Entire home
Lakefront Escape on Highland
Photo gallery for Lakefront Escape on Highland





Reviews
1010 out of 10
Exceptional
Popular amenities
- Washing machine
- Air-conditioning
- Internet access
- Dryer
- Non-smoking
Explore the area
Winchester, CT
- Highland LakePlace, Highland Lake1 min walk
- Winchester Historical SocietyPlace, Winchester Historical Society13 min walk
- Northwestern Connecticut Community CollegePlace, Northwestern Connecticut Community College3 min drive
- Hartford, CT (BDL-Bradley Intl.)Airport, Hartford, CT (BDL-Bradley Intl.)41 min drive
Rooms & beds
5 bedrooms (sleeps 14)
Bedroom 1
1 King Bed
Bedroom 2
1 King Bed
Bedroom 3
2 Double Beds
Bedroom 4
2 Double Beds
Bedroom 5
1 Double Bed
Living Room 1
1 Double Sofa Bed
4 bathrooms
Bathroom 1
Soap · Towels provided · Toilet · Shower only · Shampoo
Bathroom 2
Soap · Towels provided · Toilet · Shower only · Shampoo
Bathroom 3
Soap · Towels provided · Toilet · Shower only · Shampoo
Bathroom 4
Soap · Towels provided · Toilet · Shower only · Shampoo
About this property
Lakefront Escape on Highland
Make unforgettable memories at this one-of-a-kind, family-friendly lakehouse. Set on a private shoreline, it offers the perfect mix of relaxation, recreation, and comfort. Enjoy the cozy feel of home, resort-style fun, and natural beauty year-round, whether it’s summer on the lake, fall foliage, or a winter ski trip.
Add dates for prices
Amenities
Washing machine
Dryer
Air conditioning
Have a question?
Get instant answers with AI powered search of property information and reviews.
Similar properties

Unique 4-bedroom house with stunning views, close to all in fantastic Cornwall
Cornwall
Unique 4-bedroom house with stunning views, close to all in fantastic Cornwall
Cornwall
- Spa pool
- Washing machine
- Dryer
- Pet-friendly
10.0 out of 10, Exceptional, (1 review)
10/10
Exceptional
(1 review)

Lakefront Oasis with Spectacular Views – 3BR, 3BA, Sleeps 6, private swim dock.
New Hartford
Lakefront Oasis with Spectacular Views – 3BR, 3BA, Sleeps 6, private swim dock.
New Hartford
- Kitchen
- Washing machine
- Dryer
- Pet-friendly
9.6 out of 10, Exceptional, (5 reviews)
9.6/10
Exceptional
(5 reviews)

Mohawk Mountain Retreat: 5 Mins to Skiing
Cornwall
Mohawk Mountain Retreat: 5 Mins to Skiing
Cornwall
- Kitchen
- Washing machine
- Dryer
- Pet-friendly
10.0 out of 10, Exceptional, (1 review)
10/10
Exceptional
(1 review)

Waterfront Lake Home on Tranquil Harwinton Lake with spectacular 180⁰ view.
Northwest Harwinton
Waterfront Lake Home on Tranquil Harwinton Lake with spectacular 180⁰ view.
Northwest Harwinton
- Kitchen
- Washing machine
- Dryer
- Pet-friendly
9.8 out of 10, Exceptional, (196 reviews)
9.8/10
Exceptional
(196 reviews)

Stunning Retreat on 62 Acres, 7000 sq ft, Pool and Hot Tub
New Hartford
Stunning Retreat on 62 Acres, 7000 sq ft, Pool and Hot Tub
New Hartford
- Pool
- Spa pool
- Kitchen
- Washing machine
10.0 out of 10, Exceptional, (4 reviews)
10/10
Exceptional
(4 reviews)

Lakeside Oasis with Hot Tub; 5 min to Ski Mountain!
New Hartford
Lakeside Oasis with Hot Tub; 5 min to Ski Mountain!
New Hartford
- Pool
- Spa pool
- Kitchen
- Washing machine
10.0 out of 10, Exceptional, (2 reviews)
10/10
Exceptional
(2 reviews)

Newly renovated year-round LAKEFRONT rental on Highland Lake!!! Sleeps 8-9!
Winsted
Newly renovated year-round LAKEFRONT rental on Highland Lake!!! Sleeps 8-9!
Winsted
- Kitchen
- Washing machine
- Dryer
- Pet-friendly
10.0 out of 10, Exceptional, (22 reviews)
10/10
Exceptional
(22 reviews)

