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Beautiful, Spacious 5+ Bedroom House on Highland Lake with Spectacular views!

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Beach
5 bedrooms, desk, iron/ironing board, free WiFi
Fridge, microwave, oven, stovetop
Interior
Outdoor dining

Reviews

10 out of 10
Exceptional

Entire home

5 bedrooms4 bathroomsSleeps 12316 sq m

Popular amenities

  • Parking available
  • Barbecue grill
  • Hot Tub
  • Washer
  • Air conditioning
  • Kitchen

About this property

Entire place

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

Beautiful, Spacious 5+ Bedroom House on Highland Lake with Spectacular views!

Looking for a vacation home? This beautiful home was built in 2009 on Highland Lake, a 444-acre lake nestled in the Berkshire Mountains of Litchfield County. Located in First Bay, walking distance to the beach and boat launch, this home was designed to share and make memories with family and friends year round, but especially in the summer. This 5+ bedroom, 3 1/2 bathroom 3400 sq/ft home will sleep and dine up to 12 people comfortably. Relax and lounge in the cozy living room or peaceful sun room. Grill and eat outside on the patio and decks that overlook the lake. Cook in a state of the art fully equipped kitchen or dine out at some of New England's best restaurants. Enjoy a private dock where you can swim, fish or dock your own boat. Play games in a large yard and enjoy the jacuzzi and outdoor shower. The lower level entrance to and additional tv /rec room, half bathroom and 2nd Kitchen make it convenient to go in and out with ease. There is plenty of refrigerator space ( 1 side by side, 1 wine, 1 mini, 1 full fridge freezer on lower level )

Property manager

Amanda Zolla

Languages

English

Add dates for prices

Property amenities

Ski

  • Cross-country skiing nearby
  • Snowboarding nearby

Pool/Spa

  • Hot tub

Internet

  • Available in the house: Free WiFi

Parking and transportation

  • Parking on site

Kitchen

  • Blender
  • Coffee grinder
  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Electric kettle
  • Ice maker
  • Microwave
  • Oven
  • Paper towels
  • Refrigerator
  • Spices
  • Stovetop
  • Toaster

Dining

  • Dining table

Bedrooms

  • 5 bedrooms
  • Bedsheets provided
  • Sofa bed

Bathroom

  • 3.5 bathrooms
  • Bathtub
  • Bathtub or shower
  • Hair dryer
  • Shampoo
  • Shower
  • Soap
  • Toilet paper
  • Towels provided

Living spaces

  • Dining table
  • Fireplace
  • Living room
  • Separate dining area

Entertainment

  • Books
  • Games
  • Smart TV with cable/satellite channels
  • Video games

Outdoor areas

  • Balcony
  • Barbecue grill
  • Firepit
  • Garden
  • Outdoor furniture

Laundry

  • Washing machine

Work spaces

  • Desk
  • Desk chair

Comfort

  • Air conditioning
  • Heating

Pets

  • No pets allowed

Suitability/Accessibility

  • If you have requests for specific accessibility needs, please contact the property using the information on the reservation confirmation received after booking.
  • Wheelchair accessibility
  • Smoke-free property

Services and conveniences

  • Iron/ironing board

Location highlights

  • In the mountains
  • Near a health/beauty spa
  • Near a hospital
  • Near the marina
  • On a lake
  • On the waterfront

Things to do

  • Arcade/game room
  • Bicycles
  • Boat
  • Golf
  • Kayak
  • Snow sports gear
  • Water sports equipment
  • Basketball nearby
  • Birdwatching nearby
  • Fishing nearby
  • Golfing nearby
  • Hiking/biking trails nearby
  • Horseback riding nearby
  • Hunting nearby
  • Ice skating nearby
  • Jet skiing nearby
  • Kayaking nearby
  • Motor boating nearby
  • Mountain biking nearby
  • Rafting nearby
  • Rock climbing nearby
  • Sledding nearby
  • Snowmobiling nearby
  • Swimming nearby
  • Water skiing nearby
  • Water tubing nearby
  • Wildlife walks nearby
  • Winery tours nearby

Safety features

  • Carbon monoxide detector not reported (host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector)
  • Smoke detector (host has indicated there is a smoke detector on the property)
  • Deadbolt lock

General

  • Bicycles
  • Garden
  • Unit size: 3,400 square feet

Similar properties

Fridge, microwave, oven, stovetop

Family House On Highland Lake with Dock

  • Kitchen
  • Washer
  • Dryer
  • Free WiFi
10.0 out of 10, Exceptional, 24 reviews
Family House On Highland Lake with Dock
LIST_ALT

