Photo by Donny Campos

Search Apartments in Winchester

Start date: Check-in selected.
End date: Check-out
    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
19 Sep - 21 Sep
In two months
31 Oct - 2 Nov
In three months
28 Nov - 30 Nov
In four months
26 Dec - 28 Dec

Apartments in Winchester

Our top choices for Winchester apartments

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

Studio Apt with Full Kitchen. 1 minute stroll over picturesque bridge into town.

9.8 out of 10, Exceptional, (22)
"great location"
The price is AED 364
AED 674 total
includes taxes & fees
7 Sep - 8 Sep
Studio Apt with Full Kitchen. 1 minute stroll over picturesque bridge into town.
Lake Whitingham & Mount Snow Area Village Apartment
Property grounds

Lake Whitingham & Mount Snow Area Village Apartment

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."
The price is AED 514
AED 1,119 total
includes taxes & fees
4 Sep - 5 Sep
Lake Whitingham & Mount Snow Area Village Apartment
Spacious & Cozy Ground Floor 2/3 Bed private suite
Property grounds

Spacious & Cozy Ground Floor 2/3 Bed private suite

2.0 star property
10.0 out of 10, Exceptional, (2)
"Great property and location for a visit to Shelburne Falls. "
Spacious & Cozy Ground Floor 2/3 Bed private suite
Cozy apt in beautiful secluded spot 15 mins from Mt Snow
Property grounds

Cozy apt in beautiful secluded spot 15 mins from Mt Snow

10.0 out of 10, Exceptional, (3)
"There was a little problem with the lockbox, but Catherine was available to help solve it. We were staying in the house instead of the “cozy apartment.” Except for a somewhat difficult staircase and a couple of doors to the deck that did not have screens, we have no complaints. They location was beautiful, but a bit of a distance from places we wanted to go to. The price was very fair, and I would recommend this location to others."
The price is AED 312
AED 747 total
includes taxes & fees
30 Sep - 1 Oct
Cozy apt in beautiful secluded spot 15 mins from Mt Snow
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Winchester Hotel Reviews

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: Riverside Retreat – Cozy 2-Story Getaway!: Situated in Montague, 14.5 mi/23.3 km from the heart of Winchester. Includes free WiFi, private patios, and Smart TVs. Studio Apt with Full Kitchen. 1 minute stroll over picturesque bridge into town.: Located 23.2 mi/37.4 km away in Peterborough. Free WiFi and Smart TVs are included. Riverfront 2 Bedroom Unit 2: It's situated in Montague, 14.5 mi/23.3 km away. Includes Smart TVs. Lakefront Orange Vacation Rental - Pet Friendly!: 12.1 mi/19.4 km away in Orange. Amenities include fireplaces. Deck, Mountain Views: Colorful Retreat in Vernon!: It's located in Vernon, 8.3 mi/13.4 km from Winchester. Includes private patios.
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. Richmond Wildlife Manangement Area and Rhododendron State Park 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.