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

Woodbury Holiday Rentals

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Check prices for these dates

In two weeks
23 Oct - 25 Oct
In two months
4 Dec - 6 Dec
In three months
1 Jan - 3 Jan
In four months
29 Jan - 31 Jan

Our top choices for Woodbury holiday rentals

A white house with a wooden staircase leading to a porch.

1. Cozy One Bedroom Apartment Centrally Located in Southbury

Cozy One Bedroom Apartment Centrally Located in Southbury
Southbury
10.0 out of 10, Exceptional, (37 reviews)
"Great place. Had everything we needed and was very clean."
United States
Niki B.
The price is HK$671
HK$929 total
includes taxes & fees
14 Oct - 15 Oct
Cozy One Bedroom Apartment Centrally Located in Southbury
A modern living room with a flat-screen TV mounted on a white wall, a clock, and a minimalist design.

2. Private, Quiet, Cozy Studio Guesthouse with 75" TV WiFi etc. In Watertown.

Private, Quiet, Cozy Studio Guesthouse with 75" TV WiFi etc. In Watertown.
Watertown
8.4 out of 10, Very good, (12 reviews)
"Great night stay! Wonderful place would definitely recommend! "
United States
Laurie P.
The price is HK$769
HK$1,041 total
includes taxes & fees
3 Nov - 4 Nov
Private, Quiet, Cozy Studio Guesthouse with 75" TV WiFi etc. In Watertown.
A two-story house with a porch, a front door with a wreath, and a small garden area.

3. 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 HK$911
HK$2,668 total
includes taxes & fees
6 Oct - 7 Oct
Bear Retreat - 2-bedroom house in Waterbury
A modern kitchen with a dining area, large windows, and a TV displaying a streaming service.

4. The Perch in the Purchase -- Cozy, unique, and private

The Perch in the Purchase -- Cozy, unique, and private
Southbury
10.0 out of 10, Exceptional, (5 reviews)
"Beautiful place. Very clean & welcoming "
United States
Chris
The price is HK$1,144
HK$1,812 total
includes taxes & fees
18 Oct - 19 Oct
The Perch in the Purchase -- Cozy, unique, and private
A modern kitchen with white cabinets, stainless steel appliances, and a dining table with chairs.

5. Private Apartment in Southbury 104

Private Apartment in Southbury 104
Southbury
10.0 out of 10, Exceptional, (1 review)
"Pro Unit very clean, check in was easy and host was responsive to issues 24/7.Unit is large with new appliances in full kitchen.It is located in a beautiful rural area of CT. I highly recommend it"
United States
Daniel R.
The price is HK$1,248
HK$2,445 total
includes taxes & fees
12 Oct - 13 Oct
Private Apartment in Southbury 104
A modern kitchen with white cabinets, a black countertop, and a dining area with a table and chairs.

6. Private Apartment in Southbury 102

Private Apartment in Southbury 102
Southbury
9.0 out of 10, Wonderful, (6 reviews)
"Over all a great place. Nice to have everything on one floor. Dogs loved it. Some businesses in the building and everyone is friendly!"
United States
Debbie P.
The price is HK$1,012
HK$2,151 total
includes taxes & fees
2 Nov - 3 Nov
Private Apartment in Southbury 102
A view through a window with a clear sky and lush greenery outside.

7. Private Apartment in Southbury 101

Private Apartment in Southbury 101
Southbury
9.6 out of 10, Exceptional, (7 reviews)
"The apartment was nice, big area, loved this rental."
United States
Marissa G.
The price is HK$1,099
HK$2,258 total
includes taxes & fees
7 Oct - 8 Oct
Private Apartment in Southbury 101
A staircase with a handrail, a potted plant with yellow flowers, and a sign above the stairs.

8. 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 HK$863
HK$1,150 total
includes taxes & fees
6 Oct - 7 Oct
Cozy 1-king size bedroom house in quiet Waterbury with 75" TV in your bedroom.
A compact kitchen with wooden cabinets, a microwave, a sink, and a chair.

9. Cozy Studio apartment in delightful Waterbury with Central Air

Cozy Studio apartment in delightful Waterbury with Central Air
Waterbury
2.0 out of 10, (1 review)
"The place wasn’t how the pictures were on the app. It was hard to find the room. The keys for the room are very hard to open the room door . It’s like you have to struggle just to get inside . The room is inside of an abandoned building… some staff in the building was telling me that I shouldn’t be staying there or they wouldn’t stay there so it made me feel unsafe… the bed doesn’t match the head board. Everything just doesn’t match the images the host posted.."
United States
zynaisha
The price is HK$530
HK$766 total
includes taxes & fees
19 Oct - 20 Oct
Cozy Studio apartment in delightful Waterbury with Central Air
A modern kitchen with wooden cabinets, a stainless steel refrigerator, a built-in oven, and a large island with bar stools.

10. 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, (2 reviews)
"Clean and close to activitys"
United States
randall
The price is HK$607
HK$1,216 total
includes taxes & fees
3 Nov - 4 Nov
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.

11. 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 HK$1,719
HK$4,206 total
includes taxes & fees
6 Oct - 7 Oct
Watertown Home w/ Yard: 1 Mi to Echo Lake Park!
A modern kitchen with white cabinets, a dining area with a black table and chairs, and a large window with curtains.

12. Private Apartment in Southbury 105

Private Apartment in Southbury 105
Southbury
The price is HK$1,122
HK$2,317 total
includes taxes & fees
2 Nov - 3 Nov
Private Apartment in Southbury 105
A glass-top table with a woven placemat, a vase with white flowers, and a view of a balcony through a door with curtains.