Policies

Check-in

Minimum check-in age: 25

Special check-in instructions

You will receive an email from the host with check-in and check-out instructions

Pets

Pets not allowed

Children and extra beds

Children are welcome
Note from host: Children encouraged:)
MONETIZATION_ON

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
Onsite parties or group events are strictly prohibited
Host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector with you on the trip
Host has indicated there is a smoke detector on the property
Safety features at this property include a deadbolt lock
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

Property is also known as

Beautiful Spacious 5 Bedroom Highland Lake Spectacular Views

About the neighborhood

Map
Winchester, CT

What's nearby

  • Highland Lake - 4 min walk - 0.4 km
  • Winchester Historical Society - 12 min walk - 1.1 km
  • Northwestern Connecticut Community College - 4 min drive - 3.0 km
  • Warner Theater - 14 min drive - 17.8 km
  • Ski Sundown - 17 min drive - 15.9 km

Getting around

  • Bradley Intl. Airport (BDL) - 40 min drive

Restaurants

  • ‪McDonald's - ‬5 min drive
  • ‪Little Red Barn Brewer - ‬13 min walk
  • ‪Rowley Grill & Tap - ‬4 min drive
  • ‪Subway - ‬7 min drive
  • ‪Log House Restaurant - ‬10 min drive

Frequently asked questions

Is Beautiful, Spacious 5+ Bedroom House on Highland Lake with Spectacular views! pet-friendly?

No, pets are not allowed at this property.

Where is Beautiful, Spacious 5+ Bedroom House on Highland Lake with Spectacular views! located?

This family-friendly Winsted vacation home is located on the waterfront, within a 15-minute walk of Highland Lake and Winchester Historical Society. Laurel Lanes and Walker Field are also within 2 mi (3 km).

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Beautiful, Spacious 5+ Bedroom House on Highland Lake with Spectacular views! Reviews

Reviews

10

Exceptional

Rating 10 - Excellent. 87 out of 92 reviews
Rating 8 - Good. 5 out of 92 reviews
Rating 6 - Okay. 0 out of 92 reviews
Rating 4 - Poor. 0 out of 92 reviews
Rating 2 - Terrible. 0 out of 92 reviews

10/10

Cleanliness

Reviews

10/10 Excellent

Mah A.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great Stay
We had a wonderful time. The house has everything you need, and the view is very beautiful. We enjoyed our stay, and will definitely be back again.
Stayed 4 nights in May 2024

10/10 Excellent

Lus P., new york

Liked: Cleanliness, check-in, communication, location, listing accuracy
An amazing stay!
the house had everything we needed! very well stocked with wonderful dishes and supplies ---my family had a great time and Amanda is a fantastic host--accommodating, available, and flexible! we are looking forward to staying there again!
Stayed 8 nights in Dec 2022

10/10 Excellent

Marcella C.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Family vacation 2023
The property was Lovely with plenty of storage (clothes and groceries). The lake was beautiful, calm and great for kayaking. We would absolutely Love to stay again!
Stayed 7 nights in Jul 2023

10/10 Excellent

Karen H.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Spacious Family Stay
Lovely, large home with nice views of the lake. Kitchen is well-stocked, three levels of bedrooms gave everyone privacy. Deck was perfect for outdoor dining. Hot tub was a huge hit. Would definitely return!
Stayed 7 nights in Jun 2023

10/10 Excellent

Susan K.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Wedding 🥰😭♥️
We rented this property for my son’s wedding & it was perfect 🤩
Stayed 7 nights in Jul 2022

8/10 Good

Jean B.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Lake getaway
Highland Lake is an amazing place to have a vacation and this house was a great place to do it at. The water is clean and refreshing and it was nice to have a little beach just yards down the street for smaller children that visited. The house was clean, updated, and had plenty of room for guests. Deck was great for cooking out or just relaxing looking out over the water. Highly recommend
Stayed 7 nights in Jul 2023

10/10 Excellent

Dorothea K., Ringoes

Liked: Cleanliness, check-in, communication, location, listing accuracy
Going Home
My husband grew up in Winsted and we were looking for a place we could reconnect with family. The house is beautiful and was set up very well for our family. The owners were helpful and responsive to questions. Overall it was a great experience in a beautiful place.
Stayed 5 nights in Apr 2022

10/10 Excellent

Todd S.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Beautiful Property on Pristine Lake!
My family had a place on Highland Lake all through my childhood. While the property was sold years ago, there were many terrific memories made over the years. 20 years later, my family was able to revisit Highland Lake and relive many of those memories during our stay at this property. Many here have spoken about the property itself so I won't go into too much detail other than to say that the house, location, and amenities provided all exceeded our expectations. Terrific vacation!
Stayed 7 nights in Jul 2022

