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Top Winchester hotels

Vikings Villages Resort

Vikings Villages Resort

2 out of 5
360 Viking Village Drive Guilford VT
$161 nightly
The price is $176 total per night from Jun 3 to Jun 4
$176 total
Jun 3 - Jun 4
Total with taxes and fees
A rooftop terrace is featured at this hotel, along with free self parking. WiFi in public areas is free. A garden, a lobby fireplace, and a picnic area are also ...
Viking village is one of the most unique experiences we have had with being the most authentic and amazing Norse village in the United States. Attention to comfort and period detail along with an outdoor fire pit with Soay goats was unmatched. We didn’t want to leave. Paul and Christine were fabulous ...

Reviewed on May 2, 2026

Opens in a new windowVikings Villages Resort
The Colonial Hotel

The Colonial Hotel

3 out of 5
625 Betty Spring Road Gardner MA
Fully refundableReserve now, pay when you stay
$160 nightly
The price is $179 total per night from May 10 to May 11
$179 total
May 10 - May 11
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. ...
Restaurant food is excellent. Room has a comfortable bed and sofa. Room rate a bit high.

Reviewed on May 7, 2026

Opens in a new windowThe Colonial Hotel
Latchis Hotel

Latchis Hotel

2.5 out of 5
50 Main Street Brattleboro VT
Fully refundableReserve now, pay when you stay
$128 nightly
The price is $141 total per night from May 10 to May 11
$141 total
May 10 - May 11
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 ...
Very well run hotel, conveniently located in the heart of Brattleboro. Free parking in a lot next to the hotel was a nice touch. My only gripe would be that my room (104) had no view as the windows were made of some kind of stained glass that you can't see through and couldn't open. Also they could ...

Reviewed on May 4, 2026

Opens in a new windowLatchis 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
$140 nightly
The price is $152 total per night from May 26 to May 27
$152 total
May 26 - May 27
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 ...
Really nothing wrong with the hotel or its staff. The problem was homeless people living in the parking lot after hours. Cars running outside in the lot all night. A new security policy needs to be implemented.

Reviewed on May 2, 2026

Opens in a new windowKeene Elm City Hotel, an Ascend Collection Hotel
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
$154 nightly
The price is $167 total per night from May 10 to May 11
$167 total
May 10 - May 11
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. ...
The room was a bit dusty and a lamp didn't work. Also, when I opened the door to enter the room the stand for the suitcase was right there in the walkway, which was difficult to maneuver with full hands. Overall, the hotel needed a refresh as everything seems old and a bit unloved. Breakfast was ...

Reviewed on May 7, 2026

Opens in a new windowBest Western Plus Keene 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
$105 nightly
The price is $115 total per night from May 10 to May 11
$115 total
May 10 - May 11
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 enough for the price, owners were very nice, room was ok, internet not so good, breakfast meh…all in all, good value stay.

Reviewed on May 5, 2026

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
$122 nightly
The price is $134 total per night from Jun 7 to Jun 8
$134 total
Jun 7 - Jun 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 ...
Clean room, great included breakfast, staff was nice and overall was just a good time

Reviewed on May 7, 2026

Opens in a new windowHampton Inn Brattleboro
Econo Lodge Brattleboro South

Econo Lodge Brattleboro South

2 out of 5
515 Canal St Brattleboro VT
Fully refundableReserve now, pay when you stay
$71 nightly
The price is $78 total per night from May 14 to May 15
$78 total
May 14 - May 15
Total with taxes and fees
A seasonal outdoor pool, free self parking, and laundry facilities are featured at this motel. Guests will appreciate free perks like continental breakfast and ...
This place looks like crime scene #2. The rooms are clean, but they're also ragged as hell. Holes in the wall, lights that don't work. It's where you go when you don't have any other choices. If that's the case, you could do worse. But block the door with a chair or suitcase, because the chains are ...

Reviewed on May 6, 2026

Opens in a new windowEcono Lodge Brattleboro South
Colonial Motel And Spa

Colonial Motel And Spa

3 out of 5
889 Putney Rd Brattleboro VT
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. ...
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Opens in a new windowColonial Motel And Spa
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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 466 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 1 hour ago
Travelocity Verified Review
"Clean room, great included breakfast, staff was nice and overall was just a good time"
A verified traveler stayed at Hampton Inn Brattleboro
Hampton Inn Brattleboro

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