Woodbury Rentals

Close

Enter dates for more accurate prices

Payment Protection
Your payment for this rental is protected when you pay through FlipKey. Learn more

47 Houses

(5) Excellent 

24

Its the Perfect Weekend House just 80min from NYC!

Connecticut / Woodbury

Woodbury house

4 8 30 nights min

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

Price per night from

$193

Responds fast!
avg. 3 hours 21 minutes

Price per night from

$193

Great rentals within 20 miles that match your search

Distance approx 18.95 km from Woodbury

(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

$103

Price per night from

$103

Distance approx 13.37 km from Woodbury

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

$288

Responds fast!
avg. 10 minutes

Price per night from

$288

Distance approx 19.62 km from Woodbury

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

$716

Price per night from

$716

Distance approx 5.4 km from Woodbury Show on Map

(1) Excellent 

27

Quiet Getaway in Historic Village

Connecticut / Southbury

Southbury house

2 6 1 night min

  • 2 bedrooms
  • sleeps 6
  • 1 night min
  • Nearest beach 3 mi
  • Child Friendly
  • Car not necessary

Price per night from

$183

Price per night from

$183

Distance approx 7.43 km from Woodbury

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

$799

Price per night from

$799

Distance approx 12.31 km from Woodbury

(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

$329

Responds fast!
avg. 1 hour 37 minutes

Price per night from

$329

Distance approx 17.59 km from Woodbury

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

$862

Price per night from

$862

Distance approx 19.43 km from Woodbury

(1) Excellent 

9

Private 2 bedroom near Yale, downtown, great restaurants and parks

Connecticut / Hamden

Hamden apartment

2 4 2 nights min

  • 2 bedrooms
  • sleeps 4
  • 2 nights min
  • Air conditioning

Price per night from

$115

Price per night from

$115

Distance approx 12.56 km from Woodbury

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

$229

Responds fast!
avg. 10 minutes

Price per night from

$229

Distance approx 5.72 km from Woodbury Show on Map

(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

$919

Price per night from

$919

Distance approx 13.24 km from Woodbury

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

$229

Responds fast!
avg. 1 hour 16 minutes

Price per night from

$229

Distance approx 7.36 km from Woodbury

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

$259

Responds fast!
avg. 20 minutes

Price per night from

$259

Distance approx 5.36 km from Woodbury Show on Map

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

$229

Price per night from

$229

Distance approx 5.72 km from Woodbury Show on Map

(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

$1,031

Price per night from

$1,031

Distance approx 13.63 km from Woodbury

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

Price per night from

$161

Responds fast!
avg. 24 minutes

Price per night from

$161

Distance approx 13.88 km from Woodbury

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

$89

Responds fast!
avg. 1 hour 31 minutes

Price per night from

$89

Distance approx 18.83 km from Woodbury

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

$127

Price per night from

$127

Distance approx 11.64 km from Woodbury

(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

$403

Price per night from

$403

Distance approx 18.83 km from Woodbury

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

$171

Price per night from

$171

Distance approx 12.19 km from Woodbury

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

$401

Price per night from

$401

Distance approx 18.83 km from Woodbury

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

$172

Price per night from

$172

Distance approx 12.8 km from Woodbury

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

$1,149

Responds fast!
avg. 1 hour 0 minutes

Price per night from

$1,149

Distance approx 17.99 km from Woodbury

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

$258

Price per night from

$258

Distance approx 18.83 km from Woodbury

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

$182

Price per night from

$182

Distance approx 8.1 km from Woodbury

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

$188

Price per night from

$188

Distance approx 9.67 km from Woodbury

36

100% ROXBURY (Zoom in Map+) PoshPadsCT "PAINTER RIDGE" Mint 3BR, Pool, BBQ,Bikes

Connecticut / Washington

Washington house

3 8 min stay varies

  • 3 bedrooms
  • sleeps 8
  • min stay varies
  • Child Friendly
  • Pet Friendly

Price per night from

$264

Price per night from

$264

Distance approx 9.69 km from Woodbury

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

$773

Price per night from

$773

Distance approx 10.48 km from Woodbury

36

100% ROXBURY! (Zoom Map In++) PoshPadsCT "PAINTER HILL" Mint 4-BR,Pool,Fire,BBQ

Washington / Washington Depot

Washington Depot house

4 14 min stay varies

  • 4 bedrooms
  • sleeps 14
  • min stay varies
  • Child Friendly
  • Pet Friendly

Price per night from

$265

Price per night from

$265

Distance approx 6.35 km from Woodbury Show on Map

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

$1,006

Price per night from

$1,006

Distance approx 10.48 km from Woodbury

28

100% ROXBURY! (Zoom in Map++) PoshPadsCT "MOOSEHORN" Mint 5BR Pool, BBQ, Bikes

Washington / Washington Depot

Washington Depot house

5 12 min stay varies

  • 5 bedrooms
  • sleeps 12
  • min stay varies
  • Nearest beach 7 mi
  • Swimming pool
  • Child Friendly

Price per night from

$303

Price per night from

$303

Distance approx 10.48 km from Woodbury

38

100% ROXBURY! PoshPadsCT "NORTH ST" Private, Mint 6-BR, Pool,Views, Fire Pl, BBQ

Washington / Washington Depot

Washington Depot house

6 12 min stay varies

  • 6 bedrooms
  • sleeps 12
  • min stay varies
  • Child Friendly
  • Pet Friendly

Price per night from

$264

Price per night from

$264

Distance approx 10.48 km from Woodbury

39

100% ROXBURY! (Zoom in Map++) PoshPadsCT "SENTRY HILL"Mint 6BR Pool,4 FirePlaces

Washington / Washington Depot

Washington Depot house

6 12 min stay varies

  • 6 bedrooms
  • sleeps 12
  • min stay varies
  • Child Friendly
  • Pet Friendly

Price per night from

$303

Price per night from

$303

Distance approx 10.48 km from Woodbury

22

100% WASHINGTON! (Zoom in Map ++) PoshPadsCT "SHEARER RD" Mint 3BR, Pool, BBQ

Washington / Washington Depot

Washington Depot house

3 6 min stay varies

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

Price per night from

$227

Price per night from

$227

Distance approx 10.48 km from Woodbury

34

100% WASHINGTON! (Zoom in Map++) PoshPadsCT "51 SENFF RD" Mint 5BR, Pool, BBQ

Washington / Washington Depot

Washington Depot house

5 10 min stay varies

  • 5 bedrooms
  • sleeps 10
  • min stay varies
  • Child Friendly
  • Pet Friendly

Price per night from

$303

Price per night from

$303

Distance approx 18.83 km from Woodbury

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

$182

Price per night from

$182

Distance approx 10.48 km from Woodbury

18

100%WashingtonZOOM MAP+PoshPadsCT "Magical Barn"

Washington / Washington Depot

Washington Depot house

5 10 min stay varies

  • 5 bedrooms
  • sleeps 10
  • min stay varies
  • Child Friendly

Price per night from

$340

Price per night from

$340

Distance approx 10.48 km from Woodbury

42

100% WASHINGTON! (Zoom in Map++) PoshPadsCT "SUNNY RIDGE" 8-BR Estate, Pool, BBQ

Washington / Washington Depot

Washington Depot house

8 16 min stay varies

  • 8 bedrooms
  • sleeps 16
  • min stay varies
  • Child Friendly

Price per night from

$380

Price per night from

$380