House in Winchester, CT

Immaculate Year-Round Lakefront-Charming cottage, swimming, boating, central air

Immaculate Year-Round Lakefront-Charming cottage, swimming, boating, central air

Photo gallery for Immaculate Year-Round Lakefront-Charming cottage, swimming, boating, central air

Lone Pine Cottage Guesthouse, Highland Lake
Southerly section of Lake (Third Bay)
Lawn and dockage (right)
Deck is off living room
Living area, deck at left

Overview of Immaculate Year-Round Lakefront-Charming cottage, swimming, boating, central air

10 out of 10 Exceptional
3 bedrooms2 bathroomsSleeps 7121 sq m

Popular amenities

  • Kitchen
  • Washer
  • Dryer
  • Free WiFi
  • Air conditioning
  • Outdoor space

Explore the area

Winchester, CT
  • Popular LocationHighland Lake1 min walk
  • Popular LocationBurr Pond State Park1 min walk
  • Popular LocationPlatt Hill State Park3 min drive
  • AirportWestfield, MA (BAF-Barnes Municipal)62 min drive

Rooms & beds

3 bedrooms (sleeps 7)

2 bathrooms

Bathroom 1

Bathroom 2

Spaces

Deck or patio
Kitchen
Garden
Dining Area

About this property

Immaculate Year-Round Lakefront-Charming cottage, swimming, boating, central air


RATE NOTE: Email for reduced on rate for off-season visits for more than 6 nights (November through April) .

Antique but fully modernized cottage, located among the very best of locations at Highland Lake.

If you are aesthetically minded, if you are looking for something particularly charming and special, you will love this Victorian era waterfront cottage totally restored from the ground up in 2016. If you are seeking a very nice spot on the lake, you will love this property. Canoe, Kayak, Sunfish Sailboat, and more to enjoy.

If you have rented cottages before, you know that location on the lake makes a difference. Our cottage is located on the favored east side of the lake, with best sunshine. It is located away from the boat traffic and boat wake waves, on a quiet cove open to the largest of the lakes bays. Nice swimming area for kids. It has the important things experienced visitors to our lake recognize.

It is a Victorian beauty, but fully restored in 2016 to high standards. Toasty warm in winter with lower level radiant heated floor, air conditioned for summer.

Fully equipped kitchen, open-concept. We re-purposed original and vintage materials for this loved Victorian era cottage during our restoration. Every window and door has a story. Just ask us!

Easy to use 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,' (shallow 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.

Our area offers wonderful restaurants and grocers 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.

Of course, it's great in the summer, but fall and winter offer their own special activities. Fall leaves, apple picking, hay rides and pumpkin patches in the country. Winter snow, skiing, flannel sheets and cozy fires. Our cottage can comfortably accommodate all seasons!





Property manager

JohnSalvatoreHerman

Amenities

Kitchen
Washer
Dryer
Free WiFi
Air conditioning
Outdoor space

House Rules

Check in after 3:00 PM
Minimum age to rent: 25
Check out before 11:00 AM

Children

Children allowed: ages 0-17

Events

No events allowed

Pets

No pets allowed

Smoking

Smoking is not permitted
Not a location for wild parties. We live next door. Families are welcome - keg parties are not.
IMPORTANT - In winter months 4-wheel or All-Wheel drive vehicles are require. 2-wheel drive vehicles will not work.

Damage and incidentals

You will be responsible for any damage to the rental property caused by you or your party during your stay.

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
Onsite parties or group events are strictly prohibited
Safety features at this property include a carbon monoxide detector, a fire extinguisher, a smoke detector, and a deadbolt lock

We should mention

A car is required for transportation to and from this property

About the area

Winsted

Located in Winsted, this vacation home is on a lake. Winchester Historical Society and Warner Theater are local landmarks, and some of the area's activities can be experienced at Connecticut Valley Winery and KidsPlay Museum. Traveling with kids? Consider Laurel Lanes and Action Wildlife Foundation. Discover the area's water adventures with jet skiing and water skiing nearby, or enjoy the great outdoors with hiking and mountain biking.

What's nearby

  • Highland Lake - 1 min walk
  • Burr Pond State Park - 1 min walk
  • Platt Hill State Park - 3 min drive
  • Winchester Historical Society - 9 min drive
  • Laurel Lanes - 10 min drive

Getting around

  • Bradley Intl. Airport (BDL) - 45 min drive

Restaurants

  • McDonald's - 9 min drive
  • McDonald's - 11 min drive
  • Wendy's - 11 min drive
  • Taco Bell - 11 min drive
  • Dunkin' - 10 min drive

Reviews

10

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
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Rating 10 - Excellent. 46 out of 47 reviews" "
Rating 8 - Good. 1 out of 47 reviews" "
Rating 6 - Okay. 0 out of 47 reviews" "
Rating 4 - Poor. 0 out of 47 reviews" "
Rating 2 - Terrible. 0 out of 47 reviews" "

10/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

10/10 Excellent

Elaine C.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Highland Lake I’ve missed you
This property could not have been better. It was clean as could be and set up to be very comfortable. The kitchen is complete for all your cooking needs. The views of the lake were stunning. We have stayed in VRBOs in the States and Europe and of all of them John is the best host so far. He saw to our every need without hesitation and then some. He is a cool dude. We will stay here again! Thank you John, you rock.
Stayed 6 nights in Sep 2023

10/10 Excellent

Rick M.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Best
All excellent -- waterfront, layout, kitchen, host, feel, area! Really nice. Mattresses are on the firm side.
Stayed 7 nights in Aug 2023

10/10 Excellent

tammy g.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Lake Getaway
Clean, cute and cozy. As advertised. Only drawbacks were the weather and fish weren’t biting.
Stayed 4 nights in Jun 2023

10/10 Excellent

cathie j., milford, pa

Liked: Cleanliness, check-in, communication, location, listing accuracy
Relaxing
My sister and our two cousins rented this cottage for the week and thoroughly enjoyed it. House was very clean and lovely. Kayaking and hiking were on the to do list and was great fun. We would all highly recommend a stay here.
Stayed 7 nights in May 2022

About the host

Hosted by JohnSalvatoreHerman

Host profile image
Long time lake resident, long ago it won my heart. We made a lot of memories over the years here. When the time came to rebuild the cottage, we wanted to keep it true to the early 1900's cottage it had always been. It has all the modern conveniences now, but despite this, I hope you agree we maintained its authentic charm. It still feels like the cottage our family grew up in over those many golden summers, long to be remembered. We welcome others now to make special memories too.

Why they chose this property

Great property and location on the lake.
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