Best Outdoors near the Berkshires

Top rated by guests
FRONT OF THE HOUSE
KITCHEN/LOUNGE
Kitchen-lounge
BEDROOM
Your private side yard.
review stars
9.6Outstanding
(20 Ratings)
"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 car..."
Justine L.
Don't miss out! Price and availability may change
9.6 / 10
Outstanding(20 Ratings)

House in Winchester, CT

5 guests · 1 bedroom · 1 bath

Reasons to book

Guests love it hereGuests give this property a top rating
Well priced for this locationPriced under area average
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About this house rental

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.

Amenities at Best Outdoors near the Berkshires

Non-smoking
No pets allowed
Family friendly

Map of Winchester, CT


Ratings and reviews

9.6 / 10
Outstanding(20 Ratings)
10 / 10Outstanding·Feb 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!
10 / 10Outstanding·Jan 2026
Anna was a great host! She communicated well and the apartment was beautiful!
10 / 10Outstanding·Dec 2025
Host communicated clearly. So many wonderful plants, some were in bloom!
10 / 10Outstanding·Nov 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.

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FAQs

Is parking included with this house?

Parking is not specified as an available amenity at Best Outdoors near the Berkshires. For more information, we encourage you to contact the property about where to park.

Is there a pool at this house?

We didn’t find pool listed as an amenity for this house. It may be worth double checking if a pool is important for your stay.

Is Best Outdoors near the Berkshires pet friendly?

Unfortunately, this house is not pet-friendly. Try searching again and filter for "Pets Allowed"

What amenities are available at Best Outdoors near the Berkshires?

We found 3 amenities for this rental. This includes non-smoking, no pets allowed, and family friendly.