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Best Outdoors near the Berkshires

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FRONT OF THE HOUSE
Living Room
LIVING ROOM
BEDROOM
BEDROOM

Reviews

9.8 out of 10
Exceptional
1 bedroom1 bathroomSleeps 5

Popular amenities

  • Onsite parking available
  • Kitchen
  • Deck or patio
  • Internet access
  • Balcony or patio
  • Microwave

Explore the area

View map
Winchester, CT
  • Place, Walker Field
    ‪8 min walk‬
  • Place, Highland Lake
    ‪13 min walk‬
  • Place, Northwestern Connecticut Community College
    ‪15 min walk‬
  • Airport, Hartford, CT (BDL-Bradley Intl.)
    ‪40 min drive‬

Rooms & beds

1 bedroom (sleeps 5)

Bedroom 1

1 Queen Bed and 1 Double Bed

Living Room 1

1 Double Sofa Bed, 1 Single Futon and 1 Single Bed

1 bathroom

Bathroom

Soap · Towels provided · Bathtub or shower · Toilet · Shampoo · Hair dryer

Spaces

Deck or patio
Kitchen

About this property

Best Outdoors near the Berkshires

Looking for a quiet escape near the scenic Berkshires without being in the middle of tourist traffic? This cozy countryside apartment offers the best of both worlds—natural beauty, easy access to outdoor adventures, and close proximity to cultural gems.

The apartment with separate entrance is on the second floor, with two private staircases leading to the apartment, one is outside and the other is enclosed; they are separated by the landing/porch with the chairs to rest and enjoy the Mountain view. The staircases are wooden, with the railings on both sides. The apartment features a bright bedroom with one full and one queen bed, and a couch, a fully equipped kitchen, and a comfortable living space with one sofa bed and two couches, ideal for relaxing after a day of exploring. Outside, enjoy your own private patio with peaceful views of the rolling hills, and a very private side yard with a table and chairs.
Located just outside the Berkshires, we’re:
40 minutes from Hartford and the Wadsworth Atheneum Museum of Art. About this space
Remodeled apartment on 2nd floor of a 1910 Victorian house near the center of Winsted, CT. The apartment is unique and cozy, with large windows, some stained glass, tin ceilings, hand painted kitchen cabinets, and plants. Close proximity to all Litchfield County and the Berkshires have to offer, in all seasons. It's an easy drive from NYC or Boston. Great weekend get-away.

The space
Rooms include a full kitchen, one bedroom with one queen bed and one full sized bed, living room with a pull out bed and 4 couches throughout the apartment. Wireless internet connection. Sleeps up to 6 people. Good kitchen appliances, and updated bathroom. Private entrance with yard.

Guest access
Access is thru the left side of the house to the 2nd floor apartment. Parking is on the same side as the entrance. Use of the side and front yards is encouraged. A grill is provided for cooking outdoors.

Other things to note
Doors on the inside of the apartment lead to the main hallway of the house. In case of fire, the main hallway doors will provide an additional escape route.
70 minutes from Yale University and New Haven’s historic downtown.
30 minutes from Great Barrington and the trailheads of Bash Bish Falls
Within easy reach of Tanglewood, skiing, and charming New England towns
With fast Wi-Fi, free parking, and a quiet, natural setting, this space is perfect for weekend getaways, remote work stays, or peaceful retreats.

Enjoy the great outdoors, explore nearby culture, and return each day to a calm, comfortable retreat.
We have our own outdoor gems (see the pictures), where you can swim in the lake or the river, kayak (rental is available), and hike to the beautiful waterfalls and lookouts. We’ll give you our locals-only lead.
Our Town has the only “Movie and Dinner” theater, and a variety of restaurants and brewery, as well as Artists’ Gallery with open studios weekends, and antique stores.Healthfood store, farmer’s market and a local a supermarket will help you with food shopping.
You’ll be glad you chose this part of New England for your stay.

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About the area

Winsted

Located in Winsted, this holiday home is in a rural area. Winchester Historical Society and American Mural Project are cultural highlights, and some of the area's landmarks include Warner Theater and Goshen Historic District. Laurel Lanes and KidsPlay Museum are also worth visiting.
Map
Winchester, CT

What's nearby

  • Winchester Historical Society - 6 min walk - 0.6 km
  • Walker Field - 8 min walk - 0.7 km
  • Highland Lake - 13 min walk - 1.1 km
  • Rowley Fields - 13 min walk - 1.1 km
  • Northwestern Connecticut Community College - 15 min walk - 1.3 km

Getting around

  • Hartford, CT (BDL-Bradley Intl.) - 43 min drive

Restaurants

  • ‪McDonald's - ‬18 min walk
  • ‪Dunkin' - ‬9 min walk
  • ‪Subway - ‬5 min drive
  • ‪Little Red Barn Brewer - ‬8 min walk
  • ‪Dunkin' - ‬18 min walk

Reviews

9.8

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window
Rating 10 - Excellent. 15 out of 17 reviews
Rating 8 - Good. 2 out of 17 reviews
Rating 6 - Okay. 0 out of 17 reviews
Rating 4 - Poor. 0 out of 17 reviews
Rating 2 - Terrible. 0 out of 17 reviews

10/10

Cleanliness

9.8/10

Check-in

10/10

Communication

9.6/10

Location

10/10

Listing accuracy

Reviews

Verified

10/10 Excellent

Lana A.

