Entire home·Private host

Best Outdoors near the Berkshires

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Photo gallery for Best Outdoors near the Berkshires

Exterior
Outdoor dining
1 bedroom, iron/ironing board, WiFi, bed sheets
Dining
Hair dryer, towels, soap, toilet paper

Reviews

10 out of 10
Exceptional

Entire home

1 bedroom1 bathroom84 sq m

Popular amenities

  • Kitchen
  • Outdoor space
  • Parking available

Explore the area

View in a map
Winchester, CT
  • Place, Winchester Historical Society
    ‪6 min walk‬
  • Place, Highland Lake
    ‪13 min walk‬
  • Place, Northwestern Connecticut Community College
    ‪15 min walk‬
  • Airport, Hartford, CT (BDL-Bradley Intl.)
    ‪40 min drive‬

Room options

Similar properties

About this property

Entire place

You'll have the entire home to yourself and will only share it with other guests in your party.

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. 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.
During your stay at this vacation home, you're just a quick walk from Winchester Historical Society. The vacation home includes amenities such as a kitchen and a patio.
  • The vacation home offers a kitchen, a patio, and a Smart TV
  • Within a 10-minute walk of Winchester Historical Society and Laurel Lanes

Property amenities

Internet

  • Available in the house: WiFi

Parking and transport

  • Parking on site

Kitchen

  • Hob
  • Microwave
  • Oven

Bedrooms

  • Bedroom
  • Bedsheets provided

Bathroom

  • 1 bathroom
  • Bathtub or shower
  • Hair dryer
  • Soap
  • Toilet paper
  • Towels provided

Entertainment

  • Smart TV

Outdoor areas

  • Patio

Comfort

  • Heating

Pets

  • No pets allowed

Suitability/Accessibility

  • Smoke-free property

Services and conveniences

  • Iron/ironing board

Location highlights

  • In a rural location

Things to do

  • Kayak

Safety features

  • No carbon monoxide detector or gas appliances (host has indicated there are no carbon monoxide detectors or gas appliances on the property)
  • Smoke detector (host has indicated there is a smoke detector on the property)

General

  • Unit size: 900 square feet

Policies

Check-in

Check-in time starts at 3:00 PM
Minimum check-in age: 18

Check-out

Check-out before 11:00 AM

Special check-in instructions

You will receive an email from the host with check-in and check-out instructions
Information provided by the property may be translated using automated translation tools

Rules

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.

Pets

  • No pets allowed

Children and extra beds

  • Children are welcome.

Events

No events allowed

Smoking

Smoking is not permitted

Important information

You need to know

This property is managed by a private host (a party not acting within their trade, business or profession). EU consumer law, including the right of withdrawal, will not apply to your booking. The cancellation policy set by the private host will cover your booking.
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
Onsite parties or group events are strictly prohibited
Long-term renters welcome
Host has indicated there are no carbon monoxide detectors or gas appliances on the property
Host has indicated there is a smoke detector on the property
This property has outdoor spaces, such as balconies, patios, terraces which may not be suitable for children; if you have concerns, we recommend contacting the property prior to your arrival to confirm they can accommodate you in a suitable room
This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation
You will receive an email from the host with check-in and check-out instructions. You will also receive an email from Vrbo with a link to a Vrbo account which will enable you to manage your booking.

Best Outdoors near the Berkshires Reviews

Reviews

10

Exceptional

Rating 10 - Excellent. 14 out of 15 reviews
Rating 8 - Good. 1 out of 15 reviews
Rating 6 - Okay. 0 out of 15 reviews
Rating 4 - Poor. 0 out of 15 reviews
Rating 2 - Terrible. 0 out of 15 reviews

10/10

Cleanliness

Reviews

10/10 Excellent

Lauren R., Austin, Texas, USA

Liked: Cleanliness
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!
Stayed 1 night in Mar 2026

10/10 Excellent

Mary C.

Liked: Cleanliness
Beautiful, eclectic apartment. Plenty of room for several people. Easy to check in. Quiet location.
Stayed 1 night in Mar 2026

10/10 Excellent

Paul S.

Liked: Cleanliness
very good all around
Stayed 2 nights in Feb 2026

10/10 Excellent

Justine L., Hawley, Pennsylvania

Liked: Cleanliness
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!
Stayed 2 nights in Feb 2026

10/10 Excellent

Leslie H.

Liked: Cleanliness
Anna was a great host! She communicated well and the apartment was beautiful!
Stayed 1 night in Dec 2025

10/10 Excellent

Rowland D.

Liked: Cleanliness
Host communicated clearly. So many wonderful plants, some were in bloom!
Stayed 4 nights in Dec 2025

10/10 Excellent

Rachel B.

Liked: Cleanliness
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.
Stayed 1 night in Nov 2025

10/10 Excellent

Willow K.

Liked: Cleanliness
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!
Stayed 2 nights in Nov 2025

10/10 Excellent

Madelaine L.

Liked: Cleanliness
Clean and extremely stylish! The host Anna was communicative. We really enjoyed our night here.
Stayed 1 night in Oct 2025

10/10 Excellent

Scott G.

Liked: Cleanliness
Clean space, good location, dining options around were nice
Stayed 5 nights in Oct 2025

10/10 Excellent

Anne M.

Liked: Cleanliness
Interesting
Stayed 1 night in Sep 2025

10/10 Excellent

Sean B.

Liked: Cleanliness
Wonderful property. Adorable details all around and in every nook and cranny. We immediately felt at home in this cozy space.
Stayed 1 night in Sep 2025

10/10 Excellent

Roberta W.

Liked: Cleanliness
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.
Stayed 1 night in Sep 2025

10/10 Excellent

Rachel B.

Liked: Cleanliness

Great stay

Great stay and wonderful house.
Stayed 1 night in Aug 2025

8/10 Good

Jack H.

Liked: Cleanliness

Wonderful ambience.

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.
Stayed 1 night in Jun 2025