Deals on vacations and trips to Winchester

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Top Winchester hotel deals

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 $88 per night
$88
per night
May 30 - May 31
This smoke-free motel features a full-service spa, 2 indoor pools, and a restaurant. Business travelers can take advantage of the free WiFi in public areas. Enjoy the gym and perks like free self parking.
Hot Tub
Pet friendly
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 $160 per night
$160
per night
Jun 2 - Jun 3
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.
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 $72 per night
$72
per night
Jun 6 - Jun 7
This hotel features free self parking and free WiFi in public areas. Enjoy the free self-serve breakfast each morning.
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 $152 per night
$152
per night
Jun 17 - Jun 18
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 spa tub and perks like free self parking.
Hot Tub
Pet friendly
Days Inn by Wyndham Keene NH

Days Inn by Wyndham Keene NH

2 out of 5
3 Ash Brook Road, Keene, NH
Free Cancellation
Reserve now, pay when you stay
The price is $94 per night
$94
per night
Jun 2 - Jun 3
This hotel doesn't skimp on freebies - guests receive free on-the-go breakfast, free WiFi, and free self parking. Business travelers can take advantage of the 24-hour business center. There's a gym on site, and a snack bar/deli and a picnic area are also provided.
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 $128 per night
$128
per night
Jun 5 - Jun 6
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.
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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.

Photos of local treasures

Photo by Donny Campos
Photo by Donny Campos

Frequently asked questions

How much are vacation packages to Winchester?
Your vacation daydreams can come to life in Winchester for as low as . Vacation packages include flights and hotels, and they’ll make booking your trip nice and easy. The only thing you’ll have to concentrate on is having an incredible time.
Where can I get the best vacation package deals for Winchester?
You can pick up amazing Winchester package deals with Travelocity. Choose from as many as 400 air carriers and 1,000,000 properties worldwide and turn those vacation dreams into a reality.
Why should I book my Winchester vacation bundle via Travelocity?
Because we believe in crafting unforgettable vacation experiences. From flights and hotels to car rentals and activities, our packages make it a breeze to save. Our customer care is on hand 24/7 to make sure you’ll never wander alone. We also offer a Price Match Guarantee, so you can secure your trip knowing you’ve landed the best deal possible.
Can I save on my Winchester car rental if I bundle it with my hotel or flight?
With a Winchester vacation package, you can bundle your car, flight and hotel bookings and save a whole lot. If you want to uncover the best of this fantastic region, why not head to Fenway Park? This well-known attraction is 70 mi from Winchester. With your own set of wheels, you’ll be there soon enough.
What is the best time of year to go to Winchester?
Head off in and you can spend more money on memorable experiences, not your hotel room. This is the cheapest month to arrange your stay. Prices are at their highest in , so try to avoid this time if you’re hoping to save. June, July and August are the high season months for Winchester. You’ll need to book beforehand and be ready to pay more. October, November and December are the least popular months to travel.
Which airport is best for Winchester?
Bradley Intl. Airport (BDL) is a main hub. You’ll find it approximately 60 mi south of Winchester. Other options worth considering are Manchester-Boston Regional Airport (MHT) (50 mi away from central Winchester) and Lebanon Municipal Airport (LEB) (60 mi away from central Winchester).
Where should I stay when visiting Winchester?
Many people stay at the Stay At A Craft Brewery In Winchester Nh Close To Mountains. It’s a great base for your Winchester vacation.