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

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
The price is €205
includes taxes & fees
31 Oct - 1 Nov
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 €189
includes taxes & fees
3 Nov - 4 Nov
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 €234
includes taxes & fees
26 Oct - 27 Oct
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 €164
includes taxes & fees
25 Oct - 26 Oct
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 €172
includes taxes & fees
9 Nov - 10 Nov
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 €321
includes taxes & fees
9 Nov - 10 Nov
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 €176
includes taxes & fees
25 Oct - 26 Oct
Rose room Victorian home queen bed private bath
Room

8. Balcony Room in Victorian Home private bath

Balcony Room in Victorian Home private bath
Shelburne Falls
The price is €182
includes taxes & fees
25 Oct - 26 Oct
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 €573
includes taxes & fees
26 Oct - 27 Oct
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

Vikings Villages Resort

Vikings Villages Resort

10/10 Excellent
"This is a unique property. Perfect for getting away. Quite, very little to do on the property which is perfect for a truely relaxing get away. Kitchen is set up for cooking your own meals. There is no food available on the premises but a great breakfast spot close by and Brattleboro is also an easy drive away."
Tom 2-night trip
Posted less than an hour ago
Vikings Villages Resort

Find out more about Winchester

Winchester Apartments information

Number of reviews
92
Accommodation
42 Apartments
Lowest Price
€164
Highest Price
€573

Frequently asked questions

What's it like to stay at an apartment in Winchester?
You'll find 6 accommodation options in Winchester. Though there aren't many apartments, we can help you find accommodation with similar amenities. When you search for a place to stay on Expedia, you can use the filters to search for a kitchen— one of the conveniences often found in an apartment. You can also filter by similar property types like holiday homes, condos or guest houses. Why not take time to appreciate the lakeside during your visit?
How do you know if an apartment is the right choice for you?
Offering a kitchen for convenient meals, an apartment is often more spacious than a traditional hotel room. Apartments are a good option for couples who want to live like locals, but also for families wanting the conveniences of home.
What's a favourite apartment I should consider for a stay in Winchester?
Listed below are some of the top apartments in the area to choose from: 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 a Smart TV . Lakefront Orange Vacation Rental - Pet Friendly!: Located 12.1 mi/19.4 km away in Orange . Amenities include a fireplace . 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 . A patio and a Smart TV are included . Access to on-site laundry facilities is available on site .
What will the weather be like in 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 temperature of 19°C, while the coldest months are January and February, with an average of -2°C. The snowiest months in Winchester are January, March, February and November, with each month seeing an average of 26 cm 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.