Immaculate year-round lakefront at Highland Lake


Entire guesthouse hosted by Jack

  1. 7 guests
  2. 3 bedrooms
  3. 4 beds
  4. 2 baths
Entire home
You’ll have the guesthouse to yourself.
Enhanced Clean
This Host committed to Airbnb's 5-step enhanced cleaning process.
Great location
100% of recent guests gave the location a 5-star rating.
Great check-in experience
100% of recent guests gave the check-in process a 5-star rating.
"Lone Pine Cottage" Very special 3 bedroom / 2 full bath, 2016 ground-up restoration in Victorian cottage style. Magnificent in all four seasons. Desired direct waterfront spot on quiet east side cove. Perfect for couples or families. Kayaks, Canoe, sailboat. Central air, radiant heated floors, gas fireplace, washer/dryer, large deck with gas grill. Lawn area, good swimming area and dockage for you boat in front of the cottage.

Strict no-pet and no-smoking inside the cottage policy

The space
Three-bedroom, 2 full bath cottage with fully equipped kitchen, open-concept (entirely restored cottage 2016). We repurposed original and vintage materials from this loved early 1900's cottage during our restoration. Every window has a story. Just ask us!

Known as "Lone Pine Cottage," it now has central air throughout, radiant heat and an easy-to-use beautiful brick, gas fireplace. Great for crisp mornings.

Bedrooms include: one queen, one full and 2 bunks. Wake up in the queen and full bedrooms to sunrise on the lake. Spectacular views. Also upstairs, is a comfortable reading area and desk, a full bathroom with a 2 person, fully tiled shower, while the downstairs bath boasts a sparkling new, claw foot soaking tub.

Downstairs, you will find a fully equipped kitchen, full-sized fridge, dual-fuel stove (gas stove top/electric oven), dishwasher and apron farm sink. Guests can dine on the old world dining table and Hitchcock chairs made locally, or at the kitchen peninsula. We have an open concept kitchen/dining/living room area which opens, through french doors, onto a large deck, just steps from the lake front. Enjoy the gas grill and picnic table for afternoon BBQs or glowing white lights and sunsets for a lovely evening dinner party.

Bring your boat or jetski and tie up at our lakefront dock. This lake is great for swimming, boating, water-skiing and fishing. Private lawn and water front. Sunny side of the lake. The cottage is close to 'the Secret Spot,' (a nice area great for small children to play in the water). We live next door to the cottage. Our boat is parked on the south side of the dock in front of our place, your boat, if you bring one, is docked on the right north side directly in front of your cottage.

Where you'll sleep

Bedroom 1
1 queen bed
Bedroom 2
1 double bed
Bedroom 3
1 bunk bed

What this place offers

Free parking on premises
TV with standard cable
Air conditioning
Indoor fireplace
Hair dryer

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48 reviews
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4.98 out of 5 stars from 48 reviews


Where you’ll be

Winchester, Connecticut, United States

The area offers pleasant restaurants and grocers some using locally produced food, Farmer's Markets (don't miss Litchfield's Saturday Farmer's Market!), the Gilson Cinema/Cafe, Antiquing, nearby fly-fishing, hiking, and biking. Stop in at a local farm for just picked corn or tomatoes, or an after dinner ice-cream cone.

For anyone up for a Berkshires experience, we are less than a one hour, country drive from Tanglewood, Shakespeare and Co., Stockbridge, Great Barrington, Lenox, and the Outlets at Lenox.

During the summer, we request a minimum 7 day booking, Saturday to Saturday. Also, we cannot accommodate pets, due to potential allergies of renters. However, there is a highly respected kennel close to the other side of the lake.

Contact us for quick response, or a specific quote on longer time periods.

NOTE: During off season (all dates other than in June, July, August), rentals of 3 days + have a reduced rate of $200 per night).

On Sundays, the early part of the day can be busy on the lake, but once"quiet time" commences at 5PM, boaters start to leave making it nice for canoeing and kayaking. The cottage has a preferred location on the lake in a quiet, wide and sunny cove.

Hosted by Jack

  1. Joined in June 2016
  • 48 Reviews
  • Identity verified
  • Superhost
Easy going owner intent who wants to see his guests enjoy their stay and come back again.

During your stay

We also own the house next door, and can help if you should need assistance. If you are nearby, feel welcome to visit our cottage to see it with your own eyes.

Jack is a Superhost

Superhosts are experienced, highly rated hosts who are committed to providing great stays for guests.
  • Languages: English, Español
  • Response rate: 100%
  • Response time: within a few hours
To protect your payment, never transfer money or communicate outside of the Airbnb website or app.

Things to know

House rules

Check-in: After 3:00 PM
Checkout: 11:00 AM
No smoking
No pets
No parties or events

Health & safety

Committed to Airbnb's enhanced cleaning process. Show more
Airbnb's social-distancing and other COVID-19-related guidelines apply
Carbon monoxide alarm
Smoke alarm
Security Deposit - if you damage the home, you may be charged up to $200

Cancellation policy