We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.
We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Vacation Rentals in Woodbury, CT and nearby

Map
Satellite
Map updates are paused. Zoom in to see updated info.
Reset zoom
Updating Map...
Your filters are still active.
There are no pins in your viewport. Try moving the map or changing your filters.
mm/dd/yyyy mm/dd/yyyy
    There are no pins in your viewport. Try moving the map or changing your filters.
    • {providername} {price}
    {providername} {price}
      {listitems}
    {sold_out_text}
    We can't find prices for this accommodation
    From {rate_price} {rate_periodicity}
    List your property
    Payment Protection
    Use a credit card to book with our Peace of Mind Protection.Learn more
    Find a rental
    Price per night
    Min
    to
    Max
    Bedrooms
    Any
    Amenities
    Select
    Payment
    Select
    Go to map view
    More filters
    All 16 Rentals in the Woodbury Area
    loading...
    Don't let other travelers get your favorite Woodbury area vacation rental. You're so close to securing your perfect getaway. Book today.
    Sort by

    The following rentals are within 20 miles of Woodbury, Connecticut.

    From
    $300
    Per Night
    View Details
    1 / 20
    5 of 5 stars (1) Excellent
    New Preston
    3 Bedrooms / 2 Bathrooms / Sleeps 6
    traveler have booked this property
    Overview Reviews (1) Make Inquiry
    From
    $1,200
    Per Week
    View Details
    1 / 20
    5 of 5 stars (1) Excellent
    New Milford
    3 Bedrooms / 1 Bathroom / Sleeps 6
    traveler have booked this property
    Overview Reviews (1) Make Inquiry
    From
    $500
    Per Week
    View Details
    1 / 14
    Hamden
    1 Bedroom / 1 Bathroom / Sleeps 3
    traveler have booked this property
    Overview Make Inquiry
    From
    $289
    Per Night
    View Details
    1 / 29
    5 of 5 stars (4) Excellent
    New Milford
    4 Bedrooms / 2 Bathrooms / Sleeps 8
    travelers have booked this property
    Overview Reviews (4) Make Inquiry
    Amenities & Details
    • DVD Player
    • Stereo System
    • Deck
    • Air Conditioning
    • Satellite TV
    • Wi-Fi
    • Private Outdoor...
    • Fireplace
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    LITCHFIELD COUNTY, New Milford, CONNECTICUT Beautiful!! very private country setting; four bedrooms, large family room with cathedral ceilings and grand piano. All amenities: cable TV, CD, DVD,VCR, internet and air conditioning. Deck--including a screen house; gas grill. 20x40 inground pool with... View all property information
    Make Inquiry
    Location Information
    New Milford, Connecticut 06776
    5 of 5 stars Reviewed June 27, 2015
    When reminiscing about our amazing holiday a couple of years ago, we realised we hadn't left a (now long overdue) review for this fantastic property. The pool is great, the house...
    5 of 5 stars Reviewed August 10, 2014
    This is a spacious 4 bedroom property. it is high above the local road and is surrounded by trees. Neighbours are a good distance away, so the loudest sounds are from the local...
    See all reviews
    From
    $159
    Per Night
    View Details
    1 / 27
    5 of 5 stars (1) Excellent
    Southbury
    2 Bedrooms / 1 Bathroom / Sleeps 6
    travelers have booked this property
    Overview Reviews (1) Make Inquiry
    Amenities & Details
    • Washer
    • Internet Access
    • Refrigerator
    • Mountain Views
    • Patio
    • Dryer
    • Satellite TV
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    Charming, recently renovated, two-story, 1,200 square-foot coach house built in 1795 and set in a tranquil 3-acres of lawns, gardens, orchards and forest at the heart of the historic Village of South Britain founded in 1715 by settlers from the south of England, This vacation home an hour and a... View all property information
    Make Inquiry
    Location Information
    Southbury, Connecticut 06488
    5 of 5 stars Reviewed January 7, 2015
    My husband and I, and our doggies, enjoyed the Coach House so much. We became friends with the owner who was very accomodating. He even loaned us his ornaments, so we could...
