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Search Apartments in Winchester

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Compare 18 Apartments in Winchester with updated reviews, rates, and availability.

Lakefront Orange Vacation Rental - Pet Friendly!
Orange Vacation Rental | 1BR | 1BA | 902 Sq Ft | Access Only By Stairs
Lakefront Orange Vacation Rental - Pet Friendly!
10.0 out of 10, Exceptional, (8)
"It’s a wonderful place to stay!!"
Lakefront Orange Vacation Rental - Pet Friendly!
Updated Vintage Apartment < 1/2 Mi to Main St
Keene Vacation Rental | 2BR | 1BA | 1,100 Sq Ft | Steps Required for Entry
Updated Vintage Apartment < 1/2 Mi to Main St
9.8 out of 10, Exceptional, (8)
"Place is great! Pricing is deceiving…fees were double the actual rent. Small ramp from kitchen to living room is dangerous!"
Updated Vintage Apartment < 1/2 Mi to Main St
Unique People & Pet-Welcoming Country Haven
Cavalier Cottage, a superb getaway for all seasons and reasons!
Unique People & Pet-Welcoming Country Haven
9.8 out of 10, Exceptional, (198)
"Patricia was gracious and welcoming and her property was lovely. My mother and stepfather had a great stay. Thank you."
Unique People & Pet-Welcoming Country Haven
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Quiet Neighborhood, For Bird Lovers
Golf
Quiet Neighborhood, For Bird Lovers
10.0 out of 10, Exceptional, (42)
"We booked the cottage for our son's graduation weekend at Deerfield Academy. It was clean, well-appointed, and close to the school. We had everything we needed and more. The fridge was stocked with snacks and breakfast items. The master bedroom was spacious, and the bed was super comfortable. The pullout was perfect for our son who was with us. It is a beautiful property and gracious owners. Thank you so much! Hope to be back for our next graduation weekend."
Quiet Neighborhood, For Bird Lovers
Studio Apt with Full Kitchen. 1 minute stroll over picturesque bridge into town.
Exterior
Studio Apt with Full Kitchen. 1 minute stroll over picturesque bridge into town.
10.0 out of 10, Exceptional, (2)
"Very clean and centrally located in Peterborough. Check in was flexible and easy. Hosts were very friendly."
Studio Apt with Full Kitchen. 1 minute stroll over picturesque bridge into town.
'Red Sweetheart Barn Studio' w/ Mtn & River Views!
Westminster Vacation Rental | Studio | 1BA | Stairs Required | 500 Sq Ft
'Red Sweetheart Barn Studio' w/ Mtn & River Views!
10.0 out of 10, Exceptional, (3)
"It was cozy and beautiful and very inviting loved every part"
'Red Sweetheart Barn Studio' w/ Mtn & River Views!
"The Murdock Suite @ The Large House"
Interior
"The Murdock Suite @ The Large House"
9.6 out of 10, Exceptional, (4)
"This was a great place to stay for an extended weekend while attending a family event. Swanzey is literally 5 miles from from Keene, NH. The 2 bed upstairs unit offered plenty of seating in both the (very comfortable) living room and the nice sized (6 seat) dining room. The bedrooms were nearly identical and the Americana decor is fresh. The mattresses were comfortable. Having laundry available was a great relief. The finishes are beautiful and the basic supplies were “spot on”. The owner...
"The Murdock Suite @ The Large House"
Studio Close to Downtown w/ Trail Access
Sofa turns into a comfy sleeper (for one person, twin size)
Studio Close to Downtown w/ Trail Access
Studio Close to Downtown w/ Trail Access
HeART Barn, 35-60 m. to skiing @ Mt. Snow, Stratton, Okemo, Magic & Bromley
Living area
HeART Barn, 35-60 m. to skiing @ Mt. Snow, Stratton, Okemo, Magic & Bromley
10.0 out of 10, Exceptional, (1)
"The apartment is charming. Very clean, with everything I needed for a nice stay. The bed was very comfortable and the building was very quiet. I can’t wait to go back."
HeART Barn, 35-60 m. to skiing @ Mt. Snow, Stratton, Okemo, Magic & Bromley
1 BR Apt in Wilmington
Exterior
1 BR Apt in Wilmington
10.0 out of 10, Exceptional, (1)
"Clean and comfy and near the mtn!"
1 BR Apt in Wilmington
The Covey House 2BR Apt
Master bedroom, queen bed, overlooks village green. Large closet and dresser
The Covey House 2BR Apt
10.0 out of 10, Exceptional, (1)
"We thoroughly enjoyed the spaciousness of this apartment. Plentiful amenities make it feel like a home away from home. Very comfortable beds. Multiple tables and abundant chairs for meals and board games. Lots of closet space. We cooked many of our meals in and enjoyed them in the comfort of the apartment which includes a full dining room. The hosts were attentive, helpful, and friendly. We’re looking forward to returning again in a couple months."
The Covey House 2BR Apt
Updated Vintage Apartment < 1/2 Mi to Main St
Living area
Updated Vintage Apartment < 1/2 Mi to Main St
3.0 star property
Updated Vintage Apartment < 1/2 Mi to Main St
Quiet New England neighborhood-Greenfield, Ma.
Exterior
Quiet New England neighborhood-Greenfield, Ma.
10.0 out of 10, Exceptional, (5)
"The property was very clean and had everything I would ever need. The landlord was very nice and took care of trash weekly! A perfect stay"
Quiet New England neighborhood-Greenfield, Ma.
The Covey House Retreat with InfraRed Sauna
Room
The Covey House Retreat with InfraRed Sauna
The Covey House Retreat with InfraRed Sauna
'red Sweetheart Barn Studio' w/ Mtn & River Views!
View from property
'red Sweetheart Barn Studio' w/ Mtn & River Views!
3.0 star property
'red Sweetheart Barn Studio' w/ Mtn & River Views!
Relax peacefully in Gardner Ma, near Mt Wachusett
Private kitchen
Relax peacefully in Gardner Ma, near Mt Wachusett
Relax peacefully in Gardner Ma, near Mt Wachusett
The Pines Cabin | New Tiny Home Near Mt Snow!
The Pines Cabin | New Tiny Home Near Mt Snow!
The Pines Cabin | New Tiny Home Near Mt Snow!
Lakefront Orange Vacation Rental - Pet Friendly!
Living area
Lakefront Orange Vacation Rental - Pet Friendly!
3.0 star property
Lakefront Orange Vacation Rental - Pet Friendly!
Don't see what you're looking for?
See all available properties in Winchester
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.

