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Waterfront Cottage Highland Lake-Litchfield Hills swimming fishing kyaking sail

Bedrooms 3
Property type house
Minimum Stay 5 - 7 nights
Popular Features
  • Internet
  • Parking
  • Outdoor Grill
  • non smoking only
  • Fireplace
  • children welcome


About the property

3 bedrooms/1 bath Great Room overlooks 3RD Bay East Side of lake sleeps 6

Litchfield County - Highland Lake three-bedroom lakefront cottage with private dock. Located on the east side of lake -enjoy beautiful sunsets right on your private dock. Beautiful, clean lake 3.5 miles long. Trophy trout lake. Great bass fishing lake. Areas of lake are 85 feet deep. The water is so clean you can see bottom in 30 feet of water. Enjoy boating, wind surfing and canoeing in beautiful third bay or any of the five quiet coves. Cottage is fully furnished with an all-glass great room overlooking the lake. Enjoy a beautiful view of the Berkshire Mountains, magnificent sunsets on your private back yard.

Best Sunsets,Clean, Recreational & Private. : Magnificent Lake with a very private waterfront lakehouse. get away to a new lease on life less than 2 hours from NYC. Best sunset over the Berkshires. Trophy Trout Lake.

More Details

Richard Synnott
Member since: 2004
Speaks: english
Response time:
Within a day
Response rate:
Calendar last updated:
March 12, 2017

About Richard Synnott

I own a Travel Agency for 30 years and love to travel. I really have been fortunate to see the world but I believe the most beautiful spot is this cottage which I live four doors away from-it is hard to describe the new lease on life you obtain after a week of being on the water and going to sleep after the most beautiful sunsets over the Berkshire Mountains. I am also a licensed realtor with the State of CT to sell and list properties

Richard Synnott purchased this house in 2001

Why Richard Synnott chose Litchfield County

It is in the best location of the lake with beautiful sunsets on your very private dock. Views from the great room are spectacular overlooking the lake. There is a vacant lot next door to you to add to the privacy. You are 240 feet off the road which is great for safety and serenity.

What makes this house unique

Stationary dock that does not bob with lake motion. Open kitchen and great room overlooking the lake. Extremely private for a lake house. Private deck overlooking dock with gas grill.


Winsted House Accommodation and Amenities

Property Type:
  • house
  • Guests provide their own meals
  • Housekeeper Optional
Floor Area:
  • 1000 sq. ft.
House Rules:
  • Max. occupancy 6
  • non smoking only
  • pets not allowed
  • Minimum Age Limit for Renters ...
  • children welcome
Location Type:
  • Downtown ...
  • Lake ...
  • Lake View ...
  • Lakefront ...
  • Monument View ...
  • Mountain View ...
  • Rural ...
  • Village ...
  • Water View ...
  • Waterfront ...
  • Waterfront ...
  • Away From It All
  • Family
  • Tourist Attractions
  • Activities Guide
  • Alarm Clock
  • Basic Soaps
  • Ceiling Fans
  • Fireplace
  • Heating
  • Internet
  • Living Room
  • Local Restaurant Guide
  • Mobile Phone
  • Paper Towels
  • Parking
  • Parking Off Street
  • Telephone
  • Toilet Paper
  • Wireless Internet
  • 4 Ring Stove
  • Coffee Maker
  • Cooking Utensils
  • Grill
  • Microwave
  • Refrigerator
  • Toaster
  • Dining Area
  • seating for 6 people
  • 1 Bathroom
  • Bathroom - toilet , shower
  • New three years ago
  • 3 Bedrooms, Sleeps 6
  • Bedroom - 1 double
    Bedroom - 1 double
    Bedroom - 1 double
  • Cozy clean bedrooms
  • Books
  • DVD Player
  • Satellite / Cable
  • Television
  • VCR
  • Balcony
  • Barbecue
  • Beach Chairs
  • Boat
  • Boat Dock
  • Boat with Paddles
  • Canoe
  • Fish Cleaning Table
  • Golf ...
  • Outdoor Grill
  • Outdoor Grill Gas
  • Porch / Veranda
  • Raft
  • Terrace
  • Walkway to Water
  • Wood Deck
  • 6 garden chairs
  • 3 beach chairs
  • Long-term Renters Welcome
  • wheelchair inaccessible
  • autumn foliage
  • churches
  • library
  • restaurants
  • winery tours
Leisure Activities:
  • antiquing
  • bird watching
  • horseback riding
  • scenic drives
  • sight seeing
  • sledding
  • walking
Local Services & Businesses:
  • groceries
Sports & Adventure Activities:
  • cycling
  • fishing
  • fly fishing
  • freshwater fishing
  • golf
  • golf privileges optional
  • hiking
  • hunting
  • mountain biking
  • mountain climbing
  • pier fishing
  • sailing
  • scuba diving or snorkeling
  • skiing
  • snorkeling
  • surf fishing
  • swimming
  • water skiing
  • wind-surfing
3 full beds- sleeps 6 comfortably. Canoe with paddles. .