Liked: Cleanliness, check-in, communication, location, listing accuracy
This was a gorgeous home and a great place to stay! Check-in and out was very easy, would definitely stay again!
Stayed 1 night in Apr 2026
Response from VrboOwner on 12 May 2026
Thank you, Lana!
Verified

10/10 Excellent

Rachel B.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great stay

Great stay and wonderful house.
Stayed 1 night in Aug 2025
Verified

10/10 Excellent

Mary C.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Beautiful, eclectic apartment. Plenty of room for several people. Easy to check in. Quiet location.
Stayed 1 night in Mar 2026
Verified

10/10 Excellent

Scott G.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Clean space, good location, dining options around were nice
Stayed 5 nights in Oct 2025
Verified

10/10 Excellent

Paul S.

Liked: Cleanliness, check-in, communication, location, listing accuracy
very good all around
Stayed 2 nights in Feb 2026
Verified

10/10 Excellent

Leslie H.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Anna was a great host! She communicated well and the apartment was beautiful!
Stayed 1 night in Dec 2025
Verified

10/10 Excellent

Willow K.

Liked: Cleanliness, check-in, communication, location, listing accuracy
This home was beautiful and had everything we needed to enjoy our weekend away! Great spots to see nature and downtown is super cute as well with great shopping. Thanks so much, Anna!
Stayed 2 nights in Nov 2025
Verified

10/10 Excellent

Madelaine L.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Clean and extremely stylish! The host Anna was communicative. We really enjoyed our night here.
Stayed 1 night in Oct 2025
Verified

10/10 Excellent

Lauren R.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Quick anniversary trip. The apartment was whimsical with a dash of kitsch- in all the best ways. It was super clean! We had tickets for the Gilson, but, saw how accommodating the kitchen would have been if we'd decide to go to the grocery instead. A true gem! Also, Anna was very responsive and helpful. We will be back!
Stayed 1 night in Mar 2026
Verified

10/10 Excellent

Justine L.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Host was very communicative and welcoming. The place felt like a magic secret garden, close to downtown Winstead. When you open the door, it feels like a breathe of fresh air. Super clean and well cared for home, decorated beautifully, charming. Thank you!
Stayed 2 nights in Feb 2026
Verified

10/10 Excellent

Rowland D.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Host communicated clearly. So many wonderful plants, some were in bloom!
Stayed 4 nights in Dec 2025
Verified

10/10 Excellent

Roberta W.

Liked: Cleanliness, check-in, communication, location, listing accuracy
It is a home away from home. The second floor apartment felt like a well loved and personalized space with a warm, welcoming vibe. We would definitely choose to stay there again.
Stayed 1 night in Sep 2025
Verified

10/10 Excellent

Rachel B.

Liked: Cleanliness, check-in, communication, location, listing accuracy
We have stayed here a couple times now. We love this place. They are so welcoming and accommodating. They are great with communication and directions. I would definitely highly recommend them to anyone staying in the area. We look forward to our next visit up there with them.
Stayed 1 night in Nov 2025
Verified

10/10 Excellent

Sean B.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Wonderful property. Adorable details all around and in every nook and cranny. We immediately felt at home in this cozy space.
Stayed 1 night in Sep 2025
Verified

10/10 Excellent

Anne M.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Interesting
Stayed 1 night in Sep 2025
Verified

8/10 Good

Jack H.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Wonderful ambience.

We loved the many plants, hangings, pillows, etc. - kind of magical for our young grandchildren. Sleeping arrangements for five of us (grandparents, our daughter, two grandkids) weren't great - once opened the hide-a-bed blocked the single entrance. Kitchen has everything you could need.Perfect for a couple. Quiet neighborhood, but short walk to cafe etc.
Stayed 1 night in Jun 2025
Verified

8/10 Good

Parson W.

Liked: Cleanliness, check-in, communication, listing accuracy
It was a little unusual check in compared to other vrbo rental I have used and there was little clarity about how it worked but all worked out well. Either I missed it or the listing omitted to say it was a second floor apt. Not usually an issue but in this case the stairwell was steep narrow and awkward. The accommodations were fine the decor eclectic but interesting to say the least..TV was an enigma. Wi fi was great.
Stayed 2 nights in Apr 2026
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