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36 Houses

17

Roxbury "Judd's Bridge" 5-BR with Heated Pool, PoshPadsCT

Connecticut / Roxbury

Roxbury house

4 10 min stay varies

  • 4 bedrooms
  • sleeps 10
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$877

Price per night from

$877

7

2 Bedroom Suite with Kitchen

Connecticut / Roxbury

Roxbury hotel apartment

2 4 1 night min

  • 2 bedrooms
  • sleeps 4
  • 1 night min
  • Child Friendly
  • Air conditioning
  • Private garden

Price per night from

$250

Price per night from

$250

Great rentals within 20 miles that match your search

Distance approx 6.32 km from Roxbury

(5) Excellent 

19

Its the Perfect Weekend House just 80min from NYC!

Connecticut / Woodbury

Woodbury house

4 8 2 nights min

  • 4 bedrooms
  • sleeps 8
  • 2 nights min
  • Beach / lakeside relaxation
  • Air conditioning
  • Private garden

Price per night from

$160

Responds fast!
avg. 3 hours 21 minutes

Price per night from

$160

Distance approx 9.09 km from Roxbury

24

Unique New Fairfield House w/ Deck & Lake Views!

Connecticut / New Fairfield

New Fairfield house

3 10 min stay varies

  • 3 bedrooms
  • sleeps 10
  • min stay varies
  • Child Friendly
  • Air conditioning

Price per night from

$250

Responds fast!
avg. 53 minutes

Price per night from

$250

Distance approx 19.66 km from Roxbury

(6) Excellent 

12

Quiet first floor apartment in Torrington

Connecticut / Torrington

Torrington apartment

1 2 2 nights min

  • 1 bedroom
  • sleeps 2
  • 2 nights min

Price per night from

$90

Price per night from

$90

Distance approx 7.02 km from Roxbury

(1) Excellent 

27

Quiet Getaway in Historic Village

Connecticut / Southbury

Southbury house

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Nearest beach 3 mi
  • Child Friendly
  • Car not necessary

Price per night from

$160

Price per night from

$160

Distance approx 14.36 km from Roxbury

29

Lake House Rental On Your Own Private Lake

New York / Wingdale

Wingdale villa

4 11 4 nights min

  • 4 bedrooms
  • sleeps 11
  • 4 nights min
  • Beach / lakeside relaxation
  • Child Friendly
  • Air conditioning

Price per night from

$625

Price per night from

$625

Distance approx 4.05 km from Roxbury

30

South Street 4-BR Cottage with Heated Pool

Connecticut / Washington

Washington house

4 8 2 nights min

  • 4 bedrooms
  • sleeps 8
  • 2 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$695

Price per night from

$695

Distance approx 15.1 km from Roxbury

24

Prana Residence - Spa

Connecticut / Cornwall Bridge

Cornwall Bridge house

3 7 2 nights min

  • 3 bedrooms
  • sleeps 7
  • 2 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

Price per night from

$751

Price per night from

$751

Distance approx 18.35 km from Roxbury

(9) Very Good 

20

Lake Bliss the Perfect Getaway

New York / Holmes

Holmes house

3 10 1 night min

  • 3 bedrooms
  • sleeps 10
  • 1 night min
  • Beach / lakeside relaxation
  • Child Friendly
  • Air conditioning

Price per night from

$250

Price per night from

$250

Distance approx 8.95 km from Roxbury

24

Lakefront New Preston Cottage w/Dock & Fire Pit!

Connecticut / New Preston

New Preston cottage

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Child Friendly
  • Pet Friendly

Price per night from

$201

Responds fast!
avg. 33 minutes

Price per night from

$201

Distance approx 7.95 km from Roxbury

14

Lake Cottage with Views and Fireplace

Connecticut / Sherman

Sherman house

2 5 2 nights min

  • 2 bedrooms
  • sleeps 5
  • 2 nights min
  • Beach / lakeside relaxation
  • Child Friendly