    See all reviews
    From
    $900
    Per Night
    View Details
    1 / 16
    Bethlehem
    6 Bedrooms / 4 Bathrooms / Sleeps 12
    Overview Make Inquiry
    Amenities & Details
    • DVD Player
    • Internet Access
    • Private Outdoor...
    • Satellite TV
    • Private Tennis Court
    • Fireplace
    • Air Conditioning
    • Washer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    This sophisticated and modernized 18th Century rambling farmhouse is set amount towering tress, huge lawns, flower beds, parterre vegetable and herb gardens, 2 ponds, stone walls, pasture and woods. There are five bedrooms, including one huge family suite with a Q bed, twin bed and a crib. All... View all property information
    Make Inquiry
    Location Information
    Bethlehem, Connecticut 06751
    From
    $250
    Per Night
    View Details
    1 / 14
    New Preston
    1 Bedroom / 1 Bathroom / Sleeps 4
    Overview Make Inquiry
    Amenities & Details
    • Fireplace
    • Waterfront
    • Internet Access
    • Patio
    • Satellite TV
    • Water Views
    • DVD Player
    • Grill
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    'Little Wheel' is the guest cottage on the historic Riverdance MIll property (circa 1875) in the charming village of New Preston, CT. The cottage has been totally reconstructed recently. It is bright and airy in the Spring and Summer, cozy and warm in the Fall and Winter and ALWAYS romantic! The... View all property information
    Make Inquiry
    Location Information
    New Preston, Connecticut 06777
    From
    $275
    Per Night
    View Details
    1 / 14
    New Milford
    4 Bedrooms / 2 Bathrooms / Sleeps 7
    Overview Make Inquiry
    Amenities & Details
    • TV
    • DVD Player
    • Air Conditioning
    • Stereo System
    • Wi-Fi
    • Housekeeping...
    • Mountain Views
    • Watersports Nearby
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Nature Lovers Paradise! Light filled, private and peaceful location with fantastic mountain views! Unique seven and a half acre property, with various flowering trees and shrubs. A different scent for different seasons! ***Note: There is also a two bedroom apartment available at same location!****... View all property information
    Make Inquiry
    Location Information
    New Milford, Connecticut 06776
    From
    $119
    Per Night
    View Details
    1 / 12
    Orange
    4 Bedrooms / 3 Bathrooms / Sleeps 8
    Overview Make Inquiry
    Amenities & Details
    • Air Conditioning
    • Wi-Fi
    • Hairdryer
    • Shared Outdoor Pool...
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    This is a beautifully furnished, single-storey villa with 4 bedrooms and 2 full bathrooms plus shower room with vanity and toilet, which is accessible from Pool Deck. It has additional privacy being on a corner plot, in a cul de sac with the advantage of all the PS3 games, DVD's and Internet all at... View all property information
    Make Inquiry
    Location Information
    Orange, Connecticut CONNECTICUT
    From
    $249
    Per Night
    View Details
    1 / 32
    New Haven
    4 Bedrooms / 2 Bathrooms / Sleeps 9
    Overview Make Inquiry
    Amenities & Details
    • Watersports Nearby
    • Skiing: Property Is...
    • DVD Player
    • Hot Tub
    • Air Conditioning
    • Wi-Fi
    • TV
    • Housekeeping...
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    Unique 2500sf 4 br, 2.5 bath Home on the Quinnipiac river just 5-10 minute drive to downtown New Haven and Yale. on the bus line. Master suite with steam shower, laundry big private yard with Hot tub, River view porch, directly next to park. 1890 victorian on the Quinnipiac river with all the New... View all property information
    Make Inquiry
    Location Information
    New Haven, Connecticut 06513
    List your property for free!
    List your vacation rental where TripAdvisor travelers can find it.
    Add a Listing
    From
    $136
    Per Night
    View Details
    1 / 21
    Orange
    5 Bedrooms / 4 Bathrooms / Sleeps 10
    Overview Make Inquiry
    Amenities & Details
    • Air Conditioning
    • Hairdryer
    • Shared Outdoor Pool...
