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Southbury Holiday Rentals

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Check prices for these dates

In two weeks
28 Aug - 30 Aug
In two months
9 Oct - 11 Oct
In three months
6 Nov - 8 Nov
In four months
4 Dec - 6 Dec

Our top choices for Southbury holiday rentals

Exterior

1. Cozy One Bedroom Apartment Centrally Located in Southbury

Cozy One Bedroom Apartment Centrally Located in Southbury
Southbury
10.0 out of 10, Exceptional, (35 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$727
HK$993 total
includes taxes & fees
9 Sept - 10 Sept
Cozy One Bedroom Apartment Centrally Located in Southbury
Interior

2. 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 HK$1,108
HK$2,269 total
includes taxes & fees
8 Sept - 9 Sept
Private Apartment in Southbury 101
Interior

3. Private Apartment in Southbury 105

Private Apartment in Southbury 105
Southbury
The price is HK$1,177
HK$2,387 total
includes taxes & fees
2 Sept - 3 Sept
Private Apartment in Southbury 105
Outdoor dining

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, (3 reviews)
"Beautiful place. Very clean & welcoming "
United States
Chris
The price is HK$1,144
HK$1,827 total
includes taxes & fees
25 Aug - 26 Aug
The Perch in the Purchase -- Cozy, unique, and private
Coffee/tea maker, fridge, microwave, oven

5. Private Apartment in Southbury 104

Private Apartment in Southbury 104
Southbury
10.0 out of 10, Exceptional, (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$1,073
HK$2,229 total
includes taxes & fees
8 Sept - 9 Sept
Private Apartment in Southbury 104
Coffee/tea maker, fridge, microwave, oven

6. Private Apartment in Southbury 103

Private Apartment in Southbury 103
Southbury
10.0 out of 10, Exceptional, (4 reviews)
"Property management team was very quick to respond to any question or issue I had. Excellent location around eateries and activities "
United States
Dominick S.
The price is HK$1,073
HK$2,229 total
includes taxes & fees
8 Sept - 9 Sept
Private Apartment in Southbury 103
Interior

7. Private Apartment in Southbury 102

Private Apartment in Southbury 102
Southbury
9.0 out of 10, Wonderful, (6 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 HK$1,003
HK$2,139 total
includes taxes & fees
8 Sept - 9 Sept
Private Apartment in Southbury 102
Interior

8. 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
8.8 out of 10, Excellent, (11 reviews)
"Great night stay! Wonderful place would definitely recommend! "
United States
Laurie P.
The price is HK$855
HK$1,140 total
includes taxes & fees
8 Sept - 9 Sept
Private, Quiet, Cozy Studio Guesthouse with 75" TV WiFi etc. In Watertown.
Cookware/dishes/utensils

9. Awesome Lake Home with tons of fun!

Awesome Lake Home with tons of fun!
New Fairfield
9.8 out of 10, Exceptional, (11 reviews)
"Nicole is a wonderful host. We had a fantastic stay at her house. The home was beautifully prepared, and we felt very comfortable throughout our visit. Even though it was a rainy weekend, we were still able to enjoy the huge hot tub and had a great time playing the card games and board games provided. Thank you!!"
United States
W Y.
The price is HK$3,177
HK$5,588 total
includes taxes & fees
16 Aug - 17 Aug
Awesome Lake Home with tons of fun!
Outdoor dining

10. Candlewood Lake Retreat with Private Dock

Candlewood Lake Retreat with Private Dock
New Milford
10.0 out of 10, Exceptional, (56 reviews)
"Great property for a family to enjoy the lake!"
United States
Jenny B.
The price is HK$11,255
HK$18,094 total
includes taxes & fees
25 Aug - 26 Aug
Candlewood Lake Retreat with Private Dock
Front of property

11. Beechmont - Perfect for Family Retreat!

Beechmont - Perfect for Family Retreat!
5.0 star property
North End
The price is HK$6,390
HK$10,094 total
includes taxes & fees
18 Aug - 19 Aug
Beechmont - Perfect for Family Retreat!
Exterior

