A snow-covered town with a river running through it, surrounded by mountains and trees.

Apartments in Winchester for Rent

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Check prices for these dates

In two weeks
Aug 7 - Aug 9
In two months
Sep 18 - Sep 20
In three months
Oct 16 - Oct 18
In four months
Nov 13 - Nov 15

Our top choices for Winchester apartments

Exterior detail

Charming Country-Chic 1BR in Greenfield – King Bed, Rain Shower, Near Berkshires

Charming Country-Chic 1BR in Greenfield – King Bed, Rain Shower, Near Berkshires
Greenfield
9.6 out of 10, Exceptional, (9 reviews)
"We had a great"
United States
Meredith B.
The price is ￥22,117
￥48,679 total
includes taxes & fees
Aug 15 - Aug 16
Charming Country-Chic 1BR in Greenfield – King Bed, Rain Shower, Near Berkshires
Exterior

Light-filled treetop apartment close to downtown Greenfield and Highland Park

Light-filled treetop apartment close to downtown Greenfield and Highland Park
Greenfield
9.8 out of 10, Exceptional, (8 reviews)
"Nice place"
United States
Tom
The price is ￥23,299
￥29,686 total
includes taxes & fees
Aug 2 - Aug 3
Light-filled treetop apartment close to downtown Greenfield and Highland Park
Exterior detail

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

Studio Apt with Full Kitchen. 1 minute stroll over picturesque bridge into town.
Peterborough
9.8 out of 10, Exceptional, (39 reviews)
"Wonderful stay! Amazing location!"
United States
Basmattee B.
The price is ￥12,533
￥26,041 total
includes taxes & fees
Jul 27 - Jul 28
Studio Apt with Full Kitchen. 1 minute stroll over picturesque bridge into town.
Exterior

Rose room Victorian home queen bed private bath

Rose room Victorian home queen bed private bath
Shelburne Falls
The price is ￥16,956
￥31,750 total
includes taxes & fees
Aug 17 - Aug 18
Rose room Victorian home queen bed private bath
Living area

Stay in this historic Automotive-themed huge Apt. Located in charming Whitingham

Stay in this historic Automotive-themed huge Apt. Located in charming Whitingham
Whitingham
9.0 out of 10, Wonderful, (4 reviews)
"This apartment is very efficient and really wowed everyone based on the automotive inspired design. It was an impeccable space, well stocked, and the beds were even extremely comfortable. We enjoyed the bar/grill within walking distance, too. Would stay here again. "
United States
Ben B.
The price is ￥53,671
￥98,094 total
includes taxes & fees
Aug 24 - Aug 25
Stay in this historic Automotive-themed huge Apt. Located in charming Whitingham
Exterior

2 Twin beds on 1st floor with En-suite bathroom.

2 Twin beds on 1st floor with En-suite bathroom.
Shelburne Falls
The price is ￥17,333
￥32,353 total
includes taxes & fees
Aug 17 - Aug 18
2 Twin beds on 1st floor with En-suite bathroom.
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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Top Winchester Hotel Reviews

Vikings Villages Resort

Vikings Villages Resort

10/10 Excellent
"A charming and unexpected stop! Beautiful property, very comfortable, outdoor games to play and sheep to watch. Everyone was really kind and helpful."
Sally 1-night trip
Posted 1 hour ago
Vikings Villages Resort

Find out more about Winchester

Winchester Apartments information

Number of reviews
60
Accommodation
44 Apartments
Lowest Price
￥26,041
Highest Price
￥98,094

Frequently asked questions

What's it like to stay at an apartment in Winchester?
You'll find 7 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?
Here are some of the top apartments in the area: Lake-View Spofford Apartment w/ Shared Dock!: Situated in Spofford, 9.5 mi/15.4 km from the heart of Winchester. Light-filled treetop apartment close to downtown Greenfield and Highland Park: Located 16.8 mi/27.1 km away in Greenfield. Private balconies and jetted bathtubs are included. Studio Apt with Full Kitchen. 1 minute stroll over picturesque bridge into town.: 23.2 mi/37.4 km away in Peterborough. Free WiFi and Smart TVs are included.
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. Loring Field and Birch Point are a couple of lovely local spots to get outside and enjoy nature. Pisgah State Park and New England Sweetwater Farm & Distillery are other places to visit while you're in town.