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Check prices for these dates

In two weeks
Jun 12 - Jun 14
In two months
Jul 24 - Jul 26
In three months
Aug 21 - Aug 23
In four months
Sep 18 - Sep 20

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)
"Fully equipped kitchen, comfortable open floor plan, easy walk to downtown and very hospitable—thank you—we’d like to stay here again next year!"
United States
Mark
The price is CA $124
CA $240 total
includes taxes & fees
May 26 - May 27
Studio Apt with Full Kitchen. 1 minute stroll over picturesque bridge into town.
Exterior

Rose wisteria 4 guests 2 bedrooms-full+queen beds

Rose wisteria 4 guests 2 bedrooms-full+queen beds
Shelburne Falls
The price is CA $224
CA $426 total
includes taxes & fees
May 26 - May 27
Rose wisteria 4 guests 2 bedrooms-full+queen beds
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 CA $168
CA $387 total
includes taxes & fees
May 31 - Jun 1
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
9.6 out of 10, Exceptional, (5 reviews)
"Nice place"
United States
Tom
The price is CA $202
CA $256 total
includes taxes & fees
Jun 22 - Jun 23
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.
The price is CA $117
CA $283 total
includes taxes & fees
May 31 - Jun 1
Cozy apt in beautiful secluded spot 15 mins from Mt Snow
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 CA $503
CA $891 total
includes taxes & fees
May 26 - May 27
Stay in this historic Automotive-themed huge Apt. Located in charming Whitingham
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, (1 review)
"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 CA $311
CA $662 total
includes taxes & fees
May 26 - May 27
Terrific 3-bedroom unit in charming Leverett with AC
Exterior

Rose room Victorian home queen bed private bath

Rose room Victorian home queen bed private bath
Shelburne Falls
The price is CA $143
CA $269 total
includes taxes & fees
May 26 - May 27
Rose room Victorian home queen bed private bath
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 CA $127
CA $248 total
includes taxes & fees
May 27 - May 28
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
"The room was comfortable and the bed was excellent. Bathroom had a lack of counter space. There was a good bit of noise from people walking upstairs."
Melvin 2-night trip
Posted 11 hours ago
The Colonial Hotel

Find out more about Winchester

Winchester Apartments information

Number of reviews
56
Accommodation
40 Apartments
Lowest Price
CA $240
Highest Price
CA $891

Frequently asked questions

What's it like to stay at an apartment in Winchester?
You'll find 7 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: Light-filled treetop apartment close to downtown Greenfield and Highland Park: Located 16.8 mi/27.1 km away in Greenfield. Amenities include private balconies. 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 Smart TVs are included. Stay in this historic Automotive-themed huge Apt. Located in charming Whitingham: It's situated in Jacksonville, 22.3 mi/35.9 km from Winchester.
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. Rhododendron State Park and Loring Field 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.

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