10/10 Excellent

Leslie W.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Family Vacation
This is a beautiful property and spacious enough for all of us. The kids had fun playing games and using the toys for the lake. The adults enjoyed the chefs kitchen and large dining room table. We all spent hours at the dock enjoying the lake and we rented a pontoon boat from the local marina. I called Amanda with a minor problem and she and her husband responded immediately. I highly recommend this house, it's perfect!!!!!
Stayed 7 nights in Jul 2023

10/10 Excellent

Louise A.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Family gathering
We gathered from as close as West Hartford and as far as Montreal, Florida and California. The house was perfect with large open areas like the kitchen/dining/living area for the whole group and lots of smaller places for more intimate chats, private online work and/or homework assignments. The multiple fridges, ovens, bathrooms meant that everyone had their needs met without long waits. Long walks, dips in the lake or the hot tub, etc., it all added up to a lovely week over too soon!
Stayed 7 nights in Jul 2023

10/10 Excellent

Rita R.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Highland Lake Getaway
This Highland Lake property was magical with its beyond beautiful fall colors rising above the lake & into the hills above. Our friends stated over & over “this place is better than we ever expected”!! A few of my friends commented several times how relaxing it felt to be by the lake & wake up to its beauty every morning! It was the perfect getaway for us 4 couples each having our own bedroom. The kitchen was so spacious & equipped with most everything we needed for preparing meals & dishes to eat off & plenty of silverware. The dining room table held 10 - 12 people easily. There was plenty of living space in the living room & sun room. Plus there were 3 1/2 bathrooms for all our bathroom needs. This was definitely the VRBO to go to with a family get together or a friends get together. Amanda was so easy to contact & go over things with. A great host indeed! My party all voted this VRBO to get a 5 Star rating for sure!!🎉👍
Stayed 7 nights in Oct 2023

10/10 Excellent

Phillip M., United States

Liked: Cleanliness, check-in, communication, location, listing accuracy
The “BEST” rental yet
The 5 bedroom home on Highland Lake in Winsted CT was by far the best rental we have had in the last 20 years. We have rented Oceanfront, Lakefront and Mountainside properties in the past and this place surpassed all of them. Starting with the extra large “Gourmet Kitchen”, spacious Dining room, living room and comfy enclosed porch overlooking the lake, down to the five spacious bedrooms, our stay was perfect. Even with the inclement weather we encountered the spaciousness inside the home guaranteed a fun and relaxing time for everyone from our 3 year old granddaughter right up through the grandparents. Amanda and her husband Larry were extremely helpful and always just a phone call away. When we mentioned the propane tanks felt a little low Larry was there the next morning and had them both filled. We rented a pontoon boat at the local Marina (2 minutes away) and all 9 of us headed out to explore Highland Lake and made a stop at the 3rd Bay sandbar where we all jumped in and had a great time. Our 5 year old grandson went fishing from the dock and caught his first fish along with many more during our weeklong stay. You will not be disappointed if you rent here and we are definitely coming back in the future.
Stayed 7 nights in Aug 2023

10/10 Excellent

Gwen S.

Liked: Cleanliness, check-in, communication, location, listing accuracy
A superb and memorable vacation!
11 of us elderly brothers and sisters (59-84) from church had a wonderful time in this great property for four nights. Amanda is extremely accommodating and friendly. A super host indeed! The house is in a safe, quiet, and very friendly neighborhood. The scenery is amazing and the view from the property is excellent. We strolled around the lake a few times. The balcony is very comfortable and well equipped. The house has three canons, a fishing rod, and three bikes for use. The house is new and very clean. We felt at home at once. All the appliances are superb. The kitchen is meticulously equipped with all kinds of utensils and everything is very clean. This made our cooking efficient and enjoyable. The dining room and the living room are of the right size, comfortable, and are just right for us. The bedrooms are very clean and the beds are very comfortable. The master bedroom is excellent. The bathrooms are big and very clean. The TV works very well and has many popular programs. Hot water and Aircon are both excellent. The washer and dryer are quiet and worked very well. The dish washer was good. This house would be PERFECT if four things would be improved: 1) Reinstalling a few blinds that fell off. 2) Having shampoo in the bathroom on the 2/F. 3) Correcting the bathroom door on the second level: it cannot lock or close very tightly, having a 1/4 inch gap. 4) the stairs are a bit slippery. We highly recommend the host and this property!! Amanda, thank you so much!
Stayed 4 nights in May 2024

