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Winsted Vacation Rentals

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Bedrooms

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Distance from

5 mi
49 rentals in Winsted.
Enjoy a restful stay with fast internet, smart TV and the company of your pet., vacation rental in Winsted
Enjoy a restful stay with fast internet, smart TV and the company of your pet., vacation rental in Winsted
Enjoy a restful stay with fast internet, smart TV and the company of your pet., vacation rental in Winsted

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

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Beautiful, Spacious 5+ Bedroom House on Highland Lake with Spectacular views!, vacation rental in Winsted
Beautiful, Spacious 5+ Bedroom House on Highland Lake with Spectacular views!, vacation rental in Winsted
Beautiful, Spacious 5+ Bedroom House on Highland Lake with Spectacular views!, vacation rental in Winsted

Beautiful, Spacious 5+ Bedroom House on Highland Lake with Spectacular views!

Rental Home
5 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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Getaway for a weekend!, vacation rental in Winsted
Getaway for a weekend!, vacation rental in Winsted
Getaway for a weekend!, vacation rental in Winsted

Getaway for a weekend!

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Cottage Ease. Quaint cottage nestled in on Higland lake Winsted, Ct., vacation rental in Winsted
Cottage Ease. Quaint cottage nestled in on Higland lake Winsted, Ct., vacation rental in Winsted
Cottage Ease. Quaint cottage nestled in on Higland lake Winsted, Ct., vacation rental in Winsted

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

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Beautiful Highland lake in Connecticut, vacation rental in Winsted
Beautiful Highland lake in Connecticut, vacation rental in Winsted
Beautiful Highland lake in Connecticut, vacation rental in Winsted

Beautiful Highland lake in Connecticut

Rental Home
2 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
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The Inn at Highland Lake, 1st Floor, waterfront yard with a boat dock, vacation rental in Winsted
The Inn at Highland Lake, 1st Floor, waterfront yard with a boat dock, vacation rental in Winsted
The Inn at Highland Lake, 1st Floor, waterfront yard with a boat dock, vacation rental in Winsted

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

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Our Cottage - Small in size, Big in character, On beautiful Highland Lake, vacation rental in Winsted
Our Cottage - Small in size, Big in character, On beautiful Highland Lake, vacation rental in Winsted
Our Cottage - Small in size, Big in character, On beautiful Highland Lake, vacation rental in Winsted

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

Rental Home
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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The Cottage at Highland Lake, year-round, waterfront with a boat dock, vacation rental in Winsted
The Cottage at Highland Lake, year-round, waterfront with a boat dock, vacation rental in Winsted
The Cottage at Highland Lake, year-round, waterfront with a boat dock, vacation rental in Winsted

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

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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The Inn at Highland Lake, 2nd Floor, waterfront yard with a boat dock, vacation rental in Winsted
The Inn at Highland Lake, 2nd Floor, waterfront yard with a boat dock, vacation rental in Winsted
The Inn at Highland Lake, 2nd Floor, waterfront yard with a boat dock, vacation rental in Winsted

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

Condo/Apartment
3 bedrooms
1 bathroom
Sleeps 3
Match: Sleeps
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Cozy Waterfront Cottage on Highland Lake, Northwestern CT, vacation rental in Winsted
Cozy Waterfront Cottage on Highland Lake, Northwestern CT, vacation rental in Winsted
Cozy Waterfront Cottage on Highland Lake, Northwestern CT, vacation rental in Winsted

Cozy Waterfront Cottage on Highland Lake, Northwestern CT

Rental Home
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Newly renovated year-round LAKEFRONT rental on Highland Lake!!! Sleeps 8-9!, vacation rental in Winsted
Newly renovated year-round LAKEFRONT rental on Highland Lake!!! Sleeps 8-9!, vacation rental in Winsted
Newly renovated year-round LAKEFRONT rental on Highland Lake!!! Sleeps 8-9!, vacation rental in Winsted

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

Rental Home
4 bedrooms
0 bathrooms
Sleeps 4
Match: Sleeps
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Newly Renovated Family House On Highland Lake with Dock, vacation rental in Winsted
Newly Renovated Family House On Highland Lake with Dock, vacation rental in Winsted
Newly Renovated Family House On Highland Lake with Dock, vacation rental in Winsted

