A park with a paved walkway, trees, and historic buildings in the background.

Holiday Homes in Woodbury

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Check prices for these dates

In two weeks
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

Our top choices for Woodbury holiday homes

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

1. 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)
"I had an emergency and was only able to stay one night, but enjoyed my stay "
United States
Dirk N.
The price is €133
includes taxes & fees
4 Oct - 5 Oct
Cozy 1-king size bedroom house in quiet Waterbury with 75" TV in your bedroom.
A two-story house with a porch, a front door with a wreath, and a small garden area.

2. Bear Retreat - 2-bedroom house in Waterbury

Bear Retreat - 2-bedroom house in Waterbury
Waterbury
10.0 out of 10, Exceptional, (9 reviews)
"Perfect, spacious area. Super clean. Communication was great. Would definitely book here again."
United States
Radha
The price is €292
includes taxes & fees
8 Oct - 9 Oct
Bear Retreat - 2-bedroom house in Waterbury
A modern kitchen with wooden cabinets, a stainless steel refrigerator, a built-in oven, and a large island with bar stools.

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, (1 review)
"Clean and close to activitys"
United States
randall
The price is €145
includes taxes & fees
13 Oct - 14 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.

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)
"In town to visit our new grandchild. It was just my husband and me. It had more then enough room and was very comfortable."
United States
Elizabeth H.
The price is €471
includes taxes & fees
2 Oct - 3 Oct
Watertown Home w/ Yard: 1 Mi to Echo Lake Park!
A modern living room with a sofa, coffee table, and a TV mounted on the wall.

5. 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)
"Excellent option for a short stay near the heart of it all in Wallingford."
United States
Jeanette W.
The price is €262
includes taxes & fees
4 Oct - 5 Oct
Once the old Schools house now a newly furnished Apartment
A front view of a house with a wooden staircase leading to a front door, a small porch area, and a garage door.

6. 1-bedroom vacation home 22 minutes from Quinnipiac University

1-bedroom vacation home 22 minutes from Quinnipiac University
Wolcott
9.6 out of 10, Exceptional, (4 reviews)
"Very clean and the host was great "
United States
David G.
The price is €361
includes taxes & fees
2 Oct - 3 Oct
1-bedroom vacation home 22 minutes from Quinnipiac University
Room

7. #37 - Luxury Collection

#37 - Luxury Collection
Stratford
8.4 out of 10, Very good, (5 reviews)
"Peaceful spot, conveniently located."
United States
Katherine
The price is €416
includes taxes & fees
8 Oct - 9 Oct
#37 - Luxury Collection
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.

8. 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)
"Very serene location, the host was very responsive and helpful."
United States
Stephen L.
The price is €311
includes taxes & fees
18 Oct - 19 Oct
Lakehouse, Boat Dock, Kayaks, Fire-Pit, King Bed, 1 Hour & 15 Min from NYC etc!
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.

9. 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 €429
includes taxes & fees
4 Oct - 5 Oct
Luxurious-Modern feel w/ custom features - AC, short walk to Shelton
A living room with a grey sofa, red and yellow cushions, a wooden coffee table, and a TV on a wooden cabinet.

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, (10 reviews)
"Very Clean with everything I needed. I will stay here again."
United States
David M.
The price is €262
includes taxes & fees
5 Oct - 6 Oct
Newly Remodeled 1-BR Close to Everything yet Very Private
A room with a built-in bench along a wall with large windows, a door, and a tiled floor.

11. 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 €714
includes taxes & fees
5 Oct - 6 Oct
The Lorelai at Middle Street Manor: Walk to Town Green, Gazebo, Shops & Dining
A modern living room with a fireplace, leather sofas, a blue armchair, and large windows.

12. #30 - Spacious & Cozy!

#30 - Spacious & Cozy!
Southington
6.8 out of 10, (5 reviews)
"the house was great for our needs - it was nicely furnished fully stocked with the essentials in the kitchen. the host checked in when it was especially cold to ensure the heat and water were working correctly. the living room was very comfortable with leather reclining chairs and a gas fireplace that heated the room very well. We enjoyed how easy our stay was and recommend this location "
United States
Kaity B.
The price is €434
includes taxes & fees
7 Oct - 8 Oct
#30 - Spacious & Cozy!
A room with a wooden floor, a white door, and a closet with hanging clothes and a folded towel.

13. 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 €405
includes taxes & fees
7 Oct - 8 Oct
Quiet 1st-Floor 2BR Haven w/ King Bed, Desks, In-Unit Laundry & 2-Car Parking | Walk to Yale
A modern kitchen with stainless steel appliances, a central island, and a dining area with a sofa.

14. #27- Luxury Collection

#27- Luxury Collection
Southington
10.0 out of 10, Exceptional, (4 reviews)
"Beautiful home, well designed and spacious rooms. Host was fantastic and communication was great! Thank you"
United States
C B.
The price is €405
includes taxes & fees
20 Oct - 21 Oct
#27- Luxury Collection
A patio with a table and chairs, a grill, and a view of a lake.

15. 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, (73 reviews)
"Wow! What a great place! The house is lovely, very clean, comfy beds and cozy seating. Amazing view and an unbeatable location!"
United States
Kristi M.
The price is €465
includes taxes & fees
19 Oct - 20 Oct
Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville
A living room with a sectional sofa, a small side table, and a floor lamp.

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

Lakehaven • Hot Tub, Decks, Fires & More
Plymouth
The price is €764
includes taxes & fees
5 Oct - 6 Oct
Lakehaven • Hot Tub, Decks, Fires & More
A bedroom with a bed, a nightstand, a lamp, and a wooden wardrobe.

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

The Cottage by the Woods -private getaway to relax
Meriden
The price is €566
includes taxes & fees
2 Oct - 3 Oct
The Cottage by the Woods -private getaway to relax
A covered porch with a wicker chair and a potted plant.

18. 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, (6 reviews)
"Great stay!"
United States
Mark S.
The price is €406
includes taxes & fees
7 Oct - 8 Oct
3-bedroom house just walking distance from Yale and Downtown
A modern kitchen with a central island, pendant lights, and a view of the outdoors.

19. Renovated Retreat with Heated Pool

Renovated Retreat with Heated Pool
Redding
9.4 out of 10, Exceptional, (3 reviews)
"Beautiful house, very clean, spacious and a great host!!!"
United States
Alejandro A.
The price is €633
includes taxes & fees
4 Oct - 5 Oct
Renovated Retreat with Heated Pool
A hot tub in a backyard with a house, trees, and a clear sky.

20. Las Flores Villa

Las Flores Villa
5.0 star property
New Preston
10.0 out of 10, Exceptional, (1 review)
The price is €3,094
includes taxes & fees
2 Oct - 3 Oct
Las Flores Villa
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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Top Woodbury Hotel Reviews

Ethan Allen Hotel

Ethan Allen Hotel

10/10 Excellent
"Sold my home and im using the hotel as a temporary residence. Very comfortable and staff especially the front desk and house keeping folks have been amazing."
Angelo 3-night trip
Posted 11 hours ago
Ethan Allen Hotel

Find out more about Woodbury

Woodbury Holiday Homes information

Number of reviews
174
Accommodation
248 Holiday Homes
Lowest Price
€133
Highest Price
€3,094