10/10 Excellent

Carolyn I.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Stunning, spacious home by the water.
Stunning, comfortable and beautifully furnished home. Great getaway for our blended family with 5 young adult children and their partners. Kitchen is super-spacious with plenty of cabinet and food prep space. Loved the lighting design, could customize according to use and time of day. Two ovens, gas cooktop, outdoor grill, additional small fridge, and wine fridge make cooking for a crowd easy. Yet another fridge downstairs! Master suite is expansive with a small study with skylight and a sound reducing slider; walk in closet/changing room; bath w jetted soaking tub and separate shower. Master BR has tons of windows to your lake view and a slider to a small balcony. Upstairs bedrooms are roomy and comfortable and afford privacy. Deck and patio have plenty of chairs. Hot tub is a real treat. Downstairs tv room has 2 futons for extra sleeping space. Dock is just past the edge of the yard; we hung out there every day. The lake water is stunningly clear and we entertained ourselves by swimming, kayaking, enjoying the view, and watching the fish and birds (including a huge, stunning heron). Amanda is a responsive and thoughtful host. This property and its management are a real winner. Highly recommended!
Stayed 7 nights in Jun 2021

10/10 Excellent

Heather M.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Mrs.
Beautiful spot on the lake. Great house.
Stayed 10 nights in Aug 2024

10/10 Excellent

Bethany F.

Liked: Cleanliness, check-in, communication, location, listing accuracy
A week at the lake!
My family and I had the best week at Highland Lake. The house location was perfect and had everything we needed to enjoy lake life! Amanda was an excellent host and made the whole process very easy! We can’t wait to go back!
Stayed 7 nights in Jul 2024

10/10 Excellent

Gary and Jane H.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Best vacation ever
This property was exactly as advertised. Spacious , welcoming and very well equipped. I would highly recommend this property for all ages.
Stayed 7 nights in Jul 2024

10/10 Excellent

Kathy G.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Fabulous!
This house was perfect for our families (12 people)! Great access to lake, both dock and beach. Hot tub was a huge hit! Beautifully designed and decorated. Felt very cozy in a grand way. What a kitchen!!
Stayed 7 nights in Jun 2024

10/10 Excellent

Greg W.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Fantastic House On Highland Lake
We loved our stay on Highland Lake. The house was awesome, clean, had lake views, had a big yard, had its own private dock, was clean, and everything you'd want for a vacation or a quick getaway. Highly recommend this place and the host, Amanda, was great. Her communication was top notch. Love this place!
Stayed 15 nights in Jun 2024

10/10 Excellent

Daniel C.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Family Thanksgiving Dinner
The house worked out perfect for not only staying the week but had 20+ family members join us for Thanksgiving. Plenty of room. great kitchen and the double oven and multiple refrigerators were a life saver. Property manager was awesome and met us at the house when we got there after our 12 hour drive. As nice as this place was in November it must be really nice when you can take advantage of the lake.
Stayed 6 nights in Nov 2022

10/10 Excellent

Kevin B.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Perfect Fall Getaway
We had an incredible experience staying at this property. Amanda was very helpful with any questions that we had and went out of her way to be in touch with information about how to operate the heating a cooling systems, as they weather fluctuated throughout our October weekend. The house is amazingly spacious, to the point where we didn't even utilize every space that we had available to us. The house slept 12 with space to spare. We made use of the large backyard and the kids loved rolling down the grassy hill multiple times a day. The hot tub was an added bonus that helped melt away the pains from spending time at the batting cages and duckpin bowling that was just minutes away. Highland Lake and the surrounding community are beautiful and Amanda was so welcoming in sharing it with our family!
Stayed 4 nights in Oct 2022

10/10 Excellent

Jen Z.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great place!
Has no problems with wheelchair accessibility. There is no Hoyer lift so we rented a manual one. If you can’t transfer yourself the shower is a bit tricky but we got it figured out. Overall an excellent experience.
Stayed 5 nights in Sep 2022

10/10 Excellent

Rick K.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Lake Paradise
The property was amazing! Plenty of space for our group with indoor and outdoor seating options for dining. The hot tub was great to relax in after a day on the water. With easy access to the water to swim and fish this property has it all. Amanda was a great host and was quick to answer any questions we had. Highly recommend this property!
Stayed 7 nights in Aug 2022

10/10 Excellent

Lou B.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Very accommodating !!!
The property worked very well for our family of 10 . Would definitely recommend it .
Stayed 7 nights in Aug 2022

10/10 Excellent

David W.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Wonderful house
We had a wonderful time at the lake and were so happy with the house. Amanda was exceptional in allowing us to check in early and keeping in touch to make sure there were no issues. We would definitely stay there again.
Stayed 7 nights in Jul 2022