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
$141 nightly
The price is $158 total per night from Dec 26 to Dec 27
$158 total
Dec 26 - Dec 27
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 ...
Very clean and comfortable. Very quiet in offseason.

Reviewed on Dec 7, 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
$158 nightly
The price is $177 total per night from Dec 29 to Dec 30
$177 total
Dec 29 - Dec 30
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. ...
Parking is convenient and free. Staff were friendly. My room was clean and comfortable. The pool and fitness area were clean and well kept. There's also a mini arcade area with air hockey and a few games. Overall, I had a pleasant stay and look forward to my next visit.

Reviewed on Dec 20, 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
$188 nightly
The price is $210 total per night from Dec 30 to Dec 31
$210 total
Dec 30 - Dec 31
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 ...
Lovely night.

Reviewed on Dec 10, 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
$117 nightly
The price is $129 total per night from Dec 28 to Dec 29
$129 total
Dec 28 - Dec 29
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 ...
I arrived far before published check-in time and only had to wait a reasonable amount of time to get into my room. Desk clerks were efficient and friendly. Clean, comfortable room.

Reviewed on Dec 18, 2025

Opens in a new windowComfort Inn & Suites Brattleboro I-91
Keene Elm City Hotel, an Ascend Collection Hotel

Keene Elm City Hotel, an Ascend Collection Hotel

2.5 out of 5
175 Key Rd Keene NH
Fully refundable
$118 nightly
The price is $128 total per night from Dec 28 to Dec 29
$128 total
Dec 28 - Dec 29
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 ...
The room was perfect, and the food was great

Reviewed on Dec 15, 2025

Opens in a new windowKeene Elm City Hotel, an Ascend Collection Hotel
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 Dec 30 to Dec 31
$103 total
Dec 30 - Dec 31
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 ...
clean room. nice staff

Reviewed on Dec 22, 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
$123 nightly
The price is $136 total per night from Dec 25 to Dec 26
$136 total
Dec 25 - Dec 26
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 ...
Staff was courteous, and the room was clean. The rug was outdated as as the furniture!

Reviewed on Dec 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
$147 nightly
The price is $161 total per night from Dec 30 to Dec 31
$161 total
Dec 30 - Dec 31
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 ...
Convenient, clean. Staff was very friendly and helpful. Close to Highway. Keys weren’t working when we returned from a long day out. TV was also not working, but luckily we were in the room for only a short time before heading out for dinner.

Reviewed on Dec 8, 2025

Opens in a new windowHampton 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
$89 nightly
The price is $98 total per night from Dec 25 to Dec 26
$98 total
Dec 25 - Dec 26
Total with taxes and fees
Free WiFi in public areas is available at this hotel. Take advantage of the free self parking.
Front Desk boy was super cute, but no breakfast served. Very quiet for being such a busy street.

Reviewed on Dec 21, 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 $98. 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 441 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

The Putney Inn

The Putney Inn

5 out of 5
Posted 2 days ago
Travelocity Verified Review
"clean room. nice staff"
A verified traveler stayed at The Putney Inn
The Putney Inn

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