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
Nov 6 - Nov 8
In two months
Dec 18 - Dec 20
In three months
Jan 15 - Jan 17
In four months
Feb 12 - Feb 14

Our top choices for Winchester apartments

A two-story house with a front porch, a staircase, and a small garden area.

1. Central Large 2-bedrooms with office in Keene

Central Large 2-bedrooms with office in Keene
Keene
9.6 out of 10, Exceptional, (9 reviews)
"Friendly hosts and excellent location to walk to downtown."
United States
Joshua
Central Large 2-bedrooms with office in Keene
A blue house with a porch, a wooden bench, and a door.

2. 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
9.4 out of 10, Exceptional, (11 reviews)
"Very satisfied with the stay . Clean quiet and relaxing stay."
United States
JAMES S.
The price is ￥10,156
￥32,528 total
includes taxes & fees
Nov 3 - Nov 4
Charming Country-Chic 1BR in Greenfield – King Bed, Rain Shower, Near Berkshires
A house with a staircase leading to a porch, surrounded by snow and string lights.

3. 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, (13 reviews)
"Nice place"
United States
Tom
The price is ￥31,766
￥40,038 total
includes taxes & fees
Oct 26 - Oct 27
Light-filled treetop apartment close to downtown Greenfield and Highland Park
A two-story house with a front porch, a staircase leading to the entrance, and a well-maintained garden.

4. 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 ￥14,432
￥28,210 total
includes taxes & fees
Oct 25 - Oct 26
2 Twin beds on 1st floor with En-suite bathroom.
A house entrance with a mailbox labeled '9B Mail', a wooden door, and a brick wall interior visible through the open door.

5. 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, (47 reviews)
"Wonderful stay! Amazing location!"
United States
Basmattee B.
The price is ￥15,687
￥28,935 total
includes taxes & fees
Nov 17 - Nov 18
Studio Apt with Full Kitchen. 1 minute stroll over picturesque bridge into town.
A living room with a beige sofa, a patterned rug, and a wooden floor.

6. Spacious & Cozy Ground Floor 2/3 Bed private suite

Spacious & Cozy Ground Floor 2/3 Bed private suite
Shelburne Falls
9.6 out of 10, Exceptional, (5 reviews)
"Wonderful property with an exceptional host!"
United States
Russ D.
The price is ￥25,256
￥56,599 total
includes taxes & fees
Nov 16 - Nov 17
Spacious & Cozy Ground Floor 2/3 Bed private suite
A two-story house with a front porch, a staircase leading to the entrance, and a large tree in the foreground.

7. Rose room Victorian home queen bed private bath

Rose room Victorian home queen bed private bath
Shelburne Falls
8.0 out of 10, Very good, (1 review)
"Very cute and welcoming B&B guest house. It was not clear to me that our private bathroom was across the hall. Some are and some not so check for that."
United States
Mikaela M.
The price is ￥16,236
￥30,401 total
includes taxes & fees
Oct 25 - Oct 26
Rose room Victorian home queen bed private bath
A two-story house with a front porch, a staircase leading to the entrance, and a large tree in the foreground.

8. Balcony Room in Victorian Home private bath

Balcony Room in Victorian Home private bath
Shelburne Falls
The price is ￥17,138
￥31,584 total
includes taxes & fees
Oct 25 - Oct 26
Balcony Room in Victorian Home private bath
A cozy living room with a fireplace, leather sofas, and a television mounted on the wall.

9. 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
8.8 out of 10, Excellent, (6 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 ￥57,050
￥101,110 total
includes taxes & fees
Oct 27 - Oct 28
Stay in this historic Automotive-themed huge Apt. Located in charming Whitingham
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

Otherland Hotel

Otherland Hotel

10/10 Excellent
"Love the Nordik style accommodations and very comfortable bed!"
Debi 1-night trip
Posted 3 hours ago
Otherland Hotel

Find out more about Winchester

Winchester Apartments information

Number of reviews
92
Accommodation
41 Apartments
Lowest Price
￥28,210
Highest Price
￥101,110

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?
Here are some of the top apartments in the area: Studio Apt with Full Kitchen. 1 minute stroll over picturesque bridge into town.: Situated in Peterborough, 23.2 mi/37.4 km from the heart of Winchester. Includes free WiFi and Smart TVs. Lakefront Orange Vacation Rental - Pet Friendly!: Located 12.1 mi/19.4 km away in Orange. Amenities include fireplaces. Quiet Neighborhood, For Bird Lovers: It's located in South Deerfield, 22.4 mi/36.1 km away. Charming Country-Chic 1BR in Greenfield – King Bed, Rain Shower, Near Berkshires: Located 16.6 mi/26.7 km away in Greenfield. Private patios and Smart TVs are included. Access to onsite laundry facilities is available on site.
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 Cass Pond are a couple of lovely local spots to get outside and enjoy nature. Winchester Speedpark and New England Sweetwater Farm & Distillery are other places to visit while you're in town.