Best Outdoors near the Berkshires

Winchester, Connecticut
$139 avg/night
Bed 1

Bed

Bath 1

Bath

Home Private Vacation Home

Property Type

Sleep 5

Max Sleeps

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 enjoythe 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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  • Feature Features
  • Map Map
  • School District Rates & Availability
  • Review Review

Feature Features

  • PETS

    No Pets Allowed
  • SAFETY

    No Carbon Monoxide Detector (host Has Indicated There Is No Carbon Monoxide Detector Or Gas Appliances On The Property) Smoke Detector Installed (host Has Indicated There Is A Smoke Detector On The Property)
  • BEDROOM

    1 Bedroom Bed Sheets Provided
  • GENERAL

    Unit Size: 900 Sq Ft (84 Sq M)
  • KITCHEN

    Microwave Oven Stovetop
  • PARKING

    Onsite Parking
  • INTERNET

    WiFi Available
  • OUTDOORS

    Patio
  • BATHROOMS

    1 Bathroom Bathtub Or Shower Hair Dryer Soap Toilet Paper Towels Provided
  • THINGS TO DO

    Kayak On Site
  • ENTERTAINMENT

    Smart TV
  • LIVING SPACES

    Living Room
  • CLIMATE CONTROL

    Heating
  • LOCATION HIGHLIGHTS

    In A Rural Location
  • SERVICES AND CONVENIENCES

    Iron/ironing Board
  • SUITABILITY/ACCESSIBILITY

    Smoke-free Property

CheckIn Check-in : 03:00 PM CheckOut Check-out : 11:00 AM
No Wheelchair No smoking No pets Children allowed
Occupancy Max occupancy : 5

Map Map

School District Rates & Availability

Review Review

  • Justine L.

    Submitted Feb 10, 2026

    Stayed Feb 6, 2026

    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!

  • Leslie H.

    Submitted Jan 1, 2026

    Stayed Dec 31, 2025

    Anna was a great host! She communicated well and the apartment was beautiful!

  • Rowland D.

    Submitted Dec 30, 2025

    Stayed Dec 24, 2025

    Host communicated clearly. So many wonderful plants, some were in bloom!

  • Rachel B.

    Submitted Nov 20, 2025

    Stayed Nov 7, 2025

    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.

  • Willow K.

    Submitted Nov 17, 2025

    Stayed Nov 14, 2025

    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!

  • Madelaine L.

    Submitted Nov 1, 2025

    Stayed Oct 31, 2025

    Clean and extremely stylish! The host Anna was communicative. We really enjoyed our night here.

  • Scott G.

    Submitted Oct 19, 2025

    Stayed Oct 14, 2025

    Clean space, good location, dining options around were nice

  • Anne M.

    Submitted Oct 1, 2025

    Stayed Sep 27, 2025

    Interesting

  • Sean B.

    Submitted Sep 14, 2025

    Stayed Sep 13, 2025

    Wonderful property. Adorable details all around and in every nook and cranny. We immediately felt at home in this cozy space.

  • Roberta W.

    Submitted Sep 13, 2025

    Stayed Sep 12, 2025

    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.

  • Rachel B.

    Submitted Aug 9, 2025

    Stayed Aug 8, 2025

    Great stay and wonderful house.

  • Jack H.

    Submitted Jun 25, 2025

    Stayed Jun 7, 2025

    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.

Your dates are Available!

Total

Includes taxes and fees
$139+
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