Entire home
Family-Friendly Highland Lake Waterfront w/ Private Dock & Shallow Walk-In — 5BR
Choose dates to view prices
Photo gallery for Family-Friendly Highland Lake Waterfront w/ Private Dock & Shallow Walk-In — 5BR
Entire home
5 bedrooms4 bathrooms
Popular amenities
- Kitchen
- Washer
- Dryer
- Pet friendly
- Free WiFi
- Air conditioning
Explore the area
Winchester, CT
- Highland LakePlace, Highland Lake1 min walk
- The Marina at Highland LakePlace, The Marina at Highland Lake9 min walk
- Laurel LanesPlace, Laurel Lanes17 min walk
- Hartford, CT (BDL-Bradley Intl.)Airport, Hartford, CT (BDL-Bradley Intl.)41 min drive
Room options
About the neighborhood
Winsted
This vacation home places you next to Highland Lake and within a 10-minute walk of The Marina at Highland Lake. The vacation home includes a kitchen, a balcony, and a Smart TV.
What's nearby
- Highland Lake - 1 min walk - 0.1 miles
- The Marina at Highland Lake - 9 min walk - 0.5 miles
- Winchester Historical Society - 16 min walk - 0.8 miles
- Laurel Lanes - 17 min walk - 0.9 miles
- Northwestern Connecticut Community College - 3 min drive - 1.2 miles
Getting around
- Bradley Intl. Airport (BDL) - 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
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.
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.
The vacation home is air-conditioned and features a kitchen, 3.5 bathrooms, and a balcony, and there's space to spread out with 5 bedrooms. Guests can enjoy a Smart TV and stay connected with free WiFi. The bathroom offers a jetted tub, hair dryers, and bidets. Other standard amenities include a washing machine, an ironing board, and a travel crib.
Similar properties
Berkshires Retreat with Private Pickleball Court – Perfect for Large Groups!
Sheffield
Berkshires Retreat with Private Pickleball Court – Perfect for Large Groups!
Sheffield
- Kitchen
- Washer
- Dryer
- Pet friendly
Property amenities
Beach
- Beach nearby
Ski
- Cross-country skiing nearby
- Snowboarding nearby
Internet
- Available in the house: Free WiFi
Parking and transportation
- 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
- Smoking not allowed
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
- This property welcomes pets
- Dogs and cats only
- 2 total pets
- Service animals exempt from fees
Children and extra beds
Children allowed: ages 0-17
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 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
- Check-in: 3:00 PM
- Check-out: 10:00 AM
- Minimum check-in age: 18
We should mention
Details about charges, deposits, or other important information:
- This property is managed by a professional host. The provision of housing is linked to their trade, business, or profession.
- 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.
- Charges for extra guests may apply and vary depending on the property's policy.
- A cash deposit, credit card, or debit card for incidental charges, as well as a government-issued photo ID, may be required at check-in.
- Special requests are subject to availability at the time of check-in and can't be guaranteed. Certain requests may come with additional charges.
- Parties and events (including family gatherings, birthday parties and weddings) are allowed on site. Maximum attendees: 50.
- Onsite safety features include a carbon monoxide detector, a fire extinguisher, and a smoke detector.
Additional information about polices, regulations, and more:
- There are no elevators.
Frequently asked questions
What is there to do within easy reach of this vacation home?
This vacation home in Winsted is within a 10-minute walk of Highland Lake and The Marina at Highland Lake. You'll also find Winchester Historical Society and Laurel Lanes less than a mile away.
Is there parking available at Family-Friendly Highland Lake Waterfront w/ Private Dock & Shallow Walk-In — 5BR?
No, this vacation home doesn't offer parking.
Is this vacation home next to a casino?
No, this vacation home is not connected to a casino.
Is there an indoor pool at this vacation home?
No, there is no indoor pool at this vacation home.
What amenities will couples enjoy at Family-Friendly Highland Lake Waterfront w/ Private Dock & Shallow Walk-In — 5BR?
Amenities that appeal to couples at this lakeside vacation home include a jetted bathtub, a smart TV, and a kitchen.
Does Family-Friendly Highland Lake Waterfront w/ Private Dock & Shallow Walk-In — 5BR have a hot tub?
No, but all house at this vacation home have jetted bathtubs.
Does this vacation home include breakfast service?
No, this vacation home doesn't offer breakfast.
Does this vacation home allow pets to stay free of charge?
Although cats and dogs can't stay for free, they are welcome at this vacation home.
Does Family-Friendly Highland Lake Waterfront w/ Private Dock & Shallow Walk-In — 5BR have connecting rooms available?
No, this vacation home doesn't feature connecting guestrooms.
Where is the closest airport to this vacation home?
The closest major airport to this vacation home is Bradley Intl. Airport (BDL), which is 25.7 mi away (49 minutes by car). Another top airport is Westfield, MA (BAF-Barnes Municipal), which is around 25.4 mi away.
Are there rooms with balconies at Family-Friendly Highland Lake Waterfront w/ Private Dock & Shallow Walk-In — 5BR?
Yes, every house at Family-Friendly Highland Lake Waterfront w/ Private Dock & Shallow Walk-In — 5BR comes with a balcony and some offer mountain and water views.