Newly Renovated Family House On Highland Lake with Dock

Rental Home
5 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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Luxury Highland Lake Waterfront, vacation rental in Winsted
Luxury Highland Lake Waterfront, vacation rental in Winsted
Luxury Highland Lake Waterfront, vacation rental in Winsted

Luxury Highland Lake Waterfront

Rental Home
7 bedrooms
4 bathrooms
Sleeps 16
Match: Sleeps
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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., vacation rental in Winsted
Waterfront Lake Home on Tranquil Harwinton Lake with spectacular 180⁰ view., vacation rental in Winsted
Waterfront Lake Home on Tranquil Harwinton Lake with spectacular 180⁰ view., vacation rental in Winsted

Waterfront Lake Home on Tranquil Harwinton Lake with spectacular 180⁰ view.

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Cozy house with waterfall view!, vacation rental in Winsted
Cozy house with waterfall view!, vacation rental in Winsted
Cozy house with waterfall view!, vacation rental in Winsted

Cozy house with waterfall view!

Rental Home
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Newly renovated cottage on the lake!, vacation rental in Winsted
Newly renovated cottage on the lake!, vacation rental in Winsted
Newly renovated cottage on the lake!, vacation rental in Winsted

Newly renovated cottage on the lake!

Rental Home
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Beautiful brook-side log cabin on 3 private acres, vacation rental in Winsted
Beautiful brook-side log cabin on 3 private acres, vacation rental in Winsted
Beautiful brook-side log cabin on 3 private acres, vacation rental in Winsted

Beautiful brook-side log cabin on 3 private acres

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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West Hill Cabin, vacation rental in Winsted
West Hill Cabin, vacation rental in Winsted
West Hill Cabin, vacation rental in Winsted

West Hill Cabin

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Very charming house , that will make you feel like home, vacation rental in Winsted
Very charming house , that will make you feel like home, vacation rental in Winsted
Very charming house , that will make you feel like home, vacation rental in Winsted

Very charming house , that will make you feel like home

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Relax in The Farmhouse on a a beautiful land & pond, vacation rental in Winsted
Relax in The Farmhouse on a a beautiful land & pond, vacation rental in Winsted
Relax in The Farmhouse on a a beautiful land & pond, vacation rental in Winsted

Relax in The Farmhouse on a a beautiful land & pond

Rental Home
2 bedrooms
1 bathroom
Sleeps 7
Match: Sleeps
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Zen Loft At Oak Haus 10 min to Litchfield, vacation rental in Winsted
Zen Loft At Oak Haus 10 min to Litchfield, vacation rental in Winsted
Zen Loft At Oak Haus 10 min to Litchfield, vacation rental in Winsted

Zen Loft At Oak Haus 10 min to Litchfield

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Bedrooms Single family home in a beautiful quiet Neighborhood in Torrington CT ., vacation rental in Winsted
Bedrooms Single family home in a beautiful quiet Neighborhood in Torrington CT ., vacation rental in Winsted
Bedrooms Single family home in a beautiful quiet Neighborhood in Torrington CT ., vacation rental in Winsted

Bedrooms Single family home in a beautiful quiet Neighborhood in Torrington CT .

Rental Home
2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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BEAUTIFUL APARTMENT WITH SCENIC VIEWS, vacation rental in Winsted
BEAUTIFUL APARTMENT WITH SCENIC VIEWS, vacation rental in Winsted
BEAUTIFUL APARTMENT WITH SCENIC VIEWS, vacation rental in Winsted

BEAUTIFUL APARTMENT WITH SCENIC VIEWS

Rental Home
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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One Bedroom Guest House Nestled in the mountain, vacation rental in Winsted
One Bedroom Guest House Nestled in the mountain, vacation rental in Winsted
One Bedroom Guest House Nestled in the mountain, vacation rental in Winsted

One Bedroom Guest House Nestled in the mountain

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Scenic Country Local Antique Hiking rafting, vacation rental in Winsted
Scenic Country Local Antique Hiking rafting, vacation rental in Winsted
Scenic Country Local Antique Hiking rafting, vacation rental in Winsted

