Discover Your Perfect Highland Lake Vacation Homes

Best Vacation Homes in Highland Lake

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Bed & Breakfast
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Why Choose Rent By Owner for your Highland Lake Vacation Rental Homes?

What makes our Vacation Rentals special?

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Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
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Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
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Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.

Popular Areas for Highland Lake Vacation Rentals

Where are the best neighborhoods to stay in Highland Lake?

When exploring Highland Lake in Winsted, Connecticut, choosing the right neighborhood can greatly enhance your stay. The area offers a variety of charming communities that provide a peaceful retreat while remaining close to local amenities. Whether you prefer staying near the scenic lakefront or within easy reach of Winsted’s quaint town center, you'll find neighborhoods that cater to a range of preferences. Each neighborhood in Highland Lake provides a welcoming atmosphere, making it an ideal choice for those seeking comfortable and trustworthy vacation rentals. Discover the perfect location that aligns with your vacation plans and enjoy a memorable getaway in this picturesque part of Connecticut.

Pleasant Valley

This peaceful area offers a tranquil retreat with picturesque surroundings, making it an ideal choice for those seeking relaxation while exploring the scenic region near Highland Lake. Here, you can enjoy easy access to nature and quiet comfort in your vacation rental.

View 35+ Rentals in Pleasant Valley

Northwest Harwinton

Known for its charming small-town atmosphere, this neighborhood provides a welcoming environment close to outdoor activities around Highland Lake. Booking a stay here grants you convenient proximity to the area's natural beauty and local amenities.

View 51+ Rentals in Northwest Harwinton

Collinsville

This vibrant neighborhood combines historic charm with modern attractions, offering an excellent base for discovering the highlights of Highland Lake's surrounding region. It’s perfect for travelers seeking both comfort and accessibility during their getaway.

View 46+ Rentals in Collinsville

Canton Valley

Nestled in the scenic landscape, this community provides a serene setting with easy access to outdoor pursuits near Highland Lake. Your stay here ensures a peaceful experience complemented by convenient travel options within the region.

View 53+ Rentals in Canton Valley

Best Times to Visit Highland Lake

When should you plan your Vacation Rentals stay?

Timing your visit to this charming destination can enhance your experience, allowing you to enjoy the region’s natural beauty and serene atmosphere at its best throughout the year.

Peak Season Highlights

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Summer (June to August)

During the warm summer months, this region experiences peak visitation as visitors enjoy outdoor activities around Highland Lake and explore the scenic beauty of the area. Vacation rentals are in high demand as travelers seek a relaxing lakeside escape.

Average Temperature Daytime: 75-85°F - Nighttime: 60-65°F
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Fall (September to November)

Autumn brings vibrant foliage that attracts nature lovers to this destination. The cooler weather and colorful scenery make it an ideal time for outdoor adventures and cozy stays at vacation rentals in the region.

Average Temperature Daytime: 60-70°F - Nighttime: 45-55°F

Off-Season Highlights

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Winter (December to February)

The winter months see fewer visitors as the area becomes colder and less conducive to outdoor activities. This quieter season offers a peaceful retreat with opportunities for seasonal relaxation at available vacation rentals.

Average Temperature Daytime: 30-40°F - Nighttime: 20-30°F
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Spring (March to May)

Spring ushers in milder weather and budding landscapes, but the shoulder season results in lower visitor numbers. It's an excellent time for those seeking tranquility while enjoying the area's natural renewal.

Average Temperature Daytime: 50-60°F - Nighttime: 35-45°F

Weekly Weather Forecast for Highland Lake

How to Book Your Highland Lake Vacation Rental Home

What's our booking process?

Our platform allows you to browse a curated selection of vacation rentals. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.

Booking Steps

01

Search Properties

Use our filters to find the right property that fits your needs.
02

Select a Rental

Click on your preferred listing to view details, amenities, and pricing.
03

Book Online

Follow the link to finalize your reservation directly on the partner’s website.

Explore and book the perfect rental in Highland Lake

More Top-Rated Vacation Rentals in Highland Lake Area

Common Vacation Rentals Amenities

What amenities can you expect?

Our Vacation Rentals are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:

Indoor Features

  • Fully-equipped kitchens with modern appliances
  • Comfortable living areas with flat-screen TVs
  • Free Wi-Fi for staying connected
  • Air conditioning and heating for year-round comfort
  • In-unit washers and dryers for convenience
  • Luxurious bedrooms with premium bedding
  • Spa-like bathrooms with soaking tubs or walk-in showers

Outdoor Amenities

  • Enjoy outdoor grilling opportunities with a private barbecue area.
  • Escape to scenic lakeside views from your own outdoor patio or deck.
  • Take advantage of waterfront access for swimming, kayaking, or paddleboarding on Highland Lake.
  • Relax in a cozy outdoor fire pit perfect for evening gatherings under the stars.
  • Benefit from spacious gardens or landscaped yards for outdoor activities or picnics.
  • Explore nearby walking trails and nature paths suitable for hiking and birdwatching.
  • Make use of ample parking space for boats or recreational vehicles, ideal for exploring the region’s outdoor beauty.

