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Cozy Highland Lake Cottage. Fall Foliage & Stunning Sunsets

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A house with a front porch, a staircase leading to the entrance, and a garden with flowers.
A lakeside dock with boats, a wooden pier, and a tree.
A kitchen with white cabinets, a black granite countertop, a stainless steel stove, a microwave, and pendant lights.
A garden with a stone pathway, various plants, and a small rock feature.
A view through a window with white curtains, a backyard with a pond, a blue pool, and a wooden deck.

Reviews

10 out of 10
Exceptional

Entire home

2 bedrooms1 bathroomSleeps 6624 sq ft

Popular amenities

  • Kitchen
  • Free WiFi
  • Air conditioning
  • Outdoor Space
  • Parking available
  • Barbecue grill

Explore the area

View in a map
Winchester, CT
  • Place, Highland Lake
    ‪1 min walk‬
  • Place, The Marina at Highland Lake
    ‪19 min walk‬
  • Place, Winchester Historical Society
    ‪3 min drive‬
  • Airport, Hartford, CT (BDL-Bradley Intl.)
    ‪42 min drive‬

Room options

About the neighborhood

Winsted

This cottage places you next to Highland Lake and within a mile (2 km) of The Marina at Highland Lake. The cottage includes a kitchen, a fireplace, and a patio.
View more Cottages in WinstedOpens in a new window

What's nearby

  • Highland Lake - 1 min walk - 0.1 miles
  • The Marina at Highland Lake - 19 min walk - 1.0 mile
  • American Museum of Tort Law - 3 min drive - 1.1 miles
  • Laurel Lanes - 3 min drive - 1.2 miles
  • Winchester Historical Society - 3 min drive - 1.1 miles

Getting around

  • Bradley Intl. Airport (BDL) - 42 min drive

Restaurants

  • ‪McDonald's - ‬4 min drive
  • ‪Dunkin' - ‬4 min drive
  • ‪Arcadia - ‬11 min drive
  • ‪Dunkin' - ‬4 min drive
  • ‪Skipper's - ‬4 min drive

About this property

Entire place

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

Cozy Highland Lake Cottage. Fall Foliage & Stunning Sunsets

Escape to our cozy, completely renovated cottage on beautiful Highland Lake. Small in size but big in character, it’s a peaceful waterfront getaway that’s especially loved by couples and perfect for friends or a small family.

Wake up to quiet lake views and enjoy coffee on the deck, spend the day exploring the Litchfield Hills, and come home to some truly spectacular sunsets.

Inside you’ll find two bedrooms with full-size beds, a queen sleeper sofa with memory-foam topper, and a fully equipped kitchen with double oven and full spice rack. Outside, enjoy the spacious walk-out deck, private dock, gas and charcoal grills, and—during the warmer season—kayaks, fishing and boating.

We also provide a complimentary coffee & tea setup with assorted K-Cups, ground coffee, assorted teas and chilled bottled water.

Fall is a beautiful time at Highland Lake. The summer crowds disappear, the surrounding hills change color and the lake becomes wonderfully peaceful—perfect for a romantic getaway, girls’ weekend or simply a few days away.

PLEASE NOTE: Highland Lake’s scheduled 2026/2027 drawdown begins November 1, 2026, with a maximum drawdown of 36 inches. Water levels and some lake activities may be affected.

All fees are included. No hidden fees.
The cottage is air-conditioned and features a kitchen and a patio, and there's space to spread out with 2 bedrooms. Guests can expect to find free WiFi and a Smart TV with a DVD player. Other standard amenities include a fireplace, a coffee maker, and an ironing board. Housekeeping is available on request.

