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Family-Friendly Highland Lake Waterfront w/ Private Dock & Shallow Walk-In — 5BR

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A lakeside view with a sunset, a boat dock, and a table with a fire.
Private kitchen
A spacious room with a large sliding glass door leading to an outdoor patio area.
A lakeside property with a dock, a covered outdoor seating area, and a house with a balcony overlooking the water.
A house with a stone pond, a covered porch, and a well-maintained lawn.

Reviews

10 out of 10
Exceptional

Highlights

  • On-site fitness centre
    A rare find - enjoy convenient access to fitness facilities during your stay.
  • Discover nearby landmarks
    Walk to Highland Lake
5 bedrooms3+ bathroomsSleeps 14

Popular amenities

  • Onsite parking available
  • Dogs and cats allowed
  • Kitchen
  • Washing machine
  • Air-conditioning
  • Balcony

Explore the area

View in a map
Winchester, CT
  • Place, Highland Lake
    ‪1 min walk‬
  • Place, The Marina at Highland Lake
    ‪9 min walk‬
  • Place, Northwestern Connecticut Community College
    ‪3 min drive‬
  • Airport, Hartford, CT (BDL-Bradley Intl.)
    ‪41 min drive‬

Rooms & beds

5 bedrooms (sleeps 14)

Bedroom 1

1 King Bed

Bedroom 2

1 Queen Bed

Bunk Room

2 Single Bunk Beds

Downstairs Queen Bedroom

1 Queen Bed

Lakeview Queen

1 Queen Bed

3 bathrooms, 1 half bathroom

Downstairs Full Bathroom

+1
Soap · Towels provided · Bathtub or shower · Bathtub · Bidet · Toilet · Jetted bathtub · Hair dryer

En Suite Bathroom

Soap · Towels provided · Bathtub or shower · Bathtub · Bidet · Toilet · Hair dryer

First Floor Full Bath

Soap · Towels provided · Bathtub or shower · Bathtub · Toilet · Hair dryer

Outdoor Shower

Shower only

Spaces

Deck or patio
Kitchen
Balcony
Garden

About this property

Family-Friendly Highland Lake Waterfront w/ Private Dock & Shallow Walk-In — 5BR

Wake up to lake views, spend the day swimming from your private dock, and end the evening watching sunset over Highland Lake from the fire table. This newly renovated waterfront home sleeps 12 comfortably; it is designed for memorable family vacations and group getaways, with private lake access, walk-in swimming, kayaks, a game room, and room for everyone to gather. The interior has undergone a large remodel where you will enjoy a modern kitchen, bright living room with a fireplace, a game room, and an exercise area with Peloton.

The property is thoughtfully outfitted for lake getaways, with families and large groups in mind. Enjoy:

✔Waterfront Living – Swim, float, kayak, or relax by the lake with easy walk-in water access perfect for families
✔Private Dock – Tie up your boat or jump off the dock in sheltered Hurlbut Cove, perfect for floating, paddleboarding, and swimming
✔Fully Stocked – Floats, kayaks, life jackets, and water toys ready for guests
✔ West-Facing Home – Soak up long, sunny days and epic sunsets
✔ Outdoor Spaces Made for Gathering – Start the day with coffee on the deck, gather for sunset cocktails around the lakefront gas fire table, and end the night making s’mores by the fire pit.
✔Flat, Grassy Lawn – Stretch out, read, and play lawn games with a lake view
✔Nearby Beach – Walk two minutes to Resha, a sandy beach with seasonal lifeguard coverage
✔ Room for Everyone – 5 spacious bedrooms and generous gathering spaces designed for multi-family trips and lake escapes with friends
✔ Newly Renovated Interiors – Fresh, modern spaces that feel comfortable and clean
✔ Fully Equipped Kitchen – Stocked for everything from pancake breakfasts to large family dinners
✔ Designed for Families – Includes a crib, Pack ’n Play, infant & child life vests, floats, sand toys, and kid-friendly touches throughout
✔ Easy Escape from NYC & Boston – A relaxed Litchfield County getaway just about two hours from either city
✔ Walking distance to Little Red Barn Brewery & Main Street shops and restaurants (.8 miles)
✔ Nearby marina (.25 miles) for speedboat and pontoon rentals
✔Perfect for multiple families, groups of friends, bachelor/bachelorette parties, and milestone birthdays.

