A waterfall in a forested area with autumn foliage.

Southbury Holiday Rentals

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Check prices for these dates

In two weeks
2 Oct - 4 Oct
In two months
13 Nov - 15 Nov
In three months
11 Dec - 13 Dec
In four months
8 Jan - 10 Jan

Our top choices for Southbury holiday 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, 36, (36 reviews)
"Everything was perfect and it's a great place to stay. Highly recommended and the folks there are A+."
United States
Bob
The price is HK$692
HK$952 total
includes taxes & fees
20 Sept - 21 Sept
Cozy One Bedroom Apartment Centrally Located in Southbury
A modern kitchen with white cabinets, stainless steel appliances, and a grey wooden floor.

2. Private Apartment in Southbury 103

Private Apartment in Southbury 103
Southbury
9.4 out of 10, 6, (6 reviews)
"It was amazing , clean and awesome and good time"
United States
Michael
The price is HK$826
HK$1,858 total
includes taxes & fees
16 Sept - 17 Sept
Private Apartment in Southbury 103
A modern kitchen with white cabinets, stainless steel appliances, and a dining table with chairs.

3. Private Apartment in Southbury 104

Private Apartment in Southbury 104
Southbury
10.0 out of 10, 1, (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 HK$847
HK$1,952 total
includes taxes & fees
17 Sept - 18 Sept
Private Apartment in Southbury 104
A view through a window with a clear sky and lush greenery outside.

4. Private Apartment in Southbury 101

Private Apartment in Southbury 101
Southbury
9.6 out of 10, 7, (7 reviews)
"The apartment was nice, big area, loved this rental."
United States
Marissa G.
The price is HK$1,145
HK$2,248 total
includes taxes & fees
6 Oct - 7 Oct
Private Apartment in Southbury 101
A white house with a grey roof, a balcony with a blue umbrella, and a visible chimney.

5. The Perch in the Purchase -- Cozy, unique, and private

The Perch in the Purchase -- Cozy, unique, and private
Southbury
10.0 out of 10, 3, (3 reviews)
"Beautiful place. Very clean & welcoming "
United States
Chris
The price is HK$1,144
HK$1,811 total
includes taxes & fees
22 Sept - 23 Sept
The Perch in the Purchase -- Cozy, unique, and private
A modern kitchen with white cabinets, a dining area with a black table and chairs, and a large window with curtains.

6. Private Apartment in Southbury 105

Private Apartment in Southbury 105
Southbury
The price is HK$941
HK$2,084 total
includes taxes & fees
22 Sept - 23 Sept
Private Apartment in Southbury 105
A spacious living room with large windows, a fireplace, and a view of the outdoors.

7. 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 HK$2,141
HK$4,227 total
includes taxes & fees
18 Sept - 19 Sept
Watertown Home w/ Yard: 1 Mi to Echo Lake Park!
A two-story house with a porch, a front door with a wreath, and a small garden area.

8. Bear Retreat - 2-bedroom house in Waterbury

Bear Retreat - 2-bedroom house in Waterbury
Waterbury
10.0 out of 10, 7, (7 reviews)
"Perfect, spacious area. Super clean. Communication was great. Would definitely book here again."
United States
Radha
The price is HK$1,020
HK$2,710 total
includes taxes & fees
8 Oct - 9 Oct
Bear Retreat - 2-bedroom house in Waterbury
A modern living room with a flat-screen TV mounted on a white wall, a clock, and a minimalist design.

9. 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, 12, (12 reviews)
"Great night stay! Wonderful place would definitely recommend! "
United States
Laurie P.
The price is HK$698
HK$873 total
includes taxes & fees
16 Sept - 17 Sept
Private, Quiet, Cozy Studio Guesthouse with 75" TV WiFi etc. In Watertown.
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, 6, (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 HK$1,717
HK$3,945 total
includes taxes & fees
16 Sept - 17 Sept
Watertown Home w/ Yard: 1 Mi to Echo Lake Park!
A glass-top table with a woven placemat, a vase with white flowers, and a view of a balcony through a door with curtains.

11. 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, 16, (16 reviews)
"Very clean & cozy with everything we needed!"
United States
Joe K.
The price is HK$1,686
HK$2,159 total
includes taxes & fees
17 Sept - 18 Sept
The Overlook near South Farms in Litchfield County is Hospitality, integrated.
A multi-story house with a dock and boats, surrounded by dense forest.

12. North Cliff House - Private Dock & Sauna

North Cliff House - Private Dock & Sauna
Danbury
10.0 out of 10, 8, (8 reviews)
"Enjoyed the property. Beautiful house. Great location. Reserve, stay and enjoy!"
United States
Ron P.
The price is HK$2,744
HK$8,665 total
includes taxes & fees
16 Sept - 17 Sept
North Cliff House - Private Dock & Sauna
A house with a front porch, a garage, and a well-maintained lawn.

