Book Hotels in Winchester, NH

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Top Winchester hotels

The Inn At Crumpin Fox

The Inn At Crumpin Fox

2.5 out of 5
71 Northfield Rd Bernardston MA
Fully refundableReserve now, pay when you stay
$145 nightly
The price is $162 total per night from Nov 23 to Nov 24
$162 total
Nov 23 - Nov 24
Total with taxes and fees
This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. Traveling on business? Take advantage of the business center, conference ...
Room was great, we will be back again, favorite place in the valley thus far to stay.

Reviewed on Nov 10, 2025

Opens in a new windowThe Inn At Crumpin Fox
The Colonial Hotel

The Colonial Hotel

3 out of 5
625 Betty Spring Road Gardner MA
Fully refundableReserve now, pay when you stay
$144 nightly
The price is $161 total per night from Nov 30 to Dec 1
$161 total
Nov 30 - Dec 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. ...
Yes

Reviewed on Nov 16, 2025

Opens in a new windowThe Colonial Hotel
Hampton Inn & Suites Greenfield

Hampton Inn & Suites Greenfield

2.5 out of 5
184 Shelburne Rd Greenfield MA
Fully refundableReserve now, pay when you stay
$183 nightly
The price is $205 total per night from Nov 26 to Nov 27
$205 total
Nov 26 - Nov 27
Total with 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 ...
Check in was great!

Reviewed on Nov 13, 2025

Opens in a new windowHampton Inn & Suites Greenfield
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
$110 nightly
The price is $121 total per night from Dec 7 to Dec 8
$121 total
Dec 7 - Dec 8
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 ...
Great convenient spot just off the highway. The room was clean and the amenities were just right.

Reviewed on Nov 8, 2025

Opens in a new windowComfort Inn & Suites Brattleboro I-91
The Putney Inn

The Putney Inn

2.5 out of 5
57 Putney Landing Rd Putney VT
Fully refundableReserve now, pay when you stay
$94 nightly
The price is $103 total per night from Nov 23 to Nov 24
$103 total
Nov 23 - Nov 24
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 ...
Nice rooms and quite

Reviewed on Nov 12, 2025

Opens in a new windowThe Putney Inn
Latchis Hotel

Latchis Hotel

2.5 out of 5
50 Main Street Brattleboro VT
Fully refundableReserve now, pay when you stay
$127 nightly
The price is $140 total per night from Nov 30 to Dec 1
$140 total
Nov 30 - Dec 1
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 ...
The Latchis hotel was conveniently located in Brattleboro

Reviewed on Nov 14, 2025

Opens in a new windowLatchis Hotel
Hampton Inn Brattleboro

Hampton Inn Brattleboro

2.5 out of 5
1378 Putney Road Brattleboro VT
Fully refundableReserve now, pay when you stay
$94 nightly
The price is $104 total per night from Dec 14 to Dec 15
$104 total
Dec 14 - Dec 15
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 ...
Yes

Reviewed on Nov 16, 2025

Opens in a new windowHampton Inn Brattleboro
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
$139 nightly
The price is $151 total per night from Nov 23 to Nov 24
$151 total
Nov 23 - Nov 24
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. ...
Easy check in and nice rooms

Reviewed on Nov 14, 2025

Opens in a new windowBest Western Plus Keene Hotel
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
$76 nightly
The price is $83 total per night from Nov 21 to Nov 22
$83 total
Nov 21 - Nov 22
Total with taxes and fees
This hotel features free self parking and free WiFi in public areas. Enjoy the free continental breakfast each morning.
Easy check in. Clean building and room. Conveniently located.

Reviewed on Nov 9, 2025

Opens in a new windowThe Covered Bridge Inn
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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 $83. 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 435 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.

Recent Winchester hotel reviews by fellow wanderers

Hampton Inn Brattleboro

Hampton Inn Brattleboro

5 out of 5
Posted 4 days ago
Travelocity Verified Review
"Yes"
A verified traveler stayed at Hampton Inn Brattleboro
Hampton Inn Brattleboro

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