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

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your current months are December, 2024 and January, 2025.
December 2024
January 2025

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

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

Reviews

10 out of 10

Exceptional

Entire home

5 bedrooms4 bathroomsSleeps 12316 sq m

Popular amenities

  • Hot tub
    Hot tub
  • Parking available
    Parking available
  • Washer
    Washer
  • Barbecue grill
    Barbecue grill
  • Outdoor space
    Outdoor space
  • Kitchen
    Kitchen

Explore the area

Map
Winchester, CT
  • Highland Lake
    4 min walk
  • Winchester Historical Society
    12 min walk
  • Laurel Lanes
    2 min drive
  • Great Barrington, MA (GBR-Walter J. Koladza)
    46 min drive

Room options

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 )
During your stay at this holiday home, you're just a quick walk from Highland Lake. Enjoy features like 1 hot tub and an arcade/games room. The holiday home includes amenities such as free WiFi and a kitchen.
  • Air-conditioned home with kitchen, washing machine and 3.5 bathrooms
  • Free WiFi
  • On-site recreation includes a playground
  • Just a 4-minute walk from Highland Lake and 12 minutes on foot from Winchester Historical Society
As a guest of Beautiful, Spacious 5+ Bedroom House on Highland Lake with Spectacular views!, you'll find a hot tub, barbecue grills, and an arcade/games room. The front desk is open around the clock.

Property manager

Amanda Zolla

Languages

English

Property amenities

Ski

  • Cross-country skiing nearby
  • Snowboarding nearby

Pool/Spa

  • Spa tub

Internet

  • Available in the house: Free WiFi

Parking and transport

  • Parking on site

Kitchen

  • Blender
  • Coffee grinder
  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Electric kettle
  • Hob
  • Ice maker
  • Microwave
  • Oven
  • Paper towels
  • Refrigerator
  • Spices
  • 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.
  • In-room 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
  • Cycling 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
  • 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

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

  • No pets allowed

Children and extra beds

  • Children are welcome.
  • Note from host: Children encouraged:)

Important information

You need to know

This property is managed by a private host (a party not acting within their trade, business or profession). EU consumer law, including the right of withdrawal, will not apply to your booking. The cancellation policy set by the private host will cover your booking.
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
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
You will receive an email from the host with check-in and check-out instructions. You will also receive an email from Vrbo with a link to a Vrbo account, which will enable you to manage your booking.

Property is also known as

Beautiful Spacious 5 Bedroom Highland Lake Spectacular Views

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

Reviews

10

Exceptional

Rating 10 - Excellent. 86 out of 90 reviews" "
Rating 8 - Good. 4 out of 90 reviews" "
Rating 6 - Okay. 0 out of 90 reviews" "
Rating 4 - Poor. 0 out of 90 reviews" "
Rating 2 - Terrible. 0 out of 90 reviews" "

10/10

Cleanliness

Reviews

10/10 Excellent

Heather M.

Liked: Cleanliness
Mrs.
Beautiful spot on the lake. Great house.
Stayed 10 nights in Aug 2024

10/10 Excellent

Bethany F.

Liked: Cleanliness
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
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
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
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.

Liked: Cleanliness
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.

Liked: Cleanliness
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.

Liked: Cleanliness
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
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.

Liked: Cleanliness
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.

Liked: Cleanliness
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.

Liked: Cleanliness
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.

Liked: Cleanliness
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
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

Liked: Cleanliness
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.

Liked: Cleanliness
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
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
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
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
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
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.

Liked: Cleanliness
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.

Liked: Cleanliness
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

10/10 Excellent

David C.

Liked: Cleanliness
Great family location
This property had everything you would need for a great stay.
Stayed 7 nights in Jul 2022

10/10 Excellent

Iris G.

Liked: Cleanliness
Wonderful Stay at a Beautiful House -- Memories That'll Last Forever
Amanda and Larry were the best and most attentive to our requests and inquiries, any issues or questions we had were solved immediately. Their expertise in both the house and the area around us made the stay a million times better. In addition, the house was spectacularly delightful and was fit for our party of 10 with ages ranging from 12 to "seasoned". It was well appointed and went exceedingly above our expectations. We enjoyed the location and all of its amenities, including local restaurants and activities. Thank you for this amazing family vacation, it will be one for the books forever. We hope to return someday to this beautiful house. Thank you so much!
Stayed 7 nights in Jun 2022