Discover a selection of 24 vacation rentals in Highland Lake, US that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo vacation homes have the best amenities for hanging out with the people that matter most, including swimming pools and WiFi. Prices start at $125 per night, and cottages and houses are popular options for a stay in Highland Lake. Either way, you'll find a rental for everyone's needs.
Destination guide

Enjoy gorgeous Highland Lake in scenic Winchester

If you’re looking for a lakeside getaway where you can both relax and have a great time, then you should consider taking a trip to Highland Lake, which can be found in the welcoming community of Winchester, Connecticut. Three miles long, Highland Lake is a popular spot for water activities, including fishing and boating. Just a short drive from Highland Lake, you’ll be able to enjoy a wide array of exciting activities, including several popular state parks that offer world-class hiking. If you visit Highland Lake, this spot may just become your go-to Connecticut vacation destination.

Things to do

Interesting and memorable attractions in Highland Lake

When you’re driving around the Highland Lake area, you’ll be able to enjoy many interesting attractions. If you’re a lawyer or someone who is interested in the law, then you’ll want to tour the American Museum of Tort Law. To learn about the history of Winchester, then a great Highland Lake attraction is the Winchester Historical Society. Fans of military history should be sure to visit the Soldier’s Monument and Memorial Park. If you want to browse local art, Whiting Mills is an art studio in Winchester that holds regular events and features works from the city’s painters and photographers.


Recreation and relaxation on Highland Lake

Other than high-quality Highland Lake vacation rentals, the best reason to visit this location is being able to enjoy some of the most exciting activities in Connecticut. For travelers that simply want to relax, there’s no better choice than spending a day boating on Highland Lake, enjoying the scenery and the sun. If you’re interested in going on a scenic hike or bike ride, then you should be sure to visit Sue Grossman Still River Greenway, which runs through lush, beautiful wooded areas. Those looking for dinner and a show should be sure to stop by Gilson Cinema & Café.


The top season to stay in Highland Lake

Because so many of the most popular activities near Highland Lake vacation rentals require spending time outdoors, you’ll want to visit during a time of year with pleasant weather. Like many locations in Connecticut, the best time to visit Highland Lake is in the spring or summer, which are the warmest times of the year. If you choose to visit during the fall, you can enjoy the changing foliage. Although many people avoid traveling to Highland Lake during the winter, the cold causes the lake to freeze and opens up fun activities like ice fishing and skating.

Natural features

The natural beauty of the Highland Lake area

The Highland Lake area is filled with gorgeous scenery, allowing you to connect with nature just by stepping out of your door. While not as deep as other lakes you could visit, the lake is filled with fish, and is considered a trophy trout lake. Outside of the lake area, visitors will find gorgeous forested areas that feature both hiking and biking trails. Whether you want to see one of the most pristine bodies of water in Connecticut or are interested in taking a walk through nature, you’re going to love the natural scenery around Highland Lake.

How many vacation rentals are available around Highland Lake, US?

Our 2021 property listings offer a large selection of 24 vacation rentals around Highland Lake. From 4 cottage rentals to 22 house rentals, find a unique house rental for you to enjoy a memorable holiday or a weekend with your family and friends.