Search Motels in Winchester

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Next weekend
Feb 21 - Feb 23
In two weeks
Feb 28 - Mar 2
In one month
Mar 14 - Mar 16
In two months
Apr 11 - Apr 13

Browse Select Winchester Motels

Great Wolf Lodge Boston / Fitchburg, MA
4 indoor pools, seasonal outdoor pool, cabanas (surcharge)

Great Wolf Lodge Boston / Fitchburg, MA

3.5 star property
8.4 out of 10, Very good, (887)
"Fantastic "
The price is CA $256
CA $340 total
includes taxes & fees
Mar 5 - Mar 6
Great Wolf Lodge Boston / Fitchburg, MA
Mountaineer Inn
Fireplace

Mountaineer Inn

2.0 star property
9.0 out of 10, Wonderful, (407)
"Food choice limited for continental breakfast. staff friendly. pool table had torn felt and 2 sets of balls."
The price is CA $277
CA $336 total
includes taxes & fees
Feb 25 - Feb 26
Mountaineer Inn
The Black Bear Lodge at Stratton Mountain Resort
Indoor spa tub

The Black Bear Lodge at Stratton Mountain Resort

3.0 star property
7.6 out of 10, Good, (891)
"The place was very nice but a little dated"
The price is CA $256
CA $309 total
includes taxes & fees
Mar 12 - Mar 13
The Black Bear Lodge at Stratton Mountain Resort
Mount Snow Grand Summit Resort
Exterior

Mount Snow Grand Summit Resort

3.0 star property
8.8 out of 10, Excellent, (179)
"Older, air drying in the locker rooms odd . Moisture. "
The price is CA $400
CA $479 total
includes taxes & fees
Mar 11 - Mar 12
Mount Snow Grand Summit Resort
The Colonial Hotel
Interior

The Colonial Hotel

3.0 star property
8.6 out of 10, Excellent, (1000)
"."
The price is CA $200
CA $223 total
includes taxes & fees
Feb 25 - Feb 26
The Colonial Hotel
Doubletree by Hilton Hotel Leominster
Reception

Doubletree by Hilton Hotel Leominster

4.0 star property
8.6 out of 10, Excellent, (1002)
"."
The price is CA $188
CA $210 total
includes taxes & fees
Feb 16 - Feb 17
Doubletree by Hilton Hotel Leominster
Colonial Motel And Spa
Exterior

Colonial Motel And Spa

3.0 star property
6.8 out of 10, (1003)
"Great stop-over for northern Vermont skiing. Nice pool, friendly staff, and tasty breakfast :)"
The price is CA $156
CA $171 total
includes taxes & fees
Feb 25 - Feb 26
Colonial Motel And Spa
Big Bears Lodge
Outdoor spa tub

Big Bears Lodge

3.0 star property
9.0 out of 10, Wonderful, (169)
"very friendly"
The price is CA $238
CA $262 total
includes taxes & fees
Mar 3 - Mar 4
Big Bears Lodge
The Putney Inn
Exterior

The Putney Inn

2.5 star property
8.4 out of 10, Very good, (1001)
"Great hotel for the price. Nice and quiet. "
The price is CA $121
CA $131 total
includes taxes & fees
Mar 9 - Mar 10
The Putney Inn
Comfort Inn & Suites
Lobby

Comfort Inn & Suites

2.5 star property
9.2 out of 10, Wonderful, (1002)
"Good for what we needed. "
The price is CA $182
CA $203 total
includes taxes & fees
Feb 16 - Feb 17
Comfort Inn & Suites
Comfort Inn & Suites Brattleboro I-91
Lobby

Comfort Inn & Suites Brattleboro I-91

2.5 star property
8.6 out of 10, Excellent, (580)
"We stayed here twice this snow season, and both times, breakfast was delayed. The first time (Saturday), the cook was late, causing a 20-minute delay. The second time (also Saturday), the cook disappeared, and there was no hot food at all. We frequently stay at different Comfort Inns during our ski trips, and this is the ONLY one where we've encountered such issues with breakfast service. If you rely on a timely breakfast, especially for a busy morning, you may want to consider other options."
The price is CA $148
CA $163 total
includes taxes & fees
Mar 11 - Mar 12
Comfort Inn & Suites Brattleboro I-91
Hampton Inn Brattleboro
Lobby

