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Check prices for these dates

Next weekend
9 May - 11 May
In two weeks
16 May - 18 May
In one month
30 May - 1 Jun
In two months
27 Jun - 29 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, (1001)
"Very nice clean and convenient accommodations "
The price is AED 360
AED 396 total
includes taxes & fees
18 May - 19 May
Colonial Motel And Spa
The Putney Inn
Exterior

The Putney Inn

2.5 star property
8.4 out of 10, Very Good, (1001)
"Very clean, pleasant staff."
The price is AED 380
AED 414 total
includes taxes & fees
4 May - 5 May
The Putney Inn
Travelodge by Wyndham Brattleboro VT
Reception

Travelodge by Wyndham Brattleboro VT

2.5 star property
6.0 out of 10, (666)
"No shampo no soap, two towels one roll of toilet paper,no trash barrels walls where disgusting, the floors dirty i would never go back there and ill let everybody know , plus drug addictes asking for money or cigarettes i felt scared for my wife "
The price is AED 294
AED 324 total
includes taxes & fees
5 May - 6 May
Travelodge by Wyndham Brattleboro VT
Econo Lodge Brattleboro
View from room

Econo Lodge Brattleboro

2.0 star property
5.6 out of 10, (518)
"The interior was in bad condition and bug infested The only good thing was the low price and easy access to the highway"
The price is AED 331
AED 364 total
includes taxes & fees
20 May - 21 May
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

Story Book Lake Front Chateau with Private Beach!
Miscellaneous

Story Book Lake Front Chateau with Private Beach!

10.0 out of 10, Exceptional, (6)
"We loved staying here! The property was sparkling clean and very well stocked with everything you need. Comfortable beds and space. The view was beautiful and the privacy and yard created great memories for our family. Thank you sharing your beautiful house with us!"
Story Book Lake Front Chateau with Private Beach!
GAMERS HAVEN, River Wine Inn!
Game room

GAMERS HAVEN, River Wine Inn!

2.0 star property
10.0 out of 10, Exceptional, (11)
"Such a large house with so many areas for activities. Close to a lot of fun things to do like axe throwing, an escape room, distilleries, breweries, etc."
GAMERS HAVEN, River Wine Inn!
Riverfront 2 Bedroom Unit 2
Property grounds

Riverfront 2 Bedroom Unit 2

9.6 out of 10, Exceptional, (17)
"We had a lovely time in central Mass"
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 387 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: Loring Field, Birch Point, and Rhododendron State Park. You’ll find these family-friendly sights in the area: Brattleboro Bowl, Friendly Farm, and Northern Illusion. During your trip, here are some other places to visit: New England Sweetwater Farm & Distillery, Pisgah State Park, and Ashuelot River.
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.