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Winsted Holiday Rentals

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49 rentals in Winsted.
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Lake House  - Direct Waterfront, Immaculate; charming all 4 seasons, holiday rental in Winsted

Lake House - Direct Waterfront, Immaculate; charming all 4 seasons

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Room to Roam. Modern home with all amenities + sep. cabin on 10+  wooded acres., holiday rental in Winsted

Room to Roam. Modern home with all amenities + sep. cabin on 10+ wooded acres.

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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TRANQUIL private home with garden OASIS and heated POOL, holiday rental in Winsted

TRANQUIL private home with garden OASIS and heated POOL

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Spacious family home tucked away in a rural, friendly, lake community!, holiday rental in Winsted

Spacious family home tucked away in a rural, friendly, lake community!

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Luxurious rural get away, holiday rental in Winsted

Luxurious rural get away

6 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
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Beautiful Southfield Village!, holiday rental in Winsted

Beautiful Southfield Village!

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Spacious Country Retreat With Secluded Tree Top Mountain Views, holiday rental in Winsted

Spacious Country Retreat With Secluded Tree Top Mountain Views

6 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
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Historic home located on scenic Farmington River., holiday rental in Winsted

Historic home located on scenic Farmington River.

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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North Canaan's Quiet & Cozy Home, holiday rental in Winsted

North Canaan's Quiet & Cozy Home

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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The Cottage at Great Falls, holiday rental in Winsted

The Cottage at Great Falls

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Litchfield Hills Hideaway, holiday rental in Winsted

Litchfield Hills Hideaway

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Direct Waterfront with Private Beach - Entire Home, holiday rental in Winsted

Direct Waterfront with Private Beach - Entire Home

2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Berkshires Retreat & Respite ⭐️ Walk to the water. Peaceful, renovated property., holiday rental in Winsted

Berkshires Retreat & Respite ⭐️ Walk to the water. Peaceful, renovated property.

3 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
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Sunset Place - Modern Lake House on Otis Reservoir - 5 Night Min Stay - Sleeps 6, holiday rental in Winsted

Sunset Place - Modern Lake House on Otis Reservoir - 5 Night Min Stay - Sleeps 6

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Convenient Granby Charm, holiday rental in Winsted

Convenient Granby Charm

3 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
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Lakeridge Litchfield Resort Townhome  Pool  Tennis  Skiing, holiday rental in Winsted

Lakeridge Litchfield Resort Townhome Pool Tennis Skiing

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Converted Berkshire schoolhouse on a quiet river, holiday rental in Winsted

Converted Berkshire schoolhouse on a quiet river

3 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Cozy Cape in the Litchfield Hills, holiday rental in Winsted

Cozy Cape in the Litchfield Hills

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Family Friendly Farmhouse in the Berkshires, holiday rental in Winsted

Family Friendly Farmhouse in the Berkshires

5 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Konkapot Cottage, Pastoral Bliss With Wide Views, holiday rental in Winsted

Konkapot Cottage, Pastoral Bliss With Wide Views

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Modern Farmhouse in the Southern Berkshires, holiday rental in Winsted

Modern Farmhouse in the Southern Berkshires

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Cozy Litchfield House w/ Fenced-In Yard & Fire Pit, holiday rental in Winsted

Cozy Litchfield House w/ Fenced-In Yard & Fire Pit

3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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*New* 2020 Private Modern Farmhouse in Connecticut close to center of Litchfield, holiday rental in Winsted

*New* 2020 Private Modern Farmhouse in Connecticut close to center of Litchfield

6 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Charming Ashley Falls Cottage Retreat, holiday rental in Winsted

Charming Ashley Falls Cottage Retreat

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Lake House on the Cleanest Lake in CT, holiday rental in Winsted

Lake House on the Cleanest Lake in CT

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Prana Residence - Spa, holiday rental in Winsted

Prana Residence - Spa

3 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
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Colebrook Dream, holiday rental in Winsted

Colebrook Dream

4 bedrooms
4 bathrooms
Sleeps 14
Match: Sleeps
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NEW! Woodland Retreat w/ Pool & Near Wineries!, holiday rental in Winsted

NEW! Woodland Retreat w/ Pool & Near Wineries!

