Woodbury Holiday House Rentals from AU$194: Search Holiday Homes

Woodbury Holiday Homes
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Our top choices for Woodbury holiday homes

A two-story house with a porch, a front door with a wreath, and a small garden area.

A living room with a chandelier, a sofa, a chair, and a coffee table.

A kitchen with white cabinets, stainless steel appliances, a dining table with chairs, and a window with a view of a building.

A covered outdoor deck with a grill, a round table with chairs, and a hammock.

1. Bear Retreat - 2-bedroom house in Waterbury

Bear Retreat - 2-bedroom house in Waterbury

Waterbury

10.0 out of 10, Exceptional, (10 reviews)

10/10

Exceptional

(10 reviews)

"Perfect, spacious area. Super clean. Communication was great. Would definitely book here again."

Radha

The price is AU$479

AU$479

includes taxes & fees

14 Oct - 15 Oct

Bear Retreat - 2-bedroom house in Waterbury

A staircase with a handrail, a potted plant with yellow flowers, and a sign above the stairs.

A bedroom with a bed, a chair, a small table, a floor lamp, a wall-mounted TV, and a patterned rug.

A bathroom wall with 'BATHROOM RULES' and a hand sanitizer dispenser.

A compact living space with a sofa, a dining table with chairs, a clock, a microwave, and a coffee maker.

2. Cozy 1-king size bedroom house in quiet Waterbury with 75" TV in your bedroom.

Cozy 1-king size bedroom house in quiet Waterbury with 75" TV in your bedroom.

Waterbury

8.0 out of 10, Very good, (1 review)

8.0/10

Very good

(1 review)

"I had an emergency and was only able to stay one night, but enjoyed my stay "

Dirk N.

The price is AU$213

AU$213

includes taxes & fees

14 Oct - 15 Oct

Cozy 1-king size bedroom house in quiet Waterbury with 75" TV in your bedroom.

A modern kitchen with wooden cabinets, a stainless steel refrigerator, a built-in oven, and a large island with bar stools.

A wooden deck with a staircase leading to a covered area, a garage door, and a grassy yard with fallen leaves.

A stacked washer and dryer unit in a room with a white door and light-colored walls.

A neatly made bed with a white textured bedspread, two bedside lamps, a small bedside table with a vase, and a basket with a photo frame.

3. Cozy private room in a shared home with a Full-size bed and private bathroom.

Cozy private room in a shared home with a Full-size bed and private bathroom.

New Milford

10.0 out of 10, Exceptional, (3 reviews)

10/10

Exceptional

(3 reviews)

"I really enjoyed my four night stay here."

Jim B.

The price is AU$194

AU$194

includes taxes & fees

14 Oct - 15 Oct

Cozy private room in a shared home with a Full-size bed and private bathroom.

A spacious living room with large windows, a fireplace, and a view of the outdoors.

A dining area with a wooden table, chairs, and a chandelier.

A spacious kitchen with wooden cabinets, a dining table, and a chandelier.

4. Watertown Home w/ Yard: 1 Mi to Echo Lake Park!

Watertown Home w/ Yard: 1 Mi to Echo Lake Park!

Watertown

9.0 out of 10, Wonderful, (6 reviews)

9.0/10

Wonderful

(6 reviews)

"In town to visit our new grandchild. It was just my husband and me. It had more then enough room and was very comfortable."

Elizabeth H.

The price is AU$761

AU$761

includes taxes & fees

14 Oct - 15 Oct

Watertown Home w/ Yard: 1 Mi to Echo Lake Park!

A picnic setup with a checkered blanket, a basket, and two wine glasses on a grassy area with a lake and trees in the background.

A modern bedroom with a large bed, two bedside tables with lamps, and a potted plant.

A living room with a black leather couch, a wooden coffee table, and a TV on a stand. There are three windows with a view of trees and a lake.

A lakeside cabin with a covered patio, surrounded by trees and a view of a lake and hills.

