Photo by Donny Campos

Search Motels in Winchester from CA $135

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

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, (918)
"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 CA $257
CA $342 total
includes taxes & fees
Mar 18 - Mar 19
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 CA $201
CA $225 total
includes taxes & fees
Mar 16 - Mar 17
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 CA $190
CA $230 total
includes taxes & fees
Mar 19 - Mar 20
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 CA $201
CA $224 total
includes taxes & fees
Mar 23 - Mar 24
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 CA $214
CA $256 total
includes taxes & fees
Apr 14 - Apr 15
Mount Snow Grand Summit Resort
Comfort Inn & Suites
Lobby

Comfort Inn & Suites

2.5 star property
9.2 out of 10, Wonderful, (1005)
"good"
The price is CA $177
CA $198 total
includes taxes & fees
Apr 7 - Apr 8
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 CA $157
CA $172 total
includes taxes & fees
Mar 16 - Mar 17
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 CA $192
CA $233 total
includes taxes & fees
Apr 13 - Apr 14
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 CA $147
CA $161 total
includes taxes & fees
Mar 26 - Mar 27
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)
"Perfect"
The price is CA $157
CA $172 total
includes taxes & fees
Mar 23 - Mar 24
Comfort Inn & Suites Brattleboro I-91
Quality Inn & Suites Northampton - Amherst
Deluxe Room, 2 Queen Beds, Non Smoking

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 CA $158
CA $176 total
includes taxes & fees
Mar 19 - Mar 20
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 CA $133
CA $152 total
includes taxes & fees
Apr 6 - Apr 7
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 CA $137
CA $153 total
includes taxes & fees
Apr 7 - Apr 8
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 CA $185
CA $207 total
includes taxes & fees
Mar 17 - Mar 18
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 CA $219
CA $244 total
includes taxes & fees
Mar 23 - Mar 24
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 CA $170
CA $189 total
includes taxes & fees
Apr 7 - Apr 8
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 CA $160
CA $178 total
includes taxes & fees
Mar 16 - Mar 17
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 CA $291
CA $325 total
includes taxes & fees
Mar 16 - Mar 17
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 CA $135
CA $147 total
includes taxes & fees
Mar 16 - Mar 17
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 CA $172
CA $190 total
includes taxes & fees
Mar 31 - Apr 1
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.