Wonderful! 4.8/5 -
(6 traveler reviews)

Waterfront Cottage Highland Lake-Litchfield Hills swimming fishing kyaking sail
average rating of 4.8333335 based on 6 reviews

A True Find You Just Have to Experience!!

  • 5 of 5

What an amazing week we spent at this spotless cottage. It was a pure delight! Everything, and I mean everything was exactly as Rick described. The decor and cleanliness made it a welcoming place to reside and honestly we hated to leave. The beds were so comfortable that it was easy to sleep in and relax. Yet when we felt like being active there was plenty to do. The lake itself is incredible. The view was spectacular and I can't even begin to describe the sunsets. The cottage had plenty of space to entertain both inside and out. Plenty of room for company to stay when friends and family dropped in. This cottage is so well maintained both inside and outside that it is impressive. Rick, you have thought of all the little things that make this cottage a beautiful home. Thanks for sharing your piece of heaven. I can't wait to return. I definitely recommend this property to rent. I can guarantee that you won't be sorry.


  • Submitted: Jul 7, 2016
  • Stayed: Jun 2016
  • Source: HomeAway
Owner's Response: Thank you so much for taking your valuable time to acknowledge the amenities and other features of the cottage. We love the cottage and really enjoy it when guests have a great time. Thank you again for your input as it will assist other travelers decide if this is the right property to spend their vacation. Rick
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Awesome vacation week!

  • 5 of 5

House was very roomy for five of us. Well equipped for cooking and relaxing. Nice dining room and TV area. Outside grill on landing was convenient for talking and cooking. Terrific, stable and spacious dock was great for reading, relaxing, sunning, jumping in the lake and lots of good conversation with family. Beautiful lake just the right size for walking, running and cycling. Had a great time and would stay here again.

  • Submitted: Sep 8, 2015
  • Stayed: Jul 2015
  • Source: HomeAway
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Great Place to Stay on the Lake!!

  • 5 of 5

We had such a wonderful time at your cottage! The cottage is cozy but very clean and comfortable with all the supplies we needed for the week. Rick was very attentive and a phone call away if we needed anything. The view was beautiful and the steps into the water made it easy for our children to swim and enjoy the lake. We are already planning our next vacation there next year!!

  • Submitted: Aug 21, 2015
  • Stayed: Jul 2015
  • Source: HomeAway
Owner's Response: Thank You for taking your valuable time to write a review that will help others determine if this is the correct property for them. Thanks again Rick
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Wonderful Place to Stay!!

  • 5 of 5

My family gathered in Wiinsted, CT for the Christmas Holiday, and we had need of additional housing. I am very glad we found this place!! The property is well-cared for, clean, and well equipped for everything you would need. Great views and cozy. The owner is wonderful, and made our stay fantastic. Thanks again, Rick! We will visit and stay again.