The 1782 Darling House on the Litchfield Green
Litchfield Historic District
The 1782 Darling House on the Litchfield Green
Litchfield Historic District
- Kitchen
- Washing machine
- Dryer
- Air-conditioning
9.6 out of 10, Exceptional, (5 reviews)
9.6/10
Exceptional
(5 reviews)

Cozy Lake Garda Home-Baby/Kid/Pet Friendly
Burlington
Cozy Lake Garda Home-Baby/Kid/Pet Friendly
Burlington
- Kitchen
- Washing machine
- Dryer
- Pet-friendly
9.6 out of 10, Exceptional, (4 reviews)
9.6/10
Exceptional
(4 reviews)

Sweetbrier Farm -- Gorgeous Views, Beautiful Home
Litchfield
Sweetbrier Farm -- Gorgeous Views, Beautiful Home
Litchfield
- Pool
- Pet-friendly
- Free Wi-Fi
- Air-conditioning
10.0 out of 10, Exceptional, (33 reviews)
10/10
Exceptional
(33 reviews)

Serene Salisbury Rental Home on 26 Acres w/ Deck!
Salisbury
Serene Salisbury Rental Home on 26 Acres w/ Deck!
Salisbury
- Kitchen
- Washing machine
- Dryer
- Air-conditioning
9.2 out of 10, Wonderful, (17 reviews)
9.2/10
Wonderful
(17 reviews)

Woodland Sanctuary House with Hot Tub, Fire Pit, and Woodstove
Barkhamsted
Woodland Sanctuary House with Hot Tub, Fire Pit, and Woodstove
Barkhamsted
- Spa pool
- Kitchen
- Pet-friendly
- Free Wi-Fi
10.0 out of 10, Exceptional, (10 reviews)
10/10
Exceptional
(10 reviews)

Spacious 5-bedroom house in lake community, fireplace, hot tub, washer/dryer
Goshen
Spacious 5-bedroom house in lake community, fireplace, hot tub, washer/dryer
Goshen
- Spa pool
- Kitchen
- Washing machine
- Dryer
10.0 out of 10, Exceptional, (12 reviews)
10/10
Exceptional
(12 reviews)

The Doctor's 1781 House on the Litchfield Green
Litchfield Historic District
The Doctor's 1781 House on the Litchfield Green
Litchfield Historic District
- Kitchen
- Free Wi-Fi
- Air-conditioning
- Outdoor space
10.0 out of 10, Exceptional, (26 reviews)
10/10
Exceptional
(26 reviews)

1st Floor The Inn at Highland Lake
Winsted
1st Floor The Inn at Highland Lake
Winsted
- Kitchen
- Washing machine
- Dryer
- Free Wi-Fi
10.0 out of 10, Exceptional, (14 reviews)
10/10
Exceptional
(14 reviews)

Immaculate Year-Round Lakefront-Charming cottage, swimming, boating, central air
Winchester
Immaculate Year-Round Lakefront-Charming cottage, swimming, boating, central air
Winchester
- Kitchen
- Washing machine
- Dryer
- Free Wi-Fi
10.0 out of 10, Exceptional, (56 reviews)
10/10
Exceptional
(56 reviews)

Litchfield Hills Lakefront Home! Amazing location, views and sunsets
Goshen
Litchfield Hills Lakefront Home! Amazing location, views and sunsets
Goshen
- Kitchen
- Washing machine
- Dryer
- Free Wi-Fi
10.0 out of 10, Exceptional, (49 reviews)
10/10
Exceptional
(49 reviews)

2nd Floor The Inn at Highland Lake
Winsted
2nd Floor The Inn at Highland Lake
Winsted
- Kitchen
- Washing machine
- Dryer
- Free Wi-Fi
9.6 out of 10, Exceptional, (17 reviews)
9.6/10
Exceptional
(17 reviews)

Best Outdoors near the Berkshires
Winchester
Best Outdoors near the Berkshires
Winchester
- Kitchen
- Outdoor space
- Parking available
- Microwave
10.0 out of 10, Exceptional, (15 reviews)
10/10
Exceptional
(15 reviews)

Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville
Collinsville
Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville
Collinsville
- Kitchen
- Washing machine
- Dryer
- Free Wi-Fi
10.0 out of 10, Exceptional, (63 reviews)
10/10
Exceptional
(63 reviews)

Elegant 3 Bedroom Modern Peaceful Home with Pool in CT
Harwinton
Elegant 3 Bedroom Modern Peaceful Home with Pool in CT
Harwinton
- Pool
- Washing machine
- Dryer
- Air-conditioning

Our Cottage - Small in size, Big in character, On beautiful Highland Lake
Winchester
Our Cottage - Small in size, Big in character, On beautiful Highland Lake
Winchester
- Kitchen
- Free Wi-Fi
- Air-conditioning
- Outdoor space
10.0 out of 10, Exceptional, (50 reviews)
10/10
Exceptional
(50 reviews)

