A waterfall in a forested area with autumn foliage.

Southbury Vacation Rentals

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Check prices for these dates

In two weeks
Nov 6 - Nov 8
In two months
Dec 18 - Dec 20
In three months
Jan 15 - Jan 17
In four months
Feb 12 - Feb 14

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

Cozy One Bedroom Apartment Centrally Located in Southbury
Southbury
10.0 out of 10, Exceptional, (38 reviews)
"Great place. Had everything we needed and was very clean."
United States
Niki B.
The price is ￥16,222
￥21,791 total
includes taxes & fees
Nov 2 - Nov 3
Cozy One Bedroom Apartment Centrally Located in Southbury
A modern kitchen with white cabinets, a black countertop, and a dining area with a table and chairs.

2. 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 ￥17,507
￥39,703 total
includes taxes & fees
Oct 25 - Oct 26
Private Apartment in Southbury 102
A view through a window with a clear sky and lush greenery outside.

3. 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 ￥18,981
￥41,398 total
includes taxes & fees
Nov 3 - Nov 4
Private Apartment in Southbury 101
A modern kitchen with a dining area, large windows, and a TV displaying a streaming service.

4. 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, (6 reviews)
"Beautiful place. Very clean & welcoming "
United States
Chris
The price is ￥23,719
￥37,356 total
includes taxes & fees
Oct 28 - Oct 29
The Perch in the Purchase -- Cozy, unique, and private
A modern kitchen with white cabinets, stainless steel appliances, and a black countertop.

5. Private Apartment in Southbury 105

Private Apartment in Southbury 105
Southbury
The price is ￥22,119
￥45,320 total
includes taxes & fees
Nov 17 - Nov 18
Private Apartment in Southbury 105
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

Bear Retreat - 2-bedroom house in Waterbury
Waterbury
10.0 out of 10, Exceptional, (11 reviews)
"Perfect, spacious area. Super clean. Communication was great. Would definitely book here again."
United States
Radha
The price is ￥17,632
￥52,642 total
includes taxes & fees
Nov 1 - Nov 2
Bear Retreat - 2-bedroom house in Waterbury
A living room with a flat-screen TV displaying a streaming service interface, a white sofa, a small side table, and a patterned rug.

7. 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 ￥16,628
￥22,260 total
includes taxes & fees
Nov 4 - Nov 5
Private, Quiet, Cozy Studio Guesthouse with 75" TV WiFi etc. In Watertown.
A modern kitchen with wooden cabinets, a stainless steel refrigerator, a built-in oven, and a large island with bar stools.

8. 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 ￥10,579
￥22,511 total
includes taxes & fees
Nov 3 - Nov 4
Cozy private room in a shared home with a Full-size bed and private bathroom.
A modern kitchen with white cabinets, a microwave, stove, and sink. There is a dining area with a table and chairs.

9. 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 ￥17,240
￥22,961 total
includes taxes & fees
Oct 25 - Oct 26
Cozy 1-king size bedroom house in quiet Waterbury with 75" TV in your bedroom.
A spacious living room with large windows, a fireplace, and a view of the outdoors.

10. 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 ￥34,324
￥84,164 total
includes taxes & fees
Oct 30 - Oct 31
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.

11. 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 ￥42,787
￥84,483 total
includes taxes & fees
Nov 1 - Nov 2
Watertown Home w/ Yard: 1 Mi to Echo Lake Park!
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.

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

Luxurious-Modern feel w/ custom features - AC, short walk to Shelton
Shelton
The price is ￥23,369
￥69,945 total
includes taxes & fees
Oct 25 - Oct 26
Luxurious-Modern feel w/ custom features - AC, short walk to Shelton
A kitchen with white cabinets, a black refrigerator, a double sink, and a window overlooking a wooded area.

