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Cottages, Villas, Apartments in Winsted
Holiday Rentals
USA
Connecticut (CT)
Cottages, Villas, Apartments in Winsted
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Amenities
Internet or Wifi (49)
Air Conditioning (40)
Washer/Dryer (34)
Other outdoor space (29)
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Suitability
Kid friendly (44)
Pet friendly (13)
Smoking allowed (1)
Wheelchair access (0)
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Property type
Holiday Rental House (38)
Condominium/Apartment (12)
Cabin Holiday Rental (0)
Private Room (0)
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Distinctive Features
Waterfront (11)
Boat Available (5)
Private Chef (0)
Private Beach (0)
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Distance from
5 mi
American Museum of Tort Law
Winchester Historical Society
Whiting Mills
St. Joseph's Catholic Church
Soldiers' Monument and Memorial Park
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50 rentals
in Winsted.
Enjoy a restful stay with fast internet, smart TV and the company of your pet.
15
Condo/Apartment
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1 bedroom
1 bathroom
Sleeps 3
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Beautiful, Spacious 5+ Bedroom House on Highland Lake with Spectacular views!
14
Holiday Rental House
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6 bedrooms
4 bathrooms
Sleeps 12
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Cottage Ease. Quaint cottage nestled in on Higland lake Winsted, Ct.
Holiday Rental House
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2 bedrooms
1 bathroom
Sleeps 4
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The Inn at Highland Lake, 1st Floor, waterfront yard with a boat dock
9
Condo/Apartment
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2 bedrooms
1 bathroom
Sleeps 4
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Our Cottage - Small in size, Big in character, On beautiful Highland Lake
26
Holiday Rental House
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2 bedrooms
1 bathroom
Sleeps 6
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The Cottage at Highland Lake, year-round, waterfront with a boat dock
4
Holiday Rental House
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2 bedrooms
2 bathrooms
Sleeps 4
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The Inn at Highland Lake, 2nd Floor, waterfront yard with a boat dock
7
Condo/Apartment
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3 bedrooms
1 bathroom
Sleeps 8
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Fall 2024! Cozy WATERFRONT Cottage on Highland Lake, CT - central a/c and
10
Holiday Rental House
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2 bedrooms
2 bathrooms
Sleeps 6
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Newly renovated year-round LAKEFRONT rental on Highland Lake!!! Sleeps 8-9!
6
Holiday Rental House
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4 bedrooms
2 bathrooms
Sleeps 9
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Family House On Highland Lake with Dock
13
Holiday Rental House
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6 bedrooms
4 bathrooms
Sleeps 12
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Charming 2-bedroom apartment in welcoming Winsted with WiFi, AC
Condo/Apartment
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2 bedrooms
1 bathroom
Sleeps 4
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Charming 2-bedroom apartment with AC, WiFi LAKE VIEWS!
Condo/Apartment
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2 bedrooms
1 bathroom
Sleeps 4
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The following properties within 20 miles of Winsted match all your filters:
Waterfront Lake Home on Tranquil Harwinton Lake with spectacular 180⁰ view.
38
Holiday Rental House
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2 bedrooms
1 bathroom
Sleeps 4
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Beautiful brook-side log cabin on 3 private acres - 2 bed, 1.5 bath, entire home
12
Holiday Rental House
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2 bedrooms
2 bathrooms
Sleeps 4
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Very charming house , that will make you feel like home
Holiday Rental House
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2 bedrooms
1 bathroom
Sleeps 2
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Relax in The Farmhouse on a a beautiful land & pond
9
Holiday Rental House
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2 bedrooms
1 bathroom
Sleeps 7
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Cozy Tree Haus 1 Bedroom Apt
2
Condo/Apartment
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1 bedroom
1 bathroom
Sleeps 2
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Bedrooms Single family home in a beautiful quiet Neighborhood in Torrington CT .
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2 bedrooms
2 bathrooms
Sleeps 8
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BEAUTIFUL APARTMENT WITH SCENIC VIEWS
Holiday Rental House
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3 bedrooms
1 bathroom
Sleeps 6
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One Bedroom Guest House Nestled in the mountain
10
Holiday Rental House
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1 bedroom
1 bathroom
Sleeps 2
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Scenic Country Local Antique Hiking rafting
Holiday Rental House
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2 bedrooms
1 bathroom
Sleeps 6
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Cozy Modern Farm Haus 2 Bedroom Apartment
2
Condo/Apartment
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2 bedrooms
1 bathroom
Sleeps 5
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Lakefront Tranquility/Fishermans Delight
10
Holiday Rental House
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2 bedrooms
1 bathroom
Sleeps 6
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Lakeridge Litchfield Resort Townhome Pool Tennis Skiing
10
Holiday Rental House
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2 bedrooms
2 bathrooms
Sleeps 4
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Lovely 3 Bedroom Townhouse , perfect for skiing
Condo/Apartment
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3 bedrooms
2 bathrooms
Sleeps 4
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Immaculate Year-Round Lakefront-Charming cottage, swimming, boating, central air
12
Holiday Rental House
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3 bedrooms
2 bathrooms
Sleeps 7
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Direct Waterfront with Private Beach - Entire Home
10
Holiday Rental House
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2 bedrooms
2 bathrooms
Sleeps 4
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Cherrybrook Hideaway - Book now for autumn colors!