  • Submitted: Jan 5, 2015
  • Stayed: Dec 2014
  • Source: HomeAway
Owner's Response: Hi Jim; Thank you for taking your valuable time to write a review that will help others decide if this is the right property for their vacation. Thanks again and hope your trip home was good. Please come back to Highland Lake again. Rick Synnott
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Great place for enjoying the lake!

  • 5 of 5

Wonderful cottage right on the largest of the three bays on Highland Lake. The cottage was neat and clean, had everything we needed, and the kitchen was well equipped. Beds were very comfortable, Owner stopped by early in our stay to let us know he was prepared to respond to anything we needed. It has a great dock for boating. The owner provides a canoe, and we brought two kayaks. We came for a week of fishing and relaxing, and in addition to fishing Highland Lake (great bass lake!), the location is just 10 minutes from the Farmington River (fabulous trout stream). Plenty of good restaurants right in town (Winsted is only 5 minutes away), and a great Italian restaurant (Marino's), a pizza shop, and a spirit store are within a mile from the cottage. We would definitely recommend this place to anyone who wants to enjoy water sports and relaxing in a recreational lake area.

  • Submitted: Jun 19, 2014
  • Stayed: May 2014
  • Source: HomeAway
Owner's Response: Hi Rich; Thank you for your input to help others decide if this is the right property to spend their valuable vacation time at. We try 110% to make every experience at Highland Lake a memorable one. That is what makes us happy. Thanks for acknowledging your great time. Rick Synnott
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We had a wonderful time!

  • 4 of 5

We were looking for a nice place right on the water and we were not disappointed. The cottage was cute, clean, and the kitchen was well equipped for everything you would need to cook and serve your favorite meals. When not swimming or playing cards on the dock, we enjoyed going for walks and doing puzzles as we overlooked the beautiful lake from the dining table. We were also able to take a day trip into New York City by taking a train right into Grand Central Station which was a lot of fun. Rick the manager was very helpful in making suggestions for our trip as well. The only slight complaint would be that the walls in the front two bedrooms don't extend all the way to the ceiling which can be an issue with lighting and privacy but having said that I would certainly recommend this cottage to anyone who is looking for a nice, clean cottage on a beautiful lake.

  • Submitted: Aug 3, 2013
  • Stayed: Jul 2013
  • Source: HomeAway
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Rates & Availability

Winsted House Rental Rates

Rental Basis:
per property
Owner accepts payment in:
Convert Currency
Rate Period Nightly Weekend Night Weekly Monthly Event
Nov 5 2016 - Apr 1 2017
5 night minimum stay
My Standard Rate

Changeover Day: Saturday
7 night minimum stay

Additional information about rental rates

Refundable damage deposit $400
Cleaning Fee $90

Monthly Rates during the Fall and winter months are available at a discount. Please contact for rates.

Owner's Cancellation Policy

Canceled bookings will not receive a refund
Enter dates for accurate pricing
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Nearest Airport
20 Miles
Nearest Golf
4 Miles
Nearest Train
20 Miles
Nearest Motorway
1 Miles
Route 8
Nearest Restaurant
3.8 Miles
Nearest Ski
11 Miles
Ski Sundown
Car: recommended

Close to Lenox, Stockbridge, Tanglewood. Great antique shops and restaurants all the way to Millerton, N.Y.

Enjoy Berkshire attractions-Hancock Shaker Village, The Berkshire Museum, Jimminy Peak, Clark Art Institute, Williams College Museum of Art, The Colonial Theatre, Normal Rockwell Museum, Train rides from Lenox to Stockbridge, Shakespeare & Company. The lake is so beautiful, most people never leave!

Golf: Awesome Golf Course- Greenwoods - formerly private club but you are able to pay greens fees and golf when staying at the cottage.

Ski: Ski Sundown New Hartford- 20 minutes and Butternut Basin Great Barrington, MA 50 minutes drive.

R & B Sports- mini golf, go carts, batting machines etc - 10 minute drive

Antique Shopping Downtown Winsted 10 minutes all the way to Millerton NY - one hour drive.


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