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

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 €268
includes taxes & fees
15 Aug - 16 Aug
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 €228
includes taxes & fees
27 Jul - 28 Jul
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 €165
includes taxes & fees
26 Jul - 27 Jul
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 €173
includes taxes & fees
17 Aug - 18 Aug
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 €563
includes taxes & fees
26 Jul - 27 Jul
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 €173
includes taxes & fees
17 Aug - 18 Aug
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

The Colonial Hotel

The Colonial Hotel

10/10 Excellent
"👍"
Kevin 2-night trip
Posted less than an hour ago
The Colonial Hotel

Find out more about Winchester

Winchester Apartments information

Number of reviews
60
Accommodation
44 Apartments
Lowest Price
€165
Highest Price
€563

Frequently asked questions

What's it like to stay at an apartment in Winchester?
You'll find 7 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: 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 . A balcony and in-room jetted baths 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 a Smart TV are included .
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. 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.