Other property types in Winchester

Charming Waterfront Log Cabin
Property grounds
Charming Waterfront Log Cabin
9.8 out of 10, Exceptional, (27)
"This cabin is so wonderful. The linens are exquisite and the beds are super comfortable. It is decorated so cute. There is everything you need! My favorite activity was sitting in the wooden rocking chair on the front porch each morning, drinking coffee, listening to nature (frogs, fish), and watching the lovely pond (which is so big it should be called a lake!) The owner responded to all my questions within minutes. You can even have pizza (regular AND gluten free) delivered!! If you visit, you...
The price is SAR 702
SAR 1,522 total
includes taxes & fees
18 Jum. II - 19 Jum. II
Charming Waterfront Log Cabin
Cozy 2-bedroom Unit with private backyard
Private kitchen
Cozy 2-bedroom Unit with private backyard
10.0 out of 10, Exceptional, (11)
"Very clean and neat if in the area again would definitely stay here again."
Cozy 2-bedroom Unit with private backyard
VRBO Top 10 of 2024!- Copley's Lakefront Cottage on Lake Monomonac
Exterior
VRBO Top 10 of 2024!- Copley's Lakefront Cottage on Lake Monomonac
10.0 out of 10, Exceptional, (5)
"Copley Cottage was phenomenal! Our group included family from Los Angeles, Pa and NJ. We wanted to introduce our newest family member to great grandpa who lives in the area. We were impressed with the design and lay out of the house. . High end kitchen and open concept made for easy enjoyable time together. Waking up to the views of the lake and area felt like a bit of paradise. The private beach, dock and sauna were outstanding additions. Overall a stay that will be remembered forever"
VRBO Top 10 of 2024!- Copley's Lakefront Cottage on Lake Monomonac
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.

Frequently asked questions

What's it like to stay at an apartment in Winchester?
You’ll find 5 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, April, and February, with each month seeing an average of 11 inches of snowfall.
What are the must-see places to visit in Winchester?
Winchester is known for its lakeside. Birch Point and Pisgah State Park are a couple of lovely local spots to get outside and enjoy nature. Rhododendron State Park and Ashuelot River are other places to visit while you’re in town.

Recent reviews of Winchester hotels
Expedia verified reviews

Days Inn by Wyndham Keene NH

Days Inn by Wyndham Keene NH

4/5 Good
"It was a convenient location for my trip and everything worked out great!"
A verified traveler stayed at Days Inn by Wyndham Keene NH
Posted 3 days ago
Days Inn by Wyndham Keene NH