5. Lakehouse, Boat Dock, Kayaks, Fire-Pit, King Bed, 1 Hour & 15 Min from NYC etc!

Lakehouse, Boat Dock, Kayaks, Fire-Pit, King Bed, 1 Hour & 15 Min from NYC etc!

New Fairfield

8.6 out of 10, Excellent, (36 reviews)

8.6/10

Excellent

(36 reviews)

"Very serene location, the host was very responsive and helpful."

Stephen L.

The price is AU$462

AU$462

includes taxes & fees

18 Oct - 19 Oct

Lakehouse, Boat Dock, Kayaks, Fire-Pit, King Bed, 1 Hour & 15 Min from NYC etc!

A multi-story house with a dock and boats, surrounded by dense forest.

A lakeside property with a house surrounded by dense trees, a clear view of the lake, and a small island in the distance.

A modern bathroom with a large bathtub, a wooden ceiling, and a view of the outdoors.

A covered outdoor area with a view of a lake, stone steps, and a grill.

6. North Cliff House - Private Dock & Sauna

North Cliff House - Private Dock & Sauna

Danbury

10.0 out of 10, Exceptional, (9 reviews)

10/10

Exceptional

(9 reviews)

"Enjoyed the property. Beautiful house. Great location. Reserve, stay and enjoy!"

Ron P.

The price is AU$1,680

AU$1,680

includes taxes & fees

14 Oct - 15 Oct

North Cliff House - Private Dock & Sauna

A modern kitchen with stainless steel appliances, a central island, and a dining area with a sofa.

A modern living room with a sectional sofa, a kitchen with white cabinets, and a staircase leading to another level.

A modern kitchen with white cabinets, a central island with bar stools, and a dining area with a wooden table and chairs.

A modern living room with a large flat-screen TV, a gray sofa, and a kitchen in the background.

7. #27- Luxury Collection

#27- Luxury Collection

Southington

10.0 out of 10, Exceptional, (4 reviews)

10/10

Exceptional

(4 reviews)

"Beautiful home, well designed and spacious rooms. Host was fantastic and communication was great! Thank you"

C B.

The price is AU$666

AU$666

includes taxes & fees

20 Oct - 21 Oct

#27- Luxury Collection

A living room with a sectional sofa, a small side table, and a floor lamp.

A staircase with wooden steps and a handrail, leading to a landing with a white wall.

A covered outdoor seating area with a swing seat, a table, and chairs.

A living room with a brown leather sofa, a brown leather armchair, a wooden coffee table, and a television mounted on the wall.

8. Lakehaven • Hot Tub, Decks, Fires & More

Lakehaven • Hot Tub, Decks, Fires & More

Plymouth

10.0 out of 10, Exceptional, (1 review)

10/10

Exceptional

(1 review)

"Great find!! Amazing views, house was superb!"

Iva B.

The price is AU$1,095

AU$1,095

includes taxes & fees

15 Oct - 16 Oct

Lakehaven • Hot Tub, Decks, Fires & More

A room with a built-in bench along a wall with large windows, a door, and a tiled floor.

A dining area with a round wooden table, four chairs, and a sofa. A kitchen with white cabinets and a microwave is visible in the background.

A dining area with a round wooden table and chairs, a sofa, and a pendant light.

A bedroom with a bed, a chair, a bookshelf, and a window with curtains.

9. The Lorelai at Middle Street Manor: Walk to Town Green, Gazebo, Shops & Dining

The Lorelai at Middle Street Manor: Walk to Town Green, Gazebo, Shops & Dining

New Milford

The price is AU$1,222

AU$1,222

includes taxes & fees

26 Oct - 27 Oct

The Lorelai at Middle Street Manor: Walk to Town Green, Gazebo, Shops & Dining

A living room with a grey sofa, red and yellow cushions, a wooden coffee table, and a TV on a wooden cabinet.

