Search Holiday Rentals in Woodbury

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Save instantly and earn perks with One Key
    Learn about One Key

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
20 Nov - 22 Nov
In two months
1 Jan - 3 Jan
In three months
29 Jan - 31 Jan
In four months
26 Feb - 28 Feb

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, (39 reviews)
"Charles was super responsive and the bed was amazingly comfortable. Also the shower head great water pressure :-)"
United States
Lisbeth
The price is £99
includes taxes & fees
2 Dec - 3 Dec
Cozy One Bedroom Apartment Centrally Located in Southbury
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, (13 reviews)
"Perfect, spacious area. Super clean. Communication was great. Would definitely book here again."
United States
Radha
The price is £239
includes taxes & fees
6 Nov - 7 Nov
Bear Retreat - 2-bedroom house in Waterbury
A spacious living room with large windows, a fireplace, and a view of the outdoors.

3. 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 £400
includes taxes & fees
6 Nov - 7 Nov
Watertown Home w/ Yard: 1 Mi to Echo Lake Park!
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 £381
includes taxes & fees
6 Nov - 7 Nov
Watertown Home w/ Yard: 1 Mi to Echo Lake Park!
A glass-top table with a woven placemat, a vase with white flowers, and a view of a balcony through a door with curtains.

5. 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, (21 reviews)
"Very clean & cozy with everything we needed!"
United States
Joe K.
The price is £199
includes taxes & fees
8 Nov - 9 Nov
The Overlook near South Farms in Litchfield County is Hospitality, integrated.
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
9.2 out of 10, Wonderful, (7 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 £189
includes taxes & fees
17 Nov - 18 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 £198
includes taxes & fees
6 Dec - 7 Dec
Private Apartment in Southbury 101
A modern kitchen with white cabinets, stainless steel appliances, and a dining table with chairs.

8. 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 £195
includes taxes & fees
6 Dec - 7 Dec
Private Apartment in Southbury 104
A modern kitchen with wooden cabinets, a stainless steel refrigerator, a built-in oven, and a large island with bar stools.

9. 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)
"I really enjoyed my four night stay here."
United States
Jim B.
The price is £99
includes taxes & fees
10 Nov - 11 Nov
Cozy private room in a shared home with a Full-size bed and private bathroom.
A spacious living room with a large window overlooking a lake, wooden ceiling, and comfortable seating.

10. 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, (6 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 £367
includes taxes & fees
18 Nov - 19 Nov
Escape to Bantam Lake- With Fireplace and Hot tub!
A modern kitchen with white cabinets, a microwave, stove, and sink. There is a dining area with a table and chairs.

11. 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 £105
includes taxes & fees
9 Nov - 10 Nov
Cozy 1-king size bedroom house in quiet Waterbury with 75" TV in your bedroom.
A building entrance with a brick facade, a green awning, and a glass door.

12. 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 £77
includes taxes & fees
2 Dec - 3 Dec
Cozy Studio apartment in delightful Waterbury with Central Air
A spacious kitchen with wooden cabinets, a large island with stools, and a clock on the wall.

13. The Jefferson Guest House, Spacious, Special Views

The Jefferson Guest House, Spacious, Special Views
Litchfield
10.0 out of 10, Exceptional, (9 reviews)
"I stayed here for four nights, including one with my son, and it was fantastic.Everything is brand new, clean, and beautifully appointed, with every amenity you could want."
United States
Jennifer A.
The price is £270
includes taxes & fees
8 Nov - 9 Nov
The Jefferson Guest House, Spacious, Special Views
A hot tub in a backyard with a house, trees, and a clear sky.

14. Las Flores Villa

Las Flores Villa
5.0 star property
New Preston
10.0 out of 10, Exceptional, (1 review)
The price is £1,061
includes taxes & fees
6 Nov - 7 Nov
Las Flores Villa
A living room with a white sectional sofa, a dining area with a wooden table and chairs, and a staircase leading to an upper level.

15. 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
10.0 out of 10, Exceptional, (1 review)
"Perfect!!"
United States
Jeni O.
The price is £612
includes taxes & fees
1 Dec - 2 Dec
The Lorelai at Middle Street Manor: Walk to Town Green, Gazebo, Shops & Dining
A front view of a house with a wooden staircase leading to a front door, a small porch area, and a garage door.

16. 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 £286
includes taxes & fees
30 Nov - 1 Dec
1-bedroom vacation home 22 minutes from Quinnipiac University
A modern kitchen with white cabinets, a dining area with a black table and chairs, and a large window with curtains.

17. Private Apartment in Southbury 105

Private Apartment in Southbury 105
Southbury
The price is £196
includes taxes & fees
30 Nov - 1 Dec
Private Apartment in Southbury 105
A cozy cabin interior with a wooden ceiling, a sofa, a coffee table, and a sign reading "Our Happy Place".

18. The Little Lake Cabin with hot tub

The Little Lake Cabin with hot tub
New Fairfield
10.0 out of 10, Exceptional, (6 reviews)
"Great location and lots to do despite it raining for half our stay! My dog enjoyed the yard and walks around the neighborhood. My son loved kayaking and having his first ever s’more. Honestly I wished we had booked a longer trip! "
United States
Lyndsey F.
The price is £392
includes taxes & fees
10 Nov - 11 Nov
The Little Lake Cabin with hot tub
A modern hotel room with a bed, bedside table, lamp, desk, and window.

19. 1 King Bed | Non-Smoking

1 King Bed | Non-Smoking
Bethel
10.0 out of 10, Exceptional, (3 reviews)
"We found plenty of space for our small group plus pets. Loved having a private bathroom,it made mornings smooth."
United States
Anonymous traveller
The price is £98
includes taxes & fees
10 Nov - 11 Nov
1 King Bed | Non-Smoking
A modern living room with a black sofa, white armchair, and a coffee table with a decorative centerpiece.

20. 191 Seymour, Ave. Derby · Spacious Renovated 3 bedroom near GriffinHospital

191 Seymour, Ave. Derby · Spacious Renovated 3 bedroom near GriffinHospital
Derby
8.6 out of 10, Excellent, (8 reviews)
"Great stay! Perfect location for my needs. Clean and inviting rental. Modern and well kept. Will stay again. "
United States
Bary B.
191 Seymour, Ave. Derby · Spacious Renovated 3 bedroom near GriffinHospital
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.
View all properties

Find holiday rentals that suit your style

Cottage image
Cottages
Cottages
Apartment image
Apartments
Apartments

Top Woodbury Hotel Reviews

A hotel room with a large bed, two bedside tables with lamps, and a striped wall.
The Milestone Inn

The Milestone Inn

The Milestone Inn
Woodbury

10/10 Excellent

On arrival, called number posted on office door, Jack answered, gave us lock box code and waited on phone until we were in. That simple. Room was clean, large, great facilities and in good decorative repair. Location great for food outlets and Woodbury itself. Highly ecommended.
United Kingdom
Richard
Reviewed October 4, 2019
The Milestone Inn

Find out more about Woodbury

Everything you need to know about Woodbury holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Woodbury holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Woodbury holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Woodbury holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Woodbury. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Woodbury holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Woodbury holiday rentals we have selected for you start as low as £76 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Woodbury rentals

At Expedia, we put the best Woodbury holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Woodbury rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Woodbury holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Woodbury. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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.

Explore a world of travel with Expedia