Scenic Country Local Antique Hiking rafting

Rental Home
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Charming barn style house in historic village center, vacation rental in Winsted
Charming barn style house in historic village center, vacation rental in Winsted
Charming barn style house in historic village center, vacation rental in Winsted

Charming barn style house in historic village center

Rental Home
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Cozy Modern Farmhouse 2 Bedroom Apartment, vacation rental in Winsted
Cozy Modern Farmhouse 2 Bedroom Apartment, vacation rental in Winsted
Cozy Modern Farmhouse 2 Bedroom Apartment, vacation rental in Winsted

Cozy Modern Farmhouse 2 Bedroom Apartment

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Lakefront Tranquility/Fishermans Delight, vacation rental in Winsted
Lakefront Tranquility/Fishermans Delight, vacation rental in Winsted
Lakefront Tranquility/Fishermans Delight, vacation rental in Winsted

Lakefront Tranquility/Fishermans Delight

Rental Home
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Historic house on Farmington River is an angler’s dream!, vacation rental in Winsted
Historic house on Farmington River is an angler’s dream!, vacation rental in Winsted
Historic house on Farmington River is an angler’s dream!, vacation rental in Winsted

Historic house on Farmington River is an angler’s dream!

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Lakeridge Litchfield Resort Townhome  Pool  Tennis  Skiing, vacation rental in Winsted
Lakeridge Litchfield Resort Townhome  Pool  Tennis  Skiing, vacation rental in Winsted
Lakeridge Litchfield Resort Townhome  Pool  Tennis  Skiing, vacation rental in Winsted

Lakeridge Litchfield Resort Townhome Pool Tennis Skiing

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Lovely 3 Bedroom Townhouse , perfect for skiing, vacation rental in Winsted
Lovely 3 Bedroom Townhouse , perfect for skiing, vacation rental in Winsted
Lovely 3 Bedroom Townhouse , perfect for skiing, vacation rental in Winsted

Lovely 3 Bedroom Townhouse , perfect for skiing

Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Nature House  Water View Large Deck 2 story  Gazebo 2 bed 2 bath, vacation rental in Winsted
Nature House  Water View Large Deck 2 story  Gazebo 2 bed 2 bath, vacation rental in Winsted
Nature House  Water View Large Deck 2 story  Gazebo 2 bed 2 bath, vacation rental in Winsted

Nature House Water View Large Deck 2 story Gazebo 2 bed 2 bath

Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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The River House - Collinsville, vacation rental in Winsted
The River House - Collinsville, vacation rental in Winsted
The River House - Collinsville, vacation rental in Winsted

The River House - Collinsville

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Direct Waterfront with Private Beach - Entire Home, vacation rental in Winsted
Direct Waterfront with Private Beach - Entire Home, vacation rental in Winsted
Direct Waterfront with Private Beach - Entire Home, vacation rental in Winsted

Direct Waterfront with Private Beach - Entire Home

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Cherrybrook Hideaway - 12 mins to Ski Sundown!, vacation rental in Winsted
Cherrybrook Hideaway - 12 mins to Ski Sundown!, vacation rental in Winsted
Cherrybrook Hideaway - 12 mins to Ski Sundown!, vacation rental in Winsted

Cherrybrook Hideaway - 12 mins to Ski Sundown!

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Unique and extraordinary experience! Renew your senses., vacation rental in Winsted
Unique and extraordinary experience! Renew your senses., vacation rental in Winsted
Unique and extraordinary experience! Renew your senses., vacation rental in Winsted

Unique and extraordinary experience! Renew your senses.

