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 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.
Add dates for prices
Amenities
Kitchen
Outdoor space
Parking available
Have a question?
AI iconBetaBeta
Get instant answers with AI powered search of property information and reviews.
Similar properties
Charming 2-bedroom cottage with AC and WiFi in welcoming New Hartford
New Hartford
Charming 2-bedroom cottage with AC and WiFi in welcoming New Hartford
Please, no perfume, cigarettes use inside the apartment
Wash dishes at the end of your stay.
Leave the beds undone, leave the used towels in a bathtub
Take all the trash outside and place it in the trash bin at the bottom of the staircase.
Important information
You need to know
Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
On-site parties or group events are strictly prohibited
Long-term renters welcome
Host has indicated that there are no carbon monoxide detectors or gas appliances on the property
Host has indicated that there is a smoke detector on the property
This property has outdoor spaces, such as balconies, patios and terraces, which may not be suitable for children; if you have any concerns, we recommend contacting the property prior to your arrival to confirm that they can accommodate you in a suitable room
Frequently asked questions
Is Best Outdoors near the Berkshires pet-friendly?
No, pets are not allowed at this property.
How much does it cost to stay at Best Outdoors near the Berkshires?
As of 9 Apr 2026, prices found for a 1-night stay for 2 adults at Best Outdoors near the Berkshires on 10 May 2026 start from AU$187, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.
How much is parking at Best Outdoors near the Berkshires?
On-site parking is available at the property.
What time is check-in at Best Outdoors near the Berkshires?
Check-in begins at 3:00 PM.
What time is check-out at Best Outdoors near the Berkshires?
Checkout is at 11:00 AM.
Where is Best Outdoors near the Berkshires located?
Situated in a rural location, this holiday home is within a 10-minute walk of Winchester Historical Society and Laurel Lanes. Walker Field and The Marina at Highland Lake are also within 15 minutes.
Reviews
10
Exceptional
Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
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!
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!
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.
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.
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.
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!
Clean and extremely stylish! The host Anna was communicative. We really enjoyed our night here.
Madelaine L.
Stayed 1 night in Oct 2025
About the host
Hosted by Anna
Hi there! I’m Anna — an avid hiker, kayaker, mountain biker, and general lover of just about anything that gets me outside. Hosting on Vrbo gives me the chance to share two things I truly love: this property and the incredible outdoors that surround it.
I first fell in love with this area years ago on a weekend biking trip. Something about the crisp air, winding trails, and quiet mornings on the lake just stuck with me. Eventually, I found this house that was somewhat too big for us, and decided to it with other nature lovers, turning it into a place where the guests can unplug, recharge, and explore.
When I’m not hosting, you’ll usually find me paddling at sunrise, biking the local trails, or diving into a cold river after a long hike. I am always looking for the ways to improve this place and to make it more comfortable, welcoming space that feels like home at the end of an adventure-filled day. Whether you're here for a solo trip, a romantic getaway, or a family vacation, I’m here to make sure your stay goes smoothly.
I do not charge for cleaning, as I do not believe that the guests should pay for the previous guest mass. I do ask my guests, though, to leave the space respectfully clean,Thanks for considering my place. Anna
Why they chose this property
We’ll be happy to share with you our favorite spots and hikes.
What makes this property unique
One of the things guests love most about this apartment is the privacy. You’ll have your own completely private entrance, separate from the main house, so coming and going is easy and discreet—no shared hallways, no awkward run-ins.
Just outside the entrance, you'll find a private side yard that’s all yours during your stay. Whether you're enjoying a morning coffee in the sun, reading under the shade tree, or unwinding after a day of exploring, or relaxing on a swing, it’s a peaceful little corner designed for quiet and comfort. Mature landscaping offer extra seclusion, making it feel like your own hidden retreat.
We respect your space and privacy, but we’re just a message away if you need anything! 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 (2 free parking spots) 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.