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

Apartments in Winchester

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Check prices for these dates

In two weeks
25 Sept - 27 Sept
In two months
6 Nov - 8 Nov
In three months
4 Dec - 6 Dec
In four months
1 Jan - 3 Jan

Our top choices for Winchester apartments

Exterior detail

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
9.6 out of 10, Exceptional, (9 reviews)
"We had a great"
United States
Meredith B.
The price is AU$404
includes taxes & fees
21 Sept - 22 Sept
Charming Country-Chic 1BR in Greenfield – King Bed, Rain Shower, Near Berkshires
Exterior detail

2. 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
10.0 out of 10, Exceptional, (43 reviews)
"Wonderful stay! Amazing location!"
United States
Basmattee B.
The price is AU$267
includes taxes & fees
8 Sept - 9 Sept
Studio Apt with Full Kitchen. 1 minute stroll over picturesque bridge into town.
Exterior

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

Light-filled treetop apartment close to downtown Greenfield and Highland Park
Greenfield
10.0 out of 10, Exceptional, (12 reviews)
"Nice place"
United States
Tom
The price is AU$263
includes taxes & fees
18 Sept - 19 Sept
Light-filled treetop apartment close to downtown Greenfield and Highland Park
Exterior

4. Rose room Victorian home queen bed private bath

Rose room Victorian home queen bed private bath
Shelburne Falls
The price is AU$274
includes taxes & fees
10 Sept - 11 Sept
Rose room Victorian home queen bed private bath
Living area

5. 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)
"we had a wonderful"
United States
Rini A.
The price is AU$533
includes taxes & fees
9 Sept - 10 Sept
Spacious & Cozy Ground Floor 2/3 Bed private suite
1 bedroom, desk, iron/ironing board, WiFi

6. Balcony Room in Victorian Home private bath

Balcony Room in Victorian Home private bath
Shelburne Falls
The price is AU$292
includes taxes & fees
9 Sept - 10 Sept
Balcony Room in Victorian Home private bath
Exterior

7. 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 AU$252
includes taxes & fees
16 Sept - 17 Sept
2 Twin beds on 1st floor with En-suite bathroom.
Living area

8. 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, (5 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 AU$897
includes taxes & fees
8 Sept - 9 Sept
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

Comfort Inn & Suites Brattleboro I-91

Comfort Inn & Suites Brattleboro I-91

10/10 Excellent
"Clean & nice staff. Enjoyed our stay"
pam 1-night trip
Posted 22 hours ago
Comfort Inn & Suites Brattleboro I-91

Find out more about Winchester

Winchester Apartments information

Number of reviews
6,328
Accommodation
44 Apartments
Lowest Price
AU$145
Highest Price
AU$450

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: Charming Country-Chic 1BR in Greenfield – King Bed, Rain Shower, Near Berkshires: Located in Greenfield , 16.6 mi/26.7 km from the heart of Winchester. Includes a patio and a Smart TV . Access to on-site laundry facilities is available on site . Studio Apt with Full Kitchen. 1 minute stroll over picturesque bridge into town.: Located 23.2 mi/37.4 km away in Peterborough . Free WiFi and a Smart TV are included . Lakefront Orange Vacation Rental - Pet Friendly!: 12.1 mi/19.4 km away in Orange . Amenities include a fireplace . Lakeside Spofford Retreat Near Hiking & Boating!: It's situated in Spofford , 9.5 mi/15.4 km from Winchester.
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 Pisgah State Park are other places to visit while you're in town.