Hampton Inn Brattleboro

2.5 star property
8.2 out of 10, Very good, (1000)
"Check in staff were super helpful. We did not know the hot tub and pool were not open, which bummed us out. We loved that all the rooms were animal friendly. The cookies were also Faboo!"
The price is CA $149
CA $164 total
includes taxes & fees
Mar 10 - Mar 11
Hampton Inn Brattleboro
Chalet 239
Family Room | Living area

Chalet 239

2.0 star property
9.6 out of 10, Exceptional, (57)
"Place is very new. House keeper should give little details to the inside refrigerator. Little filthy "
The price is CA $265
CA $291 total
includes taxes & fees
Feb 26 - Feb 27
Chalet 239
Best Western Springfield Hotel
Suite, 1 King Bed, Accessible, Refrigerator & Microwave (with Sofabed)

Best Western Springfield Hotel

2.5 star property
8.8 out of 10, Excellent, (741)
"Very nice hotel, close to okemo. Nice breakfast! "
The price is CA $230
CA $251 total
includes taxes & fees
Mar 10 - Mar 11
Best Western Springfield Hotel
The Ellery
Lobby

The Ellery

3.5 star property
9.0 out of 10, Wonderful, (597)
"Our room was clean and they provided a free upgrade. Unfortunately, our door would not lock. They just had a new door lock system installed. They moved us to another room and all was well. Later on, we were accidentally locked out of our room. We were able to call and they unlocked the door remotely. Perfect! The service was fab, the continental breakfast was one of the best we’ve ever seen and it’s included with the room. We could not have been happier with this experience. This is a great,...
The price is CA $199
CA $222 total
includes taxes & fees
Feb 13 - Feb 14
The Ellery
Fullerton Inn
Standard Room, 2 Double Beds

Fullerton Inn

2.5 star property
8.0 out of 10, Very good, (326)
"This is a lovely old building with a lot of character and charm. We were greeted upon arrival and given all the information we needed for parking in the back lot due to snow plowing. The room was small, which was fine and what we had reserved, no complaints there. We had a double bed and it was very, very soft if you like that sort of thing. There was some draftiness in the second floor end room we stayed in, and the heat was not running when we got there, which was an issue for an hour or two...
The price is CA $184
CA $201 total
includes taxes & fees
Mar 10 - Mar 11
Fullerton Inn
Austrian Haus Lodge
Indoor pool

Austrian Haus Lodge

2.5 star property
8.6 out of 10, Excellent, (48)
"Great stay weather caused slippery driveway "
Austrian Haus Lodge
Howard Johnson by Wyndham Amherst Hadley
Property amenity

Howard Johnson by Wyndham Amherst Hadley

2.0 star property
7.2 out of 10, Good, (1002)
"Overall it was good customer service."
The price is CA $136
CA $152 total
includes taxes & fees
Feb 25 - Feb 26
Howard Johnson by Wyndham Amherst Hadley
Inn on Boltwood
Balcony

Inn on Boltwood

3.0 star property
9.4 out of 10, Exceptional, (627)
"We had a room with fireplace, and it was perfect for a snowy night."
The price is CA $256
CA $286 total
includes taxes & fees
Feb 25 - Feb 26
Inn on Boltwood
Motel 6 Leominster, MA
Lobby

Motel 6 Leominster, MA

2.0 star property
7.8 out of 10, Good, (1003)
"The room gave us exactly what we needed. Warm, comfortable, quiet and plenty of space. "
The price is CA $122
CA $139 total
includes taxes & fees
Feb 25 - Feb 26
Motel 6 Leominster, MA
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!
TV, fireplace, DVD player, books

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

9.8 out of 10, Exceptional, (113)
"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
Fridge, microwave, oven, stovetop

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
Beautiful Adirondack Cabin with Sauna on Lake Monomonac
Exterior

Beautiful Adirondack Cabin with Sauna on Lake Monomonac

2.0 star property
10.0 out of 10, Exceptional, (15)
"Host was incredibly friendly and accommodating and the cabin was nothing short of beautiful"
The price is CA $241
CA $423 total
includes taxes & fees
Feb 25 - Feb 26
Beautiful Adirondack Cabin with Sauna on Lake Monomonac
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: 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 Moody Center.
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.