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

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
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
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.

9.4 out of 10, Exceptional, (10)
"we were staying in the area for hiking. the space was clean and exactly as described,host was very kind and helpful, and the location is perfect. town is lovely too."
The price is AED 257
AED 558 total
includes taxes & fees
8 Jan - 9 Jan
Studio Apt with Full Kitchen. 1 minute stroll over picturesque bridge into town.
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.
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 AED 1,010
AED 1,467 total
includes taxes & fees
5 Jan - 6 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, (5)
"Kevin's place is great - clean, quiet, comfortable, spacious, and it had everything we needed for a Thanksgiving visit to Greenfield. The kitchen is well equipped, and the bed and bedding top notch. The photos accurately represent the property. The space is recently constructed -- it is well built, with thoughtful details, and has lots of natural light. Kevin was easy to communicate with, and check in was easy as well. We will definitely return! "
Stylish new 2 bedroom property in enchanting Shelburne Falls Village.
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.
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!
'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!
Cozy 1-bedroom apartment in delightful Brattleboro
Living area

Cozy 1-bedroom apartment in delightful Brattleboro

Cozy 1-bedroom apartment in delightful Brattleboro
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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Other property types in Winchester

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
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
Hilltop Home with Great Views
Exterior

Hilltop Home with Great Views

9.2 out of 10, Wonderful, (12)
"Michelle made our experience super easy and memorable! Drive up a private road and a pretty steep hill (4wd a must in winter) to a secluded, beautiful house with plenty of space. Just you and nature. The house itself has all the amenities - full kitchen, sitting areas, and even a wood stove that Michelle started up before we got there. Beds are comfortable, and the bathrooms have insane mountaintop views. Michele even left a few eggs for starter breakfast which was much appreciated. You can’t...
Hilltop Home with Great 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.

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 top apartments in the area to choose from: Experience New Hampshire Country Life—Your Peaceful Escape Awaits: It’s situated in Nelson, 21.4 mi/34.5 km away. Includes free WiFi, private patios, 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.