Southbury Holiday Houses

A waterfall in a forested area with autumn foliage.

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Our top choices for Southbury holiday homes

A two-story house with a porch, a front door with a wreath, and a small garden area.

1. Bear Retreat - 2-bedroom house in Waterbury

Waterbury

Radha

includes taxes & fees

19 Oct - 20 Oct

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

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

New Milford

Jim B.

includes taxes & fees

3 Nov - 4 Nov

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

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

Waterbury

Dirk N.

includes taxes & fees

19 Oct - 20 Oct

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

Elizabeth H.

includes taxes & fees

19 Oct - 20 Oct

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.

5. Lakehouse, Boat Dock, Kayaks, Fire-Pit, King Bed, 1 Hour & 15 Min from NYC etc!

New Fairfield

Stephen L.

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.

6. Luxurious-Modern feel w/ custom features - AC, short walk to Shelton

Shelton

includes taxes & fees

2 Nov - 3 Nov

A modern living room with a sofa, coffee table, and a TV mounted on the wall.

7. Once the old Schools house now a newly furnished Apartment

Wallingford Center

Jeanette W.

includes taxes & fees

31 Oct - 1 Nov

A room with a built-in bench along a wall with large windows, a door, and a tiled floor.

8. The Lorelai at Middle Street Manor: Walk to Town Green, Gazebo, Shops & Dining

New Milford

Jeni O.

includes taxes & fees

26 Oct - 27 Oct

A swimming pool at night with blue lighting.

9. Business or Weekend escape

Stratford

Kimberly

includes taxes & fees

25 Oct - 26 Oct

A bathroom with a toilet, sink, and a small shelf with toiletries.

10. Centric property close to all the great things in the city

Brooklawn - St. Vincent

Alma B.

includes taxes & fees

19 Oct - 20 Oct

A modern kitchen with stainless steel appliances, a central island, and a dining area with a sofa.

11. #27- Luxury Collection

Southington

C B.

includes taxes & fees

21 Oct - 22 Oct

A living room with a staircase, a sofa, a coffee table, and a TV.

12. Loft •Pool • Gym • Free Parking • Near Yale

Orange

Ali B.

includes taxes & fees

19 Oct - 20 Oct

A spacious living room with a piano, a large TV, a fireplace, and a view of a lake through the windows.

13. 6BR Easton House with Pool, Hot Tub & Big Yard

Easton

includes taxes & fees

31 Oct - 1 Nov

A modern kitchen with a central island, pendant lights, and a view of the outdoors.

14. Renovated Retreat with Heated Pool

Redding

Alejandro A.

includes taxes & fees

19 Oct - 20 Oct

A living room with a sectional sofa, a small side table, and a floor lamp.

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

Plymouth

Iva B.

includes taxes & fees

19 Oct - 20 Oct

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

16. 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.

includes taxes & fees

28 Oct - 29 Oct