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Property amenities

Beach

  • Beach loungers
  • Beach towels

Internet

  • Available in the cottage: Free WiFi

Parking and transportation

  • Car recommended
  • Wheelchair-accessible parking and van parking available

Kitchen

  • Blender
  • Coffee grinder
  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Electric kettle
  • Kitchen island
  • Lobster/crab pot
  • Microwave
  • Oven
  • Paper towels
  • Refrigerator
  • Spices
  • Stovetop
  • Toaster

Bedrooms

  • 2 bedrooms
  • Bed sheets provided

Bathroom

  • 1 bathroom
  • Bathtub or shower
  • Hair dryer
  • Shampoo
  • Soap
  • Toilet paper
  • Towels provided

Living spaces

  • Fireplace
  • Living room

Entertainment

  • Books
  • DVD player
  • Games
  • Smart TV with cable/satellite channels

Outdoor areas

  • Charcoal grill
  • Dock
  • Garden
  • Outdoor furniture
  • Patio

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.
  • 2 steps to reach entrance
  • Area rugs in public areas
  • Hardwood flooring in public areas
  • No elevator (single-level property)
  • Null
  • Single level property
  • Well-lit path to entrance
  • Wheelchair-accessible parking
  • Wheelchair-accessible path of travel
  • Wheelchair-accessible van parking
  • Smoking not allowed

Services and conveniences

  • Housekeeping (on request)
  • Iron/ironing board

Location highlights

  • In the city center
  • Near a hospital
  • On a lake
  • On the waterfront

Things to do

  • Kayak
  • Birdwatching nearby
  • Cycling nearby
  • Fishing nearby
  • Hiking/biking trails nearby
  • Jet skiing nearby
  • Kayaking nearby
  • Motor boating nearby
  • Mountain climbing nearby
  • Rafting nearby
  • Sailing nearby
  • Swimming nearby
  • Water skiing nearby
  • Water tubing nearby
  • Wildlife walks nearby
  • Windsurfing nearby
  • Winery tours nearby

Safety features

  • Carbon monoxide detector (host has indicated there is a carbon monoxide detector on the property)
  • Smoke detector (host has indicated there is a smoke detector on the property)
  • Deadbolt lock
  • Fire extinguisher
  • First aid kit

General

  • Garden
  • Housekeeping (on request)
  • Unit size: 624 square feet

Policies

Check-in

Check-in time starts at 3:00 PM
Contactless check-in available

Check-out

Check-out before 11:00 AM
Contactless check-out available

Special check-in instructions

You will receive an email from the host with check-in and check-out instructions
Information provided by the property may be translated using automated translation tools

Pets

  • This property doesn't allow pets

Children and extra beds

Children allowed: ages 0-17

Events

No events allowed

Smoking

Smoking is not permitted

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 indicated there is a carbon monoxide detector on the property
Host has indicated there is a smoke detector on the property
Safety features at this property include a fire extinguisher, a first aid kit, and a deadbolt lock
This property has outdoor spaces, such as balconies, patios, terraces which may not be suitable for children; if you have concerns, we recommend contacting the property prior to your arrival to confirm they can accommodate you in a suitable room
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
  • Check-in: 3:00 PM
  • Check-out: 11:00 AM

We should mention

Details about charges, deposits, or other important information:

  • This property is managed by a private host, not a professional engaged in trade or business.
  • This property has outdoor spaces, such as balconies, patios, terraces which may not be suitable for children. If you have concerns, we recommend contacting the property prior to your arrival to confirm they can accommodate you in a suitable room.
  • Charges for extra guests may apply and vary depending on the property's policy.
  • A cash deposit, credit card, or debit card for incidental charges, as well as a government-issued photo ID, may be required at check-in.
  • Special requests are subject to availability at the time of check-in and can't be guaranteed. Certain requests may come with additional charges.
  • Onsite parties or group events are strictly prohibited.
  • Onsite safety features include a carbon monoxide detector, a fire extinguisher, a smoke detector, a first aid kit, and a deadbolt lock.

Frequently asked questions

What's there to do within easy reach of this cottage?

