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Check prices for these dates

Next weekend
18 Apr - 20 Apr
In two weeks
25 Apr - 27 Apr
In one month
9 May - 11 May
In two months
6 Jun - 8 Jun

Compare 4 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, (1005)
"The sauna after a ski day is great"
The price is AED 360
AED 396 total
includes taxes & fees
27 Apr - 28 Apr
Colonial Motel And Spa
The Putney Inn
Exterior

The Putney Inn

2.5 star property
8.4 out of 10, Very Good, (1000)
"Good basic hotel. Very clean. Very reasonably priced"
The price is AED 343
AED 374 total
includes taxes & fees
14 Apr - 15 Apr
The Putney Inn
Travelodge by Wyndham Brattleboro VT
Reception

Travelodge by Wyndham Brattleboro VT

2.5 star property
6.0 out of 10, (666)
"Clean"
The price is AED 327
AED 360 total
includes taxes & fees
16 Apr - 17 Apr
Travelodge by Wyndham Brattleboro VT
Econo Lodge Brattleboro
View from room

Econo Lodge Brattleboro

2.0 star property
5.6 out of 10, (517)
"It was fine. We just stopped in for the night after a concert"
The price is AED 327
AED 360 total
includes taxes & fees
14 Apr - 15 Apr
Econo Lodge Brattleboro
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

GAMERS HAVEN, River Wine Inn!
Game room

GAMERS HAVEN, River Wine Inn!

2.0 star property
10.0 out of 10, Exceptional, (11)
"Great place with an elite game room. "
GAMERS HAVEN, River Wine Inn!
The Jelly Mill-A River Retreat
Exterior

The Jelly Mill-A River Retreat

10.0 out of 10, Exceptional, (47)
"Was exactly as described. Had everything we needed and more. Only thing we had hoped for that wasn’t there was some olive oil, so bring your own if you want to cook. Not quite as remote as we were anticipating, but in a good way . Was still very rural, and we were grateful for the 4wheel drive vehicle we rented. Perfect, majestic, natural location for our family retreat."
The Jelly Mill-A River Retreat
Riverfront 2 Bedroom Unit 2
Interior

Riverfront 2 Bedroom Unit 2

9.6 out of 10, Exceptional, (17)
"Overall, not bad. The host seems thoughtful about what the leave for you to use, but the apartment and exterior could use some TLC"
Riverfront 2 Bedroom Unit 2
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 381 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. Travelodge by Wyndham Brattleboro VT: Enjoy access to the 24-hour front desk, and freebies including WiFi and parking. Located 11.8 mi (19 km) from the heart of Winchester. Econo Lodge Brattleboro: Central Winchester is 10.3 mi (16.5 km) away. A seasonal outdoor pool along with freebies like breakfast, WiFi, and parking 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: Birch Point, Rhododendron State Park, and Ashuelot River. You’ll find these family-friendly sights in the area: Brattleboro Bowl, Jacobs Hill, and Friendly Farm. During your trip, here are some other places to visit: New England Sweetwater Farm & Distillery, Pisgah State Park, and Richmond Town Hall.
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.