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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.
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 $167 per night
CA $167
CA $184 total
Jan 25 - Jan 26
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 $101 per night
CA $101
CA $111 total
Jan 19 - Jan 20
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.
Parking included
Free WiFi
Vikings Villages Resort

Vikings Villages Resort

2 out of 5
360 Viking Village Drive Guilford VT
The price is CA $290 per night
CA $290
CA $338 total
Jan 19 - Jan 20
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
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 $204 per night
CA $204
CA $225 total
Feb 3 - Feb 4
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.
Latchis Hotel

Latchis Hotel

2.5 out of 5
50 Main Street Brattleboro VT
Free cancellation
Reserve now, pay when you stay
The price is CA $180 per night
CA $180
CA $199 total
Jan 22 - Jan 23
includes taxes & fees
Stay at this hotel in Brattleboro. Enjoy free WiFi, free parking, and conference space. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Latchis Theatre and Brattleboro Museum & Art Center are located nearby.
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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

Bennett Gorge

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

Bennett Gorge

Cass Pond

Commune with nature and explore the great outdoors at Cass Pond during your travels in Richmond.

Cass Pond

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

Photo by Donny Campos
Photo by Donny Campos