Search Motels in Winchester

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
20 Feb - 22 Feb
In two weeks
27 Feb - 1 Mar
In one month
13 Mar - 15 Mar
In two months
10 Apr - 12 Apr

Our top choices for Winchester motels

Standard Room, 2 Queen Beds, Refrigerator & Microwave | Desk, iron/ironing board, rollaway beds, free WiFi

The Putney Inn

The Putney Inn
2.5 star property
Putney
8.4 out of 10, Very Good, (1,003 reviews)
"perfect room, very clean and friendly staff"
Canada
Marc-André
The Putney Inn
Seasonal outdoor pool

Econo Lodge Brattleboro South

Econo Lodge Brattleboro South
2.0 star property
Brattleboro
5.4 out of 10, (618 reviews)
"Near food and shopping, ac and heater work good."
United States
Juan
The price is AED 235
AED 259 total
includes taxes & fees
1 Mar - 2 Mar
Econo Lodge Brattleboro South
Reception

Travelodge by Wyndham Brattleboro VT

Travelodge by Wyndham Brattleboro VT
2.5 star property
Brattleboro
6.0 out of 10, (749 reviews)
"Great person at front desk. Motel was nicer than expected and clean"
United States
Giovanni
The price is AED 261
AED 287 total
includes taxes & fees
11 Feb - 12 Feb
Travelodge by Wyndham Brattleboro VT
Lunch and dinner served, American cuisine

Colonial Motel And Spa

Colonial Motel And Spa
3.0 star property
Brattleboro
6.8 out of 10, (1,003 reviews)
"Clean, cozy , spacious, comfortable rooms, friendly staff, great area, excellent spa! "
United States
Ana
The price is AED 367
AED 404 total
includes taxes & fees
10 Feb - 11 Feb
Colonial Motel And Spa
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Winchester Hotel Reviews

Four Columns Inn

Four Columns Inn

10/10 Excellent
"We stayed in the John Fane room which is in the main building. It is cute as a button. Perfect for couples. "
Kathryn Mae 2-night trip
Posted 2 days ago
Four Columns Inn

Frequently asked questions

What can I expect from a motel trip to Winchester?
If you're having trouble locating a motel in Winchester, let us help you find a motel or similar property from over 446 accommodations in the larger area. Simply filter using our search tools by nightly room rate or cost-effective amenities such as free parking and free airport transportation.
What are motels like?
Motels often have free parking, and many also feature an outdoor pool. Often one or two stories tall, motels usually have exterior corridors overlooking the parking lot or an outdoor pool. In the U.S., motels became more commonplace after World War II with the popularity of car travel and road trips, peaking in the 1960s with over 60,000 properties.
What are the best motels in Winchester?
Here you'll find some of our customers' top motels in the larger area. Econo Lodge Brattleboro South is located 10.3 mi (16.5 km) from the heart of Winchester. Enjoy access to the seasonal outdoor pool, and freebies including breakfast, WiFi, and parking. The Putney Inn: A 24-hour front desk along with freebies like breakfast, WiFi, and parking are available during your stay. Central Winchester is 14.9 mi (23.9 km) away. Colonial Motel And Spa: Enjoy access to the 2 indoor pools, and freebies including WiFi and parking. Located 11.5 mi (18.5 km) from the heart of Winchester. Travelodge by Wyndham Brattleboro VT: Central Winchester is 11.8 mi (19 km) away. Free WiFi, free parking, and a 24-hour front desk are available during your stay. The Lodge At West River: 20.2 mi (32.5 km) from the heart of Winchester. Enjoy access to the snack bar/deli, and freebies including breakfast, WiFi, and parking.
What things can I to do in Winchester?
Those who've visited Winchester like the lakeside. As you're sightseeing around the area, be sure to enjoy all there is to see and do. These are some of the parks and outdoorsy places: Barden State Wildlife Management Area, Ashuelot River, and Loring Field. You'll find these family-friendly sights in the area: Brattleboro Bowl, Scott Farm Orchard, and Harlow's. During your trip, here are some other places to visit: New England Sweetwater Farm & Distillery, Bennett Gorge, and Pisgah State Park.
What's the weather like in Winchester?
Weather can make or break a roadtrip, so here's some data about year-round temperatures in Winchester to help you plan yours: The hottest months are usually July and August with an average temp of 67°F, while the coldest months are January and February with an average of 28°F. The snowiest months in Winchester are January, March, February, and November, with each month seeing an average of 10 inches of snowfall.

Explore a world of travel with Expedia