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Check prices for these dates

Next weekend
7 Saf. - 9 Saf.
In two weeks
14 Saf. - 16 Saf.
In one month
28 Saf. - 2 Rab. I
In two months
28 Rab. I - 30 Rab. I

Compare Motels in Winchester with updated reviews, rates, and availability.

Colonial Motel And Spa
Exterior

Colonial Motel And Spa

3.0 star property
6.8 out of 10, (1003)
"Great property to stay at!"
The price is SAR 409
SAR 450 total
includes taxes & fees
3 Feb - 4 Feb
Colonial Motel And Spa
The Putney Inn
Front of property

The Putney Inn

2.5 star property
8.4 out of 10, Very Good, (1008)
"Very convenient location in a charming town. "
The price is SAR 454
SAR 495 total
includes taxes & fees
8 Feb - 9 Feb
The Putney Inn
Econo Lodge Brattleboro
Exterior

Econo Lodge Brattleboro

2.0 star property
5.6 out of 10, (516)
"It was fine. We just stopped in for the night after a concert"
Econo Lodge Brattleboro
Travelodge by Wyndham Brattleboro VT
Exterior

Travelodge by Wyndham Brattleboro VT

2.5 star property
6.0 out of 10, (662)
"Clean"
The price is SAR 638
SAR 702 total
includes taxes & fees
27 Feb - 28 Feb
Travelodge by Wyndham Brattleboro VT
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.
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Other property types in Winchester

This is it! Fabulous Vermont Cabin w/ 25 Acres to Explore! Spectacular Views!
Winter wonderland!

This is it! Fabulous Vermont Cabin w/ 25 Acres to Explore! Spectacular Views!

9.8 out of 10, Exceptional, (112)
"Great place to stay with friends and family. Will be visiting again!"
This is it! Fabulous Vermont Cabin w/ 25 Acres to Explore! Spectacular Views!
Modern private home 30 acres w/ pool, river, billiards, & near 4 ski mtns
Plenty of private open space to explore with the whole family!

Modern private home 30 acres w/ pool, river, billiards, & near 4 ski mtns

10.0 out of 10, Exceptional, (51)
"This place was just about perfect with excellent hosts that were easy to communicate to. My only ask would be to get shades to block the sun in the morning in the bedroom to the left of the upstairs bathroom. We did not use that bedroom because of this reason. That being said, we loved this place so much that we already booked again for next year. "
Modern private home 30 acres w/ pool, river, billiards, & near 4 ski mtns
Stunning dog-friendly home with board games, sauna, balcony, gas grill, & deck

Stunning dog-friendly home with board games, sauna, balcony, gas grill, & deck

6.8 out of 10, (13)
"We enjoyed our stay. AWD is a must for the driveway. The number of security cameras around the property is uncomfortable."
Stunning dog-friendly home with board games, sauna, balcony, gas grill, & deck
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 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 384 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. Colonial Motel And Spa is located 11.5 mi (18.5 km) from the heart of Winchester. Enjoy access to the 2 indoor pools, and freebies including 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. Econo Lodge Brattleboro: Enjoy access to the seasonal outdoor pool, and freebies including breakfast, WiFi, and parking. Located 10.3 mi (16.5 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.
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: Pisgah State Park, Ashuelot River, and Birch Point. You’ll find these family-friendly sights in the area: Friendly Farm, Brattleboro Bowl, and Cheshire Children’s Museum. While you’re checking out the area, consider visiting Rhododendron State Park, Thomas Aquinas College, and Northfield Mount Hermon School.
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.