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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 24 Apartments in Winchester with updated reviews, rates, and availability.

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
Sweet suite in Montague near the canal and downtown Turners Falls.
1 bedroom, iron/ironing board, travel crib, WiFi

Sweet suite in Montague near the canal and downtown Turners Falls.

2.0 star property
9.6 out of 10, Exceptional, (4)
"I had a great stay at Callie’s. The room was comfortable and clean and had all the amenities one needs! "
Sweet suite in Montague near the canal and downtown Turners Falls.
Private Suite with a Sweet View. Spacious, close to town, dog friendly
Exterior

Private Suite with a Sweet View. Spacious, close to town, dog friendly

10.0 out of 10, Exceptional, (30)
"Great property with great view, cute suite with everything we needed for a short stay while getting our daughter settled back in at Amherst College. Enjoyed a nice dinner nearby at Blue Rock Shelburne Falls, a little shopping and coffee at Mocha mayas and Shelburne Falls Coffee Roasters. My husband did a little fly fishing just off the property in the Deerfield River. Thank you!"
Private Suite with a Sweet View. Spacious, close to town, dog friendly
The Covey House Retreat with InfraRed Sauna
Outdoor dining

The Covey House Retreat with InfraRed Sauna

10.0 out of 10, Exceptional, (3)
"We had an amazing stay, your place is awesome!"
The Covey House Retreat with InfraRed Sauna
Lake Whitingham & Mount Snow Area Village Apartment
Outdoor dining

Lake Whitingham & Mount Snow Area Village Apartment

2.0 star property
10.0 out of 10, Exceptional, (1)
"This place was cozy and romantic, making it the perfect escape from the hustle and bustle of city life. The location is ideal, with charming New England towns to explore in every direction. Amy and Connor were exceptional hosts, checking in with us throughout our stay to ensure we felt right at home."
The price is AED 514
AED 1,107 total
includes taxes & fees
11 Mar - 12 Mar
Lake Whitingham & Mount Snow Area Village Apartment
Entire private apartment suite in home with own entrance, views and private gym.
Interior

Entire private apartment suite in home with own entrance, views and private gym.

The price is AED 1,010
AED 1,455 total
includes taxes & fees
11 Mar - 12 Mar
Entire private apartment suite in home with own entrance, views and private gym.
Lakefront Orange Vacation Rental - Pet Friendly!
Outdoor dining

Lakefront Orange Vacation Rental - Pet Friendly!

10.0 out of 10, Exceptional, (13)
"Very cozy basement apartment overlooking the water. Quiet road. Owner was very pleasant and accommodating."
Lakefront Orange Vacation Rental - Pet Friendly!
Beautiful Townhouse In Turners Falls!
Fridge, microwave, oven, stovetop

Beautiful Townhouse In Turners Falls!

9.8 out of 10, Exceptional, (128)
"I had a Great Stay, nice place."
Beautiful Townhouse In Turners Falls!
Stylish new 2 bedroom property in enchanting Shelburne Falls Village.
Exterior

Stylish new 2 bedroom property in enchanting Shelburne Falls Village.

2.0 star property
10.0 out of 10, Exceptional, (7)
"We stayed over the long weekend and went skiing at Berkshire East (15 minutes away). The house was very clean and comfortable. It was the right size for our family of 4. "
Stylish new 2 bedroom property in enchanting Shelburne Falls Village.
Updated Vintage Apartment < 1/2 Mi to Main St
Fridge, microwave, stovetop, dishwasher

Updated Vintage Apartment < 1/2 Mi to Main St

10.0 out of 10, Exceptional, (12)
"We enjoyed our long weekend visit to Keene, NH and appreciated Hidden Gem. It was great to have such a well equipped kitchen for cooking together with fresh local foods from the nearby Monadnock Co-op. Hidden Gem was very clean and comfortable. We had 11 inches of snow overnight and the porch steps, sidewalk and driveway were cleared for us early so we could make our plane on time. Our host Sarah was helpful with any questions and needs. We would love to stay again when our travels take us back...
Updated Vintage Apartment < 1/2 Mi to Main St
Studio Apt with Full Kitchen. 1 minute stroll over picturesque bridge into town.
Fridge, microwave, oven, stovetop

Studio Apt with Full Kitchen. 1 minute stroll over picturesque bridge into town.

