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
$157 nightly
The price is $176 total per night from Sep 11 to Sep 12
$176 total
Sep 11 - Sep 12
Total with 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. ...
"It’s great hotel"

Reviewed on Aug 22, 2025

The Colonial 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
$125 nightly
The price is $136 total per night from Sep 3 to Sep 4
$136 total
Sep 3 - Sep 4
Total with 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 ...
"Great experience but our only issue was that the sink was outside of the bathroom in the sleeping area other than that I would definitely recommend this hotel and stay again. The hotel was spotless and the breakfast was very good for what we paid for the room, 9 out of 10 just because of the wash ..."

Reviewed on Aug 23, 2025

Keene Elm City Hotel, Ascend Hotel Collection
Colonial Motel And Spa

Colonial Motel And Spa

3 out of 5
889 Putney Rd, Brattleboro, VT
Fully refundableReserve now, pay when you stay
$112 nightly
The price is $123 total per night from Aug 31 to Sep 1
$123 total
Aug 31 - Sep 1
Total with 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. ...
Colonial Motel And Spa
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 Sep 7 to Sep 8
$139 total
Sep 7 - Sep 8
Total with 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 ...
Hampton Inn Brattleboro
The Putney Inn

The Putney Inn

2.5 out of 5
57 Putney Landing Rd, Putney, VT
Fully refundableReserve now, pay when you stay
$106 nightly
The price is $117 total per night from Sep 9 to Sep 10
$117 total
Sep 9 - Sep 10
Total with taxes and fees
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 ...
The Putney Inn
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
$157 nightly
The price is $170 total per night from Aug 31 to Sep 1
$170 total
Aug 31 - Sep 1
Total with 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. ...
Best Western Plus Keene Hotel
Latchis Hotel

Latchis Hotel

2.5 out of 5
50 Main Street, Brattleboro, VT
Fully refundableReserve now, pay when you stay
$135 nightly
The price is $149 total per night from Sep 2 to Sep 3
$149 total
Sep 2 - Sep 3
Total with 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 ...
Latchis Hotel
Travelodge by Wyndham Brattleboro VT

Travelodge by Wyndham Brattleboro VT

2.5 out of 5
1254 Putney Rd, Brattleboro, VT
Fully refundableReserve now, pay when you stay
$71 nightly
The price is $78 total per night from Sep 14 to Sep 15
$78 total
Sep 14 - Sep 15
Total with taxes and fees
This motel doesn't skimp on freebies - guests receive free WiFi and free self parking. Staff at the 24-hour front desk can provide around-the-clock ...
Travelodge by Wyndham Brattleboro VT
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
$131 nightly
The price is $144 total per night from Sep 2 to Sep 3
$144 total
Sep 2 - Sep 3
Total with 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 ...
Comfort Inn & Suites Brattleboro I-91
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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 $78. 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 410 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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