This cottage is located in Winsted, just steps from Highland Lake. You'll also find The Marina at Highland Lake and Northwestern Connecticut Community College Library within a short drive.

Will I be able to park at Our Cottage - Small in size, Big in character, On beautiful Highland Lake ?

Yes, there is wheelchair-accessible van parking available.

Is this cottage adjacent to a casino?

No, this cottage is not connected to a casino.

Will I find an indoor pool at this cottage?

No, there is no indoor pool at this cottage.

What do couples enjoy most about Our Cottage - Small in size, Big in character, On beautiful Highland Lake ?

Amenities that appeal to couples at this lakeside cottage include a fireplace, a kitchen, and a smart TV.

Are there hot tubs at Our Cottage - Small in size, Big in character, On beautiful Highland Lake ?

No, this cottage doesn't have a spa tub.

Does this cottage provide breakfast?

No, this cottage doesn't offer breakfast.

Will this cottage allow pets to stay for free?

No, pets aren't allowed at this cottage.

Are there connecting rooms at Our Cottage - Small in size, Big in character, On beautiful Highland Lake ?

No, there aren't connecting guestrooms at this cottage.

What is the closest airport to this cottage?

The closest major airport to this cottage is Bradley Intl. Airport (BDL), which is 25.7 mi away (42 minutes by car). Another top airport is Westfield, MA (BAF-Barnes Municipal), which is around 25.4 mi away.

Can I book a room with a balcony at Our Cottage - Small in size, Big in character, On beautiful Highland Lake ?

Yes, every cottage at Our Cottage - Small in size, Big in character, On beautiful Highland Lake comes with a patio and some offer water views.

Cozy Highland Lake Cottage. Fall Foliage & Stunning Sunsets Reviews

Reviews

10

Exceptional

Rating 10 - Excellent. 49 out of 51 reviews
Rating 8 - Good. 1 out of 51 reviews
Rating 6 - Okay. 1 out of 51 reviews
Rating 4 - Poor. 0 out of 51 reviews
Rating 2 - Terrible. 0 out of 51 reviews

10/10

Cleanliness

10/10

Amenities

10/10

Property conditions & facilities

Reviews

Verified review

10/10 Excellent

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

Special Lake Cottage

Excellent place with modern decor inside and beautiful view of lake from very nice deck. Will definitely stay again!
Stayed 3 nights in Oct 2024
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Beautiful cottage. Host was very helpful and accommodating.
Stayed 4 nights in Oct 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Wonderful lake house! Small but very comfortable for the 5 of us.
Stayed 3 nights in Sep 2025
Verified review

10/10 Excellent

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

Cozy, Quiet, Clean, & Happy

Great little place to stay! Host was easy to contact and everything lived up to expectations.
Stayed 3 nights in Oct 2024
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Easy check in and out. It was everything we hoped it would be. Had a great time!
Stayed 4 nights in Aug 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Such an amazing modern cottage. The lake view was spectacular amd the warm vibe of the cottage itself was amazing. We will for sure look to book this property again in the near future to see our cousins again.
Stayed 2 nights in Nov 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Beautifully appointed cottage on a lovely lake. We had an amazing week!
Stayed 6 nights in Jul 2025
Verified review

10/10 Excellent

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

Another great stay!!

This is our 3rd year in a row staying at Debbie’s cottage, and it was wonderful. We love having our boat docked for a week of tubing, water skiing, fishing, swimming and fishing. We are already booked for next year!
Stayed 7 nights in Jul 2022
Verified review

10/10 Excellent

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

Lake cottage

Third time we’ve stayed at this lovely cottage on Highland Lake. Immaculate, welcoming and gracious host!!Hope to be back next year!!
Stayed 2 nights in Oct 2023
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Very good
Stayed 2 nights in Sep 2025
Verified review

10/10 Excellent

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

Relaxation

2nd summer here! It has everything! Such a beautiful cottage on a beautiful lake it was very peaceful an relaxing
Stayed 4 nights in Aug 2023
Verified review

