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Holiday Rentals in Lakeville

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Bedrooms

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5 km
50 rentals in Lakeville.
In Town, walk to everything. Near lake, Hotchkiss, IMS, and Salisbury Schools, holiday rental in Lakeville
In Town, walk to everything. Near lake, Hotchkiss, IMS, and Salisbury Schools, holiday rental in Lakeville
In Town, walk to everything. Near lake, Hotchkiss, IMS, and Salisbury Schools, holiday rental in Lakeville

In Town, walk to everything. Near lake, Hotchkiss, IMS, and Salisbury Schools

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Lake House, holiday rental in Lakeville
Lake House, holiday rental in Lakeville
Lake House, holiday rental in Lakeville

Lake House

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
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Summer Lake Cottage, private beach, Berkshire Hills, small village, holiday rental in Lakeville
Summer Lake Cottage, private beach, Berkshire Hills, small village, holiday rental in Lakeville
Summer Lake Cottage, private beach, Berkshire Hills, small village, holiday rental in Lakeville

Summer Lake Cottage, private beach, Berkshire Hills, small village

Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 18
Match: Sleeps
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Babbling Brook Retreat, holiday rental in Lakeville
Babbling Brook Retreat, holiday rental in Lakeville
Babbling Brook Retreat, holiday rental in Lakeville

Babbling Brook Retreat

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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The following properties within 32 kms of Lakeville match all your filters:
Spectacular NE Summer Lakefront Cabin Just 2 Hours From NYC, holiday rental in Lakeville
Spectacular NE Summer Lakefront Cabin Just 2 Hours From NYC, holiday rental in Lakeville
Spectacular NE Summer Lakefront Cabin Just 2 Hours From NYC, holiday rental in Lakeville

Spectacular NE Summer Lakefront Cabin Just 2 Hours From NYC

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Charming Lakefront Cottage; Boat, Swim, Fish, Hike, Bike, Golf, majestic Views, holiday rental in Lakeville
Charming Lakefront Cottage; Boat, Swim, Fish, Hike, Bike, Golf, majestic Views, holiday rental in Lakeville
Charming Lakefront Cottage; Boat, Swim, Fish, Hike, Bike, Golf, majestic Views, holiday rental in Lakeville

Charming Lakefront Cottage; Boat, Swim, Fish, Hike, Bike, Golf, majestic Views

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Captivating Artisan Built Home With Spectacular Water Views, holiday rental in Lakeville
Captivating Artisan Built Home With Spectacular Water Views, holiday rental in Lakeville
Captivating Artisan Built Home With Spectacular Water Views, holiday rental in Lakeville

Captivating Artisan Built Home With Spectacular Water Views

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Dugway Hideaway Walking Distance to Lime Rock Park, holiday rental in Lakeville
Dugway Hideaway Walking Distance to Lime Rock Park, holiday rental in Lakeville
Dugway Hideaway Walking Distance to Lime Rock Park, holiday rental in Lakeville

Dugway Hideaway Walking Distance to Lime Rock Park

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Serene Salisbury Rental Home on 26 Acres w/ Deck!, holiday rental in Lakeville
Serene Salisbury Rental Home on 26 Acres w/ Deck!, holiday rental in Lakeville
Serene Salisbury Rental Home on 26 Acres w/ Deck!, holiday rental in Lakeville

Serene Salisbury Rental Home on 26 Acres w/ Deck!

Holiday Rental House
6 bedrooms
4 bathrooms
Sleeps 11
Match: Sleeps
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Pet-Friendly Millerton Home, Walk to Downtown, holiday rental in Lakeville
Pet-Friendly Millerton Home, Walk to Downtown, holiday rental in Lakeville
Pet-Friendly Millerton Home, Walk to Downtown, holiday rental in Lakeville

Pet-Friendly Millerton Home, Walk to Downtown

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Mountain View Getaway, holiday rental in Lakeville
Mountain View Getaway, holiday rental in Lakeville
Mountain View Getaway, holiday rental in Lakeville

