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

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Check prices for these dates

In two weeks
Nov 20 - Nov 22
In two months
Jan 1 - Jan 3
In three months
Jan 29 - Jan 31
In four months
Feb 26 - Feb 28

Our top choices for Winchester apartments

A blue house with a porch, a wooden bench, and a door.

1. 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 CA $121
CA $315 total
includes taxes & fees
Nov 9 - Nov 10
Charming Country-Chic 1BR in Greenfield – King Bed, Rain Shower, Near Berkshires
A two-story house with a front porch, a staircase leading to the entrance, and a well-maintained garden.

2. 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 CA $129
CA $241 total
includes taxes & fees
Nov 9 - Nov 10
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.

3. 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, (48 reviews)
"Wonderful stay! Amazing location!"
United States
Basmattee B.
The price is CA $134
CA $240 total
includes taxes & fees
Nov 30 - Dec 1
Studio Apt with Full Kitchen. 1 minute stroll over picturesque bridge into town.
A house with a staircase leading to a porch, surrounded by snow and string lights.

4. 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 CA $315
CA $383 total
includes taxes & fees
Nov 9 - Nov 10
Light-filled treetop apartment close to downtown Greenfield and Highland Park
A residential building with a wooden balcony and a window.

5. Two Bedroom Guesthouse near many attractions pet friendly with private deck

Two Bedroom Guesthouse near many attractions pet friendly with private deck
Gardner
10.0 out of 10, Exceptional, (3 reviews)
"Cute little guesthouse. Super clean and lovely decorated."
United States
Kristin R.
The price is CA $208
CA $436 total
includes taxes & fees
Dec 1 - Dec 2
Two Bedroom Guesthouse near many attractions pet friendly with private deck
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 CA $225
CA $486 total
includes taxes & fees
Nov 9 - Nov 10
Spacious & Cozy Ground Floor 2/3 Bed private suite
A cozy living room with a fireplace, leather sofas, and a television mounted on the wall.

7. 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
8.4 out of 10, Very good, (7 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 CA $509
CA $857 total
includes taxes & fees
Nov 9 - Nov 10
Stay in this historic Automotive-themed huge Apt. Located in charming Whitingham
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 CA $153
CA $266 total
includes taxes & fees
Nov 9 - Nov 10
Balcony Room in Victorian Home private bath
A two-story house with a front porch, a staircase leading to the entrance, and a large tree in the foreground.

9. 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 CA $145
CA $257 total
includes taxes & fees
Nov 9 - Nov 10
Rose room Victorian home queen bed private bath
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

The Putney Inn

The Putney Inn

10/10 Excellent
"Quiet, clean, safe area. Good breakfast- fruit, yogurt, waffles plus all the usual cereal, toast etc."
Martha 1-night trip
Posted 18 hours ago
The Putney Inn

Find out more about Winchester

Winchester Apartments information

Number of reviews
85
Accommodation
42 Apartments
Lowest Price
CA $240
Highest Price
CA $857

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.

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