Book Cheap Hotels in Winchester

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Tonight
Check prices in Winchester for tonight, Oct 15 - Oct 16
Oct 15 - Oct 16
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Oct 16 - Oct 17
This weekend
Check prices in Winchester for this weekend, Oct 16 - Oct 18
Oct 16 - Oct 18
Next weekend
Check prices in Winchester for next weekend, Oct 23 - Oct 25
Oct 23 - Oct 25

Most frequently booked Winchester hotels

2 private mountain RV pads for rent. Full hook ups

2 private mountain RV pads for rent. Full hook ups

Winchester NH
3.45 km from city centre
The price is CA $78 per night
CA $78
CA $116 total
Oct 16 - Oct 17
includes taxes & fees
Stay at this campground in Winchester. Enjoy free WiFi and a garden. Popular attractions Attleboro Mountain and Winchester Speedpark are located nearby.
Pet-friendly
Free WiFi
Colonial Motel

Colonial Motel

3 out of 5
889 Putney Rd Brattleboro VT
Free cancellation
Reserve now, pay when you stay
18.53 km from city centre
The price is CA $127 per night
CA $127
CA $139 total
Nov 1 - Nov 2
includes taxes & fees
Book a stay at this business-friendly motel in Brattleboro. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Brattleboro Bowl and New England Center for Circus Arts are located nearby.
Breakfast included
Pet-friendly
The Colonial Hotel

The Colonial Hotel

3 out of 5
625 Betty Spring Road Gardner MA
Free cancellation
Reserve now, pay when you stay
42.31 km from city centre
The price is CA $205 per night
CA $205
CA $229 total
Nov 1 - Nov 2
includes taxes & fees
Book a stay at this business-friendly hotel in Gardner. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Dunn State Park and 1761 Old Mill Gift Shop are located nearby.
Pool
Hot tub
Latchis Hotel

Latchis Hotel

2.5 out of 5
50 Main Street Brattleboro VT
Free cancellation
Reserve now, pay when you stay
16.67 km from city centre
The price is CA $202 per night
CA $202
CA $222 total
Nov 1 - Nov 2
includes taxes & fees
Stay at this hotel in Brattleboro. Enjoy free WiFi, free parking, and conference space. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Latchis Theatre and Brattleboro Museum & Art Center are located nearby.
Pet-friendly
Parking included
Best Western Plus Keene Hotel

Best Western Plus Keene Hotel

3 out of 5
401 Winchester St Keene NH
Free cancellation
Reserve now, pay when you stay
18 km from city centre
The price is CA $201 per night
CA $201
CA $218 total
Nov 1 - Nov 2
includes taxes & fees
Book a stay at this business-friendly hotel in Keene. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Ashuelot River and Redfern Arts Center are located nearby.
Pool
Breakfast included
Gardner Inn

Gardner Inn

2 out of 5
22 Pearson Blvd Gardner MA
Free cancellation
Reserve now, pay when you stay
40.24 km from city centre
The price is CA $151 per night
CA $151
CA $169 total
Nov 6 - Nov 7
includes taxes & fees
Stay at this hotel in Gardner. Enjoy free WiFi, free parking, and daily housekeeping. Popular attractions Dunn State Park and 1761 Old Mill Gift Shop are located nearby.
Pet-friendly
Parking included
Comfort Inn & Suites Brattleboro I-91

Comfort Inn & Suites Brattleboro I-91

2.5 out of 5
1186 Putney Road Brattleboro VT
Free cancellation
18.95 km from city centre
The price is CA $157 per night
CA $157
CA $173 total
Nov 15 - Nov 16
includes taxes & fees
Book a stay at this business-friendly hotel in Brattleboro. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions United States Navy Seabee Bridge and Brattleboro Bowl are located nearby.
Pool
Breakfast included
Days Inn by Wyndham Keene NH

Days Inn by Wyndham Keene NH

2 out of 5
3 Ash Brook Road Keene NH
Free cancellation
Reserve now, pay when you stay
17.88 km from city centre
The price is CA $135 per night
CA $135
CA $147 total
Oct 29 - Oct 30
includes taxes & fees
Book a stay at this business-friendly hotel in Keene. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions Ashuelot River and Cheshire Children's Museum are located nearby.
Breakfast included
Pet-friendly
The Putney Inn

The Putney Inn

2.5 out of 5
57 Putney Landing Rd Putney VT
Free cancellation
Reserve now, pay when you stay
23.92 km from city centre
The price is CA $120 per night
CA $120
CA $132 total
Oct 25 - Oct 26
includes taxes & fees
Book a stay at this business-friendly motel in Putney. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Yellow Barn and Next Stage Arts are located nearby.
Breakfast included
Pet-friendly
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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.

Winchester hotels essential information

Accommodation
477 hotels
Lowest Price
CA $116
Highest Price
CA $229
Popular hotels
2 private mountain RV pads for rent. Full hook ups, Colonial Motel, The Colonial Hotel, Latchis Hotel, Best Western Plus Keene Hotel, Gardner Inn, Comfort Inn & Suites Brattleboro I-91, Days Inn by Wyndham Keene NH, The Putney Inn

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 CA $116 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 477 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

Latchis Hotel

Latchis Hotel

5 out of 5
Posted 16 hours ago
Travelocity Verified Review
"This hotel is part of history. It was a great experience. The building and some of the original features have been preserved beautifully. The theater makes you dream of the glorious days when art was highly regarded. We got to enjoy music played on a phonograph in our room. It was like time traveling to the great Gatsby era 😉"
A verified traveller stayed at Latchis Hotel
Latchis Hotel