4 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Lakefront Granby Escape w/ Private Dock & Kayaks!, holiday rental in Winsted

Lakefront Granby Escape w/ Private Dock & Kayaks!

3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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'The Mill River Cabin’ w/ Fireplace & River View!, holiday rental in Winsted

'The Mill River Cabin’ w/ Fireplace & River View!

2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Quiet Country Contemporary Home – Ideal Respite From The City, holiday rental in Winsted

Quiet Country Contemporary Home – Ideal Respite From The City

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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East Otis Reservoir Cabin w/ Porch - Walk to Lake!, holiday rental in Winsted

East Otis Reservoir Cabin w/ Porch - Walk to Lake!

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Modern Goshen House w/ Deck, Backyard & Views, holiday rental in Winsted

Modern Goshen House w/ Deck, Backyard & Views

3 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Tentrr Signature Site - Echo Hill, holiday rental in Winsted

Tentrr Signature Site - Echo Hill

1 bedroom
1 bathroom
Sleeps 8
Match: Sleeps
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Tentrr Signature Site - Meadow Ridge Farm  Meadow, holiday rental in Winsted

Tentrr Signature Site - Meadow Ridge Farm Meadow

1 bedroom
1 bathroom
Sleeps 14
Match: Sleeps
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Tentrr Signature Site - Maple Corner Farm's Meadow Site, holiday rental in Winsted

Tentrr Signature Site - Maple Corner Farm's Meadow Site

1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
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Tentrr Signature Site - Meadow Ridge Farm Woods, holiday rental in Winsted

Tentrr Signature Site - Meadow Ridge Farm Woods

1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
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Quaint Quiet Serene !!, holiday rental in Winsted

Quaint Quiet Serene !!

1 bedroom
0 bathrooms
Sleeps 4
Match: Sleeps
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Cabin w/3 Acres, Tennis+BBall Courts by 4 Ski Mtns, holiday rental in Winsted

Cabin w/3 Acres, Tennis+BBall Courts by 4 Ski Mtns

6 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Ultimate Staycation Home in a Serene Setting, holiday rental in Winsted

Ultimate Staycation Home in a Serene Setting

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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NEW! East Otis Romantic Cottage w/ Deck & BBQ!, holiday rental in Winsted

NEW! East Otis Romantic Cottage w/ Deck & BBQ!

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Spacious Unit w/ Kitchen for Business Travel, Business Center, holiday rental in Winsted

Spacious Unit w/ Kitchen for Business Travel, Business Center

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Adventure Awaits! Modern Unit with Kitchen, Breakfast, holiday rental in Winsted

Adventure Awaits! Modern Unit with Kitchen, Breakfast

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Group Vacay! 2 Cozy Units Near Attractions, Pool, Parking, holiday rental in Winsted

Group Vacay! 2 Cozy Units Near Attractions, Pool, Parking

2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Group Vacay! 3 Cozy Units Near Attractions, Pool, Parking, holiday rental in Winsted

Group Vacay! 3 Cozy Units Near Attractions, Pool, Parking

3 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Group Vacay! 4 Cozy Units Near Attractions, Pool, Parking, holiday rental in Winsted

Group Vacay! 4 Cozy Units Near Attractions, Pool, Parking

4 bedrooms
4 bathrooms
Sleeps 16
Match: Sleeps
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Adventure Awaits! 2 Modern Units w/Kitchen, Breakfast, holiday rental in Winsted

Adventure Awaits! 2 Modern Units w/Kitchen, Breakfast

2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Tentrr Signature Site - Camping in the Woods of the Berkshires, holiday rental in Winsted

Tentrr Signature Site - Camping in the Woods of the Berkshires

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Ski Retreat -- Private Modern on 40 Acres of Land, holiday rental in Winsted

Ski Retreat -- Private Modern on 40 Acres of Land

4 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
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