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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. - Family-Friendly Highland Lake Waterfront w/ Private Dock & Shallow Walk-In — 5BR (Winchester)
A spacious room with a large sliding glass door leading to an outdoor patio area. - Family-Friendly Highland Lake Waterfront w/ Private Dock & Shallow Walk-In — 5BR (Winchester)
A living room with a sofa, a coffee table, a fireplace, and a view of the outdoors. - Family-Friendly Highland Lake Waterfront w/ Private Dock & Shallow Walk-In — 5BR (Winchester)
A house with a stone pond, a covered porch, and a well-maintained lawn. - Family-Friendly Highland Lake Waterfront w/ Private Dock & Shallow Walk-In — 5BR (Winchester)
Private kitchen - Family-Friendly Highland Lake Waterfront w/ Private Dock & Shallow Walk-In — 5BR (Winchester)
A garden, laundry facilities and a gym are just a few of the amenities provided at Family-Friendly Highland Lake Waterfront w/ Private Dock & Shallow Walk-In — 5BR. Guests can connect to free in-room WiFi.

Entire home

5 bedrooms4 bathrooms

Popular amenities

  • Kitchen
  • Washing machine
  • Dryer
  • Pet-friendly
  • Free Wi-Fi
  • Air-conditioning

Add dates for prices

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.

Property amenities

Beach

  • Beach nearby

Ski

  • Cross-country skiing nearby
  • Snowboarding nearby

Internet

  • Available in the house: Free WiFi

Parking and transport

  • Parking on site

Bedrooms

  • 5 bedrooms
  • Bedsheets provided

Bathroom

  • 3.5 bathrooms
  • Bathtub or shower
  • Bidet
  • Hair dryer
  • Jetted bathtub
  • Shampoo
  • Shower
  • Soap
  • Toilet paper
  • Towels provided

Entertainment

  • Smart TV

Outdoor areas

  • Balcony
  • Garden

Laundry

  • Laundry facilities
  • Washing machine

Comfort

  • Air conditioning
  • Heating

Pets

  • Pet friendly
  • Welcoming cats and dogs only
  • 2 pets total

Suitability/Accessibility

  • If you have requests for specific accessibility needs, please contact the property using the information on the reservation confirmation received after booking.
  • Upper floors accessible by stairs only
  • Smoke-free property

Services and conveniences

  • Iron/ironing board

Location highlights

  • In the mountains
  • Near a hospital
  • Near a river
  • Near the marina
  • On a lake
  • On the waterfront

Things to do

  • Gym
  • Birdwatching nearby
  • Fishing nearby
  • Golfing nearby
  • Hiking nearby
  • Horseback riding nearby
  • Hunting nearby
  • Ice skating nearby
  • Jet skiing nearby
  • Kayaking nearby
  • Motor boating nearby
  • Mountain biking nearby
  • Rafting nearby
  • Sailing nearby
  • Sledding nearby
  • Snowmobiling nearby
  • Surfing/bodyboarding nearby
  • Swimming nearby
  • Water skiing nearby
  • Water tubing nearby
  • Wildlife walks nearby
  • Windsurfing nearby
  • Winery tours nearby

Safety features

  • Carbon monoxide detector (host has indicated there is a carbon monoxide detector on the property)
  • Smoke detector (host has indicated there is a smoke detector on the property)
  • Fire extinguisher

General

  • Garden

Similar properties

Policies

Check-in

Check-in time starts at 3:00 PM
Minimum check-in age - 18

Check-out

Check-out before 10:00 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

Pets

Pets are allowed
Service animals are welcome, and are exempt from fees
Welcoming dogs and cats only
2 total pets

Children and extra beds

Children are welcome

Events

Events allowed: family gatherings, birthday parties, weddings

Smoking

Smoking is not permitted

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
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
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

We should mention

This property does not have any lifts

About the area

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 Mural Project 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 sledging. Visit our Winsted travel guide
View more Holiday homes in Winsted
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
  • Laurel Lanes
    17 min walk - 1.5 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
  • Skipper's
    3 min drive
  • Subway
    6 min drive
  • Little Red Barn Brewer
    17 min walk

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).

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