Photo by Richard Miska

Southbury Holiday Rentals

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Our top choices for Southbury holiday rentals

New One Bedroom Apartment Centrally Located in Southbury

Southbury
9.8 out of 10, Exceptional, (19)
"Perfect sized apartment for a short stay - very convenient to my destination"
United States
S
The price is AU$189
includes taxes & fees
10 Dec - 11 Dec
New One Bedroom Apartment Centrally Located in Southbury

Private Apartment in Southbury 101

Southbury
9.4 out of 10, Exceptional, (6)
"Great stay. Clean, open space, easy access, and a nice pond in back to bring the dog. Would come back again."
United States
Rooster D.
The price is AU$451
includes taxes & fees
17 Dec - 18 Dec
Private Apartment in Southbury 101

Private Apartment in Southbury 103

Southbury
10.0 out of 10, Exceptional, (2)
"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 AU$424
includes taxes & fees
10 Dec - 11 Dec
Private Apartment in Southbury 103

Entire guesthouse in Southbury, Connecticut 3 guests1 bedroom2 beds1 bath.

2.0 star property
Southbury
10.0 out of 10, Exceptional, (1)
"Beautiful place. Very clean & welcoming "
United States
Chris
The price is AU$291
includes taxes & fees
10 Dec - 11 Dec
Entire guesthouse in Southbury, Connecticut 3 guests1 bedroom2 beds1 bath.

Cozy cute Relaxing home

Southbury
8.8 out of 10, Excellent, (6)
"nice quiet area"
United States
Alex V.
The price is AU$510
includes taxes & fees
4 Jan - 5 Jan 2026
Cozy cute Relaxing home

The Southbury Duo Apartments

Southbury
The price is AU$831
includes taxes & fees
10 Dec - 11 Dec
The Southbury Duo Apartments

Creekside Retreat Tent

New Milford
10.0 out of 10, Exceptional, (4)
"Absolutely beautiful location and wonderful hosts very romantic spot lots of hiking trails near and on premises me and my husband loved the fact we slept by the water and can hear the water running all night very peaceful and beautiful site ."
United States
yarelis t.
The price is AU$295
includes taxes & fees
10 Dec - 11 Dec
Creekside Retreat Tent

Stylish Sheek Loft Dwntwn, Amphitheater, Park, Metro North, Ferry All 2-10min

Downtown Bridgeport
10.0 out of 10, Exceptional, (2)
"Ricardo’s place was perfect for our needs! A small, clean and cozy place, not far from our daytime destination, the apartment offers all the basics - kitchenette, nice bathroom and modern shower, a comfy Queen Size bed, and even some snacks and essentials for a comfortable stay. The area has some restraunts and bars nearby too, though we were happy to stay in and watch some Netflix. I would highly recommend this apartment to a friend, and Ricardo has been a pleasure. Thanks so much!"
United States
Anonymous traveller
The price is AU$250
includes taxes & fees
10 Dec - 11 Dec
Stylish Sheek Loft Dwntwn, Amphitheater, Park, Metro North, Ferry All 2-10min

Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.

Cheshire
9.4 out of 10, Exceptional, (13)
"Needed a place to sleep for a couple of nights and this worked for us."
United States
James (Jim) L.
Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.

Westville Stay • 2BR • Near Yale • Free Parking

West New Haven
10.0 out of 10, Exceptional, (2)
"We were only here for a short stay, but everything was smooth and comfortable for us! Hotel-like linens and blackout curtains made for a very cozy sleeping experience."
United States
ross f.
The price is AU$361
includes taxes & fees
8 Jan - 9 Jan 2026
Westville Stay • 2BR • Near Yale • Free Parking

Business or Weekend escape

Stratford
9.2 out of 10, Wonderful, (51)
"Clean room, easy check-in, parking available on-site "
United States
Cindy
The price is AU$224
includes taxes & fees
4 Jan - 5 Jan 2026
Business or Weekend escape

#26 Beautifully Renovated 2 BR Home

Plainville
10.0 out of 10, Exceptional, (4)
"We thoroughly enjoyed our stay! The space was great for our family of 4. Would recommend!"
United States
LaTanya W.
The price is AU$335
includes taxes & fees
10 Dec - 11 Dec
#26 Beautifully Renovated 2 BR Home