13. The Overlook near South Farms in Litchfield County is Hospitality, integrated.

The Overlook near South Farms in Litchfield County is Hospitality, integrated.
Morris
9.8 out of 10, Exceptional, (18 reviews)
"Very clean & cozy with everything we needed!"
United States
Joe K.
The price is HK$1,687
HK$2,176 total
includes taxes & fees
6 Oct - 7 Oct
The Overlook near South Farms in Litchfield County is Hospitality, integrated.
A spacious living room with large windows, a fireplace, and a view of the outdoors.

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

Watertown Home w/ Yard: 1 Mi to Echo Lake Park!
3.0 star property
Oakville
The price is HK$2,142
HK$4,230 total
includes taxes & fees
7 Oct - 8 Oct
Watertown Home w/ Yard: 1 Mi to Echo Lake Park!
A front view of a house with a wooden staircase leading to a front door, a small porch area, and a garage door.

15. 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 HK$1,177
HK$3,112 total
includes taxes & fees
6 Oct - 7 Oct
1-bedroom vacation home 22 minutes from Quinnipiac University
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.

16. 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 HK$918
HK$2,676 total
includes taxes & fees
18 Oct - 19 Oct
Lakehouse, Boat Dock, Kayaks, Fire-Pit, King Bed, 1 Hour & 15 Min from NYC etc!
A modern hotel room with a large bed, a desk, a flat-screen TV, and a window with curtains.

17. 1 King Bed | Non-Smoking

1 King Bed | Non-Smoking
Bethel
The price is HK$900
HK$1,035 total
includes taxes & fees
6 Oct - 7 Oct
1 King Bed | Non-Smoking
A spacious living room with a large window overlooking a lake, wooden ceiling, and comfortable seating.

18. Escape to Bantam Lake- With Fireplace and Hot tub!

Escape to Bantam Lake- With Fireplace and Hot tub!
Morris
10.0 out of 10, Exceptional, (5 reviews)
"This house is a dream. First, the views are incredible. Second, it’s beautifully decorated and very cozy. Lastly, the property location is perfect. I can’t wait to stay again!"
United States
Shannon M.
The price is HK$2,158
HK$4,291 total
includes taxes & fees
2 Nov - 3 Nov
Escape to Bantam Lake- With Fireplace and Hot tub!
A kitchen with a marble island, wooden cabinets, a clock, and a window with a view of trees.

19. The Jefferson Guest House, Spacious, Special Views

The Jefferson Guest House, Spacious, Special Views
Litchfield
10.0 out of 10, Exceptional, (9 reviews)
"Everything about Jefferson House was perfect. It was located in a beautiful part of Connecticut adjoining a state park. The house was beautifully decorated. The kitchen was fully equipped and had a large island for dining. The bed, pillows and living room furnishings were very comfortable. The house was well up-to-date with two TVs, a charging device with multiple cords, a double oven (!), and countless thoughtful touches. I cannot recommend it highly enough!"
United States
genevieve
The price is HK$2,415
HK$3,114 total
includes taxes & fees
7 Oct - 8 Oct
The Jefferson Guest House, Spacious, Special Views
A living room with a fireplace, two armchairs, a sofa, and a TV.

20. Mid Century Modern Studio w/ Full Kitchen - Newly Built

Mid Century Modern Studio w/ Full Kitchen - Newly Built
Kent
10.0 out of 10, Exceptional, (24 reviews)
"Very nice, great location in town"
United States
Lisa F.
The price is HK$1,301
HK$1,661 total
includes taxes & fees
6 Oct - 7 Oct
Mid Century Modern Studio w/ Full Kitchen - Newly Built
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

Holiday Inn Express Southington by IHG

Holiday Inn Express Southington by IHG

10/10 Excellent
"Updated hotel"
Melanie 1-night trip
Posted 2 hours ago
Holiday Inn Express Southington by IHG

Find out more about Woodbury

Search for holiday rentals in Woodbury on Expedia! You can easily find your home rentals, villas, holiday apartments in Woodbury using one of the methods below:

  • View our selection of featured holiday rentals in Woodbury
  • Use the map to find apartments and other holiday homes in the Woodbury neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Woodbury while they last

Look no further and take a look at our great range of rental properties in Woodbury!

Frequently asked questions

Are there holiday rentals in Woodbury?

Yes, there are holiday rentals in Woodbury close to Glebe House Museum and The Gertrude Jekyll Garden, or you can select a more secluded option if you're looking for a relaxing stay. Our travellers say Woodbury has a good selection of restaurants. Make sure you have time to check out the ski areas and coffee shops during your trip.

What are some of the best holiday rentals that Woodbury has to offer?

Lakehouse Boat Dock, Kayaks, Fire-Pit, Pool Table, Air Hockey, Hammock, King Bed: This holiday home rental outside of Woodbury offers a fireplace, a patio and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games.

How many holiday rentals are there in Woodbury?

With 8 Expedia holiday rentals, you're guaranteed to find just the right place for your Woodbury stay.

What can I see and do in Woodbury?

Hollow Park and Lake Quassapaug are a couple of scenic spots to enjoy the outdoors, whereas Glebe House Museum and The Gertrude Jekyll Garden is one of the cultural attractions. Other places in town to visit include Pilgrim Mall Shopping Center and Flanders Nature Center.

What are holiday rentals like in Woodbury?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Woodbury. Holiday rentals provide amenities like laundry facilities and kitchens so you'll have a home away from home. If you're concerned about a sanitised environment, a holiday rental can offer a sense of safety away from public hotel lifts and busy reception areas while still allowing you the enjoyment of travel. You'll also get more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is an attractive choice for a family getaway.