Search Apartments in Winchester

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
26 Jun - 28 Jun
In two months
7 Aug - 9 Aug
In three months
4 Sept - 6 Sept
In four months
2 Oct - 4 Oct

Our top choices for Winchester apartments

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, (35 reviews)
"Wonderful stay! Amazing location!"
United States
Basmattee B.
The price is €176
includes taxes & fees
14 Jun - 15 Jun
Studio Apt with Full Kitchen. 1 minute stroll over picturesque bridge into town.
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 €161
includes taxes & fees
22 Jun - 23 Jun
2 Twin beds on 1st floor with En-suite bathroom.
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, (8 reviews)
"Super clean and nice space with beautifully updated bathroom and kitchen. Loved staying here."
United States
Andrew R.
The price is €204
includes taxes & fees
16 Jun - 17 Jun
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, (6 reviews)
"Nice place"
United States
Tom
The price is €253
includes taxes & fees
22 Jun - 23 Jun
Light-filled treetop apartment close to downtown Greenfield and Highland Park
Interior

Cozy apt in beautiful secluded spot 15 mins from Mt Snow

Cozy apt in beautiful secluded spot 15 mins from Mt Snow
Dover
10.0 out of 10, Exceptional, (4 reviews)
"Cozy little spot that had everything we needed. Peaceful, quiet, and once the rain let up on our stay we walked out to the gorgeous little pond on the property. So serene. Catherine was great!"
United States
Erica H.
Cozy apt in beautiful secluded spot 15 mins from Mt Snow
Terrace/patio

Terrific 3-bedroom unit in charming Leverett with AC

Terrific 3-bedroom unit in charming Leverett with AC
Leverett
10.0 out of 10, Exceptional, (2 reviews)
"The apartment is lovely, so comfortable and quiet!! Caitlin was a wonderful host, very responsive. Would absolutely stay again! "
United States
Anna B.
The price is €421
includes taxes & fees
9 Jun - 10 Jun
Terrific 3-bedroom unit in charming Leverett with AC
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
8.8 out of 10, Excellent, (3 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 €504
includes taxes & fees
21 Jun - 22 Jun
Stay in this historic Automotive-themed huge Apt. Located in charming Whitingham
Exterior

Rose wisteria 4 guests 2 bedrooms-full+queen beds

Rose wisteria 4 guests 2 bedrooms-full+queen beds
Shelburne Falls
The price is €268
includes taxes & fees
10 Jun - 11 Jun
Rose wisteria 4 guests 2 bedrooms-full+queen beds
Exterior

Rose room Victorian home queen bed private bath

Rose room Victorian home queen bed private bath
Shelburne Falls
The price is €171
includes taxes & fees
10 Jun - 11 Jun
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Winchester Hotel Reviews

Comfort Inn & Suites Brattleboro I-91

Comfort Inn & Suites Brattleboro I-91

10/10 Excellent
"Nice clean spot"
Nicolas 1-night trip
Posted 10 hours ago
Comfort Inn & Suites Brattleboro I-91

Find out more about Winchester

Winchester Apartments information

Number of reviews
58
Accommodation
40 Apartments
Lowest Price
€161
Highest Price
€504

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?
Below are some of the more popular apartments in the area: 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 . Lake-View Spofford Apartment w/ Shared Dock!: It's located in Spofford , 9.5 mi/15.4 km away. Beautiful Townhouse In Turners Falls!: Located 14.7 mi/23.7 km away in Montague . A washer/dryer and a balcony 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. Rhododendron State Park and Loring Field are a couple of lovely local spots to get outside and enjoy nature. New England Sweetwater Farm & Distillery and Winchester Speedpark are other places to visit while you're in town.