Photo by Donny Campos

Search Motels in Winchester

  • Plan, book, stay with confidence

    • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Next weekend
21 Mar - 23 Mar
In two weeks
28 Mar - 30 Mar
In one month
11 Apr - 13 Apr
In two months
9 May - 11 May

Compare 4 Motels in Winchester with updated reviews, rates, and availability.

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, (917)
"We had a great time with our 4 year old grandsons. However would like more waterslides for kids under 42 inches and more non-water activities for the little ones. "
The price is AED 657
AED 875 total
includes taxes & fees
26 Mar - 27 Mar
Great Wolf Lodge Boston / Fitchburg, MA
The Colonial Hotel
Interior

The Colonial Hotel

3.0 star property
8.8 out of 10, Excellent, (1002)
"The staff were really friendly, very helpful. It was meticulously clean, the hot tub and pool area was an added bonus."
The price is AED 514
AED 574 total
includes taxes & fees
23 Mar - 24 Mar
The Colonial Hotel
Mountaineer Inn
Fireplace

Mountaineer Inn

2.0 star property
9.0 out of 10, Wonderful, (436)
"Very close to the ski resort.. fairly respectable it was clean. "
The price is AED 485
AED 588 total
includes taxes & fees
19 Mar - 20 Mar
Mountaineer Inn
Doubletree by Hilton Hotel Leominster
Reception

Doubletree by Hilton Hotel Leominster

4.0 star property
8.6 out of 10, Excellent, (1002)
"Staff are always super nice here. "
The price is AED 511
AED 571 total
includes taxes & fees
23 Mar - 24 Mar
Doubletree by Hilton Hotel Leominster
Mount Snow Grand Summit Resort
Exterior

Mount Snow Grand Summit Resort

3.0 star property
8.6 out of 10, Excellent, (189)
"Outdoor pool was great !"
The price is AED 547
AED 655 total
includes taxes & fees
14 Apr - 15 Apr
Mount Snow Grand Summit Resort
Comfort Inn & Suites
Lobby

Comfort Inn & Suites

2.5 star property
9.2 out of 10, Wonderful, (1005)
"Incredibly clean, comfortable and quiet motel. One of the better experiences we have had in our travels, lately. Will definitely return to this motel when we come back to visit the area."
The price is AED 453
AED 506 total
includes taxes & fees
7 Apr - 8 Apr
Comfort Inn & Suites
Colonial Motel And Spa
Exterior

Colonial Motel And Spa

3.0 star property
6.8 out of 10, (1004)
"Great for the price!"
The price is AED 400
AED 440 total
includes taxes & fees
18 Mar - 19 Mar
Colonial Motel And Spa
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, (896)
"appreciated the breakfast and in hotel restaurant."
The price is AED 490
AED 593 total
includes taxes & fees
13 Apr - 14 Apr
The Black Bear Lodge at Stratton Mountain Resort
Hampton Inn Brattleboro
Lobby

Hampton Inn Brattleboro

2.5 star property
8.2 out of 10, Very Good, (803)
"The whole experience was great and I will come back again."
The price is AED 371
AED 409 total
includes taxes & fees
26 Mar - 27 Mar
Hampton Inn Brattleboro
Comfort Inn & Suites Brattleboro I-91
Lobby

Comfort Inn & Suites Brattleboro I-91

2.5 star property
8.6 out of 10, Excellent, (606)
"I think the wait staff is what makes this property great. They are courteous and considerate."
The price is AED 401
AED 441 total
includes taxes & fees
23 Mar - 24 Mar
Comfort Inn & Suites Brattleboro I-91
Quality Inn & Suites Northampton - Amherst
Deluxe Room, 2 Queen Beds, Non Smoking | Desk, iron/ironing board, cribs/infant beds, rollaway beds

Quality Inn & Suites Northampton - Amherst

2.5 star property
7.2 out of 10, Good, (1001)
"Staff was very helpful and friendly "
The price is AED 403
AED 450 total
includes taxes & fees
19 Mar - 20 Mar
Quality Inn & Suites Northampton - Amherst
Motel 6 Leominster, MA
Lobby

Motel 6 Leominster, MA

2.0 star property
7.8 out of 10, Good, (1005)
"You could hear water running from beyond thr bathroom but that was my only issue."
The price is AED 340
AED 388 total
includes taxes & fees
6 Apr - 7 Apr
Motel 6 Leominster, MA
Howard Johnson by Wyndham Amherst Hadley
Property amenity