A living room with a sofa, a coffee table, a TV, and a cabinet.

A dining area with a round table, four wooden chairs, a white tablecloth, a basket, and a black trash bin.

A bedroom with a four-poster bed, a large window, and a wardrobe.

10. Newly Remodeled 1-BR Close to Everything yet Very Private

Newly Remodeled 1-BR Close to Everything yet Very Private

Wallingford

10.0 out of 10, Exceptional, (11 reviews)

10/10

Exceptional

(11 reviews)

"We really liked this property! Modernized apartment in an older home. Clean, comfortable, and close to family in the area. Karl was great to work with. We will stay here again next time we visit family!"

Alan

The price is AU$417

AU$417

includes taxes & fees

14 Oct - 15 Oct

Newly Remodeled 1-BR Close to Everything yet Very Private

A modern living room with a sofa, coffee table, and a TV mounted on the wall.

A cozy living room with a ceiling fan, a TV mounted on the wall, a sofa with colorful cushions, a coffee table, and a lamp.

A hallway with a white door, a number '174' on the wall, a glass console table, and a decorative mirror above it.

A single-story house with a front porch, a small entryway, and a mailbox.

11. Once the old Schools house now a newly furnished Apartment

Once the old Schools house now a newly furnished Apartment

Wallingford Center

9.2 out of 10, Wonderful, (15 reviews)

9.2/10

Wonderful

(15 reviews)

"Excellent option for a short stay near the heart of it all in Wallingford."

Jeanette W.

The price is AU$417

AU$417

includes taxes & fees

14 Oct - 15 Oct

Once the old Schools house now a newly furnished Apartment

A modern living room with hardwood flooring, a leather sofa, a round coffee table, and a wooden side table. There is a dining area with a table and chairs visible in the background.

A room with a wooden floor, white walls, and a door with a lock. There is a window with blinds, a ceiling vent, and a small table with a vase of flowers.

A dining table with a wooden bowl containing green spherical objects, two black candle holders, and a white table runner.

A bedroom with a bed, two bedside tables, a nightstand, a shelf with plants, and a mirror.

12. Luxurious-Modern feel w/ custom features - AC, short walk to Shelton

Luxurious-Modern feel w/ custom features - AC, short walk to Shelton

Shelton

The price is AU$652

AU$652

includes taxes & fees

9 Nov - 10 Nov

Luxurious-Modern feel w/ custom features - AC, short walk to Shelton

A kitchen with wooden cabinets, granite countertops, and a stainless steel sink.

A stainless steel refrigerator with a water dispenser, a white door with a window, and a wooden floor with a rug.

A compact, two-door laundry room with a wooden floor and a white door.

A dining area with a table and chairs, a television, and a patterned rug.

13. Welcoming 1500 square foot 3-bedroom house completely remodeled in Southington

Welcoming 1500 square foot 3-bedroom house completely remodeled in Southington

Southington

10.0 out of 10, Exceptional, (3 reviews)

10/10

Exceptional

(3 reviews)

"We had a great, relaxing Thanksgiving holiday at this spacious Southington, CT home. It was the perfect spot to visit one of my daughters and be able to have my mother-in-law stay with us so we could cook and host Thanksgiving dinner. The house was well-stocked and supplied with everything we needed, and then some; which allowed us to have a stress-free holiday as if we were in our own home. We highly recommend this home and will keep it in mind for future extended stays in the area."

Cindy M.

The price is AU$1,022

AU$1,022

includes taxes & fees

28 Oct - 29 Oct

Welcoming 1500 square foot 3-bedroom house completely remodeled in Southington

A hot tub in a backyard with a house, trees, and a clear sky.

A living room with a sofa, ottoman, glass coffee table, and a patterned rug. There are two lamps, a decorative statue, and a framed artwork on the wall.

A beach with a playground and a white building in the background.

A spacious living room with a dining area, large windows, and a chandelier.

