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Search Apartments in Winchester

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Check prices for these dates

Next weekend
25 Apr - 27 Apr
In two weeks
2 May - 4 May
In one month
16 May - 18 May
In two months
13 Jun - 15 Jun

Compare 32 Apartments in Winchester with updated reviews, rates, and availability.

Riverfront 2 Bedroom Unit 2
Property grounds

Riverfront 2 Bedroom Unit 2

9.6 out of 10, Exceptional, (17)
"Overall, not bad. The host seems thoughtful about what the leave for you to use, but the apartment and exterior could use some TLC"
Riverfront 2 Bedroom Unit 2
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
Studio w/ Trail Access ~ 10 Mi to Brattleboro!
Property grounds

Studio w/ Trail Access ~ 10 Mi to Brattleboro!

2.0 star property
10.0 out of 10, Exceptional, (1)
Studio w/ Trail Access ~ 10 Mi to Brattleboro!
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 312
AED 618 total
includes taxes & fees
22 Apr - 23 Apr
Studio Apt with Full Kitchen. 1 minute stroll over picturesque bridge into town.
Cozy apt in beautiful secluded spot 15 mins from Mt Snow
Property grounds

Cozy apt in beautiful secluded spot 15 mins from Mt Snow

10.0 out of 10, Exceptional, (1)
The price is AED 257
AED 685 total
includes taxes & fees
1 May - 2 May
Cozy apt in beautiful secluded spot 15 mins from Mt Snow
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, (15)
"Great experience. "
Updated Vintage Apartment < 1/2 Mi to Main St
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, (8)
"The place was very comfortable and in a great location. "
Stylish new 2 bedroom property in enchanting Shelburne Falls Village.
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 1,131 total
includes taxes & fees
15 Apr - 16 Apr
Lake Whitingham & Mount Snow Area Village Apartment
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
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.
'Red Sweetheart Barn Studio' w/ Mtn & River Views!
Exterior

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

9.6 out of 10, Exceptional, (4)
"We enjoyed a few night springtime stay at this beautiful cabin! The view was wonderful, and the accommodations were very nicely decorated. Some things we would love to see improvement on before staying again: there were no washcloths available in the upstairs bathroom, and no garbage can available in the downstairs one. No tissues to be found in the entire space. The bed was extremely uncomfortable, and the pillows as well. We also found fingernail clippings in the sheets, which was problematic,...
'Red Sweetheart Barn Studio' w/ Mtn & River Views!
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
Charming Ground-Floor 2/3 bedroom apartment in Shelburne Falls, MA
Living area

Charming Ground-Floor 2/3 bedroom apartment in Shelburne Falls, MA

2.0 star property
The price is AED 606
AED 1,031 total
includes taxes & fees
16 Apr - 17 Apr
Charming Ground-Floor 2/3 bedroom apartment in Shelburne Falls, MA
Lakefront Orange Vacation Rental - Pet Friendly!
Outdoor dining

Lakefront Orange Vacation Rental - Pet Friendly!

10.0 out of 10, Exceptional, (14)
"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, (130)
"Our stay made it easy to access the shops and restaurants we needed to go to. Although the main spaces of the living area were clean (living room, bedrooms, kitchen, bathrooms, tubs, showers, toilets, sinks, couch, and beds), we were surprised to see some dust accumulated throughout the unit (on lamps, light fixtures and overhead fans, as well as box fans in the bedrooms) and having to clean the tea kettle and some dishes and glasses before use. We would have given this a 5/5 star stay if we...
Beautiful Townhouse In Turners Falls!
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 1,463 total
includes taxes & fees
29 Apr - 30 Apr
Entire private apartment suite in home with own entrance, views and private gym.
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
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
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
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!
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

GAMERS HAVEN, River Wine Inn!
Game room

GAMERS HAVEN, River Wine Inn!

2.0 star property
10.0 out of 10, Exceptional, (11)
"Great place with an elite game room. "
GAMERS HAVEN, River Wine Inn!
The Jelly Mill-A River Retreat
Exterior

The Jelly Mill-A River Retreat

10.0 out of 10, Exceptional, (47)
"Was exactly as described. Had everything we needed and more. Only thing we had hoped for that wasn’t there was some olive oil, so bring your own if you want to cook. Not quite as remote as we were anticipating, but in a good way . Was still very rural, and we were grateful for the 4wheel drive vehicle we rented. Perfect, majestic, natural location for our family retreat."
The Jelly Mill-A River Retreat
Riverfront 2 Bedroom Unit 2
Property grounds

Riverfront 2 Bedroom Unit 2

9.6 out of 10, Exceptional, (17)
"Overall, not bad. The host seems thoughtful about what the leave for you to use, but the apartment and exterior could use some TLC"
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'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's a favorite apartment for a stay in Winchester?
Below are some of the more popular apartments in the area: Riverfront 2 Bedroom Unit 2: Located 14.5 mi/23.3 km away in Montague. Cozy 2-bedroom Unit with private backyard: It’s situated in Montague, 14.5 mi/23.3 km away. Includes free WiFi, private patios, and Smart TVs. Studio w/ Trail Access ~ 10 Mi to Brattleboro!: 8.2 mi/13.2 km away in Vernon. Amenities include separate dining areas. Updated Vintage Apartment < 1/2 Mi to Main St: It’s located in Keene, 12.6 mi/20.3 km from Winchester. Includes private patios.
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. Birch Point and Rhododendron State Park are a couple of lovely local spots to get outside and enjoy nature. New England Sweetwater Farm & Distillery and Pisgah State Park are other places to visit while you’re in town.