Entire home

Best Outdoors near the Berkshires

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Interior
Living area
Living area
Interior
Interior
1 bedroom1 bathroomSleeps 583.6 sq m

Popular amenities

  • Parking available

Explore the area

Map
Winchester, CT
  • Northwestern Connecticut Community College
    ‪18 min walk‬
  • Highland Lake
    ‪19 min walk‬
  • Connecticut Valley Winery
    ‪14 min drive‬
  • Hartford, CT (BDL-Bradley Intl.)
    ‪43 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

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 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
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.

Property manager

Anna

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Amenities

Parking available

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House Rules

Check in after 3:00 PM
Minimum age to rent: 18
Check out before 11:00 AM
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Children

Children allowed: ages 0–17
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Events

No events allowed
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Pets

No pets allowed
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Smoking

Smoking is not permitted
Please, no perfume use inside the apartment
Wash dishes at the end of your stay
Take trash outside and put it in the trash bin near 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

About the area

Winsted

Winsted is home to this holiday home. 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 - 8 min walk - 0.7 km
  • Northwestern Connecticut Community College - 18 min walk - 1.6 km
  • Highland Lake - 19 min walk - 1.7 km
  • Platt Hill State Park - 10 min drive - 5.4 km
  • Connecticut Valley Winery - 14 min drive - 15.0 km

Getting around

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

Restaurants

  • ‪McDonald's - ‬18 min walk
  • ‪Little Red Barn Brewer - ‬8 min walk
  • ‪Rowley Grill & Tap - ‬17 min walk
  • ‪Subway - ‬5 min drive
  • ‪Log House Restaurant - ‬8 min drive

Frequently asked questions

Is Best Outdoors near the Berkshires pet-friendly?

No, pets are not allowed at this 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 Winsted, this holiday home is within a 10-minute walk of Winchester Historical Society and Laurel Lanes. Walker Field and Tatro Pond are also within 15 minutes.

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About the host

Hosted by Anna

Host profile image
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!
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