13. Serene Country Cottage

Serene Country Cottage
Woodbridge
8.0 out of 10, Very good, (11 reviews)
"We had a great one night stay here! The place is really cute, clean and comfortable. One of the greatest parts about the stay was the host, Trent. He was welcoming and VERY responsive to questions! "
United States
felicia
The price is ￥19,970
￥33,790 total
includes taxes & fees
Nov 17 - Nov 18
Serene Country Cottage
A cozy cabin interior with a wooden ceiling, a sofa, a coffee table, and a sign reading "Our Happy Place".

14. 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 ￥53,356
￥94,224 total
includes taxes & fees
Nov 8 - Nov 9
The Little Lake Cabin with hot tub
A covered outdoor area with a view of a lake, stone steps, and a grill.

15. North Cliff House - Private Dock & Sauna

North Cliff House - Private Dock & Sauna
Danbury
10.0 out of 10, Exceptional, (9 reviews)
"Enjoyed the property. Beautiful house. Great location. Reserve, stay and enjoy!"
United States
Ron P.
The price is ￥54,434
￥196,080 total
includes taxes & fees
Oct 26 - Oct 27
North Cliff House - Private Dock & Sauna
A modern kitchen with a central island, stainless steel appliances, and pendant lighting.

16. Stylish Westville Apartment near Yale Campus

Stylish Westville Apartment near Yale Campus
West New Haven
9.0 out of 10, Wonderful, (4 reviews)
"Great location, well organized space, well decorated. I loved that there were enough places to sit and be comfortable, many VRBO’s have tiny little sofas that are so uncomfortable, but this has proper furniture. The beds are very firm."
Canada
Alex C.
The price is ￥15,248
￥38,752 total
includes taxes & fees
Oct 26 - Oct 27
Stylish Westville Apartment near Yale Campus
A glass-top table with a woven placemat, a vase with white flowers, and a view of a balcony through a door with curtains.

17. 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 ￥33,697
￥43,140 total
includes taxes & fees
Nov 2 - Nov 3
The Overlook near South Farms in Litchfield County is Hospitality, integrated.
A workspace with a desktop computer, a printer, and a chair.

18. Sunny 1 Full Bed ADA|Free parking

Sunny 1 Full Bed ADA|Free parking
MILFORD
10.0 out of 10, Exceptional, (4 reviews)
"Pool was clean and just right for a quick swim."
United States
Anonymous traveler
The price is ￥10,709
￥12,315 total
includes taxes & fees
Nov 2 - Nov 3
Sunny 1 Full Bed ADA|Free parking
A bedroom with a bed, a blue sofa, a radiator, a window with blinds, a dreamcatcher, and a framed picture on the wall.

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

One bedroom in United States of America, New Haven
Dwight
9.4 out of 10, Exceptional, (3 reviews)
"The property is immaculate and the service very responsive."
United States
Stephanie G.
The price is ￥11,427
￥27,992 total
includes taxes & fees
Oct 25 - Oct 26
One bedroom in United States of America, New Haven
A modern living room with a sofa, coffee table, and a TV mounted on the wall.

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

Once the old Schools house now a newly furnished Apartment
Wallingford Center
9.0 out of 10, Wonderful, (16 reviews)
"Excellent option for a short stay near the heart of it all in Wallingford."
United States
Jeanette W.
The price is ￥20,688
￥49,025 total
includes taxes & fees
Nov 5 - Nov 6
Once the old Schools house now a newly furnished Apartment
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.
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Top Southbury Hotel Reviews

Cambria Hotel New Haven University Area

Cambria Hotel New Haven University Area

10/10 Excellent
"Friendly"
Zoran 3-night trip
Posted less than an hour ago
Cambria Hotel New Haven University Area

Find out more about Southbury

Search for holiday rentals in Southbury on Expedia! You can easily find your home rentals, villas, holiday apartments in Southbury using one of the methods below:

  • View our selection of featured holiday rentals in Southbury
  • Use the map to find apartments and other holiday homes in the Southbury neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Southbury while they last

Look no further and take a look at our great range of rental properties in Southbury!

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.