Best Outdoors near the Berkshires

Photo gallery for Best Outdoors near the Berkshires

A cozy living room with a floral sofa, a fireplace, and various potted plants.
A window with stained glass and a view of a tree-lined street.
A cozy room with a radiator, a table with decorative items, a lamp, and a window with curtains.
A two-story house with a prominent tower section, a porch with yellow columns, and a brick chimney.
A garden with green chairs, a wooden ladder, and pink flowers.

Reviews

9.6 out of 10
Exceptional

Highlights

  • Discover nearby landmarks
    Close to Highland Lake

Popular amenities

  • Patio
  • Internet
  • Onsite parking available
  • Microwave
  • Non-smoking

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

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

Deck or patio
Kitchen
Number of living rooms

Add dates for prices

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About the area

Winsted

Located in Winsted, this holiday home is in a rural area. American Museum of Tort Law and Winchester Historical Society 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.
View more Holiday homes in WinstedOpens in a new window
Map
Winchester, CT

What's nearby

  • Winchester Historical Society - 6 min walk - 0.6 km
  • Highland Lake - 13 min walk - 1.1 km
  • The Marina at Highland Lake - 13 min walk - 1.1 km
  • Northwestern Connecticut Community College - 15 min walk - 1.3 km
  • Northwestern Connecticut Community College Library - 15 min walk - 1.3 km

Getting around

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

Restaurants

  • ‪McDonald's - ‬18 min walk
  • ‪Dunkin' - ‬9 min walk
  • ‪Arcadia - ‬9 min drive
  • ‪Dunkin' - ‬18 min walk
  • ‪Skipper's - ‬17 min walk

Frequently asked questions

Is Best Outdoors near the Berkshires pet-friendly?

No, pets are not allowed at this property.

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 American Museum of Tort Law, Winchester Historical Society and Laurel Lanes. Walker Field and The Marina at Highland Lake are also within 15 minutes.

Reviews

9.6

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window
Rating 10 - Excellent. 23 out of 27 reviews
Rating 8 - Good. 2 out of 27 reviews
Rating 6 - Okay. 1 out of 27 reviews
Rating 4 - Poor. 0 out of 27 reviews
Rating 2 - Terrible. 1 out of 27 reviews

9.8/10

Cleanliness

9.6/10

Check-in

9.6/10

Communication

9.6/10

Location

9.6/10

Listing accuracy

Reviews

Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Wonderful and comfortable space!
Stayed 3 nights in Aug 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Anna was so helpful with my family. Accommodating us during a crazy day with a wedding in town. We girls absolutely loved her place. Communication was wonderful! Love a vintage home!
Stayed 1 night in Oct 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
This was a gorgeous home and a great place to stay! Check-in and out was very easy, would definitely stay again!
Stayed 1 night in Apr 2026
Response from VrboOwner on 12 May 2026
Thank you, Lana!
Verified review

10/10 Excellent

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

Great stay

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

10/10 Excellent

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

10/10 Excellent

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

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
very good all around
Stayed 2 nights in Feb 2026
Verified review

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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
Verified review

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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

10/10 Excellent

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

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
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!
Stayed 2 nights in May 2026
Verified review

8/10 Good

Liked: Cleanliness, check-in, communication, listing accuracy
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.
Stayed 2 nights in Apr 2026
Verified review

10/10 Excellent

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

8/10 Good

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 review

2/10 Terrible

Disliked: Cleanliness, check-in, communication, listing accuracy
1. Host was nowhere to found so I was inconveniently forced to look for another accommodation. host was called numerous times but refused to respond2. Property was unkept and looked very spooky - far from what was advertised. I was really DISAPPOINTED.3. I was severely delayed for my appointment - over 3 hours - and forced to pay a higher price with additional travel mileage
Stayed 4 nights in May 2026
Response from VrboOwner on 10 Sept 2026
This guest have never stayed in my house on Vrbo, therefore, the review is irrelevant, and should not represent the assessment of the property.
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Big apartment on the second floor. Love the furnishings and plants. Beds were comfortable. Tv remote did not work but didn’t it after all. Convenient location to Winsted.
Stayed 1 night in Sep 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
This was hands-down one of our favorite stays of our entire road trip. Every corner of the home was whimsical, creative, and so thoughtfully designed. It felt like staying in someone's beloved home rather than a rental. Our host was incredibly welcoming and pointed us to nearby lakes where we enjoyed a beautiful evening walk. If you're considering booking this place, do it—you won't regret it. We would absolutely stay here again.
Stayed 1 night in Jun 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, listing accuracy
Anna's home was just what my friends and I needed for a memorable weekend away. It is a unique space filled with plants and homey touches that made it stand out from the many bland rentals that are available these days. I especially loved that the kitchen was so well appointed. The space was welcoming and Anna was very responsive when we reached out to her.
Stayed 2 nights in Jun 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
We stayed for 2 nights in June and truly enjoyed our rental experience.The apartment is located on the second floor. It is much bigger than pictured and is absolutely gorgeous. It is located on a narrow, windy street that is very quiet. The many plants, books, vintage lamps, dishes, books, and board games make it very special. The apartment was immaculate and the beds were comfortable. We enjoyed the coffee the host provided. The Roku TV had many apps and the WiFi was excellent. Truly, one of the best and most interesting rentals that we have had the pleasure to rent.
Stayed 2 nights in Jun 2026
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