Top Attractions Around Highland Lake

What attractions are nearby?

In this charming region, you can enjoy a variety of outdoor activities, including kayaking, fishing, and hiking, all just moments from your Highland Lake accommodation.

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Family Activities

  • Fishing at Highland Lake: Enjoy a relaxing day casting your line in the calm waters of Highland Lake, perfect for family fishing adventures.
  • Hiking around the region: Explore scenic trails nearby that offer great opportunities for family hikes and immersive nature experiences.
  • Boating and kayaking: Rent a boat or kayak to explore the tranquil lake, making it an ideal activity for families seeking outdoor water fun.
  • Visiting local parks: Spend quality time at nearby parks with picnic areas and playgrounds, creating memorable family outings in the area.
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Adult Activities

  • Fishing at Highland Lake: You can enjoy a relaxing day casting your line on the lake's serene waters, renowned for its excellent fishing opportunities in the area.
  • Boating and Kayaking: Explore the tranquil waters of the region by renting a boat or kayak, perfect for discovering hidden spots around Highland Lake.
  • Hiking and Nature Walks: Take advantage of nearby trails that offer scenic views and a peaceful escape into the natural beauty surrounding this destination.
  • Local Dining Experiences: Savor local cuisine at nearby restaurants and eateries, immersing yourself in the regional flavors after a day of outdoor activities.

Other Places to Stay in Highland Lake, CT

Winchester Historical Society
Winchester Historical Society Vacation Rentals
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Highland Lake Travel Tips

How Can You Make the Most of Your Stay?

  • Explore Local Outdoor Activities: Take advantage of the scenic surroundings by engaging in activities like fishing, boating, or hiking around Highland Lake to fully enjoy the natural beauty this area offers.
  • Plan Your Visit During Peak Seasons: Timing your stay during the region's prime seasons allows you to experience the best weather and community events that highlight this destination’s charm.
  • Discover Nearby Dining and Shops: Venture into the local towns to enjoy authentic regional cuisine and unique shops that add to the charm of your getaway here.
  • Engage with the Community: Connect with local residents and explore community parks or spots to gain a richer understanding of the area's culture and traditions.

Transportation Options

  • Personal Vehicles: Renting or driving your own car offers the most flexibility for exploring Highland Lake and the surrounding area at your own pace.
  • Local Taxis and Ride-Sharing Services: Convenient options like taxi services and ride-share apps provide quick transportation around this destination without the need for parking or navigation concerns.
  • Public Transportation: The region is served by local buses that connect key points around Highland Lake, making it easy to explore without a vehicle.
  • Rental Car Services: Numerous rental agencies in nearby towns offer vehicles suited for all travel needs, ensuring you have reliable transportation during your stay here.

Local Customs Options

  • Respect for Nature: Locals here value outdoor preservation, so you’ll find a strong tradition of caring for the natural landscape around Highland Lake.
  • Community Gatherings: Community events often highlight local traditions, offering an authentic experience of regional hospitality and camaraderie.
  • Fishing Etiquette: When fishing in the area, following local guidelines and practicing catch-and-release can be courteous ways to respect the region’s aquatic environment.
  • Seasonal Celebrations: Participating in seasonal festivals and holidays allows visitors to embrace the customs that embody the spirit of this destination.

Frequently Asked Questions About Highland Lake?

1. What are the top vacation rentals in Highland Lake?

There are a lot of options in Highland Lake. If you plan on staying in the Highland Lake area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Highland Lake:

2. How many Rentbyowner vacation rentals are available in Highland Lake?

Currently, the total number of properties listed by Rent By Owner in 2025 is over 45 in the Highland Lake area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Highland Lake. 

3. What is the cancellation policy for vacation rentals in Highland Lake, Winsted?

Cancellation policies vary by property; please review the specific listing details or contact the property owner directly to understand the terms related to cancellations and refunds.

4. Are there any additional fees I should expect when booking a vacation rental here?

Additional fees such as cleaning fees, service charges, or security deposits are typically outlined in the listing. It's recommended to read the detailed property description or ask the host for clarification before booking.

5. How do I find the most suitable vacation rental in this area?

To find the best option, filter your search based on amenities, guest capacity, and price range. Reviewing photos and guest reviews can also help ensure the property meets your expectations.

6. Is it possible to inquire about special requests or amenities before booking?

Yes, you can contact the property owner or manager directly through the listing to discuss any special requests or specific amenities you require during your stay.

7. What should I know about the check-in and check-out procedures for rentals here?

Check-in and check-out times are specified in each listing. For detailed instructions or to arrange early or late arrangements, it's best to communicate directly with the host prior to your arrival.

Best Vacation Homes in Highland Lake