2
Holiday Rental House
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4 bedrooms
2 bathrooms
Sleeps 6
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Unique & extraordinary experience - renew your senses. Delightful waterfront!
5
Holiday Rental House
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3 bedrooms
3 bathrooms
Sleeps 8
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River tubes, electric bikes, kayaks, skiing, more 2 minutes to the river
8
Holiday Rental House
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3 bedrooms
2 bathrooms
Sleeps 9
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Stylish Comfort in a Stunning Country Setting
Holiday Rental House
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3 bedrooms
3 bathrooms
Sleeps 8
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4 Bedroom Family Friendly Home in Riverton Paradise
1
Holiday Rental House
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4 bedrooms
2 bathrooms
Sleeps 11
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Great Family Cabin in the woods on a lake.
2
Holiday Rental House
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4 bedrooms
3 bathrooms
Sleeps 8
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Stunning Retreat on 62 Acres, 7000 sq ft, Pool and Hot Tub
4
Holiday Rental House
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5 bedrooms
4 bathrooms
Sleeps 12
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Charming 2-bedroom cottage with AC and WiFi in welcoming New Hartford
3
Holiday Rental House
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2 bedrooms
1 bathroom
Sleeps 6
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Woodland Dream House on private pond with forest and fields- Warm and Cozy
Holiday Rental House
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4 bedrooms
2 bathrooms
Sleeps 6
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Country home vacation oasis with pool, hot tub, near lake/hiking.
2
Holiday Rental House
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3 bedrooms
2 bathrooms
Sleeps 6
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3-bedroom house in Collinsville with WiFi
Holiday Rental House
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3 bedrooms
1 bathroom
Sleeps 5
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Waterfront Cabin w Firepit, Dock, Deck, BBQ. Direct Lake Access! Pet-friendly!
12
Holiday Rental House
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1 bedroom
1 bathroom
Sleeps 6
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1 bedroom in a factory converted loft, with fitness room, WiFi in Torrington
Condo/Apartment
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1 bedroom
1 bathroom
Sleeps 2
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Lakeside Oasis with Hot Tub; 5 min to Ski Mountain!
Holiday Rental House
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5 bedrooms
3 bathrooms
Sleeps 10
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Spacious 4-bedroom condo with AC and WiFi in Litchfield County
Condo/Apartment
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4 bedrooms
4 bathrooms
Sleeps 9
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Charming 3-bedroom Modern cottage with lakeside views
Holiday Rental House
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3 bedrooms
2 bathrooms
Sleeps 12
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Nature's Oasis - 15 Mins to Ski Resort
1
Holiday Rental House
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4 bedrooms
3 bathrooms
Sleeps 8
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RIVERSIDE HOMESTEAD on the Farmington River
10
Condo/Apartment
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1 bedroom
1 bathroom
Sleeps 3
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Relax or be active! The choice is yours in this pet-friendly family home.
7
Holiday Rental House
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3 bedrooms
2 bathrooms
Sleeps 8
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Private, lake community house in the serene Berkshire Foothills with pool table
4
Holiday Rental House
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3 bedrooms
3 bathrooms
Sleeps 6
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Beautiful retreat in a lake community to the enjoy the summer season.
15
Holiday Rental House
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4 bedrooms
2 bathrooms
Sleeps 8
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Charming apartment 7 minute walk to downtown
7
Condo/Apartment
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2 bedrooms
1 bathroom
Sleeps 4
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Cottage is currently rented for the year, and not available until further notice
2
Holiday Rental House
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2 bedrooms
1 bathroom
Sleeps 6
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1
Showing results 1-50 of 50
Frequently Asked Questions about Winsted
Do any holiday rentals in Winsted have a pool?
Yes, here are some popular holiday rentals in Winsted that have a pool:
Enjoy a restful stay with fast internet, smart TV and the company of your pet.
Beautiful, Spacious 5+ Bedroom House on Highland Lake with Spectacular views!
Cottage Ease. Quaint cottage nestled in on Higland lake Winsted, Ct.
See all holiday rentals with a pool in Winsted on Tripadvisor
Do any holiday rentals in Winsted have internet access?
Yes, here are some popular holiday rentals in Winsted that have internet access:
Enjoy a restful stay with fast internet, smart TV and the company of your pet.
Beautiful, Spacious 5+ Bedroom House on Highland Lake with Spectacular views!
Cottage Ease. Quaint cottage nestled in on Higland lake Winsted, Ct.
See all holiday rentals in Winsted on Tripadvisor
What are the best pet friendly rentals in Winsted?
The best pet friendly rentals in Winsted are:
Enjoy a restful stay with fast internet, smart TV and the company of your pet.
Cottage Ease. Quaint cottage nestled in on Higland lake Winsted, Ct.
Newly renovated year-round LAKEFRONT rental on Highland Lake!!! Sleeps 8-9!
See all pet friendly holiday rentals in Winsted on Tripadvisor
What are some great rentals in Winsted that are kid friendly?
Some of the most popular kid friendly rentals in Winsted are:
Enjoy a restful stay with fast internet, smart TV and the company of your pet.
Beautiful, Spacious 5+ Bedroom House on Highland Lake with Spectacular views!
The Inn at Highland Lake, 1st Floor, waterfront yard with a boat dock
See all kid friendly holiday rentals in Winsted on Tripadvisor
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