7 Ocean Vacation - Vacation Rentals in Highland Lake

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From US $278

         

10.0 (56 Reviews)

House

Immaculate Year-Round Lakefront-Charming cottage, swimming, boating, central air

• Air Conditioner
• Parking
• TV

• Winsted
• Winchester

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From US $219

         

1.0 (1 Review)

Bed & Breakfast

L&R

• Air Conditioner
• Parking
• Pool

• Connecticut
• Torrington

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From US $293

         

10.0 (50 Reviews)

Cottage

Our Cottage - Small in size, Big in character, On beautiful Highland Lake

• Air Conditioner
• Parking
• TV

• Winsted
• Winchester

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From US $360

         

10.0 (28 Reviews)

House

Family House On Highland Lake with Dock

• Air Conditioner
• Parking
• TV

• Winsted
• Winchester

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From US $159

         

10.0 (13 Reviews)

Apartment

The Inn at Highland Lake, 1st Floor, waterfront yard with a boat dock

• Air Conditioner
• Parking
• TV

• Winsted
• Winchester

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From US $217

         

9.6 (17 Reviews)

Apartment

The Inn at Highland Lake, 2nd Floor, waterfront yard with a boat dock

• Air Conditioner
• Parking
• TV

• Winsted
• Winchester

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From US $251

         

9.6 (11 Reviews)

Cottage

The Cottage at Highland Lake, year-round, waterfront with a boat dock

• Air Conditioner
• Parking
• TV

• Winsted
• Winchester

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From US $195

         

9.2 (46 Reviews)

Apartment

Enjoy a restful stay with fast internet, smart TV and the company of your pet.

• Air Conditioner
• Parking
• Pet Friendly

• Winsted
• Winchester

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From US $258

         

9.0 (2 Reviews)

House

Charming renovated 3-bedroom house in serene Winsted

• Air Conditioner
• Parking
• TV

• Winsted
• Winchester

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From US $1,073

         

New

House

Lakefront Escape on Highland

• Air Conditioner
• Security/Safety
• Bedding/Linens

• Winsted
• Winchester

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From US $339

         

10.0 (25 Reviews)

Cottage

Cozy WATERFRONT Cottage on Highland Lake, CT - central a/c & heat

• Air Conditioner
• Parking
• TV

• Winsted
• Winchester

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From US $542

         

10.0 (19 Reviews)

House

Newly renovated year-round LAKEFRONT rental on Highland Lake! Sleeps 8-9!

• Air Conditioner
• Parking
• Pet Friendly

• Winsted
• Winchester

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From US $220

         

10.0 (9 Reviews)

Cottage

Charming 2-bedroom cottage with AC and WiFi in welcoming New Hartford

• Air Conditioner
• Parking
• Security/Safety

• Torrington
• West Hill Lake

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From US $134

         

9.8 (9 Reviews)

House

Best Outdoors near the Berkshires

• Parking
• TV
• Balcony/Terrace

• Winsted
• Winchester

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From US $159

         

9.6 (13 Reviews)

House

Lakeridge Litchfield Resort Townhome Pool Tennis Skiing

• Air Conditioner
• Parking
• Pet Friendly

• Connecticut
• Torrington

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From US $427

         

New

Apartment

Charming 2-bedroom apartment with AC, WiFi LAKE VIEWS!

• Air Conditioner
• Security/Safety
• Bedding/Linens

• Winsted
• Winchester

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From US $166

         

New

Condo

Lovely 3 Bedroom Townhouse , perfect for skiing

• Air Conditioner
• Parking
• Pool

• Connecticut
• Torrington

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From US $94

         

6.0 (2 Reviews)

Apartment

Getaway for a weekend!

• Air Conditioner
• Security/Safety
• Bedding/Linens

• Winsted
• Winchester

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From US $531

         

New

House

Charming 3-bedroom lakehouse in Winchester with WiFi and AC

• Air Conditioner
• Parking
• TV

• Winsted
• Winchester

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From US $450

         

New

House

Beautiful Highland lake in Connecticut

• Air Conditioner
• TV
• View

• Winsted
• Winchester

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From US $385

         

New

Apartment

Charming 2-bedroom apartment in welcoming Winsted with WiFi, AC

• Air Conditioner
• Security/Safety
• Bedding/Linens

• Winsted
• Winchester

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From US $237

         

New

Condo

Spacious 4-bedroom condo with AC and WiFi in Litchfield County

• Air Conditioner
• Parking
• Pool

• Connecticut
• Torrington

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From US $200

         

New

Cottage

Cottage Ease. Quaint cottage nestled in on Higland lake Winsted, Ct.

• Pet Friendly
• Security/Safety
• Bedding/Linens

• Winsted
• Winchester

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From US $166

         

New

House

Cozy Fall and ski rental nestled in a gated community in the woods.

• Air Conditioner
• Bedding/Linens
• Wellness Facilities

• Connecticut
• Torrington

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