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Check prices for these dates

Next weekend
16 Jan - 18 Jan
In two weeks
23 Jan - 25 Jan
In one month
6 Feb - 8 Feb
In two months
6 Mar - 8 Mar

Our top choices for Winchester apartments

Property grounds
Lake Whitingham & Mount Snow Area Village Apartment

Lake Whitingham & Mount Snow Area Village Apartment

Lake Whitingham & Mount Snow Area Village Apartment
2.0 star property
Whitingham
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.
The price is AED 514
AED 1,119 total
includes taxes & fees
9 Jan - 10 Jan
Lake Whitingham & Mount Snow Area Village Apartment
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.

Studio Apt with Full Kitchen. 1 minute stroll over picturesque bridge into town.
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
The price is AED 298
AED 602 total
includes taxes & fees
8 Jan - 9 Jan
Studio Apt with Full Kitchen. 1 minute stroll over picturesque bridge into town.
Terrace/patio
Terrific 3-bedroom unit in charming Leverett with AC

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)
"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 AED 826
AED 1,735 total
includes taxes & fees
8 Jan - 9 Jan
Terrific 3-bedroom unit in charming Leverett with AC
Interior
Cozy apt in beautiful secluded spot 15 mins from Mt Snow

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)
"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 AED 312
AED 755 total
includes taxes & fees
31 Jan - 1 Feb
Cozy apt in beautiful secluded spot 15 mins from Mt Snow
Exterior
2 Twin beds on 1st floor with En-suite bathroom.

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 AED 323
AED 644 total
includes taxes & fees
11 Jan - 12 Jan
2 Twin beds on 1st floor with En-suite bathroom.
Exterior
Rose wisteria 4 guests 2 bedrooms-full+queen beds

Rose wisteria 4 guests 2 bedrooms-full+queen beds

Rose wisteria 4 guests 2 bedrooms-full+queen beds
Shelburne Falls
The price is AED 545
AED 1,019 total
includes taxes & fees
11 Jan - 12 Jan
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

Holiday Inn Express Hotel & Suites Brattleboro by IHG

Holiday Inn Express Hotel & Suites Brattleboro by IHG

10/10 Excellent
"Clean. Friendly staff. Corn Chowder in the lobby!"
Margaret 1-night trip
Posted 1 day ago
Holiday Inn Express Hotel & Suites Brattleboro by IHG

Frequently asked questions

What's it like to stay at an apartment in Winchester?
You'll find 8 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: Beautiful Townhouse In Turners Falls!: Located in Montague, 14.7 mi/23.7 km from the heart of Winchester. Includes laundry facilities and private balconies. Access to onsite laundry facilities is available on site. Studio Apt with Full Kitchen. 1 minute stroll over picturesque bridge into town.: It's situated in Peterborough, 23.2 mi/37.4 km away. Includes free WiFi and Smart TVs. Spacious & Cozy Ground Floor 2/3 Bed private suite: 21.4 mi/34.4 km away in Shelburne Falls. Amenities include sofa beds. Charming Country-Chic 1BR in Greenfield – King Bed, Rain Shower, Near Berkshires: It's situated in Greenfield, 16.6 mi/26.7 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 Barden State Wildlife Management Area are a couple of lovely local spots to get outside and enjoy nature. Pisgah State Park and Ashuelot River are other places to visit while you're in town.