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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.
A spacious room with a large sliding glass door leading to an outdoor patio area.
A house with a stone pond, a covered porch, and a well-maintained lawn.
A living room with a sofa, a coffee table, a fireplace, and a view of the outdoors.
Private kitchen

Entire home

5 bedrooms4 bathrooms

Popular amenities

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

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, Laurel Lanes
    ‪17 min walk‬
  • Airport, Hartford, CT (BDL-Bradley Intl.)
    ‪41 min drive‬

Room options

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About this property

Entire place

You'll have the entire home to yourself and will only share it with other guests in your party.

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.
During your stay at this vacation home, you're just a quick walk from Highland Lake. You'll find features like a gym and laundry facilities. The vacation home offers free WiFi and a jetted tub.
  • Air-conditioned home with kitchen, washing machine, and 3.5 bathrooms
  • Free WiFi
  • Amenities include laundry facilities
  • Onsite recreation includes a gym
  • Steps from Highland Lake and 9 minutes by foot from The Marina at Highland Lake
As a guest of this vacation home, you'll find a fitness center, a garden, and laundry facilities. The front desk is open around the clock.

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

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 welcome
  • Only dogs and cats are allowed
  • Maximum 2 pets
  • Service animals are exempt from fees

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

This property is managed by a professional host. The provision of housing is linked to their trade, business, or profession.
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 there is a carbon monoxide detector on the property
Host has indicated 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, terraces which may not be suitable for children; if you have concerns, we recommend contacting the property prior to your arrival to confirm 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
You will receive an email from the host with check-in and check-out instructions. You will also receive an email from Vrbo with a link to a Vrbo account which will enable you to manage your booking.
If you cancel your booking, you'll be subject to the host's cancellation policy. In accordance with EU regulations about consumer rights, property booking services are not subject to the right of withdrawal.

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