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.
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
10 / 10Outstanding·May 2026
Lovely, large apartment in a beautiful, HUGE Victorian home. Lots of fun, eclectic decorations and houseplants. The apartment contains 6 couches, so tons of seating. Be aware that this is an upstairs apartment, so you will have to climb stairs. (not a problem, just something to be aware of) The host was very responsive. We would definitely recommend this property to others!
10 / 10Outstanding·May 2026
This was a gorgeous home and a great place to stay! Check-in and out was very easy, would definitely stay again!
8 / 10Excellent·May 2026
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.
10 / 10Outstanding·Mar 2026
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!
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Top rated by guests
9.6Outstanding
(24 Ratings)
"Lovely, large apartment in a beautiful, HUGE Victorian home. Lots of fun, eclectic decorations and houseplants. The apartment contains 6 couches, so tons of seating. Be aware that this is an upstairs ..."
Cindy Z.Don't miss out! Price and availability may change