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    Relax in the Elegance and Grace of this Villa, overlooking the Conservation land and situated in the cul de sac in Essex Place, of the Shire. The Accommodation provided consists of 2 King Bedrooms, each with master bathrooms and access to the Balcony area for either the early mornings or late night... View all property information
    Make Inquiry
    Location Information
    Orange, Connecticut CONNECTICUT
    From
    $28,500
    Per Month
    View Details
    1 / 22
    New Fairfield
    5 Bedrooms / 6 Bathrooms / Sleeps 10
    Overview Make Inquiry
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    There's not much better than summertime on Candlewood Lake! Enjoy all the summer offers in New England from this magnificent waterfront home on Connecticut's largest lake. This architectural designed home is perfect for guests and ALL 5 bedrooms are en-suite! There's a living room with a massive... View all property information
    Make Inquiry
    Location Information
    New Fairfield, Connecticut 06812
    From
    $111
    Per Night
    View Details
    1 / 19
    5 of 5 stars (6) Excellent
    New Haven
    2 Bedrooms / 1 Bathroom / Sleeps 4
    Overview Reviews (6) Make Inquiry
    Amenities & Details
    • Internet Access
    • Satellite TV
    • Water Views
    • Boat Available
    • Stereo System
    • Water Park Nearby
    • DVD Player
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Charming beach cottage, clean, well maintained interior,central AC. Cottage located on dead end street, 4 houses from LI Sound. Residents share PRIVATE BEACH.Guests of property also have beach rights to adjacent PRIVATE BEACH. View of ocean and salt marsh from front porch. Short walk to TOWN BEACH... View all property information
    Make Inquiry
    Location Information
    New Haven, Connecticut 06512
    4 of 5 stars Reviewed December 5, 2014
    This is a well equipped and furnished property. It was very clean and comfortable and WiFi and telephone were included. The house is only a few yards from the beach and, for...
    See all reviews
    From
    $200
    Per Night
    View Details
    1 / 22
    5 of 5 stars (1) Excellent
    Kent
    2 Bedrooms / 2 Bathrooms / Sleeps 4
    Overview Reviews (1) Make Inquiry
    Amenities & Details
    • Patio
    • Stove
    • Air Conditioning
    • Internet Access
    • Dryer
    • Refrigerator
    • Stereo System
    • Washer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Nestled in the heart of the village, this private get-away awaits you. Relax and still be in the center of everything. 2 bedrooms, 1 1/2 baths and charming backyard. There is wifi, fully equipped kitchen and a washer dryer. Off street parking. You can walk to 4 restaurants, 2 bakeries and many... View all property information
    Make Inquiry
    Location Information
    Kent, Connecticut 06757
    5 of 5 stars Reviewed June 28, 2015
    Beautiful and brand new tastefully renovated duplex in most picturesque house on Kent's Main Street. Fully equipped and convenient. Karren, the property's owner is generous and...
    See all reviews
    From
    $271
    Per Night
    View Details
    1 / 28
    New Milford
    4 Bedrooms / 2 Bathrooms / Sleeps 8
    Overview Make Inquiry
    Amenities & Details
    • Private Outdoor...
    • Internet Access
    • DVD Player
    • Deck
    • Satellite TV
    • Fireplace
    • Air Conditioning
    • Stereo System
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    SUMMER RENTAL LITCHFIELD COUNTY, New Milford, CONNECTICUT Beautiful , very private country setting; four bedrooms, large family room with cathedral ceilings; grand piano. All amenities:cable TV, CD, DVD,VCR, internet. All rooms are with AC. Deck by the house with screen house and gas... View all property information
    Make Inquiry
    Location Information
    New Milford, Connecticut 06776
    From
    $180
    Per Night
    View Details
    1 / 10
    New Haven
    1 Bedroom / 1 Bathroom / Sleeps 2
    Overview Make Inquiry
    Amenities & Details
    • Dryer
    • TV
    • Elevator/Lift access
    • DVD Player
    • Gym
    • Wi-Fi
    • Air Conditioning
    • Washer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • Smoking allowed
    • Elder access
    • x
    About this property
    Compass Furnished Apartments at 360 State Street gives you what you’ve been looking for. 360 State Street is the second-tallest building in New Haven with 700,000 square-feet of “green” living. Our beautifully furnished apartments include oversized windows with beautiful views, Energy Star... View all property information
    Make Inquiry
    Location Information
    New Haven, Connecticut 06510