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
$122 nightly
The price is $137 total per night from Nov 1 to Nov 2
$137 total
Nov 1 - Nov 2
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 staff was amazing. Breakfast didn't open until 8 and was already luke warm by 8:15. Our room was clean and the beds were comfy. Our particular room was near the housekeeping office and laundry room. There was a propane oder in the hallway. We were told it was the laundry room. For the price we ..."

Reviewed on Oct 27, 2026

Opens in a new windowThe Colonial 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 1 to Nov 2
$115 total
Nov 1 - Nov 2
Total with taxes and fees
Free WiFi in public areas is available at this hotel. Take advantage of the free self parking.
"The room overall was ok, but the curtains were absolutely disgustingly dirty. The staff was very nice and overall, the room was fine. But looking at the dirty curtains was a real turn off to me."

Reviewed on Oct 29, 2026

Opens in a new windowGardner Inn
Travelodge by Wyndham Brattleboro VT

Travelodge by Wyndham Brattleboro VT

2.5 out of 5
1254 Putney Rd Brattleboro VT
Fully refundableReserve now, pay when you stay
$62 nightly
The price is $68 total per night from Nov 2 to Nov 3
$68 total
Nov 2 - Nov 3
Total with taxes and fees
This motel doesn't skimp on freebies - guests receive free WiFi and free self parking. Staff at the 24-hour front desk can provide around-the-clock ...
"If you are looking for a clean place to rest your head for the night this place is it!"

Reviewed on Oct 30, 2026

Opens in a new windowTravelodge by Wyndham Brattleboro VT
2 private mountain RV pads for rent. Full hook ups

2 private mountain RV pads for rent. Full hook ups

Winchester NH
$75 nightly
The price is $81 total per night from Nov 1 to Nov 2
$81 total
Nov 1 - Nov 2
Total with taxes and fees
A garden is available at this campground.
Opens in a new window2 private mountain RV pads for rent. Full hook ups
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 1 to Nov 2
$105 total
Nov 1 - Nov 2
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
$103 nightly
The price is $112 total per night from Nov 12 to Nov 13
$112 total
Nov 12 - Nov 13
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
$125 nightly
The price is $137 total per night from Dec 1 to Dec 2
$137 total
Dec 1 - Dec 2
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
Comfort Inn & Suites Brattleboro I-91

Comfort Inn & Suites Brattleboro I-91

2.5 out of 5
1186 Putney Road Brattleboro VT
Fully refundable
$110 nightly
The price is $121 total per night from Nov 22 to Nov 23
$121 total
Nov 22 - Nov 23
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 ...
Opens in a new windowComfort Inn & Suites Brattleboro I-91
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 2 to Nov 3
$154 total
Nov 2 - Nov 3
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
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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 $68. 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 474 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 Inn At Crumpin Fox

The Inn At Crumpin Fox

5 out of 5
Posted 1 hour ago
Travelocity Verified Review
"We loved it! Very clean, quiet and nice room. Loved the center gazebo, gardens and all the stone work. Highly recommend!"
A verified traveler stayed at The Inn At Crumpin Fox
The Inn At Crumpin Fox

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