Photo by Donny Campos

Search Apartments in Winchester

  • Plan, book, stay with confidence

    • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Next weekend
31 Muh. - 2 Saf.
In two weeks
7 Saf. - 9 Saf.
In one month
21 Saf. - 23 Saf.
In two months
21 Rab. I - 23 Rab. I

Compare 23 Apartments in Winchester with updated reviews, rates, and availability.

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.

9.6 out of 10, Exceptional, (11)
"I stayed a few nights for a snowboarding trip for my birthday with my partner. Wonderful food spots bearby. The location was very clean, will return 10p percent."
The price is SAR 281
SAR 590 total
includes taxes & fees
10 Feb - 11 Feb
Studio Apt with Full Kitchen. 1 minute stroll over picturesque bridge into town.
Cozy 2-bedroom Unit with private backyard
Private kitchen

Cozy 2-bedroom Unit with private backyard

10.0 out of 10, Exceptional, (21)
"Small but very clean and had everything we needed for our stay "
Cozy 2-bedroom Unit with private backyard
Studio w/ Trail Access ~ 10 Mi to Brattleboro!
Exterior

Studio w/ Trail Access ~ 10 Mi to Brattleboro!

3.0 star property
Studio w/ Trail Access ~ 10 Mi to Brattleboro!
The Covey House Retreat with InfraRed Sauna
Room

The Covey House Retreat with InfraRed Sauna

10.0 out of 10, Exceptional, (3)
"We had an amazing stay, your place is awesome!"
The Covey House Retreat with InfraRed Sauna
Lake Whitingham & Mount Snow Area Village Garden Apartment 2 BR, AC & WiFi
Living Room

Lake Whitingham & Mount Snow Area Village Garden Apartment 2 BR, AC & WiFi

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."
Lake Whitingham & Mount Snow Area Village Garden Apartment 2 BR, AC & WiFi
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, (11)
"Great host communication, everything we needed, unexpected extras (like dog treats), and a beautiful view. Would gladly stay again!"
Lakefront Orange Vacation Rental - Pet Friendly!
Quiet Neighborhood, For Bird Lovers
Property grounds

Quiet Neighborhood, For Bird Lovers

10.0 out of 10, Exceptional, (46)
" My husband and I felt at home at the opening of the door!! The location is beautiful and serene, making relaxation unavoidable! The hostess thought of every little detail! Thank you Manon for a perfectly lovely stay!!"
Quiet Neighborhood, For Bird Lovers
Experience New Hampshire Country Life—Your Peaceful Escape Awaits
Living area

Experience New Hampshire Country Life—Your Peaceful Escape Awaits

9.8 out of 10, Exceptional, (30)
"We had a short stay but the hosts were wonderful and gave us a tour when we arrived. The property is gorgeous. Definitely recommend staying here."
Experience New Hampshire Country Life—Your Peaceful Escape Awaits
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

10.0 out of 10, Exceptional, (11)
"This property was just as expected and Close to top notch restaurants. Kitchen was well equipped and I was able to bake a few casseroles for our family we were visiting.The area was nice and quiet. Will visit again."
Updated Vintage Apartment < 1/2 Mi to Main St
'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!
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, (4)
"We stayed for the weekend and absolutely loved it- it was huge! Warm and inviting- full kitchen and bathroom, crib in the closet for a wee one. It was so clean and smelled good too- great windows and easy furniture. Bed was superb! Would stay again in a heartbeat. "
HeART Barn, 35-60 m. to skiing @ Mt. Snow, Stratton, Okemo, Magic & Bromley
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. One guest only, 7 nights max.
Exterior

Quiet New England neighborhood - Greenfield, Ma. One guest only, 7 nights max.

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. One guest only, 7 nights max.
Studio w/ Trail Access ~ 10 Mi to Brattleboro!
Vernon Vacation Rental | Studio | 1BA | Steps Required | 280 Sq Ft

Studio w/ Trail Access ~ 10 Mi to Brattleboro!

2.0 star property
Studio w/ Trail Access ~ 10 Mi to Brattleboro!
Entire private apartment suite in home with own entrance, views and private gym.
Guest suite entrance and patio area with outdoor grill.

Entire private apartment suite in home with own entrance, views and private gym.

The price is SAR 747
SAR 1,140 total
includes taxes & fees
26 Jan - 27 Jan
Entire private apartment suite in home with own entrance, views and private gym.
Spacious 3/4-bedroom apt 5 minutes walk to charming Shelburne Falls center.
Room

Spacious 3/4-bedroom apt 5 minutes walk to charming Shelburne Falls center.

2.0 star property
Spacious 3/4-bedroom apt 5 minutes walk to charming Shelburne Falls center.
Stylish new 2 bedroom property in enchanting Shelburne Falls Village.
Interior

Stylish new 2 bedroom property in enchanting Shelburne Falls Village.

2.0 star property
10.0 out of 10, Exceptional, (6)
"From this location easily walked into Shelburne Falls village, enjoyed lunch by the Fallls and got groceries at Buckland. Great hiking trails in the area. Trailhead 5 minute drive away"
Stylish new 2 bedroom property in enchanting Shelburne Falls Village.
Lovely Greenfield Apartment
Living area

Lovely Greenfield Apartment

2.0 star property
8.0 out of 10, Very Good, (1)
"Very well decorated apartment. The property owner was so helpful and easy to get in touch with"
Lovely Greenfield Apartment
Sweet suite in Montague near the canal and downtown Turners Falls.
Room

Sweet suite in Montague near the canal and downtown Turners Falls.

2.0 star property
9.6 out of 10, Exceptional, (4)
"I had a great stay at Callie’s. The room was comfortable and clean and had all the amenities one needs! "
Sweet suite in Montague near the canal and downtown Turners Falls.
'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!
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.
Don't see what you're looking for?
See all available properties in Winchester
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Other property types in Winchester

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, (6)
"Everything about this property was beautiful. The home itself being located right on the water was perfect for kayaking, fishing, evenings by the fire, relaxing and reconnecting. The house is gorgeous, comfortable, and had everything you might need/want. We enjoyed the game room - jenga and family air hockey tournaments. A lovely experience and we hope to return at some point. Thank you for sharing your beautiful home with us!"
VRBO Top 10 of 2024!- Copley's Lakefront Cottage on Lake Monomonac
Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly

Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly

8.8 out of 10, Excellent, (43)
"Cabin was perfect for our long weekend. Master bed mattress needs an update, but otherwise everything was fantastic."
Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly
Charming Waterfront Log Cabin
Exterior

Charming Waterfront Log Cabin

9.6 out of 10, Exceptional, (37)
"We really appreciated the solitude and quiet retreat this cabin offered. "
Charming Waterfront Log Cabin
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 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?
Below are some of the more popular apartments in the area: Cozy 2-bedroom Unit with private backyard: Located 14.5 mi/23.3 km away in Montague. Free WiFi, private patios, and Smart TVs are included. 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. Lakefront Orange Vacation Rental - Pet Friendly!: It’s located in Orange, 12.1 mi/19.4 km from Winchester. Includes fireplaces.
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. Pisgah State Park and Ashuelot River are a couple of lovely local spots to get outside and enjoy nature. Birch Point and Rhododendron State Park are other places to visit while you’re in town.