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
Aug 21 - Aug 23
In two months
Oct 2 - Oct 4
In three months
Oct 30 - Nov 1
In four months
Nov 27 - Nov 29

Our top choices for Winchester apartments

Exterior

1. 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, (10 reviews)
"Nice place"
United States
Tom
The price is CA $316
CA $403 total
includes taxes & fees
Aug 12 - Aug 13
Light-filled treetop apartment close to downtown Greenfield and Highland Park
Exterior detail

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
9.6 out of 10, Exceptional, (9 reviews)
"We had a great"
United States
Meredith B.
The price is CA $187
CA $411 total
includes taxes & fees
Aug 31 - Sep 1
Charming Country-Chic 1BR in Greenfield – King Bed, Rain Shower, Near Berkshires
1 bedroom, desk, iron/ironing board, WiFi

3. Balcony Room in Victorian Home private bath

Balcony Room in Victorian Home private bath
Shelburne Falls
The price is CA $167
CA $300 total
includes taxes & fees
Aug 30 - Aug 31
Balcony Room in Victorian Home private bath
Living area

4. 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 CA $298
CA $605 total
includes taxes & fees
Aug 24 - Aug 25
Spacious & Cozy Ground Floor 2/3 Bed private suite
Living area

5. 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 CA $461
CA $828 total
includes taxes & fees
Aug 6 - Aug 7
Stay in this historic Automotive-themed huge Apt. Located in charming Whitingham
Exterior

6. Rose room Victorian home queen bed private bath

Rose room Victorian home queen bed private bath
Shelburne Falls
The price is CA $146
CA $273 total
includes taxes & fees
Aug 26 - Aug 27
Rose room Victorian home queen bed 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 CA $171
CA $301 total
includes taxes & fees
Aug 17 - Aug 18
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

Vikings Villages Resort

Vikings Villages Resort

10/10 Excellent
"Super fun environment. Wish we had more time to stay there. In the middle of nowhere yet still close to food places and other activities."
Kathleen 1-night trip
Posted 11 hours ago
Vikings Villages Resort

Find out more about Winchester

Winchester Apartments information

Number of reviews
18
Accommodation
42 Apartments
Lowest Price
CA $272
Highest Price
CA $828

Frequently asked questions

What's it like to stay at an apartment in Winchester?
You'll find 6 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 more popular apartments in the area: Lake-View Spofford Apartment w/ Shared Dock!: Situated in Spofford, 9.5 mi/15.4 km from the heart of Winchester. Lakefront Orange Vacation Rental - Pet Friendly!: It's situated in Orange, 12.1 mi/19.4 km away. Includes fireplaces. HeART Barn, 35-60 m. to skiing @ Mt. Snow, Stratton, Okemo, Magic & Bromley: It's located in Brattleboro, 13.8 mi/22.2 km from Winchester. Includes free WiFi.
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. Cass Pond 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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