Mountain View Getaway

Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 5
Match: Sleeps
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Antique Farmhouse Totally Restored, holiday rental in Lakeville
Antique Farmhouse Totally Restored, holiday rental in Lakeville
Antique Farmhouse Totally Restored, holiday rental in Lakeville

Antique Farmhouse Totally Restored

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 16
Match: Sleeps
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The Perfect Escape From The City, holiday rental in Lakeville
The Perfect Escape From The City, holiday rental in Lakeville
The Perfect Escape From The City, holiday rental in Lakeville

The Perfect Escape From The City

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Gorgeous Modern Ranch in the Hudson Valley NY with incredible views!, holiday rental in Lakeville
Gorgeous Modern Ranch in the Hudson Valley NY with incredible views!, holiday rental in Lakeville
Gorgeous Modern Ranch in the Hudson Valley NY with incredible views!, holiday rental in Lakeville

Gorgeous Modern Ranch in the Hudson Valley NY with incredible views!

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
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Rustic House w/ Heating + Pool, holiday rental in Lakeville
Rustic House w/ Heating + Pool, holiday rental in Lakeville
Rustic House w/ Heating + Pool, holiday rental in Lakeville

Rustic House w/ Heating + Pool

Condo/Apartment
0 bedrooms
0 bathrooms
Sleeps 10
Match: Sleeps
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Private creek side farm stay — walkable to Salisbury, holiday rental in Lakeville
Private creek side farm stay — walkable to Salisbury, holiday rental in Lakeville
Private creek side farm stay — walkable to Salisbury, holiday rental in Lakeville

Private creek side farm stay — walkable to Salisbury

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Quiet, sweet house in the heart of Litchfield/the Berkshires, holiday rental in Lakeville
Quiet, sweet house in the heart of Litchfield/the Berkshires, holiday rental in Lakeville
Quiet, sweet house in the heart of Litchfield/the Berkshires, holiday rental in Lakeville

Quiet, sweet house in the heart of Litchfield/the Berkshires

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Private Lakeville/Salisbury Converted Barn, holiday rental in Lakeville
Private Lakeville/Salisbury Converted Barn, holiday rental in Lakeville
Private Lakeville/Salisbury Converted Barn, holiday rental in Lakeville

Private Lakeville/Salisbury Converted Barn

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
More info
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Salisbury Cottage Retreat, holiday rental in Lakeville
Salisbury Cottage Retreat, holiday rental in Lakeville
Salisbury Cottage Retreat, holiday rental in Lakeville

Salisbury Cottage Retreat

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Barbell Brook, holiday rental in Lakeville
Barbell Brook, holiday rental in Lakeville
Barbell Brook, holiday rental in Lakeville

Barbell Brook

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
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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, holiday rental in Lakeville
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

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
More info
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Secluded Cabin for the Perfect Weekend Escape, holiday rental in Lakeville
Secluded Cabin for the Perfect Weekend Escape, holiday rental in Lakeville
Secluded Cabin for the Perfect Weekend Escape, holiday rental in Lakeville

Secluded Cabin for the Perfect Weekend Escape

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
More info
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Adirondack-Style/Cottage-Beautiful Lake & Mountain Views-Peaceful!, holiday rental in Lakeville
Adirondack-Style/Cottage-Beautiful Lake & Mountain Views-Peaceful!, holiday rental in Lakeville
Adirondack-Style/Cottage-Beautiful Lake & Mountain Views-Peaceful!, holiday rental in Lakeville

Adirondack-Style/Cottage-Beautiful Lake & Mountain Views-Peaceful!

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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The Cottage at Great Falls, holiday rental in Lakeville
The Cottage at Great Falls, holiday rental in Lakeville
The Cottage at Great Falls, holiday rental in Lakeville

The Cottage at Great Falls

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Two Bedroom Cottage Close To Town, holiday rental in Lakeville
Two Bedroom Cottage Close To Town, holiday rental in Lakeville
Two Bedroom Cottage Close To Town, holiday rental in Lakeville

Two Bedroom Cottage Close To Town

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Close to Lime Rock, Prep Schools, 3 Ski Areas, holiday rental in Lakeville
Close to Lime Rock, Prep Schools, 3 Ski Areas, holiday rental in Lakeville
Close to Lime Rock, Prep Schools, 3 Ski Areas, holiday rental in Lakeville

Close to Lime Rock, Prep Schools, 3 Ski Areas

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
More info
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Newly renovated charming home , Brand new chefs kitchen very comfortable home ., holiday rental in Lakeville
Newly renovated charming home , Brand new chefs kitchen very comfortable home ., holiday rental in Lakeville
Newly renovated charming home , Brand new chefs kitchen very comfortable home ., holiday rental in Lakeville

Newly renovated charming home , Brand new chefs kitchen very comfortable home .

