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
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
Similar properties

Simsbury 1820 House
Simsbury Center
Simsbury 1820 House
Simsbury Center
- Pool
- Breakfast included
- Pet friendly
- Parking included
4.7 out of 5, Exceptional, 1,003 reviews
4.7
Exceptional
1,003 reviews
$204 nightly
The price is $235
$235 total
Jul 28 - Jul 29
Total with taxes and fees

The Litchfield Inn
Litchfield
The Litchfield Inn
Litchfield
- Pool
- Breakfast included
- Spa
- Pet friendly
4.6 out of 5, Wonderful, 1,005 reviews
4.6
Wonderful
1,005 reviews
$360 nightly
The price is $414
$414 total
Jul 30 - Jul 31
Total with taxes and fees

The Abner Hotel
Litchfield Historic District
The Abner Hotel
Litchfield Historic District
- Breakfast included
- Pet friendly
- Parking included
- Free WiFi
4.8 out of 5, Exceptional, 81 reviews
4.8
Exceptional
81 reviews
$261 nightly
The price is $301
$301 total
Aug 23 - Aug 24
Total with taxes and fees

Blackberry River Inn
Norfolk
Blackberry River Inn
Norfolk
- Pool
- Breakfast included
- Parking included
- Free WiFi
4.7 out of 5, Exceptional, 199 reviews
4.7
Exceptional
199 reviews
$164 nightly
The price is $189
$189 total
Jul 28 - Jul 29
Total with taxes and fees

Americas Best Value Inn Torrington CT
Torrington
Americas Best Value Inn Torrington CT
Torrington
- Parking included
- Free WiFi
- Air conditioning
- Gym
2.8 out of 5, 806 reviews
2.8
806 reviews
$110 nightly
The price is $127
$127 total
Jul 28 - Jul 29
Total with taxes and fees

Charming renovated 3-bedroom house in serene Winsted
Winsted
Charming renovated 3-bedroom house in serene Winsted
Winsted
- Kitchen
- Washer
- Dryer
- Free WiFi
4.0 out of 5, Very Good, 4 reviews
4.0
Very Good
4 reviews

Sunny Peace Homestay
Harwinton
Sunny Peace Homestay
Harwinton
- Pool
- Parking included
- Free WiFi
4.7 out of 5, Exceptional, 9 reviews
4.7
Exceptional
9 reviews
$192 nightly
The price is $221
$221 total
Aug 12 - Aug 13
Total with taxes and fees

1st Floor The Inn at Highland Lake
Winsted
1st Floor The Inn at Highland Lake
Winsted
- Kitchen
- Washer
- Dryer
- Free WiFi
5.0 out of 5, Exceptional, 14 reviews
5
Exceptional
14 reviews

Waterfront House & Guest House Available in Winchester, CT!
Winchester
Waterfront House & Guest House Available in Winchester, CT!
Winchester
- Kitchen
- Washer
- Dryer
- Free WiFi

Stylish, renovated 3 bed 3.5 bath 1812 Colonial
Colebrook
Stylish, renovated 3 bed 3.5 bath 1812 Colonial
Colebrook
- Air conditioning
- Parking available
- Laundry
About the neighborhood
Winsted
With a stay at this vacation home in Winsted, you'll be on the waterfront, just a 1-minute walk from Highland Lake and 9 minutes by foot from The Marina at Highland Lake. .This vacation home is 0.8 mi (1.3 km) from Winchester Historical Society and 0.9 mi (1.5 km) from Walker Field.
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.
Make yourself comfortable in this air-conditioned vacation home, which has a kitchen. There's a private balcony. Complimentary wireless internet access keeps you connected, and a Smart television is provided for your entertainment. The bathroom has a jetted bathtub and a bidet.
Enjoy recreation amenities such as a fitness center or take in the view from a garden.
Guests will find features like internet access and onsite parking.
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
Pets 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 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
We should mention
This property does not have elevators