12. Angelica’s safe haven @ west haven

Angelica’s safe haven @ west haven
West Haven
10.0 out of 10, Exceptional, (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$1,059
HK$2,636 total
includes taxes & fees
11 Aug - 12 Aug
Angelica’s safe haven @ west haven
1 bedroom, Internet, bed sheets

13. Welcome to Sweet Abby Rose!

Welcome to Sweet Abby Rose!
Brewster
10.0 out of 10, Exceptional, (1 review)
"The place is super comfortable and has a great outdoor area for chatting; I would definitely like to come back and stay longer."
United States
Yasmin G.
The price is HK$784
HK$1,445 total
includes taxes & fees
11 Aug - 12 Aug
Welcome to Sweet Abby Rose!
Interior

14. 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, (13 reviews)
"The property was very clean and inviting and the owner was very welcoming and helpful!"
United States
Sarah
The price is HK$1,687
HK$2,159 total
includes taxes & fees
16 Aug - 17 Aug
The Overlook near South Farms in Litchfield County is Hospitality, integrated.
Coffee/tea maker, fridge, microwave, oven

15. Renovated Retreat with Heated Pool

Renovated Retreat with Heated Pool
Redding
10.0 out of 10, Exceptional, (2 reviews)
"Beautiful house, very clean, spacious and a great host!!!"
United States
Alejandro A.
The price is HK$5,405
HK$9,422 total
includes taxes & fees
2 Sept - 3 Sept
Renovated Retreat with Heated Pool
1 bedroom, desk, iron/ironing board, free WiFi

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

Lovely Bohemian Loft Downtwn, Amphitheater,Seaside Park,Metro North,2-10min walk
Downtown Bridgeport
9.8 out of 10, Exceptional, (16 reviews)
"I was surprised by the large size of this apt, and that it had everything I needed for my stay. The location was perfect and very close to the event I was there for. Excellent host and I'm looking forward to booking this place again next year."
United States
Shamel
The price is HK$1,098
HK$1,820 total
includes taxes & fees
11 Aug - 12 Aug
Lovely Bohemian Loft Downtwn, Amphitheater,Seaside Park,Metro North,2-10min walk
Coffee/tea maker, fridge, microwave, oven

17. The Jefferson Guest House, Spacious, Special Views

The Jefferson Guest House, Spacious, Special Views
Litchfield
10.0 out of 10, Exceptional, (8 reviews)
"I stayed here for four nights, including one with my son, and it was fantastic.Everything is brand new, clean, and beautifully appointed, with every amenity you could want."
United States
Jennifer A.
The price is HK$2,288
HK$2,978 total
includes taxes & fees
3 Sept - 4 Sept
The Jefferson Guest House, Spacious, Special Views
Coffee/tea maker, fridge, microwave, oven

18. Modern home with a private Heated pool and jacuzzi

Modern home with a private Heated pool and jacuzzi
Hamden
The price is HK$6,747
HK$10,049 total
includes taxes & fees
16 Aug - 17 Aug
Modern home with a private Heated pool and jacuzzi
Lobby

19. Spacious Bohemian Nook

Spacious Bohemian Nook
West New Haven
8.4 out of 10, Very good, (8 reviews)
"The place was incredibly clean. The instructions were clear for entering and locking up. Great experience! Thanks Dylan. "
United States
Andrew P.
The price is HK$883
HK$2,009 total
includes taxes & fees
11 Aug - 12 Aug
Spacious Bohemian Nook
TV, books

20. 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 HK$1,355
HK$3,931 total
includes taxes & fees
12 Aug - 13 Aug
Luxurious-Modern feel w/ custom features - AC, short walk to Shelton
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

Hotel Marcel New Haven, Tapestry Collection By Hilton

Hotel Marcel New Haven, Tapestry Collection By Hilton

10/10 Excellent
"Great hotel, clean and modern"
Anastasiya 2-night trip
Posted less than an hour ago
Hotel Marcel New Haven, Tapestry Collection By Hilton

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?

Cozy 1-bedroom house in lovely New Haven with AC close to Yale University: This holiday home rental outside of Southbury is equipped with a patio, air conditioning and a Smart TV to help you feel comfortable during your stay.

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 Lillinonah and Housatonic River 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 Kettletown 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.