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Lakeville Holiday Rentals

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50 rentals in Lakeville.
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Lake House, holiday rental in Lakeville

Lake House

5 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
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Babbling Brook Retreat, holiday rental in Lakeville

Babbling Brook Retreat

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Close To Skiing!  Beautiful +Family Friendly - W Tree House & Tennis Court, holiday rental in Lakeville

Close To Skiing! Beautiful +Family Friendly - W Tree House & Tennis Court

4 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
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Elegant Historic Hudson Valley Gilded Age Mansion On 4+ Parklike Acres, holiday rental in Lakeville

Elegant Historic Hudson Valley Gilded Age Mansion On 4+ Parklike Acres

10 bedrooms
10 bathrooms
Sleeps 22
Match: Sleeps
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Antique Farmhouse Totally Restored, holiday rental in Lakeville

Antique Farmhouse Totally Restored

4 bedrooms
3 bathrooms
Sleeps 16
Match: Sleeps
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Pet & Kid Friendly, Solar, 13 Acres, Salt Water Pool, River Views, holiday rental in Lakeville

Pet & Kid Friendly, Solar, 13 Acres, Salt Water Pool, River Views

3 bedrooms
4 bathrooms
Sleeps 9
Match: Sleeps
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Spacious Country Retreat With Secluded Tree Top Mountain Views, holiday rental in Lakeville

Spacious Country Retreat With Secluded Tree Top Mountain Views

6 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
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North Canaan's Quiet & Cozy Home, holiday rental in Lakeville

North Canaan's Quiet & Cozy Home

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Modern Antique Farmhouse in the Hudson Valley, holiday rental in Lakeville

Modern Antique Farmhouse in the Hudson Valley

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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The Cottage at Great Falls, holiday rental in Lakeville

The Cottage at Great Falls

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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TRANQUIL private home with garden OASIS and heated POOL, holiday rental in Lakeville

TRANQUIL private home with garden OASIS and heated POOL

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Waterfront Perfection!, holiday rental in Lakeville

Waterfront Perfection!

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Harmony House, Lakeville, Connecticut, holiday rental in Lakeville

Harmony House, Lakeville, Connecticut

6 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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The Little House in the Woods, holiday rental in Lakeville

The Little House in the Woods

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Beautiful Mountainside House with nearby Lake and Hiking Trails, holiday rental in Lakeville

Beautiful Mountainside House with nearby Lake and Hiking Trails

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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TREEMENDOUS VIEWS COTTAGE, holiday rental in Lakeville

TREEMENDOUS VIEWS COTTAGE

4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Have it all! Lakefront, Pool & Skiing! 5 Bedrooms, holiday rental in Lakeville

Have it all! Lakefront, Pool & Skiing! 5 Bedrooms

6 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
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Lakefront Home in Hudson Valley Dutchess County, Pine Plains, New York, holiday rental in Lakeville

Lakefront Home in Hudson Valley Dutchess County, Pine Plains, New York

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Mountainview - Vacation Rental in Sharon, CT, holiday rental in Lakeville

Mountainview - Vacation Rental in Sharon, CT

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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The Barn - Rustic Chic Loft - Rehabed 1890 Hay Barn - Near Lakes & Hotchkiss, holiday rental in Lakeville

The Barn - Rustic Chic Loft - Rehabed 1890 Hay Barn - Near Lakes & Hotchkiss

2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Contemporary Lakefront, Ski, Tennis and Boat Cozy 3 Bedrooms, holiday rental in Lakeville

Contemporary Lakefront, Ski, Tennis and Boat Cozy 3 Bedrooms

4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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PRIVATE PENINSULA 2ac surrounded by water min from hiking skiing theater music, holiday rental in Lakeville

PRIVATE PENINSULA 2ac surrounded by water min from hiking skiing theater music

3 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
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Newly Renovated Country Retreat-Berkshires, holiday rental in Lakeville

Newly Renovated Country Retreat-Berkshires

3 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
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New England Winter Wonderland - 2 Hrs from NYC, holiday rental in Lakeville

New England Winter Wonderland - 2 Hrs from NYC

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Beautiful Berkshire Home - Enjoy all Summer, Fall & Winter Attractions, holiday rental in Lakeville

