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

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Beautiful 5BR Lake House on Highland Lake

A beautiful location for a vacation, reunion, party or even a wedding!

Overview
Amenities
Policies
Location
Host

Exceptional

5 bedrooms3+ bathroomsSleeps 12315.9 sq m

Popular amenities

Parking available
Air conditioning
Barbecue grill
Kitchen
Fireplace

Explore the area

Winchester, CT

Highland Lake
‪4 min walk‬
Winchester Historical Society
‪12 min walk‬
Platt Hill State Park
‪8 min drive‬
Hartford, CT (BDL-Bradley Intl.)
‪40 min drive‬

Rooms & beds

5 bedrooms (sleeps 12)

Blue Room

1 Queen Bed

Master Bedroom

1 King Bed

Nature

1 Queen Bed

Nautical

1 Queen Bed

Trundle

2 Single Beds

Tv room / efficiency kitchen

1 Double Futon

3 bathrooms, 1 half bathroom

2nd Floor

Bathtub or shower · Toilet

Lower level

Toilet

Main Floor

Toilet · Shower only

Master

Bathtub · Toilet · Shower only

Spaces

Deck or patio

Porch or lanai

Kitchen

Balcony

Separate dining area

Outdoor play area

Garden

Dining area

About this property

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

Premier Host

Languages

English

Add dates for prices

Amenities

Hot tub

Kitchen

Washer

Dryer

Free WiFi

Air conditioning

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Kitchen
Washer
Dryer
Free WiFi

House Rules

Minimum age to rent: 25

Children

Children allowed: ages 0–17

Children encouraged:)

Events

No events allowed

Pets

No pets allowed

Smoking

Smoking is not permitted

Must have a phone call with owner within 48 hours of booking.

Traveler must provide photo ID within 48 hours of booking, if requested.

Absolutely no parties or large events.

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 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 that there is a smoke detector on the property

Safety features at this property include a deadlock

About the area

Winsted

Located in Winsted, this holiday home is in the mountains and on the waterfront. Winchester Historical Society and Warner Theater are local landmarks, and some of the area's attractions include Laurel Lanes and KidsPlay Museum. Travelling with kids? Consider Action Wildlife Foundation and Flamig Farm. Make sure you get close to the area's animals with activities such as game walks and birdwatching.

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
Platt Hill State Park - 8 min drive - 5.0 km
Warner Theater - 14 min drive - 17.8 km

Getting around

Hartford, CT (BDL-Bradley Intl.) - 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 holiday 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 miles (3 km).

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.

Learn more

10/10

Cleanliness

10/10

Check-in

10/10

Communication

9.8/10

Location

10/10

Listing accuracy

8/10 Good

Theresa T.

20 Mar 2025

Liked: Cleanliness, check-in, communication, location, listing accuracy

Winter Retreat

The spacious house and view of the frozen lake were wonderful for our family gathering. It was unfortunate the hot tub was broken and there were some water issues, but the hostess was gracious in trying to accommodate us.

Stayed 4 nights in Feb 2025

10/10 Excellent

Jeremy R.

7 Jan 2025

Liked: Cleanliness, check-in, communication, location, listing accuracy

Amazing house, responsive host

The house exceeded all out expectations. Beautiful, convenient to services, stunning location on the lake, plenty of off street parking. The host and I spoke multiple times throughout the stay regarding small things like trash and recycling expectations, etc.

Stayed 8 nights in Dec 2024

10/10 Excellent

Heather M.

8 Sept 2024

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.

4 Aug 2024

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.

27 July 2024

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.

8 July 2024

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.

8 July 2024

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

Mah A.

8 June 2024

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

Gwen S.

5 June 2024

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

Rita R.

24 Oct 2023

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

20 Aug 2023

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

Marcella C.

16 Aug 2023

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

8/10 Good

Jean B.

9 Aug 2023

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

Karen H.

22 July 2023

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

Leslie W.

19 July 2023

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.

17 July 2023

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

Lus P., new york

11 Jan 2023

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

Daniel C.

7 Dec 2022

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.

21 Oct 2022

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.

3 Oct 2022

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.

21 Aug 2022

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.

16 Aug 2022

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.

10 Aug 2022

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

10/10 Excellent

Todd S.

9 Aug 2022

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

Barbara P.

2 Aug 2022

Liked: Cleanliness, check-in, communication, location, listing accuracy

Special Family Fun Time

July 23-30 This was our 4th family vacation at this lake house. (Would of been 5th but Covid took away 1 summer vacation) As always my family loves being together and having a house big enough to allow all members to be under 1 roof and reconnect. It’s like a family reunion. The weather was great and that allowed all the water and boating activities to be sooo much fun. This lake house is awesome in so many ways. It has the space we needed, the lake and all the water activities included ( kayaks, floats, dock , water toys, swimming, beach ( with lifeguards) and a beautiful house with space for all of us. Also police boats monitor the lake and make it safe for all. The house is equipped with so many amenities that you feel like you’re on vacation. Then of course there’s the hot tub that is so relaxing at the end of the day. Smores and a fire at night tops off a great day. We always enjoy our vacation and Amanda is always there if needed. We greatly appreciate how well the house is taken care. Barbara

Stayed 7 nights in Jul 2022

About the host

Hosted by Amanda Zolla

My name is Amanda and I have had the pleasure of caring for a lovely woman named Sarah who was injured in a terrible car accident a few years ago. She and her husband John, the owners, built and lived in this beautiful house since 2009. They have recently made the decision to move to San Antonio, TX, to trade in CT winters for a warmer year round climate. Although they are too far away now for me to continue to aide in Sarah's care, I am excited and happy for the opportunity to care for and welcome people into this home built for making memories.
Here are a few words from John and Sarah about their home:
The house is 8 years old and incorporates all of the energy efficiencies possible at the time it was built; active and passive solar, radiant heat, instant hot water, eight zone heating and air-conditioning control. In addition we installed hardwood or tile floors to minimize allergens. We consciously chose Highland Lake for its pristine water quality, excellent fishing and proximity to world famous arts/culture and year round recreational sport venues. We moved to Texas this fall so this will be the first time we rented the house. We hope you and your families will enjoy this wonderful place as much as we have.

Why they chose this property

pristine water quality, excellent fishing and proximity to world famous arts/culture and year round recreational sport venues

What makes this property unique

active and passive solar, radiant heat, instant hot water, eight zone heating and air-conditioning control

Languages:

English

Premier Host

They consistently provide great experiences for their guests

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

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

Reviews

Popular amenities

Explore the area

Rooms & beds

5 bedrooms (sleeps 12)

Blue Room

Master Bedroom

Nature

Nautical

Trundle

Tv room / efficiency kitchen

3 bathrooms, 1 half bathroom

2nd Floor

Lower level

Main Floor

Master

Spaces

About this property