Entire home

Best Outdoors near the Berkshires

Photo gallery for Best Outdoors near the Berkshires

Exterior - Best Outdoors near the Berkshires (Winchester)
Outdoor dining - Best Outdoors near the Berkshires (Winchester)
1 bedroom, iron/ironing board, WiFi, bed sheets - Best Outdoors near the Berkshires (Winchester)
Dining - Best Outdoors near the Berkshires (Winchester)
Hair dryer, towels, soap, toilet paper - Best Outdoors near the Berkshires (Winchester)
Best Outdoors near the Berkshires provides everything that you need. Stay connected with in-room WiFi.

Reviews

10 out of 10
Exceptional

Entire home

1 bedroom1 bathroom900 sq ft

Popular amenities

  • Kitchen
  • Outdoor space
  • Parking available
The current price is £110
includes taxes & fees
14 May - 15 May

Add dates for prices

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.

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

Similar properties

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

Pets not 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
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
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

About the area

Located in Winchester, this holiday home is in a rural area. 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. Visit our Winsted travel guide
View more Holiday homes in Winsted
Map
Winchester, CT

What's nearby

  • Winchester Historical Society
    6 min walk - 0.4 miles
  • Highland Lake
    13 min walk - 0.7 miles
  • The Marina at Highland Lake
    13 min walk - 0.7 miles
  • Rowley Fields
    13 min walk - 0.7 miles
  • Northwestern Connecticut Community College
    15 min walk - 0.8 miles

Getting around

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

Restaurants

  • McDonald's
    18 min walk
  • Dunkin'
    9 min walk
  • Subway
    5 min drive
  • Little Red Barn Brewer
    8 min walk
  • Dunkin'
    18 min walk

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 30 Apr 2026, prices found for a 1-night stay for 2 adults at Best Outdoors near the Berkshires on 14 May 2026 start from £110, 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.

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Best Outdoors near the Berkshires Reviews

Reviews

Exceptional

All reviews shown are from real guest experiences. Only travellers who have booked a stay with us can submit a review. We verify reviews according to our guidelines and publish all reviews, positive or negative.
More informationOpens in a new window
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

Cleanliness

9.6

Location

Reviews

Verified

10/10 Excellent

Willow K.

Liked: Cleanliness, check-in, communication, location, listing accuracy
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
Verified

10/10 Excellent

Rachel B.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great stay

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

10/10 Excellent

Scott G.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Clean space, good location, dining options around were nice
Stayed 5 nights in Oct 2025
Verified

10/10 Excellent

Leslie H.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Anna was a great host! She communicated well and the apartment was beautiful!
Stayed 1 night in Dec 2025
Verified

10/10 Excellent

Rowland D.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Host communicated clearly. So many wonderful plants, some were in bloom!
Stayed 4 nights in Dec 2025
Verified

10/10 Excellent

Rachel B.

Liked: Cleanliness, check-in, communication, location, listing accuracy
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
Verified

10/10 Excellent

Roberta W.

Liked: Cleanliness, check-in, communication, location, listing accuracy
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
Verified

10/10 Excellent

Sean B.

Liked: Cleanliness, check-in, communication, location, listing accuracy
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
Verified

10/10 Excellent

Anne M.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Interesting
Stayed 1 night in Sep 2025
Verified

8/10 Good

Jack H.

Liked: Cleanliness, check-in, communication, location, listing accuracy

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
Verified

10/10 Excellent

Madelaine L.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Clean and extremely stylish! The host Anna was communicative. We really enjoyed our night here.
Stayed 1 night in Oct 2025