A multi-tiered waterfall with cascading water over rocks, surrounded by bare trees and a cloudy sky.

Southbury Vacation Rentals

Dates

November 2026

December 2026

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Our top choices for Southbury 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 modern kitchen with white cabinets, stainless steel appliances, and a dining table with chairs.

2. 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.

3. 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.

4. Private Apartment in Southbury 101

Southbury

Marissa G.

AED 991 total

includes taxes & fees

6 Dec - 7 Dec

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

5. Private Apartment in Southbury 105

Southbury

AED 870 total

includes taxes & fees

16 Nov - 17 Nov

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

6. Bear Retreat - 2-bedroom house in Waterbury

Waterbury

Radha

AED 1,201 total

includes taxes & fees

22 Nov - 23 Nov

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

7. 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.

8. 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

Deck: Comfortable outdoor sofa sets for outdoor conversations

9. Serenity Haven: A Modern Retreat

Monroe

Tresha J.

A compact room with a kitchenette, a bed, a wall decorated with photos and a mirror, and a 'No Fishing From Bridge' sign.

10. Welcome to Sweet Abby Rose!

Brewster

Fernanda

AED 665 total

includes taxes & fees

21 Nov - 22 Nov

A bedroom with a bed, a blue sofa, a radiator, a window with blinds, a dreamcatcher, and a framed picture on the wall.

11. One bedroom in United States of America, New Haven

Dwight

Stephanie G.

AED 635 total

includes taxes & fees

8 Dec - 9 Dec

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

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

Watertown

Elizabeth H.

AED 1,892 total

includes taxes & fees

11 Nov - 12 Nov

A kitchen with white cabinets, a black refrigerator, a double sink, and a window overlooking a wooded area.

13. Serene Country Cottage

Woodbridge

felicia

AED 729 total

includes taxes & fees

2 Dec - 3 Dec

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

Oakville

AED 1,980 total

includes taxes & fees

10 Nov - 11 Nov

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.

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

Shelton

A bedroom with a large arched window, a bed, a bedside table with a lamp, and a small seating area with cushions and a plant.

16. Lovely Bohemian Loft Downtwn, Amphitheater,Seaside Park,Metro North,2-10min walk

Downtown Bridgeport

Kim F.

AED 815 total

includes taxes & fees

16 Nov - 17 Nov

A bedroom with a large bed, a dresser, a chair, and a mirror.

17. Modern Westville Home near Yale and Hospitals

West New Haven

Thomas B.

A hotel lobby with a reception desk, seating area, and a large window providing a view of the outdoors.

18. 2 FULL BEDS | NON-SMOKING

MILFORD

AED 287 total

includes taxes & fees

29 Nov - 30 Nov

A row of brick townhouses with wooden front doors, black railings, and a sidewalk.

19. Prime Yale Studio Steps to Sallys Apizza

Downtown New Haven

Milton W.

AED 901 total

includes taxes & fees

17 Nov - 18 Nov

A swimming pool at night with blue lighting.

20. Business or Weekend escape

Stratford

Kimberly

AED 530 total

includes taxes & fees

11 Nov - 12 Nov

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Find vacation rentals that suit your style

Top Southbury Hotel Reviews

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 covered porch with white columns and black hanging lanterns.

The Milestone Inn

Woodbury

10/10 Excellent

Elin

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 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

Comfort Inn Naugatuck-Shelton, CT

Naugatuck

10/10 Excellent

Marta

A modern dining area with multiple tables and chairs, a kitchen area with appliances, and a seating area with a large window.

Holiday Inn Express Hotel & Suites Danbury - I-84 by IHG

Danbury

10/10 Excellent

Robert

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 modern lobby with a high ceiling, brick walls, and a glass enclosure. There are seating areas with tables and chairs, and a kitchen area in the background.

Best Western Danbury/Bethel

Bethel

10/10 Excellent

Mark

A modern building entrance with a covered walkway, a white car parked in front, and two people near the entrance.

Hotel Marcel New Haven, Tapestry Collection By Hilton

Long Wharf

10/10 Excellent

Matthew

A stone building with a covered patio area, outdoor seating, and a fire feature.

Homewood Suites by Hilton Orange New Haven

Orange

10/10 Excellent

Meyra

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

Econo Lodge Bethel - Danbury

Bethel

10/10 Excellent

David O

Frequently Asked Questions

Can I find vacation rentals in Southbury?

Yes, we have vacation rentals near top sights in Southbury, or you can choose a more remote option if you're looking for a relaxing stay. The spas and bars are several reasons why visitors like Southbury. While you're here, grab a bite or have a drink at the restaurants.

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

Lakehouse Boat Dock, Kayaks, Fire-Pit, Pool Table, Air Hockey, Hammock, King Bed: This vacation home rental near Southbury 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.

How many vacation rentals are there in Southbury?

Expedia has 3 vacation rentals for your stay in Southbury.

What can I see and do in Southbury?

Housatonic River and Lake Quassapaug are a couple of scenic spots to enjoy the outdoors, whereas Vicinanza Studios & Gallery is one of the cultural attractions. While here, Southford Falls State Park and Lake Lillinonah are other places worth a visit.

What are vacation rentals like in Southbury?

Vacation rentals are private accommodations you can stay in for a few days or a quick weekend in Southbury. Vacation rentals provide amenities such as patios, hot tubs, and fire pits so you'll have all the conveniences of home. If you're concerned about a sanitized environment, a vacation rental can offer a sense of safety away from shared hotel elevators and busy front desks while still allowing you the excitement and enjoyment of travel. You'll also get more space in a vacation rental than in a hotel, which makes a vacation rental an attractive choice for a small group gathering.

Southbury Vacation Rentals

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Southbury vacation rentals

1. Cozy One Bedroom Apartment Centrally Located in Southbury

2. Private Apartment in Southbury 104

3. Private Apartment in Southbury 102

4. Private Apartment in Southbury 101

5. Private Apartment in Southbury 105

6. Bear Retreat - 2-bedroom house in Waterbury

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

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

9. Serenity Haven: A Modern Retreat

10. Welcome to Sweet Abby Rose!

11. One bedroom in United States of America, New Haven

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

13. Serene Country Cottage

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

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

16. Lovely Bohemian Loft Downtwn, Amphitheater,Seaside Park,Metro North,2-10min walk

17. Modern Westville Home near Yale and Hospitals

18. 2 FULL BEDS | NON-SMOKING

19. Prime Yale Studio Steps to Sallys Apizza

20. Business or Weekend escape

Find vacation rentals that suit your style

Top Southbury Hotel Reviews

Heritage Hotel, Golf & Conference Center

10/10 Excellent

Frequently Asked Questions

Can I find vacation rentals in Southbury?

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

How many vacation rentals are there in Southbury?

What can I see and do in Southbury?

What are vacation rentals like in Southbury?