Book Hotels in Winchester, NH

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Top Winchester hotels

The Colonial Hotel

The Colonial Hotel

3 out of 5
625 Betty Spring Road, Gardner, MA
Fully refundableReserve now, pay when you stay
$140 nightly
The price is $156 total per night from Jul 20 to Jul 21
$156 total
Jul 20 - Jul 21
Total includes taxes and fees
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. ...
"Nice place. Grounds, buildings and rooms are high quality."

Reviewed on Jul 7, 2025

The Colonial Hotel
Comfort Inn & Suites Brattleboro I-91

Comfort Inn & Suites Brattleboro I-91

2.5 out of 5
1186 Putney Road, Brattleboro, VT
Fully refundableReserve now, pay when you stay
$139 nightly
The price is $152 total per night from Aug 6 to Aug 7
$152 total
Aug 6 - Aug 7
Total includes taxes and fees
This hotel features an indoor pool, a gym, and a restaurant. Traveling on business? Take advantage of the business center and free WiFi in public areas. Guests ...
"We are having a good time here"

Reviewed on Jul 5, 2025

Comfort Inn & Suites Brattleboro I-91
Hampton Inn & Suites Greenfield

Hampton Inn & Suites Greenfield

2.5 out of 5
184 Shelburne Rd, Greenfield, MA
$178 nightly
The price is $199 total per night from Aug 11 to Aug 12
$199 total
Aug 11 - Aug 12
Total includes taxes and fees
This hotel doesn't skimp on freebies - guests receive free buffet breakfast, free WiFi, and free self parking. Traveling for business? Take advantage of the ...
"Excellent service"

Reviewed on Jul 5, 2025

Hampton Inn & Suites Greenfield
Latchis Hotel

Latchis Hotel

2.5 out of 5
50 Main Street, Brattleboro, VT
Fully refundableReserve now, pay when you stay
$115 nightly
The price is $127 total per night from Jul 14 to Jul 15
$127 total
Jul 14 - Jul 15
Total includes taxes and fees
A restaurant and a bar/lounge are featured at this hotel. Guests will appreciate free perks like free self parking and WiFi in public areas. Free parking and ...
"Amazing building with very knowledgeable and keen staff. Bustling city Centre but delivers comfort & an experience."

Reviewed on Jul 4, 2025

Latchis Hotel
Best Western Plus Keene Hotel

Best Western Plus Keene Hotel

3 out of 5
401 Winchester St, Keene, NH
Fully refundableReserve now, pay when you stay
$134 nightly
The price is $145 total per night from Jul 14 to Jul 15
$145 total
Jul 14 - Jul 15
Total includes taxes and fees
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. ...
"My Daughter And I Stayed 3 Days 4th Of July And Loved Pretty Much Everything!! Staff Were Great,Breakfast Wow Awesome, Indoor Pool,Beautiful Gazebo And Other Outdoor Lights!! Our Only Note*Rotate The Mattresses 1Side Of Bed Sinks,The Other Side Firm!! Tyvm 😁 😊 We Will Be Returning Soon!! Maureen ..."

Reviewed on Jul 6, 2025

Best Western Plus Keene Hotel
Keene Elm City Hotel, Ascend Hotel Collection

Keene Elm City Hotel, Ascend Hotel Collection

2.5 out of 5
175 Key Rd, Keene, NH
Fully refundableReserve now, pay when you stay
$112 nightly
The price is $121 total per night from Jul 20 to Jul 21
$121 total
Jul 20 - Jul 21
Total includes taxes and fees
This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Guests will appreciate ...
"All was good. The room, the breakfast are all very good."

Reviewed on Jul 7, 2025

Keene Elm City Hotel, Ascend Hotel Collection
Hampton Inn Brattleboro

Hampton Inn Brattleboro

2.5 out of 5
1378 Putney Road, Brattleboro, VT
Fully refundableReserve now, pay when you stay
$127 nightly
The price is $139 total per night from Jul 20 to Jul 21
$139 total
Jul 20 - Jul 21
Total includes taxes and fees
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 hot ...
"Great hotel, friendly staff and very comfortable."