9.6 out of 10, Exceptional, (12)
"Great location, a short walk to downtown Peterborough.the rental had everything i needed. Ben and Maryann were helpful with any questions i had. I would stay here again if in the area."
The price is AED 294
AED 598 total
includes taxes & fees
12 Mar - 13 Mar
Studio Apt with Full Kitchen. 1 minute stroll over picturesque bridge into town.
Studio w/ Trail Access ~ 10 Mi to Brattleboro!
Property grounds

Studio w/ Trail Access ~ 10 Mi to Brattleboro!

2.0 star property
Studio w/ Trail Access ~ 10 Mi to Brattleboro!
'Red Sweetheart Barn Studio' w/ Mtn & River Views!
Exterior

'Red Sweetheart Barn Studio' w/ Mtn & River Views!

10.0 out of 10, Exceptional, (3)
"It was cozy and beautiful and very inviting loved every part"
'Red Sweetheart Barn Studio' w/ Mtn & River Views!
HeART Barn, 35-60 m. to skiing @ Mt. Snow, Stratton, Okemo, Magic & Bromley
Exterior detail

HeART Barn, 35-60 m. to skiing @ Mt. Snow, Stratton, Okemo, Magic & Bromley

10.0 out of 10, Exceptional, (4)
"We stayed for the weekend and absolutely loved it- it was huge! Warm and inviting- full kitchen and bathroom, crib in the closet for a wee one. It was so clean and smelled good too- great windows and easy furniture. Bed was superb! Would stay again in a heartbeat. "
HeART Barn, 35-60 m. to skiing @ Mt. Snow, Stratton, Okemo, Magic & Bromley
Quiet Neighborhood, For Bird Lovers
Fridge, microwave, oven, stovetop

Quiet Neighborhood, For Bird Lovers

10.0 out of 10, Exceptional, (46)
" My husband and I felt at home at the opening of the door!! The location is beautiful and serene, making relaxation unavoidable! The hostess thought of every little detail! Thank you Manon for a perfectly lovely stay!!"
Quiet Neighborhood, For Bird Lovers
Ground floor 2/3 bed apartment
Living area

Ground floor 2/3 bed apartment

2.0 star property
The price is AED 749
AED 1,199 total
includes taxes & fees
11 Mar - 12 Mar
Ground floor 2/3 bed apartment
Studio w/ Trail Access ~ 10 Mi to Brattleboro!
Interior

Studio w/ Trail Access ~ 10 Mi to Brattleboro!

3.0 star property
Studio w/ Trail Access ~ 10 Mi to Brattleboro!
Updated Vintage Apartment < 1/2 Mi to Main St
Apartment (2 Bedrooms) | Private kitchen | Microwave, oven, stovetop, dishwasher

Updated Vintage Apartment < 1/2 Mi to Main St

3.0 star property
Updated Vintage Apartment < 1/2 Mi to Main St
Experience New Hampshire Country Life—Your Peaceful Escape Awaits
1 bedroom, desk, iron/ironing board, free WiFi

Experience New Hampshire Country Life—Your Peaceful Escape Awaits

9.8 out of 10, Exceptional, (30)
"We had a short stay but the hosts were wonderful and gave us a tour when we arrived. The property is gorgeous. Definitely recommend staying here."
Experience New Hampshire Country Life—Your Peaceful Escape Awaits
The Pines Cabin | New Tiny Home Near Mt Snow!
Property grounds

The Pines Cabin | New Tiny Home Near Mt Snow!

The Pines Cabin | New Tiny Home Near Mt Snow!
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

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, (26)
"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's it like to stay at an apartment in Winchester?
You’ll find 6 hotels and other accommodations in Winchester. Though there aren’t many apartments, we can help you find accommodations with similar amenities. When you search for a place to stay on Expedia, you can use the filters to search for conveniences you might find in an apartment like a kitchen. You can also search for similar property types like condos, vacation homes, or cottages. Why not take time to appreciate the lakeside during your visit?
How do you know if an apartment is the right choice for you?
An apartment features a kitchen for convenient meals, and often has more space than a traditional hotel room. Apartments are a good option for solo travelers who want to stay in at night and plan out their next day, but also for families wanting the conveniences of home.
What will the weather be like when I travel to Winchester?
Weather is only one factor, but it can really affect your travel plans, especially if you’re planning an extended stay in Winchester. 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.
What are the must-see places to visit in Winchester?
Winchester is known for its lakeside. Barden State Wildlife Management Area and Rhododendron State Park are a couple of lovely local spots to get outside and enjoy nature. Bennett Gorge and Pisgah State Park are other places to visit while you’re in town.