Beautiful Berkshire Home - Enjoy all Summer, Fall & Winter Attractions

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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CAMP HOUSE on Twin Lakes, holiday rental in Lakeville

CAMP HOUSE on Twin Lakes

6 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Modern Farmhouse in the Southern Berkshires, holiday rental in Lakeville

Modern Farmhouse in the Southern Berkshires

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Charming 2+2 Lakeside Cottage on Best Lake in CT, holiday rental in Lakeville

Charming 2+2 Lakeside Cottage on Best Lake in CT

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Riverwood - Cozy Carriage House in the Woods, holiday rental in Lakeville

Riverwood - Cozy Carriage House in the Woods

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Hudson Valley - Picardy Farm: Entire Estate, holiday rental in Lakeville

Hudson Valley - Picardy Farm: Entire Estate

10 bedrooms
8 bathrooms
Sleeps 20
Match: Sleeps
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Large Country Home, Sleeps 10! Enjoy the Firepit and Ski Butternut, holiday rental in Lakeville

Large Country Home, Sleeps 10! Enjoy the Firepit and Ski Butternut

5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Charming Ashley Falls Cottage Retreat, holiday rental in Lakeville

Charming Ashley Falls Cottage Retreat

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Quiet Country Contemporary Home – Ideal Respite From The City, holiday rental in Lakeville

Quiet Country Contemporary Home – Ideal Respite From The City

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Exclusive Rental in Beautiful Amenia!, holiday rental in Lakeville

Exclusive Rental in Beautiful Amenia!

3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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The FarmHouse, holiday rental in Lakeville

The FarmHouse

2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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1790 Classic Colonial Center Hall home, holiday rental in Lakeville

1790 Classic Colonial Center Hall home

5 bedrooms
3 bathrooms
Sleeps 11
Match: Sleeps
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Tentrr Signature Site - Glacial Erratic at Moore Brook, holiday rental in Lakeville

Tentrr Signature Site - Glacial Erratic at Moore Brook

1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
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Tentrr Signature Site - Echo Hill, holiday rental in Lakeville

Tentrr Signature Site - Echo Hill

1 bedroom
1 bathroom
Sleeps 8
Match: Sleeps
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Tentrr Signature Site - Driftways Farm, holiday rental in Lakeville

Tentrr Signature Site - Driftways Farm

1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
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Tentrr Signature Site - Hudson Valley Hilltop 1, holiday rental in Lakeville

Tentrr Signature Site - Hudson Valley Hilltop 1

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Konkapot Cottage, Pastoral Bliss With Wide Views, holiday rental in Lakeville

Konkapot Cottage, Pastoral Bliss With Wide Views

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Waterfront Working From Home, holiday rental in Lakeville

Waterfront Working From Home

2 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
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Ski Retreat -- Private Modern on 40 Acres of Land, holiday rental in Lakeville

Ski Retreat -- Private Modern on 40 Acres of Land

4 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
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Tentrr State Park Site - Taconic State Park: High Valley Rd Site F, holiday rental in Lakeville

Tentrr State Park Site - Taconic State Park: High Valley Rd Site F

1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
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Tentrr State Park Site - Taconic State Park: High Valley Rd Site E, holiday rental in Lakeville

Tentrr State Park Site - Taconic State Park: High Valley Rd Site E

1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
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Tentrr State Park Site - Taconic State Park: High Valley Rd Site C, holiday rental in Lakeville

Tentrr State Park Site - Taconic State Park: High Valley Rd Site C

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Tentrr State Park Site - Taconic State Park: High Valley Rd Site B, holiday rental in Lakeville

Tentrr State Park Site - Taconic State Park: High Valley Rd Site B

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Tentrr State Park Site - Taconic State Park: High Valley Rd Site A, holiday rental in Lakeville

Tentrr State Park Site - Taconic State Park: High Valley Rd Site A

1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
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Tentrr State Park Site - Taconic State Park: High Valley Rd Site D, holiday rental in Lakeville

Tentrr State Park Site - Taconic State Park: High Valley Rd Site D

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Tentrr Signature Site - Hudson Valley Hilltop 2, holiday rental in Lakeville

Tentrr Signature Site - Hudson Valley Hilltop 2

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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