Winchester apartments
We found 57 apartments — enter your dates for availability
Explore Winchester condo rentals

Peaceful Mountain View Retreat
Sleeps 4 · 2 bedrooms · 1 bathroom

Riverfront 2 floors 2 Bedrooms
Sleeps 5 · 2 bedrooms · 1 bathroom

Cozy 1-bdrm apartment in Colonial Home in Richmond, NH.
Sleeps 2 · 1 bedroom · 1 bathroom

Deck, Mountain Views: Colorful Retreat in Vernon!
Sleeps 5 · 2 bedrooms · 2 bathrooms

Studio w/ Trail Access ~ 10 Mi to Brattleboro!
Sleeps 2 · 1 bathroom

Unique second floor Private Studio with Coded Locks
Sleeps 2 · 1 bedroom · 1 bathroom
Find spaces that suit your style
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- More quality timeFrom booking to staying, the whole process is simple and enjoyable
- All the privacy of homeEnjoy full kitchens, laundry, pools, gardens and more
- More for lessMore space, more privacy, more amenities — more value
Frequently asked questions
What's it like to stay at an apartment in Winchester?
You'll find 6 accommodation options in Winchester. Though there aren't many apartments, we can help you find accommodation with similar amenities. When you search for a place to stay on Expedia, you can use the filters to search for a kitchen— one of the conveniences often found in an apartment. You can also filter by similar property types like holiday homes, condos or guest houses. Why not take time to appreciate the lakeside during your visit?
How do you know if an apartment is the right choice for you?
Offering a kitchen for convenient meals, an apartment is often more spacious than a traditional hotel room. Apartments are a good option for couples who want to live like locals, but also for families wanting the conveniences of home.
What will the weather be like in 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 temperature of 19°C, while the coldest months are January and February, with an average of -2°C. The snowiest months in Winchester are January, March, February and November, with each month seeing an average of 26 cm 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.
