Book Hotels in Winchester, NH

Cabins, apartments, houseboats! We offer comfortable & private vacation rentals

Save an extra 10% or more on select hotels with Member Discounts

Access exclusive hotel deals, only with the Travelocity app

Filter by

Guest rating
Guest rating
Star rating
Payment type
Payment type
Property type
Property type
Neighborhood
Neighborhood
Traveler experience
Traveler experience
Popular locations
Popular locations
Meal plans available
Meal plans available
Property amenities
Property amenities
Accessibility
Accessibility

Top Winchester hotels

Comfort Inn & Suites Brattleboro I-91

Comfort Inn & Suites Brattleboro I-91

2.5 out of 5
1186 Putney Road Brattleboro VT
Fully refundable
$112 nightly
The price is $124 total per night from Nov 15 to Nov 16
$124 total
Nov 15 - Nov 16
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 welcome, nice and convenient location. Clean, quiet, updated room with a comfortable bed."

Reviewed on Nov 5, 2026

Opens in a new windowComfort Inn & Suites Brattleboro I-91
2 private mountain RV pads for rent. Full hook ups

2 private mountain RV pads for rent. Full hook ups

Winchester NH
A garden is available at this campground.
Get rates
Opens in a new window2 private mountain RV pads for rent. Full hook ups
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 24 to Nov 25
$161 total
Nov 24 - Nov 25
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. ...
Opens in a new windowThe Colonial Hotel
Colonial Motel

Colonial Motel

3 out of 5
889 Putney Rd Brattleboro VT
Fully refundableReserve now, pay when you stay
$95 nightly
The price is $105 total per night from Nov 8 to Nov 9
$105 total
Nov 8 - Nov 9
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 ...
Opens in a new windowColonial Motel
Days Inn by Wyndham Keene NH

Days Inn by Wyndham Keene NH

2 out of 5
3 Ash Brook Road Keene NH
Fully refundableReserve now, pay when you stay
$97 nightly
The price is $105 total per night from Nov 9 to Nov 10
$105 total
Nov 9 - Nov 10
Total with taxes and fees
This hotel doesn't skimp on freebies - guests receive free on-the-go breakfast, free WiFi, and free self parking. Business travelers can take advantage of the ...
Opens in a new windowDays Inn by Wyndham Keene NH
Latchis Hotel

Latchis Hotel

2.5 out of 5
50 Main Street Brattleboro VT
Fully refundableReserve now, pay when you stay
$114 nightly
The price is $125 total per night from Nov 9 to Nov 10
$125 total
Nov 9 - Nov 10
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 ...
Opens in a new windowLatchis Hotel
Gardner Inn

Gardner Inn

2 out of 5
22 Pearson Blvd Gardner MA
Fully refundableReserve now, pay when you stay
$103 nightly
The price is $115 total per night from Nov 9 to Nov 10
$115 total
Nov 9 - Nov 10
Total with taxes and fees
Free WiFi in public areas is available at this hotel. Take advantage of the free self parking.
Opens in a new windowGardner 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
$142 nightly
The price is $154 total per night from Nov 9 to Nov 10
$154 total
Nov 9 - Nov 10
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. ...
Opens in a new windowBest Western Plus Keene Hotel
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 refundableReserve now, pay when you stay
$134 nightly
The price is $145 total per night from Nov 8 to Nov 9
$145 total
Nov 8 - Nov 9
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 ...
Opens in a new windowKeene Elm City Hotel, an Ascend Collection Hotel
Don't see what you're looking for?
See all available properties in Winchester
View all properties
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 $105. 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 467 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 5 hours ago
Travelocity Verified Review
"Great stay in a newly renovated room. Clean and comfortable. I have stayed before the renovation and will happily stay again."
A verified traveler stayed at Hampton Inn Brattleboro
Hampton Inn Brattleboro

Explore More Ways to Travel with Travelocity