFi, free parking, and free bicycles on site. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Billings Park and Trail and Red Wagon Toy Company are located nearby.
Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
Price was CA $3,323, price is now CA $2,814 per person
CA $2,814
per person
Jan 24 - Jan 31
found 6 hours ago
Roundtrip flight included
Toronto (YTO) to Springfield (VSF)
Book a stay at this luxury resort in Woodstock. Enjoy free WiFi, free valet parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular attractions Middle Covered Bridge and Woodstock Town Hall Theatre are located nearby.
Sinclair Inn Bed and Breakfast

Sinclair Inn Bed and Breakfast

4 out of 5
Price was CA $1,696, price is now CA $1,560 per person
CA $1,560
per person
Dec 28 - Jan 3
found 15 hours ago
Roundtrip flight included
Philadelphia (PHL) to Springfield (VSF)
Stay at this B&B in Jericho. Enjoy free breakfast, free WiFi, and in-room massages. Our guests praise the breakfast in our reviews. Popular attractions Veterans' Park and Mills Riverside Park are located nearby.

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
Get rates
Book a stay at this business-friendly hotel in Gardner. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Wachusett Mountain Ski Area and Dunn State Park are located nearby.
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
The price is CA $128 per night
CA $128
CA $140 total
Dec 7 - Dec 8
includes taxes & fees
Book a stay at this business-friendly hotel in Brattleboro. Enjoy free breakfast, free parking, and a fitness center. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions United States Navy Seabee Bridge and Brattleboro Bowl are located nearby.
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
The price is CA $256 per night
CA $256
CA $286 total
Nov 26 - Nov 27
includes taxes & fees
Book a stay at this business-friendly hotel in Greenfield. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions Old Greenfield Village and Museum of Our Industrial Heritage are located nearby.
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
The price is CA $154 per night
CA $154
CA $170 total
Dec 7 - Dec 8
includes taxes & fees
Book a stay at this business-friendly hotel in Brattleboro. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions United States Navy Seabee Bridge and Brattleboro Bowl are located nearby.
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
The price is CA $103 per night
CA $103
CA $113 total
Nov 20 - Nov 21
includes taxes & fees
Book a stay at this business-friendly hotel in Brattleboro. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions United States Navy Seabee Bridge and Brattleboro Bowl are located nearby.
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
Get rates
Book a stay at this business-friendly motel in Putney. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Yellow Barn and Next Stage Arts are located nearby.
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

Winchester Vacations

Get your vacation off to an amazing start by learning a bit about Winchester before you head off.

You'll find this town 10 miles (16 kilometers) from Brattleboro and 12 miles (19 kilometers) away from Keene.

Forget the big-name attractions — it's the locals that make a place tick. In this part of New Hampshire, you'll find 2,000 of them.

Places to visit in Winchester

Bridges are often iconic local symbols. Stop at Schell Bridge and learn when and how it was built and the part its played throughout history. Still need some more options? Of all the roads you take in life, make sure some of them are dirt! So slip into those boots, fill up your water bottle and tackle the hikes of Metacomet-Monadnock Trail.

Where do you fly into for Winchester?

There's nothing like the feeling of finally touching down in a new, unknown destination. If you're heading to Winchester, there's a good chance you'll fly into Manchester-Boston Regional Airport (MHT). It's about 50 miles (80 kilometers) to the east of the downtown area. Collect your belongings and get set to kick-start your vacation!

Frequently asked questions

How much are vacation packages to Winchester?
CA $1,111 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 113 kilometers 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) (97 kilometers away from the downtown area), Manchester-Boston Regional Airport (MHT) (80 kilometers away from central Winchester) and Lebanon Municipal Airport (LEB) (97 kilometers 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