Charming 2-bedroom cottage with AC and WiFi in welcoming New Hartford
New Hartford
Charming 2-bedroom cottage with AC and WiFi in welcoming New Hartford
New Hartford
- Kitchen
- Air-conditioning
- Parking available
- Barbecue
10.0 out of 10, Exceptional, (10 reviews)
10/10
Exceptional
(10 reviews)

Lakefront Tranquility/Fishermans Delight
New Hartford
Lakefront Tranquility/Fishermans Delight
New Hartford
- Kitchen
- Free Wi-Fi
- Outdoor space
- Parking available
10.0 out of 10, Exceptional, (21 reviews)
10/10
Exceptional
(21 reviews)

Charming renovated 3-bedroom house in serene Winsted
Winsted
Charming renovated 3-bedroom house in serene Winsted
Winsted
- Kitchen
- Washing machine
- Dryer
- Free Wi-Fi
8.0 out of 10, Very good, (3 reviews)
8.0/10
Very good
(3 reviews)

Waterfront Cabin w Firepit, Dock, Deck, BBQ. Direct Lake Access! Pet-friendly!
Northwest Harwinton
Waterfront Cabin w Firepit, Dock, Deck, BBQ. Direct Lake Access! Pet-friendly!
Northwest Harwinton
- Kitchen
- Pet-friendly
- Free Wi-Fi
- Air-conditioning
8.8 out of 10, Excellent, (28 reviews)
8.8/10
Excellent
(28 reviews)

Iconic Cabin in the Berkshires
Sandisfield
Iconic Cabin in the Berkshires
Sandisfield
- Pool
- Kitchen
- Washing machine
- Dryer
6.0 out of 10, (2 reviews)
6.0/10
(2 reviews)

Mint restored historic Simsbury 4BR estate; optional 1BR apt; all new amenities
Simsbury Center
Mint restored historic Simsbury 4BR estate; optional 1BR apt; all new amenities
Simsbury Center
- Kitchen
- Washing machine
- Dryer
- Free Wi-Fi
10.0 out of 10, Exceptional, (2 reviews)
10/10
Exceptional
(2 reviews)

Enjoy a restful stay with fast internet, smart TV and the company of your pet.
winsted
Enjoy a restful stay with fast internet, smart TV and the company of your pet.
winsted
- Kitchen
- Pet-friendly
- Free Wi-Fi
- Air-conditioning
9.2 out of 10, Wonderful, (47 reviews)
9.2/10
Wonderful
(47 reviews)

Beautiful retreat in a lake community to the enjoy the summer season.
Tolland
Beautiful retreat in a lake community to the enjoy the summer season.
Tolland
- Kitchen
- Dryer
- Free Wi-Fi
- Parking available
10.0 out of 10, Exceptional, (45 reviews)
10/10
Exceptional
(45 reviews)
House Rules
Check in after 4:00 PM
Minimum age to rent: 25
Check out before 11:00 AM
Children
Children allowed: ages 0–17
Events
No events allowed
Pets
No pets allowed
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
On-site parties or group events are strictly prohibited
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
About the area
Winsted
Winchester is home to this holiday home. Winchester Historical Society and American Mural Project are cultural highlights, and some of the area's attractions include Laurel Lanes and KidsPlay Museum. Action Wildlife Foundation and Flamig Farm are also worth visiting.
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 - 13 min walk - 1.1 km
- Rowley Fields - 2 min drive - 1.5 km
- Northwestern Connecticut Community College - 3 min drive - 1.8 km
Getting around
- Hartford, CT (BDL-Bradley Intl.) - 45 min drive
Restaurants
- McDonald's - 4 min drive
- Dunkin' - 3 min drive
- Subway - 6 min drive
- Little Red Barn Brewer - 17 min walk
- Dunkin' - 4 min drive
Frequently asked questions
Is Lakefront Escape on Highland pet-friendly?
No, pets are not allowed at this property.
How much does it cost to stay at Lakefront Escape on Highland?
As of 23 Apr 2026, prices found for a 1-night stay for 2 adults at Lakefront Escape on Highland on 23 Apr 2026 start from AU$1,187, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.
What time is check-in at Lakefront Escape on Highland?
Check-in begins at 4:00 PM.
What time is check-out at Lakefront Escape on Highland?
Checkout is at 11:00 AM.
Where is Lakefront Escape on Highland located?
Situated in Winchester, 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).
About the host
Your host
Tell us how we can improve our siteShare feedback
