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
Oct 2 - Oct 4
In two months
Nov 13 - Nov 15
In three months
Dec 11 - Dec 13
In four months
Jan 8 - Jan 10

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)
"Super clean and nice space with beautifully updated bathroom and kitchen. Loved staying here."
United States
Andrew R.
The price is CA $154
CA $372 total
includes taxes & fees
Sep 21 - Sep 22
Charming Country-Chic 1BR in Greenfield – King Bed, Rain Shower, Near Berkshires
Exterior

2. Central Large 2-bedrooms with office in Keene

Central Large 2-bedrooms with office in Keene
Keene
9.8 out of 10, Exceptional, (6 reviews)
"Friendly hosts and excellent location to walk to downtown."
United States
Joshua
The price is CA $176
CA $222 total
includes taxes & fees
Sep 21 - Sep 22
Central Large 2-bedrooms with office in Keene
Exterior detail

3. 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, (44 reviews)
"Wonderful stay! Amazing location!"
United States
Basmattee B.
The price is CA $137
CA $241 total
includes taxes & fees
Sep 21 - Sep 22
Studio Apt with Full Kitchen. 1 minute stroll over picturesque bridge into town.
Exterior

4. 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 CA $315
CA $398 total
includes taxes & fees
Sep 21 - Sep 22
Light-filled treetop apartment close to downtown Greenfield and Highland Park
Exterior

5. Rose room Victorian home queen bed private bath

Rose room Victorian home queen bed private bath
Shelburne Falls
The price is CA $145
CA $270 total
includes taxes & fees
Sep 21 - Sep 22
Rose room Victorian home queen bed private bath
Exterior

6. 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 $129
CA $252 total
includes taxes & fees
Sep 21 - Sep 22
2 Twin beds on 1st floor with En-suite bathroom.
Living area

7. 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 $295
CA $599 total
includes taxes & fees
Sep 28 - Sep 29
Spacious & Cozy Ground Floor 2/3 Bed private suite
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 CA $458
CA $834 total
includes taxes & fees
Oct 3 - Oct 4
Stay in this historic Automotive-themed huge Apt. Located in charming Whitingham
1 bedroom, desk, iron/ironing board, WiFi

9. Balcony Room in Victorian Home private bath

Balcony Room in Victorian Home private bath
Shelburne Falls
The price is CA $159
CA $289 total
includes taxes & fees
Sep 28 - Sep 29
Balcony Room in Victorian Home 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.
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Top Winchester Hotel Reviews

Best Western Plus Keene Hotel

Best Western Plus Keene Hotel

10/10 Excellent
"Everything was excellent and will definitely come back"
robert 1-night trip
Posted 13 hours ago
Best Western Plus Keene Hotel

Find out more about Winchester

Winchester Apartments information

Number of reviews
75
Accommodation
42 Apartments
Lowest Price
CA $222
Highest Price
CA $834

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 top apartments in the area: Studio Apt with Full Kitchen. 1 minute stroll over picturesque bridge into town.: Situated in Peterborough, 23.2 mi/37.4 km from the heart of Winchester. Includes free WiFi and Smart TVs. Lakefront Orange Vacation Rental - Pet Friendly!: Located 12.1 mi/19.4 km away in Orange. Amenities include fireplaces. Lakeside Spofford Retreat Near Hiking & Boating!: It's located in Spofford, 9.5 mi/15.4 km away. Charming Country-Chic 1BR in Greenfield – King Bed, Rain Shower, Near Berkshires: Located 16.6 mi/26.7 km away in Greenfield. Private patios and Smart TVs are included. Access to onsite laundry facilities is available on site. Quiet Neighborhood, For Bird Lovers: It's situated in South Deerfield, 22.4 mi/36.1 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. Birch Point and Cass Pond are a couple of lovely local spots to get outside and enjoy nature. Winchester Speedpark and New England Sweetwater Farm & Distillery are other places to visit while you're in town.

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