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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
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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
Colonial Motel And Spa

Colonial Motel And Spa

3 out of 5
889 Putney Rd Brattleboro VT
Free cancellation
Reserve now, pay when you stay
The price is CA $130 per night
CA $130
CA $143 total
Mar 1 - Mar 2
includes taxes & fees
Book a stay at this spa motel in Brattleboro. Enjoy free WiFi, free parking, and 2 indoor pools. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Brattleboro Bowl and United States Navy Seabee Bridge 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 $156 per night
CA $156
CA $171 total
Mar 4 - Mar 5
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
Vikings Villages Resort

Vikings Villages Resort

2 out of 5
360 Viking Village Drive Guilford VT
The price is CA $262 per night
CA $262
CA $306 total
Mar 29 - Mar 30
includes taxes & fees
Stay at this hotel in Brattleboro. Enjoy free WiFi, free parking, and a rooftop terrace. Our guests praise the helpful staff in our reviews. Popular attractions Sweet Pond State Park and Shattuck Brook Wildlife Management Area are located nearby.
Parking included
Free WiFi
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 $158 per night
CA $158
CA $174 total
Mar 28 - Mar 29
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
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
The price is CA $163 per night
CA $163
CA $177 total
Feb 27 - Feb 28
includes taxes & fees
Book a stay at this business-friendly hotel in Keene. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Ashuelot River and Thorne Sagendorph Art Gallery are located nearby.
Pool
Breakfast included
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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

Barden State Wildlife Management Area

Explore the great outdoors at Barden State Wildlife Management Area, a lovely green space in Richmond.

Barden State Wildlife Management Area

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

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?
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

Winchester, New Hampshire in winter
Winchester, New Hampshire in winter
covered bridge in winter -Ashuelot Covered Bridge, Winchester, New Hampshire
Black and white Lattice work detail on The Ashuelot Covered Bridge crosses the Ashuelot River and Bolton Road in Winchester New Hampshire
The Ashuelot Covered Bridge is a historic wooden covered bridge over the Ashuelot River on Bolton Road, just south of its intersection with NH 119 in Ashuelot, New Hampshire, an unincorporated village of Winchester.