Roxbury Vacation Rentals, Houses & More


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1 / 7

2 Bedroom Suite with Kitchen

  • 2
  • 4
  • 1 night min

$249

Details

Great rentals within 30 miles that match your search

1 / 30

South Street 4-BR Cottage with Heated Pool

  • 4
  • 8
  • Min stay varies

$696

Details

1 / 20

Five Bedroom Country Home

  • 5
  • 10
  • 3 nights min

$475

Details

3
1 / 22

Its the Perfect Weekend House just 80min from NYC!

  • 4
  • 8
  • Min stay varies

$130

Details

1 / 16

Wits End Farm

  • 6
  • 12
  • 3 nights min

$900

Details

1 / 14

Wits End Farm B&B

  • 5
  • 10
  • Min stay varies

$800

Details

1 / 11

The Charm of a Historic Home and Gardens in a Historic Village near NYC

  • 3
  • 8
  • 1 night min

$230

Details

1
1 / 27

Quiet Getaway in Historic Village

  • 2
  • 6
  • 1 night min

$152

Details

4
1 / 24

20'x40' inground private pool just for you&house with 4bedrooms

  • 4
  • 8
  • 7 nights min

$286

Details

1 / 29

Charming Farmhouse on 160 Acre Beautiful Vineyard

  • 3
  • 6
  • 2 nights min

$299

Details

1 / 14

Lake Cottage with Views and Fireplace

  • 2
  • 5
  • 2 nights min

$199

Details

1
1 / 23

Rhubarb Hill, a Charming 1850's Farmhouse

  • 3
  • 6
  • 3 nights min

$250

Details

1 / 24

Exceptional Beauty on the Water! House Sleeps 6 Wifi, Hot Tub, billiards

  • 3
  • 6
  • 14 nights min

$515

Details

1 / 24

NEW! 3BR New Preston Cottage - Lakefront w/ Dock!

  • 3
  • 6
  • Min stay varies

$256

Details

1 / 27

Country Estate newly renovated that sleeps 16!

  • 5
  • 16
  • Min stay varies

$225

Details

1 / 57

‘Carriage House’ Lakefront Warren 7BR on 25 Acres!

  • 7
  • 16
  • 4 nights min

$795

Details

1 / 25

Superb Views in Modern 1820 Farmhouse

  • 3
  • 5
  • 2 nights min

$260

Details

1 / 26

NEW! 3BR Litchfield House on Half Acre of Land!

  • 3
  • 7
  • Min stay varies

$235

Details

1 / 29

Lake House Rental On Your Own Private Lake

  • 4
  • 11
  • 4 nights min

$625

Details

11
1 / 73

Pawling 1900 house near Darryl house,Thunder ridge

  • 3
  • 6
  • 2 nights min

$174

Details

1 / 21

Prana Residence - Spa

  • 3
  • 7
  • 2 nights min

$750

Details

1 / 54

New! 3BR Cornwall Bridge Villa w/Spa & Indoor Pool

  • 3
  • 7
  • Min stay varies

$650

Details

1 / 18

Private Lakefront & Pool DeeLuxGlamping. NYC Getaway

  • 2
  • 12
  • Min stay varies

$157

Details

1 / 15

Apartment in great location, suburban

  • 1
  • 6
  • 3 nights min

$120

Details

1 / 6

Charming Cottage in a lovely lake community

  • 2
  • 4
  • 7 nights min

$200

Details

1
1 / 17

5BR Woodridge Lake Rental House

  • 5
  • 12
  • 7 nights min

$158

Details

9
1 / 20

Lake Bliss the Perfect Getaway

  • 3
  • 10
  • 1 night min

$250

Details

3
1 / 12

Quiet first floor apartment in Torrington

  • 1
  • 2
  • 2 nights min

$90

Details

1 / 16

Charming COTTAGE near NYC!

  • 1
  • 5
  • 1 night min

$295

Details

1 / 13

Quiet Country Contemporary Home on 5 Private Acres

  • 3
  • 10
  • 2 nights min

$375

Details

1 / 42

Spectacular Modern Home Near NYC

  • 5
  • 8
  • 2 nights min

$895

Details

1 / 10

Royal Master Suite

  • 1
  • 2
  • 1 night min

$90

Details

1 / 5

Adorable Guest Cottage

  • 2
  • 4
  • 1 night min

$155

Details

3
1 / 23

Comfortable Rustic Cottage on 4 Wooded Acres with Brook

  • 2
  • 6
  • 2 nights min

$150

Details

1 / 4

Exclusive Rental in Beautiful Amenia!

  • 3
  • 6
  • 30 nights min

$134

Details

1 / 37

Unique, Modern, & Private 3 bedroom on 6 acres

  • 3
  • 8
  • 3 nights min

$299

Details

1 / 20

LAKEFRONT COTTAGE ON PRISTINE LAKE

  • 2
  • 4
  • 7 nights min

$225

Details

1 / 26

Luxury Executive Estate 1 Hr from New York City

  • 6
  • 20
  • 2 nights min

$700

Details

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