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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
The price is CA $194 per night
CA $194
CA $216 total
includes taxes & fees
Apr 22 - Apr 23
Stay at this 3-star 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 Dunn State Park and 1761 Old Mill Gift Shop 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 $155 per night
CA $155
CA $170 total
includes taxes & fees
Apr 28 - Apr 29
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
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 $136 per night
CA $136
CA $149 total
includes taxes & fees
May 4 - May 5
Stay at this 3-star 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
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
The price is CA $129 per night
CA $129
CA $141 total
includes taxes & fees
Apr 21 - Apr 22
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
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 $150 per night
CA $150
CA $165 total
includes taxes & fees
Apr 22 - Apr 23
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
Courtyard by Marriott Keene Downtown

Courtyard by Marriott Keene Downtown

3 out of 5
75 Railroad St, Keene, NH
Free cancellation
Reserve now, pay when you stay
The price is CA $192 per night
CA $192
CA $209 total
includes taxes & fees
Apr 24 - Apr 25
Stay at this 3-star business-friendly hotel in Keene. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Colonial Theatre and Central Square are located nearby.
Pool
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

Richmond Town Hall

After visiting Richmond Town Hall, make a plan to see the other sights and activities in Richmond.

Richmond Town Hall

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

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