Charming & Private 1-bed & 1 ba ,sleeps 2, on 1st floor of a 5 bed 3ba House,

Shelton
9.0 out of 10, Wonderful, (2)
"The house was very clean. Rudolph and his son were very personable and welcoming. Very much enjoyed our stay."
United States
Alex C.
The price is AU$300
includes taxes & fees
4 Jan - 5 Jan 2026
Charming & Private 1-bed & 1 ba ,sleeps 2, on 1st floor of a 5 bed 3ba House,

Private, Quiet, Cozy Studio Guesthouse with 75" TV WiFi etc. In Watertown.

Watertown
9.0 out of 10, Wonderful, (8)
"Great night stay! Wonderful place would definitely recommend! "
United States
Laurie P.
The price is AU$187
includes taxes & fees
10 Dec - 11 Dec
Private, Quiet, Cozy Studio Guesthouse with 75" TV WiFi etc. In Watertown.

Renovated 2BR Retreat / Modern Comforts Included

West End - West Side
10.0 out of 10, Exceptional, (2)
"Very pretty, clean place for us to stay while visiting family. Communication was very timely. Would definitely stay here again"
United States
Deborah
The price is AU$439
includes taxes & fees
10 Dec - 11 Dec
Renovated 2BR Retreat / Modern Comforts Included

All New Private and Cozy in great location

Wallingford
8.8 out of 10, Excellent, (6)
"The pictures must have been old. Very deceiving. Expected it to be more spacious. Hard to get in and out because of the busy road"
United States
ROBERT P.
The price is AU$440
includes taxes & fees
13 Dec - 14 Dec
All New Private and Cozy in great location

One bedroom apartment in United States of America, New Haven

Dwight
10.0 out of 10, Exceptional, (1)
"Apartment was very clean and well supplied, host very responsive. Location is convenient to Yale and restaurants. As noted in the listing, you'll have to carry your luggage up 4 flights of stairs. There is some street noise as is typical for that part of the city. Very happy with it overall and plan to stay again."
United States
Philip S.
The price is AU$315
includes taxes & fees
11 Dec - 12 Dec
One bedroom apartment in United States of America, New Haven

Urban Oasis 3BR Parking Washer & Dryer Yale East Rock

East Rock
9.6 out of 10, Exceptional, (10)
"Thanks to the detailed information from the host check-in couldn’t have been easier. The home was clean and well-appointed. Great location with access to the Yale tram and local markets and restaurants. "
United States
Denyce D.
The price is AU$348
includes taxes & fees
10 Dec - 11 Dec
Urban Oasis 3BR Parking Washer & Dryer Yale East Rock

Once the old Schools house now a newly furnished Apartment

Wallingford Center
9.0 out of 10, Wonderful, (13)
"Excellent option for a short stay near the heart of it all in Wallingford."
United States
Jeanette W.
The price is AU$439
includes taxes & fees
10 Dec - 11 Dec
Once the old Schools house now a newly furnished Apartment

Angelica’s safe haven @ west haven

West Haven
10.0 out of 10, Exceptional, (6)
"Quiet place with spacious living room perfect for movie nights. Also just a 10-minute drive from the beach and multiple dining options. Host was very accommodating and communicative. Would stay here again."
United States
Veronica
The price is AU$510
includes taxes & fees
10 Dec - 11 Dec
Angelica’s safe haven @ west haven
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

Find out more about Southbury

Everything you need to know about Southbury holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Southbury holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Southbury holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Southbury holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Southbury. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Southbury holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Southbury holiday rentals we have selected for you start as low as AU$189 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Southbury rentals

At Expedia, we put the best Southbury holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Southbury rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Southbury holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Southbury. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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?

Lakeside/Sleeps20/HotTub/GameRoom/2Acres/Firepit: This holiday home rental outside of Southbury is located on a lake, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 6 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a garden, an arcade/games room and 1 hot tub so that you can immerse yourself in your holiday.

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?

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 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.