13. Angelica’s safe haven @ west haven

Angelica’s safe haven @ west haven
West Haven
10.0 out of 10, 7, (7 reviews)
"We had a great stay. Comfortable home with a large living room. Beds were great. "
United States
Jason V.
The price is HK$1,176
HK$2,676 total
includes taxes & fees
16 Sept - 17 Sept
Angelica’s safe haven @ west haven
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, 4, (4 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 HK$2,579
HK$4,601 total
includes taxes & fees
30 Sept - 1 Oct
The Little Lake Cabin with hot tub
A room with a large window, wooden furniture, and a vase with a plant.

15. VintageGem: Prime East Rock 5 mins to Yale 5 beds

VintageGem: Prime East Rock 5 mins to Yale 5 beds
East Rock
9.4 out of 10, 3, (3 reviews)
"Met all expectations and the location is excellent."
United States
James D.
The price is HK$1,278
HK$3,155 total
includes taxes & fees
16 Sept - 17 Sept
VintageGem: Prime East Rock 5 mins to Yale 5 beds
A sunroom with large windows, wicker furniture, and a ceiling fan.

16. Welcome to Dove Haven — a peaceful and stylish retreat in the heart of Westville. Relax in the private hot tub, enjoy cozy sun-filled spaces, and walk to charming cafés, top restaurants, and beautiful Edgewood Park. Minutes from Yale and downtown.

Welcome to Dove Haven — a peaceful and stylish retreat in the heart of Westville. Relax in the private hot tub, enjoy cozy sun-filled spaces, and walk to charming cafés, top restaurants, and beautiful Edgewood Park. Minutes from Yale and downtown.
West New Haven
10.0 out of 10, 15, (15 reviews)
"Beautiful house, convenient location, great amenities, responsive host."
United States
Niels G.
The price is HK$4,705
HK$8,925 total
includes taxes & fees
16 Sept - 17 Sept
Welcome to Dove Haven — a peaceful and stylish retreat in the heart of Westville. Relax in the private hot tub, enjoy cozy sun-filled spaces, and walk to charming cafés, top restaurants, and beautiful Edgewood Park. Minutes from Yale and downtown.
A patio with a round table and chairs, overlooking a body of water and a forested area during sunset.

17. Candlewood Lake Retreat with Private Dock

Candlewood Lake Retreat with Private Dock
New Milford
10.0 out of 10, 60, (60 reviews)
"Great property for a family to enjoy the lake!"
United States
Jenny B.
Candlewood Lake Retreat with Private Dock
A front view of a house with a wooden staircase leading to a front door, a small porch area, and a garage door.

18. 1-bedroom vacation home 22 minutes from Quinnipiac University

1-bedroom vacation home 22 minutes from Quinnipiac University
Wolcott
9.6 out of 10, 4, (4 reviews)
"Very clean and the host was great "
United States
David G.
The price is HK$1,176
HK$3,023 total
includes taxes & fees
3 Oct - 4 Oct
1-bedroom vacation home 22 minutes from Quinnipiac University
A cozy living room with a grey sofa, a coffee table with books and a vase of flowers, and bookshelves filled with books and decorative items.

19. Spacious Bohemian Nook

Spacious Bohemian Nook
West New Haven
8.4 out of 10, 9, (9 reviews)
"We had a good time. Did some relaxing, a little beachtime and ate some good food."
United States
Erin S.
The price is HK$882
HK$1,922 total
includes taxes & fees
16 Sept - 17 Sept
Spacious Bohemian Nook
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, 14, (14 reviews)
"Excellent option for a short stay near the heart of it all in Wallingford."
United States
Jeanette W.
The price is HK$925
HK$2,288 total
includes taxes & fees
23 Sept - 24 Sept
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

New Haven Hotel

New Haven Hotel

8/10 Good
"Quiet clean and comfortable"
Avery 1-night trip
Posted 5 hours ago
New Haven Hotel

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 holiday rentals in Southbury?

Yes, there are holiday rentals close to the most popular sights in Southbury, or you can select a more secluded 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 holiday rentals that Southbury has to offer?

Lakehouse Boat Dock, Kayaks, Fire-Pit, Pool Table, Air Hockey, Hammock, King Bed: This holiday home rental outside of Southbury offers a fireplace, a patio and a BBQ 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 that you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games.

How many holiday rentals are there in Southbury?

Expedia has 3 holiday rentals for your stay in Southbury.

What can I see and do in Southbury?

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

What are holiday rentals like in Southbury?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Southbury. Holiday rentals provide amenities such as WiFi and washers and dryers so you'll feel right at home. If you're concerned about a clean environment, holiday rentals can offer a sense of safety away from shared hotel lifts and lobbies bustling with people while still allowing you the experience of travel. You'll also find more space in a holiday rental than in a traditional hotel, which makes a holiday rental an attractive choice for small groups.