Apartments in Winchester for Rent

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In two weeks
Dec 19 - Dec 21
In two months
Jan 30 - Feb 1
In three months
Feb 27 - Mar 1
In four months
Mar 27 - Mar 29

Apartments in Winchester

Fridge, microwave, oven, stovetop
Studio Apt with Full Kitchen. 1 minute stroll over picturesque bridge into town.

Apartment in Peterborough

9.8 out of 10, Exceptional, (30)
"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
$124 nightly
The price is $135
Dec 9 - Dec 10
Total with taxes and fees
Studio Apt with Full Kitchen. 1 minute stroll over picturesque bridge into town.
Exterior detail
Charming Country-Chic 1BR in Greenfield – King Bed, Rain Shower, Near Berkshires

Apartment in Greenfield

8.8 out of 10, Excellent, (3)
"We had an amazing stay! The property was spotless and comfortable. We felt right at home and can’t wait to stay here again! "
United States
Garth P.
$186 nightly
The price is $208
Dec 8 - Dec 9
Total with taxes and fees
Charming Country-Chic 1BR in Greenfield – King Bed, Rain Shower, Near Berkshires
Property grounds
Lake Whitingham & Mount Snow Area Village Apartment

Apartment in Whitingham

2.0 star property
10.0 out of 10, Exceptional, (1)
"This place was cozy and romantic, making it the perfect escape from the hustle and bustle of city life. The location is ideal, with charming New England towns to explore in every direction. Amy and Connor were exceptional hosts, checking in with us throughout our stay to ensure we felt right at home."
United States
Anicia K.
$273 nightly
The price is $306
Dec 8 - Dec 9
Total with taxes and fees
Lake Whitingham & Mount Snow Area Village Apartment
Property grounds
Cozy apt in beautiful secluded spot 15 mins from Mt Snow

Apartment in Dover

10.0 out of 10, Exceptional, (4)
"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.
$182 nightly
The price is $206
Dec 31 - Jan 1, 2026
Total with taxes and fees
Cozy apt in beautiful secluded spot 15 mins from Mt Snow
Exterior
2 Twin beds on 1st floor with En-suite bathroom.

Apartment in Shelburne Falls

$135 nightly
The price is $151
Dec 8 - Dec 9
Total with taxes and fees
2 Twin beds on 1st floor with En-suite bathroom.
Exterior
Terrific 3-bedroom unit in charming Leverett with AC

Apartment in Leverett

10.0 out of 10, Exceptional, (1)
"The apartment is lovely, so comfortable and quiet!! Caitlin was a wonderful host, very responsive. Would absolutely stay again! "
United States
Anna B.
$395 nightly
The price is $441
Dec 16 - Dec 17
Total with taxes and fees
Terrific 3-bedroom unit in charming Leverett with AC
Interior
Entire private apartment suite in home with own entrance, views and private gym.

Apartment in Keene

$363 nightly
The price is $394
Dec 28 - Dec 29
Total with taxes and fees
Entire private apartment suite in home with own entrance, views and private gym.
Exterior
Rose wisteria 4 guests 2 bedrooms-full+queen beds

Apartment in Shelburne Falls

$224 nightly
The price is $250
Dec 8 - Dec 9
Total with taxes and fees
Rose wisteria 4 guests 2 bedrooms-full+queen beds
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

Keene Elm City Hotel, an Ascend Collection Hotel

Keene Elm City Hotel, an Ascend Collection Hotel

10/10 Excellent
"The customer service at this hotel is consistently exceptional. Every staff member is friendly, professional, and welcoming, creating an atmosphere that feels truly comfortable. The property is impeccably clean, and the breakfast offerings are always enjoyable. I have had an excellent experience during each of my visits, and I highly recommend this hotel to others"
qader 2-night trip
Posted 7 days ago
Keene Elm City Hotel, an Ascend Collection Hotel

Find out more about Winchester

Winchester Apartments information

Number of reviews
35
Accommodation
35 Apartments
Lowest Price
$135
Highest Price
$441

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 is a popular apartment in the area to consider: Walk to Trails: Artsy Mtn-view Getaway in Vernon!: Located in Vernon, 8.3 mi/13.4 km from Winchester. Includes private patios. Access to free parking is available on site.
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 Ashuelot River 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.

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