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

Woodbury Vacation Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 Jan

Our top choices for Woodbury vacation rentals

Exterior

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 AED 324
AED 446 total
includes taxes & fees
27 Sep - 28 Sep
Cozy One Bedroom Apartment Centrally Located in Southbury
Interior

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 AED 327
AED 449 total
includes taxes & fees
28 Sep - 29 Sep
Private, Quiet, Cozy Studio Guesthouse with 75" TV WiFi etc. In Watertown.
Exterior detail

3. Bear Retreat - 2-bedroom house in Waterbury

Bear Retreat - 2-bedroom house in Waterbury
Waterbury
10.0 out of 10, Exceptional, (8 reviews)
"Perfect, spacious area. Super clean. Communication was great. Would definitely book here again."
United States
Radha
The price is AED 477
AED 1,269 total
includes taxes & fees
8 Oct - 9 Oct
Bear Retreat - 2-bedroom house in Waterbury
Coffee/tea maker, fridge, microwave, oven

4. Private Apartment in Southbury 103

Private Apartment in Southbury 103
Southbury
9.4 out of 10, Exceptional, (6 reviews)
"It was amazing , clean and awesome and good time"
United States
Michael
The price is AED 529
AED 1,077 total
includes taxes & fees
28 Sep - 29 Sep
Private Apartment in Southbury 103
Interior

5. 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 AED 433
AED 953 total
includes taxes & fees
28 Sep - 29 Sep
Private Apartment in Southbury 101
House (3 Bedrooms) | Interior

6. 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 AED 1,003
AED 1,980 total
includes taxes & fees
24 Sep - 25 Sep
Watertown Home w/ Yard: 1 Mi to Echo Lake Park!
Outdoor dining

7. 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 AED 536
AED 848 total
includes taxes & fees
29 Sep - 30 Sep
The Perch in the Purchase -- Cozy, unique, and private
Interior

8. 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 AED 804
AED 1,903 total
includes taxes & fees
24 Sep - 25 Sep
Watertown Home w/ Yard: 1 Mi to Echo Lake Park!
Coffee/tea maker, fridge, microwave, oven

9. 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 AED 569
AED 1,128 total
includes taxes & fees
7 Oct - 8 Oct
Private Apartment in Southbury 104
Interior

10. 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, (17 reviews)
"Very clean & cozy with everything we needed!"
United States
Joe K.
The price is AED 790
AED 1,011 total
includes taxes & fees
27 Sep - 28 Sep
The Overlook near South Farms in Litchfield County is Hospitality, integrated.
Interior

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 AED 404
AED 538 total
includes taxes & fees
24 Sep - 25 Sep
Cozy 1-king size bedroom house in quiet Waterbury with 75" TV in your bedroom.
Interior

12. Private Apartment in Southbury 105

Private Apartment in Southbury 105
Southbury
The price is AED 433
AED 964 total
includes taxes & fees
25 Sep - 26 Sep
Private Apartment in Southbury 105
TV

13. #43- Modern Luxury Log Cabin Retreat - Fire Pit

#43- Modern Luxury Log Cabin Retreat - Fire Pit
Prospect
9.4 out of 10, Exceptional, (3 reviews)
"3.5 rounding up to 4. We had a good stay overall. I travel fairly often and tend to reserve 5 stars for places where every detail of the guest experience feels really thoughtfully considered. This home was comfortable and worked fine for our trip, but it felt a bit more basic compared to some other rentals I’ve stayed in."
United States
Lauren P.
The price is AED 703
AED 1,657 total
includes taxes & fees
24 Sep - 25 Sep
#43- Modern Luxury Log Cabin Retreat - Fire Pit
Exterior

14. Cozy Modern Farmhouse Private Apt - 3 Beds

Cozy Modern Farmhouse Private Apt - 3 Beds
Torrington
10.0 out of 10, Exceptional, (4 reviews)
"My husband and I came down from Boston for Christmas to see family and couldn’t find one decent hotel in the area. We were relieved to find this place. Cute, comfortable, clean environment and just what we needed. "
United Kingdom
Louisa A.
The price is AED 474
AED 1,496 total
includes taxes & fees
28 Sep - 29 Sep
Cozy Modern Farmhouse Private Apt - 3 Beds
Coffee/tea maker, fridge, microwave, oven

15. Renovated 2 bedroom entire apartment w/parking

Renovated 2 bedroom entire apartment w/parking
Ansonia
10.0 out of 10, Exceptional, (2 reviews)
"Host was very attentive making sure everything was going well, apartment was great would definitely stay again "
United States
Sophia
The price is AED 582
AED 1,008 total
includes taxes & fees
27 Sep - 28 Sep
Renovated 2 bedroom entire apartment w/parking
Coffee/tea maker, fridge, microwave, oven

16. 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 AED 1,131
AED 1,443 total
includes taxes & fees
28 Sep - 29 Sep
The Jefferson Guest House, Spacious, Special Views
Exterior detail

17. 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 AED 551
AED 1,456 total
includes taxes & fees
1 Oct - 2 Oct
1-bedroom vacation home 22 minutes from Quinnipiac University
Interior

18. Cozy Studio apartment in delightful Waterbury with Central Air

Cozy Studio apartment in delightful Waterbury with Central Air
Waterbury
The price is AED 334
AED 457 total
includes taxes & fees
9 Oct - 10 Oct
Cozy Studio apartment in delightful Waterbury with Central Air
Apartment (1 Bedroom) | Interior

19. Bristol Condo Near Espn HQ & Lake Compounce!

Bristol Condo Near Espn HQ & Lake Compounce!
3.5 star property
Bristol
The price is AED 643
AED 1,153 total
includes taxes & fees
27 Sep - 28 Sep
Bristol Condo Near Espn HQ & Lake Compounce!
TV

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.
The price is AED 666
AED 1,125 total
includes taxes & fees
24 Sep - 25 Sep
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
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Woodbury Hotel Reviews

Courtyard by Marriott Waterbury Downtown

Courtyard by Marriott Waterbury Downtown

8/10 Good
"The room was clean and very up-to-date decor-wise."
Karen 1-night trip
Posted 14 hours ago
Courtyard by Marriott Waterbury Downtown

Frequently asked questions

Are there vacation rentals in Woodbury?

Yes, we offer vacation rentals in Woodbury close to Glebe House Museum and The Gertrude Jekyll Garden, or you can choose a more secluded option if you're looking for a relaxing stay. Our travelers say Woodbury has a good selection of restaurants. Make sure you have time to check out the ski areas and coffeehouses during your trip.

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

Lakehouse Boat Dock, Kayaks, Fire-Pit, Pool Table, Air Hockey, Hammock, King Bed: This vacation home near Woodbury offers a fireplace, a patio, and a barbecue grill 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 you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games. Our travelers also rate Charming 1760 Cape Nestled in the Foothills of Litchfield County as a favorite home for rent in Woodbury.

How many vacation rentals are there in Woodbury?

With 8 Expedia vacation rentals, you're sure 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 vacation rentals like in Woodbury?

Vacation rentals are privately owned properties you can book for a couple days or more in Woodbury. Vacation rentals feature extras like laundry facilities and kitchens so you'll have all the comforts of home. If you're concerned about a clean environment, a vacation rental can offer a sense of privacy away from public hotel elevators and busy reception areas while still allowing you to travel. You'll also have more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is a great choice for small groups.