A snow-covered residential area with large white houses and a tall evergreen tree.

Woodbury Vacation Rentals

Dates

November 2026

December 2026

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Our top choices for Woodbury vacation rentals

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

1. Cozy One Bedroom Apartment Centrally Located in Southbury

Southbury

Lisbeth

AED 443 total

includes taxes & fees

20 Nov - 21 Nov

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

Waterbury

Radha

AED 1,201 total

includes taxes & fees

22 Nov - 23 Nov

A modern kitchen with white cabinets, stainless steel appliances, and a dining table with chairs.

3. Private Apartment in Southbury 104

Southbury

Daniel R.

AED 940 total

includes taxes & fees

1 Dec - 2 Dec

A modern kitchen with white cabinets, a black countertop, and a dining area with a table and chairs.

4. Private Apartment in Southbury 102

Southbury

Debbie P.

AED 899 total

includes taxes & fees

1 Dec - 2 Dec

A view through a window with a clear sky and lush greenery outside.

5. Private Apartment in Southbury 101

Southbury

Marissa G.

AED 991 total

includes taxes & fees

6 Dec - 7 Dec

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

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

New Milford

Jim B.

AED 479 total

includes taxes & fees

12 Nov - 13 Nov

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

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

Waterbury

Dirk N.

AED 509 total

includes taxes & fees

13 Nov - 14 Nov

A building entrance with a brick facade, a green awning, and a glass door.

8. Cozy Studio apartment in delightful Waterbury with Central Air

Waterbury

"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.."

zynaisha

AED 336 total

includes taxes & fees

2 Dec - 3 Dec

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

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

Watertown

Elizabeth H.

AED 1,892 total

includes taxes & fees

10 Nov - 11 Nov

A modern kitchen with white cabinets, a dining area with a black table and chairs, and a large window with curtains.

10. Private Apartment in Southbury 105

Southbury

AED 870 total

includes taxes & fees

16 Nov - 17 Nov

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

Oakville

AED 1,980 total

includes taxes & fees

10 Nov - 11 Nov

A glass-top table with a woven placemat, a vase with white flowers, and a view of a balcony through a door with curtains.

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

Morris

Joe K.

AED 971 total

includes taxes & fees

16 Nov - 17 Nov

A front view of a house with a wooden staircase leading to a front door, a small porch area, and a garage door.

13. 1-bedroom vacation home 22 minutes from Quinnipiac University

Wolcott

David G.

AED 1,409 total

includes taxes & fees

30 Nov - 1 Dec

A spacious living room with a large window overlooking a lake, wooden ceiling, and comfortable seating.

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

Morris

Shannon M.

AED 2,037 total

includes taxes & fees

22 Nov - 23 Nov

A modern hotel room with a bed, bedside table, lamp, desk, and window.

15. 1 Queen Bed | Non-Smoking

Bethel

Anonymous traveler

AED 459 total

includes taxes & fees

10 Nov - 11 Nov

A kitchen with a marble island, wooden cabinets, a clock, and a window with a view of trees.

16. The Jefferson Guest House, Spacious, Special Views

Litchfield

Jennifer A.

AED 1,384 total

includes taxes & fees

18 Nov - 19 Nov

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

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

Southington

"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.

AED 1,715 total

includes taxes & fees

20 Nov - 21 Nov

A living room with a fireplace, two armchairs, a sofa, and a TV.

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

Kent

benjamin

AED 672 total

includes taxes & fees

10 Nov - 11 Nov

Deck: Comfortable outdoor sofa sets for outdoor conversations

19. Serenity Haven: A Modern Retreat

Monroe

Tresha J.

A two-story house with a front porch, a small balcony, and a white picket fence.

20. Cozy Attic 10 min to Llitchfield

Torrington

Nicole N.

AED 1,300 total

includes taxes & fees

10 Nov - 11 Nov

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Find vacation rentals that suit your style

Top Woodbury Hotel Reviews

A covered porch with white columns and black hanging lanterns.

The Milestone Inn

Woodbury

10/10 Excellent

Elin

A spacious hotel lobby with wooden beams, a central seating area, and large windows offering a view.

Heritage Hotel, Golf & Conference Center

Southbury

10/10 Excellent

Always a good stay. Been coming to this hotel with the family for at least a decade and I also worked here in my young adult life. The staff is always pleasant, the place is always clean. The pool was a little overcrowded for once and we were given wrist bands for the first time ever. There was a staff member checking we had them on yet 75% of the people there did not have them which I thought was odd. We did not get too enjoy the pool as much as we would have wanted, it’s a great pool but there...

Luz

A hotel lobby with a modern design, featuring a seating area with sofas, a fireplace, and a television mounted on the wall.

Courtyard by Marriott Waterbury Downtown

Waterbury

10/10 Excellent

Courtney

A spacious living room with hardwood floors, a large dining area, and a cozy seating area with a red sofa and matching cushions.

Homestead Inn

New Milford

10/10 Excellent

This is my second time staying at the Inn, and everytime that out do themselves from the time before. Gave me a call to see if there was anything special I may need prior to my arrival. Room is spotless, probably the cleanest room I have ever experience. Convenient to the New Milford Green, plenty of good places to eat. Very quiet and restful. I will be staying at the end at least once a month over the next year, Highly recommend!!!

Bob

A hotel room with two beds, a desk, a chair, and a window with curtains.

Rocky River Inn

New Milford

10/10 Excellent

Zoe

Comfort Inn Naugatuck-Shelton, CT

Naugatuck

10/10 Excellent

Marta

A restaurant with wooden tables and chairs, a bar area, and hanging spherical light fixtures.

The Abner Hotel

Litchfield Historic District

10/10 Excellent

Karen

A hotel room with a bed, a chair, a small table with a plant, and a mirror.

La Quinta Inn & Suites by Wyndham Danbury

Danbury

10/10 Excellent

Louis

A hotel room with a bed, a desk, a chair, a TV, and a window with curtains.

Microtel Inn & Suites by Wyndham Bethel/Danbury

Bethel

10/10 Excellent

Vincent

An outdoor patio with a fire pit, wicker furniture, and a pergola structure.

Homewood Suites by Hilton Southington, CT

Southington

10/10 Excellent

Suzanne Martin

An outdoor seating area with fire pits and umbrellas, surrounded by modern buildings with large windows.

DoubleTree by Hilton Hotel Bristol, Connecticut

Bristol

10/10 Excellent

Susan

A large, two-story house with a wrap-around porch, a central entrance, and a flag.

Belden House & Mews

Litchfield Historic District

10/10 Excellent

Anthony

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.

Woodbury Vacation Rentals

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Woodbury vacation rentals

1. Cozy One Bedroom Apartment Centrally Located in Southbury

2. Bear Retreat - 2-bedroom house in Waterbury

3. Private Apartment in Southbury 104

4. Private Apartment in Southbury 102

5. Private Apartment in Southbury 101

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

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

8. Cozy Studio apartment in delightful Waterbury with Central Air

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

10. Private Apartment in Southbury 105

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

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

13. 1-bedroom vacation home 22 minutes from Quinnipiac University

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

15. 1 Queen Bed | Non-Smoking

16. The Jefferson Guest House, Spacious, Special Views

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

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

19. Serenity Haven: A Modern Retreat

20. Cozy Attic 10 min to Llitchfield

Find vacation rentals that suit your style

Top Woodbury Hotel Reviews

The Milestone Inn

10/10 Excellent

Frequently Asked Questions

Are there vacation rentals in Woodbury?

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

How many vacation rentals are there in Woodbury?

What can I see and do in Woodbury?

What are vacation rentals like in Woodbury?