Price per night from

$200

Responds fast!
avg. 1 hour 16 minutes

Price per night from

$200

Distance approx 6.1 km from Roxbury

(1) Excellent 

14

Wits End Farm B&B

Connecticut / Bethlehem

Bethlehem b and b

5 10 4 nights min

  • 5 bedrooms
  • sleeps 10
  • 4 nights min
  • Child Friendly

Price per night from

$800

Price per night from

$800

Distance approx 6.91 km from Roxbury

(4) Excellent 

36

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

Connecticut / New Milford

New Milford house

4 8 7 nights min

  • 4 bedrooms
  • sleeps 8
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 13 mi
  • Swimming pool
“Wonderful experience!!!” My wife and our two children (10 and 7)spent a wonderful time at this beautiful New Milford retreat. The house was spacious and nicely decorated and we loved the privacy of the place. You couldn't see any neighbors and yet sho
…see more

Price per night from

$287

Responds fast!
avg. 1 hour 37 minutes

Price per night from

$287

Distance approx 9.54 km from Roxbury

27

Country Estate newly renovated that sleeps 16!

Connecticut / Bethlehem

Bethlehem house

5 16 3 nights min

  • 5 bedrooms
  • sleeps 16
  • 3 nights min
  • Child Friendly

Price per night from

$225

Responds fast!
avg. 20 minutes

Price per night from

$225

Distance approx 13.87 km from Roxbury

(1) Excellent 

24

Litchfield House on Half Acre - 1 Mile to Town!

Connecticut / Litchfield

Litchfield house

3 7 min stay varies

  • 3 bedrooms
  • sleeps 7
  • min stay varies
  • Ski
  • Child Friendly
  • Air conditioning

Price per night from

$213

Responds fast!
avg. 10 minutes

Price per night from

$213

Distance approx 6.94 km from Roxbury

12

A Historic Home for Guests and Lawns/Facilities for Gatherings such as Weddings

Connecticut / Southbury

Southbury house

3 8 1 night min

  • 3 bedrooms
  • sleeps 8
  • 1 night min
  • Air conditioning
  • Private garden

Price per night from

$199

Price per night from

$199

Distance approx 6.1 km from Roxbury

(1) Excellent 

16

Wits End Farm

Connecticut / Bethlehem

Bethlehem house

6 12 3 nights min

  • 6 bedrooms
  • sleeps 12
  • 3 nights min
  • Nearest beach 3 mi
  • Swimming pool
  • Child Friendly

Price per night from

$900

Price per night from

$900

Distance approx 12.9 km from Roxbury

24

Victorian Newtown Apt w/Fire Pit 20 Mi to Jennings

Connecticut / Newtown

Newtown apartment

1 4 min stay varies

  • 1 bedroom
  • sleeps 4
  • min stay varies
  • Ski
  • Suitable for children age 5+

Price per night from

$140

Responds fast!
avg. 53 minutes

Price per night from

$140

Distance approx 17.85 km from Roxbury

27

Apartment in great location, suburban

Connecticut / Seymour

Seymour house

1 6 3 nights min

  • 1 bedroom
  • sleeps 6
  • 3 nights min
  • Nearest beach 4 mi
  • Child Friendly
  • Air conditioning

Price per night from

$77

Price per night from

$77

Distance approx 14.29 km from Roxbury

8

Kent Victorian Room 3

Connecticut / Kent

Kent room

1 2 2 nights min

  • 1 bedroom
  • sleeps 2
  • 2 nights min
  • Air conditioning
  • Private garden

Price per night from

$149

Price per night from

$149

Distance approx 14.29 km from Roxbury

8

Kent Victorian Room 4

Connecticut / Kent

Kent room

1 2 2 nights min

  • 1 bedroom
  • sleeps 2
  • 2 nights min
  • Air conditioning
  • Private garden

Price per night from

$110

Price per night from

$110

Distance approx 7.91 km from Roxbury

(1) Excellent 

23

Rhubarb Hill, a Charming 1850's Farmhouse

Connecticut / New Preston

New Preston house

3 6 3 nights min

  • 3 bedrooms
  • sleeps 6
  • 3 nights min
  • Child Friendly
  • Car not necessary
  • Pet Friendly

Price per night from

$350

Price per night from

$350

Distance approx 14.29 km from Roxbury

8

Kent Victorian Room 2

Connecticut / Kent

Kent room

1 2 2 nights min

  • 1 bedroom
  • sleeps 2
  • 2 nights min
  • Air conditioning
  • Private garden

Price per night from

$149

Price per night from

$149

Distance approx 6.78 km from Roxbury

29

Very private,4bdrm house,20x40inground pool, pool house. Paradise!

