Family-Friendly Highland Lake Waterfront w/Private Dock & Shallow Walk-In — 5BR | House in Winchester
5 Bedroom House in Winchester
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.
Family-Friendly Highland Lake Waterfront w/Private Dock & Shallow Walk-In — 5BR is located in Winchester. Family-Friendly Highland Lake Waterfront w/Private Dock & Shallow Walk-In — 5BR provides accommodation, featuring Ocean View, Balcony/Terrace, Oceanfront, among other amenities. This House features Ocean View, Balcony/Terrace, Oceanfront, to make your stay a comfortable one.
Family-Friendly Highland Lake Waterfront w/Private Dock & Shallow Walk-In — 5BR has 5 Bedrooms , 3 Bathrooms, and max occupancy of 14 people. The minimum rental for this property is 1 nights, but this can change depending on the season you plan on staying. Previous guests have given good rated it, and VRBO labeled it a top-rated House because of the excellent services rendered by the owner or manager of this House, and has consistently provided great experiences for their guests. Most families or guests that use it recommend it to their friends and some of them are repeat guests. House has a friendly neighborhood, and the Winchester has interesting places to visit. If you want to learn more about the House in Winchester, such as places to visit and things to do nearby, you can check below to learn more.
This Property is OneKey Eligible
Earn OneKeyCash for every dollar spent on eligible vacation rentals, villas, cottages, cabins, and more when you book on Vrbo.
Amenities
Facility Overview
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Air conditioning
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Heating
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Jetted bathtub
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Shampoo
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Towels provided
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Bidet
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3+ bathrooms
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Soap
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Hair dryer
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Bathtub or shower
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Toilet paper
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5 bedrooms
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Bed sheets provided
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Laundry facilities
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Washing machine and dryer
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Near the beach
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Onsite parking
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Pet friendly
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2 total pets
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Welcoming cats and dogs only
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Upper floors accessible by stairs only
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Smoke-free property
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If you have requests for specific accessibility needs, please contact the property using the information on the reservation confirmation received after booking.
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No elevators
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Windsurfing nearby
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Kayaking nearby
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Surfing/body boarding nearby
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Fitness center
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Sledding nearby
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Sailing nearby
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Swimming nearby
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Ice skating nearby
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Water skiing nearby
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Cycling nearby
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Smart TV
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Near a river
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On the lake
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On the waterfront
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Near a hospital
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In the mountains
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Travel crib
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Stair gate
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Baby monitor
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Iron/ironing board
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Free WiFi
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Balcony
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Garden
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Fire extinguisher
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Carbon monoxide detector installed (host has indicated there is a carbon monoxide detector on the property)
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Smoke detector installed (host has indicated there is a smoke detector on the property)
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Snowboarding and cross-country skiing nearby
Policies
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 host has indicated there is a carbon monoxide detector on the property host has indicated there is a smoke detector on the property parties and events (including family gatherings, birthday parties and weddings) are allowed on site; maximum attendees: 50 safety features at this property include a fire extinguisher special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed 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
FAQ's
Is this Winchester house pet-friendly for guests?
Yes, pets are allowed at this property. Check the guest reviews to learn what guests had to share.
Does the Winchester house have a swimming pool?
No, this Winchester house does not have a swimming pool. Check the Facility Overview section for details about the pool and other available facilities.
How much does it cost per night to stay in Winchester house?
Best-rates for the Winchester house starts from $1,260 per night with includes Wellness Facilities, Fireplace/Heating, Child Friendly, Hot Tub, Internet, Air Conditioner, Parking, TV, View, Security/Safety, Bedding/Linens, Pet Friendly, Ocean View, Balcony/Terrace, Oceanfront, Laundry, Kitchen with all other facilities. matches every traveler with their perfect accommodation, whether you are traveling with a group, friends, family, or pets.
Is Winchester house a family-friendly place to stay?
Based on the information we have received from the owner or our partner, this is considered to be a family-friendly property. Families have rated this house Good or guests have recommended them suitable for families. As reported by the owner or manager, the house has specified that children are welcome. Please see details about suitability for your family or inquire with the property to learn more.
Is the Winchester house wheelchair accessible or offer services for disabled guests?
Based on the information received from our partner, the Winchester house has not specified they are wheelchair accessible. Likewise, there is not an elevator specified as being available at the property. Specific accessibility details may be addressed in the property details section of this page.
What is the minimum night stay policy for the Winchester house?
Based on the information reported by the owner or manager, the Winchester house indicates 1 day stay policy at this house. Guests are cautioned that the minimum stay policy may differ based on seasonality or availability and may be at the discretion of the owner or manager.
What cancellation policy is in place for Winchester house?
Guests are cautioned that the cancellation policy may differ based on seasonality, availability, or current travel restrictions. Guests should also be aware that this policy may be subject to change and should be confirmed prior to booking. More details may be available on this page in the property description. However, early check-in or late check-out can sometimes be negotiated between the guest and the owner or the manager of this property.