14. Las Flores Villa

Las Flores Villa

5.0 star property

New Preston

10.0 out of 10, Exceptional, (1 review)

10/10

Exceptional

(1 review)

The price is AU$5,019

AU$5,019

includes taxes & fees

26 Oct - 27 Oct

Las Flores Villa

A modern kitchen with a central island, pendant lights, and a view of the outdoors.

A modern living room with a fireplace, comfortable seating, and a large window offering a view of the outdoors.

A modern kitchen with a marble countertop, stainless steel appliances, and a wooden floor.

A modern dining area with a wooden table, white chairs, a chandelier, and a painting on the wall.

15. Renovated Retreat with Heated Pool

Renovated Retreat with Heated Pool

Redding

9.4 out of 10, Exceptional, (3 reviews)

9.4/10

Exceptional

(3 reviews)

"Beautiful house, very clean, spacious and a great host!!!"

Alejandro A.

The price is AU$1,042

AU$1,042

includes taxes & fees

11 Nov - 12 Nov

Renovated Retreat with Heated Pool

A bedroom with a bed, a nightstand, a lamp, and a wooden wardrobe.

A bedroom with a bed, a window with blinds, a painting of bulls, and a door leading to another room.

A room with a wooden floor, a desk with a printer, a chair, and a lamp.

A living room with a brick fireplace, white furniture, and a patterned rug.

16. The Cottage by the Woods -private getaway to relax

The Cottage by the Woods -private getaway to relax

Meriden

The price is AU$892

AU$892

includes taxes & fees

15 Oct - 16 Oct

The Cottage by the Woods -private getaway to relax

A room with a wooden floor, a white door, and a closet with hanging clothes and a folded towel.

A bedroom with a bed, a door, and a wall-mounted shelf.

A living room with a sofa, coffee table, dining table, chairs, and artwork on the walls.

A kitchen with a gas stove, a microwave, wooden cabinets, and various kitchen utensils.

17. Quiet 1st-Floor 2BR Haven w/ King Bed, Desks, In-Unit Laundry & 2-Car Parking | Walk to Yale

Quiet 1st-Floor 2BR Haven w/ King Bed, Desks, In-Unit Laundry & 2-Car Parking | Walk to Yale

Newhallville

The price is AU$565

AU$565

includes taxes & fees

14 Oct - 15 Oct

Quiet 1st-Floor 2BR Haven w/ King Bed, Desks, In-Unit Laundry & 2-Car Parking | Walk to Yale

A patio with a table and chairs, a grill, and a view of a lake.

A two-story house with a garage, a driveway, and a river in the background.

A living room with a large window, a ceiling fan, a television, a glass coffee table, a patterned rug, and two chairs.

A room with a large bay window overlooking a lake, a patterned armchair, and a glass table with a decorative bowl.

18. Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville

Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville

Collinsville

10.0 out of 10, Exceptional, (74 reviews)

10/10

Exceptional

(74 reviews)

"What a wonderful spot and exceptional host. Loved our stay and hope to visit again soon. "

Mike

The price is AU$735

AU$735

includes taxes & fees

21 Oct - 22 Oct

Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville

A covered porch with a wicker chair and a potted plant.

A compact kitchen with wooden cabinets, a white refrigerator, a stove, and a dining area with a table and two chairs.

A living room with a black leather sofa, a glass coffee table, and a dining area with a chandelier.

A dining area with a glass table surrounded by four upholstered chairs, a decorative vase, and a small side table with a lamp.

19. 3-bedroom house just walking distance from Yale and Downtown

3-bedroom house just walking distance from Yale and Downtown

Dixwell

10.0 out of 10, Exceptional, (7 reviews)

10/10

Exceptional

(7 reviews)

"Great stay!"

Mark S.

The price is AU$637

AU$637

includes taxes & fees

19 Oct - 20 Oct

3-bedroom house just walking distance from Yale and Downtown

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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