Book Cheap Hotels in Winchester

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Check hotel availability in Winchester

Tonight
Check prices in Winchester for tonight, Dec 13 - Dec 14
Dec 13 - Dec 14
Tomorrow night
Check prices in Winchester for tomorrow night, Dec 14 - Dec 15
Dec 14 - Dec 15
Next weekend
Check prices in Winchester for next weekend, Dec 19 - Dec 21
Dec 19 - Dec 21

Most frequently booked Winchester hotels

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
Get rates
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 Wachusett Mountain Ski Area and Dunn State Park are located nearby.
Pool
Hot tub
The Covered Bridge Inn

The Covered Bridge Inn

2.5 out of 5
1043 Putney Road Brattleboro VT
Free cancellation
Reserve now, pay when you stay
18.68 km from city centre
The price is CA $109 per night
CA $109
CA $120 total
Jan 7 - Jan 8, 2026
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 breakfast and the helpful staff in our reviews. Popular attractions United States Navy Seabee Bridge and Brattleboro Bowl are located nearby.
Parking included
Free WiFi
Hampton Inn & Suites Greenfield

Hampton Inn & Suites Greenfield

2.5 out of 5
184 Shelburne Rd Greenfield MA
Free cancellation
Reserve now, pay when you stay
28.52 km from city centre
The price is CA $252 per night
CA $252
CA $282 total
Jan 11 - Jan 12, 2026
includes taxes & fees
Book a stay at this business-friendly hotel in Greenfield. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions Old Greenfield Village and Museum of Our Industrial Heritage are located nearby.
Breakfast included
Pet-friendly
Hampton Inn Brattleboro

Hampton Inn Brattleboro

2.5 out of 5
1378 Putney Road Brattleboro VT
Free cancellation
Reserve now, pay when you stay
19.03 km from city centre
The price is CA $197 per night
CA $197
CA $217 total
Jan 7 - Jan 8, 2026
includes taxes & fees
Book a stay at this business-friendly hotel in Brattleboro. Enjoy free breakfast, free parking, and a fitness center. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions United States Navy Seabee Bridge and Brattleboro Bowl are located nearby.
Pool
Hot tub
Comfort Inn & Suites Brattleboro I-91

Comfort Inn & Suites Brattleboro I-91

2.5 out of 5
1186 Putney Road Brattleboro VT
Free cancellation
Reserve now, pay when you stay
18.95 km from city centre
The price is CA $147 per night
CA $147
CA $162 total
Dec 21 - Dec 22
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
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
Free cancellation
18.3 km from city centre
The price is CA $158 per night
CA $158
CA $172 total
Dec 15 - Dec 16
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 Cheshire Children's Museum are located nearby.
Pool
Breakfast included
Hampton Inn & Suites Keene

Hampton Inn & Suites Keene

2.5 out of 5
126 Key Rd Keene NH
Free cancellation
Reserve now, pay when you stay
18.21 km from city centre
The price is CA $203 per night
CA $203
CA $220 total
Dec 24 - Dec 25
includes taxes & fees
Book a stay at this business-friendly hotel in Keene. Enjoy free breakfast, free parking, and room service. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Ashuelot River and Cheshire Children's Museum are located nearby.
Pool
Breakfast included
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
Get rates
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
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 $191 per night
CA $191
CA $208 total
Dec 14 - Dec 15
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 Thorne Sagendorph Art Gallery are located nearby.
Pool
Breakfast included
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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
440 hotels
Lowest Price
CA $120
Highest Price
CA $282
Popular hotels
The Colonial Hotel, The Covered Bridge Inn, Hampton Inn & Suites Greenfield, Hampton Inn Brattleboro, Comfort Inn & Suites Brattleboro I-91, Keene Elm City Hotel, an Ascend Collection Hotel, Hampton Inn & Suites Keene, The Putney Inn, Best Western Plus Keene Hotel

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 $120 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

Latchis Hotel

Latchis Hotel

5 out of 5
Posted 5 days ago
Travelocity Verified Review
"Our room was very clean. Comfy bed. Loved the uniqueness of this hotel! Will come again!"
A verified traveller from Plymouth stayed at Latchis Hotel
Latchis Hotel

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Areas of Winchester