10/10 Excellent

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

Definitely a must

Great communication and amenities. We had a great time as a family and can’t wait to see what next year brings! Love that it’s right on the water. The kids swam for the whole week every day even in the rain
Stayed 7 nights in Aug 2022
Verified review

10/10 Excellent

Liked: Cleanliness, amenities, property conditions & facilities, communication
This place was spotless. Newly rebuilt I would guess. So well stocked that I cannot even imagine something that was not there. We came in the Fall so it was very quiet. The host was fantastic and offered to let us come in early. When we got a flat tire from in town on our last morning she offered to let us stay inside all day as we waited for AAA. She could not have been more accommodating. We would easily stay here again.
Stayed 4 nights in Oct 2025
Verified review

10/10 Excellent

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

Came to see the fall in October.

Excellent, well appointed, lakeside property close to many superb state parks showing off their leaf colours. Property has a good view of the lake A great few days. Good value.
Stayed 4 nights in Oct 2022
Verified review

10/10 Excellent

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

Fall Getaway

Overall great trip with my wife and daughter. Nice little cottage along the lake. Place is small, but we knew that going into it when we reserved. Everything worked out great. She even brought in an outdoor gas firepit for us!!
Stayed 3 nights in Oct 2022
Verified review

10/10 Excellent

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

Great location

Such a beautiful area & the place was perfect, neat, clean, comfortable. Easy communication with owner!
Stayed 7 nights in Oct 2022
Verified review

10/10 Excellent

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

Beautiful location right on the water!

My father and brother were visiting from out of state and found this cottage to be the perfect size to meet their needs. Very calming to be by the water with a gorgeous view.
Stayed 14 nights in Sep 2022
Verified review

10/10 Excellent

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

Perfect

Can’t say enough good things. The cottage is beautifully decorated and had everything for a perfect lake getaway with my family. Right on the water! And the host is awesome, she is so nice and accessible to reach. Tells you all you need to know. Place is a true gem Can’t wait to come back
Stayed 5 nights in Sep 2022
Verified review

10/10 Excellent

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

Terrific

Perfect rental in every way Cleanliness, decorations, host interaction, location etc
Stayed 3 nights in Oct 2021
Verified review

10/10 Excellent

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

Great place for a little get away! Right on the water just like they said! Enjoyed a lot

The host was great and replied quickly for any thing we needed, got in the house and immediately were amazed by the view, went on the canoe in the lake which was absolutely beautiful. And nothing beats waking up in the morning and having coffee with this view. 5/5 all across the board!
Stayed 2 nights in Oct 2021
Verified review

10/10 Excellent

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

Lovely cottage

Enjoyed immensely.
Stayed 3 nights in Oct 2021
Verified review

10/10 Excellent

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

Cozy Cottage

Adorable cottage on the lake. Clean, comfortable and quiet with everything one could need. Great host!
Stayed 11 nights in Oct 2021
Verified review

6/10 Okay

Liked: Cleanliness, check-in, communication, location

Lake cottage

Clean and nice cottage on Highland Lake. We had a good time here but it should be noted that space is very limited, there’s no washing/drying machine or dishwasher and wifi was weak (we had trouble with Zoom and streaming).
Stayed 13 nights in Sep 2021
Verified review

10/10 Excellent

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

Awesome week at the cottage!

This was our family’s second year staying at the cottage, and it was another fun week! We bring our own boat, so it was great to have it docked there all week to fish, water ski, go tubing, and going on evening rides around the lake. We love the cottage, and it has everything we need for our small family.
Stayed 7 nights in Aug 2021
Verified review

10/10 Excellent

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

Perfect get away!

The view from this home is gorgeous as is the whole property!!! Even when you're in the house The water view is complete as the home is very close to the water. I can't think of a single thing that was lacking.
Stayed 3 nights in Oct 2020