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
$158 nightly
The price is $177 total per night from Jan 11 to Jan 12
$177 total
Jan 11 - Jan 12, 2026
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. ...
Clean, courteous.

Reviewed on Dec 9, 2025

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

Hampton Inn & Suites Keene

2.5 out of 5
126 Key Rd Keene NH
Fully refundableReserve now, pay when you stay
$147 nightly
The price is $160 total per night from Dec 23 to Dec 24
$160 total
Dec 23 - Dec 24
Total with taxes and fees
This hotel features an indoor pool and a 24-hour gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Guests ...
Clean comfy nice staff

Reviewed on Dec 6, 2025

Opens in a new windowHampton Inn & Suites Keene
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 Dec 19 to Dec 20
$205 total
Dec 19 - Dec 20
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 ...
The Hampton Inn let us check-in two hours early after a winter snowstorm closed all the places we were to visit that day. We then hunkered down and watched the snow pile up from our room.

Reviewed on Dec 3, 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
$107 nightly
The price is $118 total per night from Dec 14 to Dec 15
$118 total
Dec 14 - Dec 15
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 ...
Staff was friendly and pool was nice

Reviewed on Dec 1, 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
$115 nightly
The price is $125 total per night from Dec 14 to Dec 15
$125 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 business center and free WiFi in public areas. Guests will appreciate ...
Over all a good stay. The pool window as left open over night so it as very cool in the pool area the next morning. Suggest staff check for that after the pool closes at 10 each night. Thanks

Reviewed on Dec 2, 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 21 to Dec 22
$103 total
Dec 21 - Dec 22
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 motel.

Reviewed on Nov 30, 2025

Opens in a new windowThe Putney Inn
Hampton Inn Brattleboro

Hampton Inn Brattleboro

2.5 out of 5
1378 Putney Road Brattleboro VT
Fully refundableReserve now, pay when you stay
$143 nightly
The price is $158 total per night from Dec 18 to Dec 19
$158 total
Dec 18 - Dec 19
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
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 Dec 14 to Dec 15
$151 total
Dec 14 - Dec 15
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. ...
Staff was accommodating. Got a Free upgrade to my room

Reviewed on Nov 25, 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
$79 nightly
The price is $87 total per night from Dec 22 to Dec 23
$87 total
Dec 22 - Dec 23
Total with taxes and fees
Free WiFi in public areas is available at this hotel. Take advantage of the free self parking.
Room very nice, comfortable clean

Reviewed on Nov 29, 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 $87. 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 440 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 Colonial Hotel

The Colonial Hotel

5 out of 5
Posted 4 days ago
Travelocity Verified Review
"Clean, courteous. "
A verified traveler from Hingham stayed at The Colonial Hotel
The Colonial Hotel

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