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Private forest retreat minutes from charming downtown Millerton, holiday rental in Lakeville
Private forest retreat minutes from charming downtown Millerton, holiday rental in Lakeville
Private forest retreat minutes from charming downtown Millerton, holiday rental in Lakeville

Private forest retreat minutes from charming downtown Millerton

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Brindlewood Sunny Upstate Escape 3BRs on 7.5 Acres, holiday rental in Lakeville
Brindlewood Sunny Upstate Escape 3BRs on 7.5 Acres, holiday rental in Lakeville
Brindlewood Sunny Upstate Escape 3BRs on 7.5 Acres, holiday rental in Lakeville

Brindlewood Sunny Upstate Escape 3BRs on 7.5 Acres

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Peaceful Lakeville Retreat Located Within Minutes to Local Schools, holiday rental in Lakeville
Peaceful Lakeville Retreat Located Within Minutes to Local Schools, holiday rental in Lakeville
Peaceful Lakeville Retreat Located Within Minutes to Local Schools, holiday rental in Lakeville

Peaceful Lakeville Retreat Located Within Minutes to Local Schools

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
More info
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Kellogg Haus, holiday rental in Lakeville
Kellogg Haus, holiday rental in Lakeville
Kellogg Haus, holiday rental in Lakeville

Kellogg Haus

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Country living with a Lake View, holiday rental in Lakeville
Country living with a Lake View, holiday rental in Lakeville
Country living with a Lake View, holiday rental in Lakeville

Country living with a Lake View

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
More info
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Bluebird Valley Farmhouse, holiday rental in Lakeville
Bluebird Valley Farmhouse, holiday rental in Lakeville
Bluebird Valley Farmhouse, holiday rental in Lakeville

Bluebird Valley Farmhouse

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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Gorgeous Luxury Farmhouse in the Hudson Valley New York, holiday rental in Lakeville
Gorgeous Luxury Farmhouse in the Hudson Valley New York, holiday rental in Lakeville
Gorgeous Luxury Farmhouse in the Hudson Valley New York, holiday rental in Lakeville

Gorgeous Luxury Farmhouse in the Hudson Valley New York

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
More info
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BEAUTIFUL 4-SEASON RENTAL DIRECTLY ON TWIN LAKES, holiday rental in Lakeville
BEAUTIFUL 4-SEASON RENTAL DIRECTLY ON TWIN LAKES, holiday rental in Lakeville
BEAUTIFUL 4-SEASON RENTAL DIRECTLY ON TWIN LAKES, holiday rental in Lakeville

BEAUTIFUL 4-SEASON RENTAL DIRECTLY ON TWIN LAKES

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Modern Barn secluded in nature with Views for as far as the eye can see., holiday rental in Lakeville
Modern Barn secluded in nature with Views for as far as the eye can see., holiday rental in Lakeville
Modern Barn secluded in nature with Views for as far as the eye can see., holiday rental in Lakeville

Modern Barn secluded in nature with Views for as far as the eye can see.

Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 7
Match: Sleeps
More info
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Curated Contemporary for lakes, forest & ski hills, holiday rental in Lakeville
Curated Contemporary for lakes, forest & ski hills, holiday rental in Lakeville
Curated Contemporary for lakes, forest & ski hills, holiday rental in Lakeville

Curated Contemporary for lakes, forest & ski hills

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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150 year old cottage on 120 acres of land next to a stream, holiday rental in Lakeville
150 year old cottage on 120 acres of land next to a stream, holiday rental in Lakeville
150 year old cottage on 120 acres of land next to a stream, holiday rental in Lakeville

150 year old cottage on 120 acres of land next to a stream

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
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The Country Retreat House, holiday rental in Lakeville
The Country Retreat House, holiday rental in Lakeville
The Country Retreat House, holiday rental in Lakeville

The Country Retreat House

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Private Country Retreat in Lovely Lakeville CT, holiday rental in Lakeville
Private Country Retreat in Lovely Lakeville CT, holiday rental in Lakeville
Private Country Retreat in Lovely Lakeville CT, holiday rental in Lakeville

Private Country Retreat in Lovely Lakeville CT

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
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Mountain View Farmhouse, pool/hot tub, fire pit, 4 seasons porch, game room, holiday rental in Lakeville
Mountain View Farmhouse, pool/hot tub, fire pit, 4 seasons porch, game room, holiday rental in Lakeville
Mountain View Farmhouse, pool/hot tub, fire pit, 4 seasons porch, game room, holiday rental in Lakeville

Mountain View Farmhouse, pool/hot tub, fire pit, 4 seasons porch, game room

Holiday Rental House
5 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
More info
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BEAUTIFUL TWIN LAKES 4-SEASON RENTAL, holiday rental in Lakeville
BEAUTIFUL TWIN LAKES 4-SEASON RENTAL, holiday rental in Lakeville
BEAUTIFUL TWIN LAKES 4-SEASON RENTAL, holiday rental in Lakeville

BEAUTIFUL TWIN LAKES 4-SEASON RENTAL

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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Litchfield Hills Estate with a Pool, holiday rental in Lakeville
Litchfield Hills Estate with a Pool, holiday rental in Lakeville
Litchfield Hills Estate with a Pool, holiday rental in Lakeville

Litchfield Hills Estate with a Pool

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Luxurious, modernist barn in peaceful northwestern Connecticut - private swim!, holiday rental in Lakeville
Luxurious, modernist barn in peaceful northwestern Connecticut - private swim!, holiday rental in Lakeville
Luxurious, modernist barn in peaceful northwestern Connecticut - private swim!, holiday rental in Lakeville

Luxurious, modernist barn in peaceful northwestern Connecticut - private swim!

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 7
Match: Sleeps
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Modern Sharon Farmhouse: Spacious, Patio, Views, holiday rental in Lakeville
Modern Sharon Farmhouse: Spacious, Patio, Views, holiday rental in Lakeville
Modern Sharon Farmhouse: Spacious, Patio, Views, holiday rental in Lakeville

Modern Sharon Farmhouse: Spacious, Patio, Views

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 11
Match: Sleeps
More info
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An acclaimed photographers country estate, arts community, near private schools!, holiday rental in Lakeville
An acclaimed photographers country estate, arts community, near private schools!, holiday rental in Lakeville
An acclaimed photographers country estate, arts community, near private schools!, holiday rental in Lakeville

An acclaimed photographers country estate, arts community, near private schools!

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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CAMP HOUSE on Twin Lakes, holiday rental in Lakeville
CAMP HOUSE on Twin Lakes, holiday rental in Lakeville
CAMP HOUSE on Twin Lakes, holiday rental in Lakeville

CAMP HOUSE on Twin Lakes

Holiday Rental House
6 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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5BR Farmhouse☆King Size Bed☆Mountain View☆28 Acres, holiday rental in Lakeville
5BR Farmhouse☆King Size Bed☆Mountain View☆28 Acres, holiday rental in Lakeville
5BR Farmhouse☆King Size Bed☆Mountain View☆28 Acres, holiday rental in Lakeville

5BR Farmhouse☆King Size Bed☆Mountain View☆28 Acres

Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 12
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, holiday rental in Lakeville
Charming 2+2 Lakeside Cottage on Best Lake in CT, holiday rental in Lakeville

Charming 2+2 Lakeside Cottage on Best Lake in CT

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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The FarmHouse, holiday rental in Lakeville
The FarmHouse, holiday rental in Lakeville
The FarmHouse, holiday rental in Lakeville

The FarmHouse

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
More info
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Showing results 1-50 of 50
Frequently Asked Questions about Lakeville