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Check prices for these dates

In two weeks
30 Jan - 1 Feb
In two months
13 Mar - 15 Mar
In three months
10 Apr - 12 Apr
In four months
8 May - 10 May

Our top choices for Winchester apartments

Living area

Apartment in Shelburne Falls

Spacious Ground Floor 2/3 Bed private suite 5 minutes walk to Bridge of Flowers
2.0 star property
9.6 out of 10, Exceptional, (4 reviews)
"Great property and location for a visit to Shelburne Falls. "
United States
Kevin K.
The price is AED 566
AED 1,292 total
includes taxes & fees
18 Jan - 19 Jan
Spacious Ground Floor 2/3 Bed private suite 5 minutes walk to Bridge of Flowers
Property grounds

Apartment in Whitingham

Lake Whitingham & Mount Snow Area Village Apartment
2.0 star property
10.0 out of 10, Exceptional, (1 review)
"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 1,123 total
includes taxes & fees
18 Jan - 19 Jan
Lake Whitingham & Mount Snow Area Village Apartment
Exterior detail

Apartment in Peterborough

Studio Apt with Full Kitchen. 1 minute stroll over picturesque bridge into town.
9.8 out of 10, Exceptional, (31 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 AED 349
AED 658 total
includes taxes & fees
4 Feb - 5 Feb
Studio Apt with Full Kitchen. 1 minute stroll over picturesque bridge into town.
Terrace/patio

Apartment in Leverett

Terrific 3-bedroom unit in charming Leverett with AC
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 AED 826
AED 1,735 total
includes taxes & fees
18 Jan - 19 Jan
Terrific 3-bedroom unit in charming Leverett with AC
Exterior

Apartment in Shelburne Falls

2 Twin beds on 1st floor with En-suite bathroom.
The price is AED 323
AED 644 total
includes taxes & fees
19 Jan - 20 Jan
2 Twin beds on 1st floor with En-suite bathroom.
Living area

Apartment in Whitingham

Free HOT Breakfast for each guest everyday! Located in charming Whitingham
2.0 star property
The price is AED 1,203
AED 2,146 total
includes taxes & fees
19 Jan - 20 Jan
Free HOT Breakfast for each guest everyday! Located in charming Whitingham
Exterior

Apartment in Shelburne Falls

Rose wisteria 4 guests 2 bedrooms-full+queen beds
The price is AED 545
AED 1,007 total
includes taxes & fees
18 Jan - 19 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

Hampton Inn Brattleboro

Hampton Inn Brattleboro

10/10 Excellent
"Fantastic experience! Great staff! Very comfortable room. Thanks . "
Ronaldo 1-night trip
Posted 7 days ago
Hampton Inn Brattleboro

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 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 Barden State Wildlife Management Area are a couple of lovely local spots to get outside and enjoy nature. New England Sweetwater Farm & Distillery and Bennett Gorge are other places to visit while you're in town.