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Highland Lake gorgeous sunset 3RD east BAY side, Private dock.

Bedrooms 3
Space 1,000 sq ft
Property type house
Minimum Stay 7 nights


About the property

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

Ask about great discounts for multi week reservations!!!!!

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 lake house. get away to a new lease on life less than 2 hours from NYC. Best sunset over the Berkshires. Best location for Paddle Boarding in quiet cove.

In event you have to cancel- a full refund will be given if the property is re-rented.

More Details

Member since: 2004
Speaks english
Response time:
Within 12 hours
Response rate:
Calendar last updated:
July 13, 2018

About The Owner

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

The Owner purchased this house in 2001

Why The Owner chose Winchester

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 with Brazilian Hardwood. Dock does not bob up and down from occasional boat waves- safe and great for that book you planned on finishing ages ago. Open kitchen and great room overlooking the lake. Extremely private for a lake house. Private deck overlooking dock with gas grill.


Accommodation and Amenities for this vacation house rental in Winchester, Connecticut

Property Type:
  • house
  • Guests provide their own meals
  • Housekeeper Optional
Floor Area:
  • 1000 sq ft
House Rules:
  • Check-in: 3:00 PM
  • /
  • Check-out: 10:00 AM
  • Max. occupancy: 6
  • Children welcome
  • Parties/events not allowed
  • Pets not allowed
  • Non smoking only
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
  • Air Conditioning ...
  • Alarm Clock
  • soaps basic
  • Ceiling Fans
  • Fireplace ...
  • Heating ...
  • Internet ...
  • Linens Provided ...
  • Living Room ...
  • restaurant dining guide
  • cell phone
  • Paper Towels
  • Parking ...
  • Parking Off Street
  • Telephone ...
  • Toilet Paper
  • Towels Provided ...
  • Wireless Internet ...
  • 4 Ring Stove
  • Coffee Maker
  • Cooking Utensils ...
  • Grill
  • Microwave
  • Refrigerator
  • Toaster
  • Dining ...
  • 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
  • Deck / Patio ...
  • Fish Cleaning Table
  • Golf ...
  • Lawn / Garden
  • Outdoor Grill ...
  • Outdoor Grill Gas
  • porch/lanai
  • Raft
  • Terrace
  • Walkway to Water
  • deck wood
  • 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! 4.9/5 -
(7 traveler reviews)

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Highland Lake gorgeous sunset 3RD east BAY side, Private dock.
average rating of 4.857143 based on 7 reviews

We had a great time at the lake house!

  • 5 of 5

House is cozy and the the location on the lake is amazing! Spent most of our time enjoying all of the activities outside!

  • Submitted: 14-Jul-2018
  • Stayed: June 2018
  • Source: VRBO, from HomeAway
Owner's Response: Hi Lori; Thank you for taking your valuable time to write a review that will help others decide if this is the best property for their vacation. We live four doors away for 28 years now and love the location on the lake-gorgeous sunsets right on your private stationary dock. Our cove offers a beautiful view of the lake and Berkshire Mountains and is not a busy part of the lake. Thank you again for writing a review. Rick
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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: 7-Jul-2016
  • Stayed: June 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: 8-Sep-2015
  • Stayed: July 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: 21-Aug-2015
  • Stayed: July 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: 5-Jan-2015
  • Stayed: December 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: 19-Jun-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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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.


Rates & Availability

Rental Rates for this vacation house rental in Winchester, Connecticut

Rental Basis:
per property
Owner accepts payment in:
Convert Currency
Rate Period Nightly Weekend Night Weekly Monthly Event
Apr 2 2018 - Nov 1 2018
7 night minimum stay
Quiet Mellow
Nov 2 2018 - Apr 1 2019
7 night minimum stay
My Standard Rate

Changeover Day: Saturday
7 night minimum stay

Additional information about rental rates

Refundable Damage Deposit C$530.6
Cleaning Fee C$119.38

Monthly Rates during the Fall and winter months are available at a discount. Please contact for rates. In case of cancellation we will refund all payments if property rerented.

Owner's Cancellation Policy

  • 100% refund if canceled at least 60 days before arrival date.
  • Service Fee fully refunded on cancellations that qualify for 100% refund.
Contact Owner