Rental Home
3 bedrooms
3 bathrooms
Sleeps 3
Match: Sleeps
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River tubes, electric bikes, kayaks, skiing, more 
4 minutes to the river, vacation rental in Winsted
River tubes, electric bikes, kayaks, skiing, more 
4 minutes to the river, vacation rental in Winsted
River tubes, electric bikes, kayaks, skiing, more 
4 minutes to the river, vacation rental in Winsted

River tubes, electric bikes, kayaks, skiing, more 4 minutes to the river

Rental Home
3 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
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Stylish Comfort in a Stunning Country Setting, vacation rental in Winsted
Stylish Comfort in a Stunning Country Setting, vacation rental in Winsted
Stylish Comfort in a Stunning Country Setting, vacation rental in Winsted

Stylish Comfort in a Stunning Country Setting

Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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4 Bedroom Family Friendly Home in Riverton Paradise, vacation rental in Winsted
4 Bedroom Family Friendly Home in Riverton Paradise, vacation rental in Winsted
4 Bedroom Family Friendly Home in Riverton Paradise, vacation rental in Winsted

4 Bedroom Family Friendly Home in Riverton Paradise

Rental Home
4 bedrooms
2 bathrooms
Sleeps 11
Match: Sleeps
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Spacious country home minutes from Litchfield Green and downtown Torrington, vacation rental in Winsted
Spacious country home minutes from Litchfield Green and downtown Torrington, vacation rental in Winsted
Spacious country home minutes from Litchfield Green and downtown Torrington, vacation rental in Winsted

Spacious country home minutes from Litchfield Green and downtown Torrington

Rental Home
4 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Berkshire Retreat Near Hiking, Outdoors, and Walkable to Town, vacation rental in Winsted
Berkshire Retreat Near Hiking, Outdoors, and Walkable to Town, vacation rental in Winsted
Berkshire Retreat Near Hiking, Outdoors, and Walkable to Town, vacation rental in Winsted

Berkshire Retreat Near Hiking, Outdoors, and Walkable to Town

Rental Home
4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Waterfront renovated country house with deck, close to hiking, skiing, vacation rental in Winsted
Waterfront renovated country house with deck, close to hiking, skiing, vacation rental in Winsted
Waterfront renovated country house with deck, close to hiking, skiing, vacation rental in Winsted

Waterfront renovated country house with deck, close to hiking, skiing

Rental Home
3 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
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Pristine Private Lake Cottage in West Hartland CT - Three Season Rentals, vacation rental in Winsted
Pristine Private Lake Cottage in West Hartland CT - Three Season Rentals, vacation rental in Winsted
Pristine Private Lake Cottage in West Hartland CT - Three Season Rentals, vacation rental in Winsted

Pristine Private Lake Cottage in West Hartland CT - Three Season Rentals

Rental Home
5 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Great Family Cabin in the woods on a lake., vacation rental in Winsted
Great Family Cabin in the woods on a lake., vacation rental in Winsted
Great Family Cabin in the woods on a lake., vacation rental in Winsted

Great Family Cabin in the woods on a lake.

Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Beautiful Farmhouse on 14 Acres, vacation rental in Winsted
Beautiful Farmhouse on 14 Acres, vacation rental in Winsted
Beautiful Farmhouse on 14 Acres, vacation rental in Winsted

Beautiful Farmhouse on 14 Acres

Rental Home
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Serene Berkshire Retreat, vacation rental in Winsted
Serene Berkshire Retreat, vacation rental in Winsted
Serene Berkshire Retreat, vacation rental in Winsted

Serene Berkshire Retreat

Rental Home
4 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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Stunning Retreat on 62 Acres, 7000 sq ft, Pool and Hot Tub, vacation rental in Winsted
Stunning Retreat on 62 Acres, 7000 sq ft, Pool and Hot Tub, vacation rental in Winsted
Stunning Retreat on 62 Acres, 7000 sq ft, Pool and Hot Tub, vacation rental in Winsted

Stunning Retreat on 62 Acres, 7000 sq ft, Pool and Hot Tub

Rental Home
5 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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Lakeside Cottage in the Berkshires, vacation rental in Winsted
Lakeside Cottage in the Berkshires, vacation rental in Winsted
Lakeside Cottage in the Berkshires, vacation rental in Winsted

Lakeside Cottage in the Berkshires

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Beautiful retreat to the woods to enjoy the winter season., vacation rental in Winsted
Beautiful retreat to the woods to enjoy the winter season., vacation rental in Winsted
Beautiful retreat to the woods to enjoy the winter season., vacation rental in Winsted

Beautiful retreat to the woods to enjoy the winter season.

Rental Home
5 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Showing results 1-49 of 49
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