Guests will have access to the whole house and yard space. Private waterfront location with dock.

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House Rules

Check in after 3:00 PM
Minimum age to rent: 18
Check out before 10:00 AM
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Children

Children allowed: ages 0–17
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Events

Events allowed: family gatherings, birthday parties, weddings
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Pets

Pets allowed: dogs and cats (limit 2 total)
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Smoking

Smoking is not permitted

Important information

You need to know

Property # 5322666vb
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
Parties and events (including family gatherings, birthday parties and weddings) are allowed on site. Maximum attendees: 50
Host has indicated that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher
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

About the area

Winsted

Located in Winsted, this holiday home is in the mountains and on the waterfront. The area's natural beauty can be seen at Tatro Pond and Platt Hill State Park, while Winchester Historical Society and American Museum of Tort Law are cultural highlights. Laurel Lanes and KidsPlay Museum are also worth visiting. Enjoy the area's slopes with cross-country skiing and snowboarding, and don't miss out on the snowmobiling and ice skating.
Map
Winchester, CT

What's nearby

  • Highland Lake - 1 min walk - 0.1 km
  • The Marina at Highland Lake - 9 min walk - 0.8 km
  • Winchester Historical Society - 16 min walk - 1.3 km
  • Northwestern Connecticut Community College Library - 2 min drive - 1.9 km
  • Northwestern Connecticut Community College - 3 min drive - 1.8 km

Getting around

  • Hartford, CT (BDL-Bradley Intl.) - 49 min drive

Restaurants

  • ‪McDonald's - ‬4 min drive
  • ‪Dunkin' - ‬3 min drive
  • ‪Arcadia - ‬10 min drive
  • ‪Skipper's - ‬3 min drive
  • ‪Dunkin' - ‬4 min drive

Frequently asked questions

Is Family-Friendly Highland Lake Waterfront w/ Private Dock & Shallow Walk-In — 5BR pet-friendly?

Yes, this property allows cats and dogs (limit 2 total).

How much is parking at Family-Friendly Highland Lake Waterfront w/ Private Dock & Shallow Walk-In — 5BR?

On-site parking is available at the property.

What time is check-in at Family-Friendly Highland Lake Waterfront w/ Private Dock & Shallow Walk-In — 5BR?

Check-in begins at 3:00 PM.

What time is check-out at Family-Friendly Highland Lake Waterfront w/ Private Dock & Shallow Walk-In — 5BR?

Checkout is at 10:00 AM.

Where is Family-Friendly Highland Lake Waterfront w/ Private Dock & Shallow Walk-In — 5BR located?

Situated on the waterfront, this holiday home is within a 10-minute walk of Highland Lake and The Marina at Highland Lake. Winchester Historical Society and Laurel Lanes are also within 1 mile (2 km).

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. 3 out of 3 reviews
Rating 8 - Good. 0 out of 3 reviews
Rating 6 - Okay. 0 out of 3 reviews
Rating 4 - Poor. 0 out of 3 reviews
Rating 2 - Terrible. 0 out of 3 reviews

10/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
This is a perfect property for a group wanting to spend time on the lake! The house was beautiful and easily fit our group of 10. The hosts had generously supplied plenty of clean towels and fresh linens so you don't have to bring your own. There were all the usual amenities such as shampoo, conditioner, coffee, as well as plenty of plates, utensils, and cookware. The double dishwashers were very handy (and remarkablely quiet). The technologically advanced toilet seats were an interesting experience that could be a challenge for kids to resist. All those buttons . . . That being said, kids will have plenty to do with all the other indoor and outdoor activities available. The lake is absolutely beautiful and the house is situated on a quiet cove that gets little motorized boat traffic. Great for paddle boarding and kayaking. The 3 paddle boards and 3 kayaks that were available for our use were in very good condition. The neighborhood is very walkable and people seemed very friendly. Being able to bring our dog made this a true family getaway. Hosts were easy to contact and responded promptly to our questions. Overall we had a wonderful stay and would recommend this property.
Stayed 4 nights in Aug 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Pet friendly beautiful clean house on lake. Host is very easy to work with.
Stayed 5 nights in Sep 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, listing accuracy
Stayed 3 nights in Jul 2026

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