Reviewed on Jul 11, 2025

Hampton Inn Brattleboro
The Covered Bridge Inn

The Covered Bridge Inn

2.5 out of 5
1043 Putney Road, Brattleboro, VT
Fully refundableReserve now, pay when you stay
$104 nightly
The price is $114 total per night from Jul 21 to Jul 22
$114 total
Jul 21 - Jul 22
Total includes taxes and fees
This hotel features free self parking and free WiFi in public areas. Enjoy the free self-serve breakfast each morning.
"Clean, convenient, comfortable and good price."

Reviewed on Jul 11, 2025

The Covered Bridge Inn
Colonial Motel And Spa

Colonial Motel And Spa

3 out of 5
889 Putney Rd, Brattleboro, VT
Fully refundableReserve now, pay when you stay
$109 nightly
The price is $120 total per night from Jul 14 to Jul 15
$120 total
Jul 14 - Jul 15
Total includes taxes and fees
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. ...
"This is my go to place to stay. Its always clean, check in is quick and easy. The staff has always been polite and helpful when something has come up. The price is the best around."

Reviewed on Jul 8, 2025

Colonial Motel And Spa
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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.

Frequently asked questions

What are the top kid-friendly hotels in Winchester?
From carefully considered amenities to extra room, kid-friendly hotels are equipped with features that can help turn a great family vacation into a fabulous one. These Winchester properties make vacationing with little ones a piece of cake: You have found a clean and bright home on the water. will help make your vacation the best one yet. It features plenty of conveniences geared toward families, such as a playground and a nearby beach. Otherwise, spend your evenings in Winchester at Magical Lakefront Home on Forest Lake. Make the most of a firepit, pet-friendly facilities and more here.
Where can I find cheap hotels in Winchester?
At Travelocity you'll find really nice hotels in Winchester at great prices. We source incredible prices with our trusted partners, so you have a tempting selection of cheap hotels to choose from. If you can be flexible on dates and location, consider staying at a hotel near Winchester rather than in Winchester. We may find you even better rates, too.
How do I find the best Winchester hotel deals?
Simple! On Travelocity, look through the fantastic offers we've already found in Winchester then use our filters to find a great deal that's perfect for you. Enter your travel dates, select the number of rooms you need, and we'll do the rest. You can get great discounts on flights and car hire, too, when you bundle.
How much does it cost to stay in a hotel in Winchester?
The cheapest hotel in Winchester is $114. This price was available within the past 7 days, for stays with a check-in date within the next year. Of course, the price you pay depends on your dates of travel, the length of your stay, and the hotel's location. Prices and availability are subject to change. Additional terms apply.
How many hotels are in Winchester?
There are 412 hotels in Winchester on Travelocity.
What are the best hotels in Winchester?
Winchester has so many great hotels to choose from at Travelocity --- and it's so easy to find the perfect one. Just choose one of our popular pre-selected hotels with great reviews, or you can refine your search to build your ideal stay. Simply filter hotels based on price or star rating, or select properties with a pool, a hot tub, or a range of other amenities and pick the best place to stay in Winchester for you!
When is the best time to visit Winchester?
If you want the joy of a fun-filled trip in peak season, visit Winchester during June, July and August. If you'd prefer the peace of off-season, book a stay during quieter months, such as October, November and December.
When is the cheapest time to stay in Winchester?
Based on historic data is usually the cheapest month to visit Winchester. However, we have incredible deals all year round, so we're confident you'll find a room in your budget whenever you choose to travel.
Are there any great family-friendly hotels in Winchester?
There are multiple hotels in Winchester that will please the whole family. Do you need adjoining rooms, babysitting services or a swimming pool? We've got you covered. Use our family filter to narrow your search down and use guest reviews to help you pick the perfect place for your next family trip to Winchester. We have plenty of kid-friendly hotels in Winchester to choose from on Travelocity!
Why book a hotel in Winchester through Travelocity?
Because we have the top hotels in Winchester! We want to help you travel more and worry less. That's why we've put the most amazing hotel, car rental, and flight deals in one place. When you search for hotels with us, you know you're getting fantastic prices with no hidden fees and free cancellation on most properties up to 24 hours before your stay. If you become a Travelocity member, you also get exclusive member discounts. Sign up today!
How do I cancel my hotel booking in Winchester on Travelocity?
Canceling your booking with Travelocity is easy. Sign into your account and select My Trips. Here, you will see your cancellation options. We offer free cancellation on many properties.

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