Connecticut / New Milford

New Milford house

4 8 3 nights min

  • 4 bedrooms
  • sleeps 8
  • 3 nights min
  • Child Friendly

Price per night from

$350

Price per night from

$350

Distance approx 9.53 km from Roxbury

25

Lakefront Warren 'Carriage House' on 25 Acres!

Connecticut / Warren

Warren house

7 14 4 nights min

  • 7 bedrooms
  • sleeps 14
  • 4 nights min
  • Ski
  • Child Friendly
  • Air conditioning

Price per night from

$1,000

Responds fast!
avg. 53 minutes

Price per night from

$1,000

Distance approx 19.41 km from Roxbury

16

Direct Waterfront Lake Home on Tranquil Harwinton

Connecticut / Harwinton

Harwinton cottage

2 4 3 nights min

  • 2 bedrooms
  • sleeps 4
  • 3 nights min
  • Child Friendly
  • Air conditioning
  • Pet Friendly

Price per night from

$225

Price per night from

$225

Distance approx 14.29 km from Roxbury

8

Kent Victorian Room 5

Connecticut / Kent

Kent room

2 3 2 nights min

  • 2 bedrooms
  • sleeps 3
  • 2 nights min
  • Air conditioning
  • Private garden

Price per night from

$160

Price per night from

$160

Distance approx 16.63 km from Roxbury

(1) Excellent 

31

Private Lakefront & Pool DeeLuxGlamping. NYC Getaway

New York / Pawling

Pawling camper van

2 8 1 night min

  • 2 bedrooms
  • sleeps 8
  • 1 night min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$158

Price per night from

$158

Distance approx 14.29 km from Roxbury

6

Kent Victorian Room 1

Connecticut / Kent

Kent room

1 2 2 nights min

  • 1 bedroom
  • sleeps 2
  • 2 nights min
  • Air conditioning
  • Private garden

Price per night from

$159

Price per night from

$159

Distance approx 8.23 km from Roxbury

21

Washington - "Senff 8-BR Estate" Heated Pool, Private Scenic Estate Neighborhood

Connecticut / Washington

Washington house

8 14 min stay varies

  • 8 bedrooms
  • sleeps 14
  • min stay varies
  • Nearest beach 5 mi
  • Swimming pool
  • Child Friendly

Price per night from

$1,202

Price per night from

$1,202

Distance approx 4.78 km from Roxbury

12

Washington - "Kirby Road" 3-Bedroom Carriage House on the Green - PoshPadsCT

Connecticut / Washington

Washington house

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Child Friendly
  • Air conditioning
  • Private garden

Price per night from

$450

Price per night from

$450

Distance approx 4.28 km from Roxbury

18

Washington "Plumb Hill" 5-Bedroom, Heated Pool, PoshPadsCT

Connecticut / Washington

Washington house

5 10 min stay varies

  • 5 bedrooms
  • sleeps 10
  • min stay varies
  • Nearest beach 5 mi
  • Swimming pool
  • Child Friendly

Price per night from

$875

Price per night from

$875

Distance approx 8.08 km from Roxbury

14

Washington "Shearer" 3-Bedroom Country Cottage - PoshPadsCT

Connecticut / Washington

Washington house

3 7 min stay varies

  • 3 bedrooms
  • sleeps 7
  • min stay varies
  • Child Friendly
  • Air conditioning
  • Pet Friendly

Price per night from

$676

Price per night from

$676

Distance approx 6.96 km from Roxbury

8

Library Bed Room with Fireplace, Dressing Room and Separate Entry from outside

Connecticut / Southbury

Southbury room

1 2 2 nights min

  • 1 bedroom
  • sleeps 2
  • 2 nights min
  • Private garden

Price per night from

$90

Price per night from

$90

Distance approx 5.87 km from Roxbury

(1)  

32

Must Love Garden and the Sound of Stream

New York / Lanesville

Lanesville house

4 9 1 night min

  • 4 bedrooms
  • sleeps 9
  • 1 night min
  • Child Friendly
  • Pet Friendly

Price per night from

$251

Price per night from

$251