Howard Johnson by Wyndham Amherst Hadley

2.0 star property
7.2 out of 10, Good, (1000)
"Nice and clean"
The price is AED 350
AED 391 total
includes taxes & fees
7 Apr - 8 Apr
Howard Johnson by Wyndham Amherst Hadley
The Ellery
Lobby

The Ellery

3.5 star property
9.0 out of 10, Wonderful, (630)
"Love the breakfast!"
The price is AED 474
AED 529 total
includes taxes & fees
17 Mar - 18 Mar
The Ellery
Homewood Suites by Hilton Hadley Amherst
Terrace/patio

Homewood Suites by Hilton Hadley Amherst

3.0 star property
9.4 out of 10, Exceptional, (625)
"Nice location. Clean room "
The price is AED 559
AED 624 total
includes taxes & fees
26 Mar - 27 Mar
Homewood Suites by Hilton Hadley Amherst
Fairfield Inn & Suites Springfield Northampton/Amherst
Exterior

Fairfield Inn & Suites Springfield Northampton/Amherst

3.0 star property
9.2 out of 10, Wonderful, (932)
"Perfect place for an overnight business stay. Staff was wonderful, the room was nice, clean and quiet."
The price is AED 433
AED 484 total
includes taxes & fees
7 Apr - 8 Apr
Fairfield Inn & Suites Springfield Northampton/Amherst
Red Roof Inn PLUS+ South Deerfield – Amherst
Desk, laptop workspace, blackout drapes, iron/ironing board

Red Roof Inn PLUS+ South Deerfield – Amherst

2.5 star property
7.2 out of 10, Good, (1001)
"Easy access "
The price is AED 408
AED 456 total
includes taxes & fees
23 Mar - 24 Mar
Red Roof Inn PLUS+ South Deerfield – Amherst
Inn on Boltwood
Balcony

Inn on Boltwood

3.0 star property
9.4 out of 10, Exceptional, (633)
"Great"
The price is AED 746
AED 833 total
includes taxes & fees
23 Mar - 24 Mar
Inn on Boltwood
The Putney Inn
Exterior

The Putney Inn

2.5 star property
8.4 out of 10, Very Good, (1004)
"It was a spur of the moment for a trip to Vermont and New Hampshire with our 2 dogs still had snow so couldn't walk around. Nice room bed comfy. "
The price is AED 345
AED 376 total
includes taxes & fees
18 Mar - 19 Mar
The Putney Inn
Latchis Hotel
Interior

Latchis Hotel

2.5 star property
8.4 out of 10, Very Good, (720)
"The Latchis Hotel was amazing. There is so much history within the walls and the decor. Not to mention the pictures of the hotel back in 1939. As well as the theater being built. Being right in downtown was great. There was plenty of dining as well as different stores for everyone. I will most definitely be back. "
The price is AED 440
AED 484 total
includes taxes & fees
7 Apr - 8 Apr
Latchis Hotel
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.
Don't see what you're looking for?
See all available properties in Winchester
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Other property types in Winchester

Secluded Lakefront Vacation Home
Smart TV, fireplace, books, printers

Secluded Lakefront Vacation Home

9.8 out of 10, Exceptional, (69)
"Once again I was placed into a state of memories starting from childhood when I used to swim in Lake Sunshine(now lake Contoocook! The scenery is mesmerizing and I love staring at the trees and lake which takes me back to days of freedom and wonderment. The sunrises are spectacular and make me begin a new day with energy and hope for this unsettled world."
Secluded Lakefront Vacation Home
Cozy 2-bedroom Unit with private backyard
Fridge, microwave, oven, stovetop

Cozy 2-bedroom Unit with private backyard

10.0 out of 10, Exceptional, (21)
"Small but very clean and had everything we needed for our stay "
Cozy 2-bedroom Unit with private backyard
Bright three-level home with water views, jetted tub, firepit, and pool table
Fridge, microwave, oven, stovetop

Bright three-level home with water views, jetted tub, firepit, and pool table

8.4 out of 10, Very Good, (27)
"Had a fantastic weekend at this cabin. Beautifully maintained, sparking clean and beautiful cabin. Everything was exactly as pictured and is even better in person. Would stay here again x100"
Bright three-level home with water views, jetted tub, firepit, and pool table
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 373 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: Ashuelot River, Barden State Wildlife Management Area, and Rhododendron State Park. You’ll find these family-friendly sights in the area: Brattleboro Bowl, Scott Farm Orchard, and Friendly Farm. During your trip, here are some other places to visit: New England Sweetwater Farm & Distillery, Winchester Speedpark, 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.