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Southbury Holiday Rentals

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Check prices for these dates

In two weeks
19 Dec - 21 Dec
In two months
30 Jan - 1 Feb
In three months
27 Feb - 1 Mar
In four months
27 Mar - 29 Mar

Holiday Rentals in Southbury

Exterior
New One Bedroom Apartment Centrally Located in Southbury

Apartment in 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 HK$701
HK$961 total
includes taxes & fees
5 Dec - 6 Dec
New One Bedroom Apartment Centrally Located in Southbury
Interior
Private Apartment in Southbury 101

Apartment in 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 HK$872
HK$2,228 total
includes taxes & fees
7 Dec - 8 Dec
Private Apartment in Southbury 101
Fridge, microwave, oven, stovetop
Private Apartment in Southbury 103

Apartment in 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 HK$825
HK$2,167 total
includes taxes & fees
7 Dec - 8 Dec
Private Apartment in Southbury 103
Property grounds
Private Apartment in Southbury 102

Apartment in Southbury

9.6 out of 10, Exceptional, (4)
"Overall we had a great stay, the split unit air conditioner stopped working after a few days but the property manager quickly resolved the problem as temperatures were rising. Kitchen in the apartment is equipped for a long stay as it had most of what we needed. Would recommend. "
United States
Jared G.
Private Apartment in Southbury 102
Terrace/patio
Cozy cute Relaxing home

Holiday Home in Southbury

8.8 out of 10, Excellent, (6)
"nice quiet area"
United States
Alex V.
The price is HK$1,401
HK$2,584 total
includes taxes & fees
20 Dec - 21 Dec
Cozy cute Relaxing home
TV
Entire guesthouse in Southbury, Connecticut 3 guests1 bedroom2 beds1 bath.

Apartment in Southbury

2.0 star property
The price is HK$1,246
HK$1,812 total
includes taxes & fees
22 Dec - 23 Dec
Entire guesthouse in Southbury, Connecticut 3 guests1 bedroom2 beds1 bath.
Fridge, microwave, oven, dishwasher
The Southbury Duo Apartments

Apartment in Southbury

The price is HK$1,821
HK$4,235 total
includes taxes & fees
16 Dec - 17 Dec
The Southbury Duo Apartments
Property grounds
Creekside Retreat Tent

Camping in 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 HK$1,168
HK$1,498 total
includes taxes & fees
7 Dec - 8 Dec
Creekside Retreat Tent
1 bedroom, desk, iron/ironing board, free WiFi
Stylish Sheek Loft Dwntwn, Amphitheater, Park, Metro North, Ferry All 2-10min

Apartment in 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 HK$662
HK$1,275 total
includes taxes & fees
8 Dec - 9 Dec
Stylish Sheek Loft Dwntwn, Amphitheater, Park, Metro North, Ferry All 2-10min
1 bedroom, iron/ironing board, WiFi, bed sheets
Once the old Schools house now a newly furnished Apartment

Holiday Home in 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 HK$895
HK$2,244 total
includes taxes & fees
6 Dec - 7 Dec
Once the old Schools house now a newly furnished Apartment
1 bedroom, desk, iron/ironing board, WiFi
One bedroom apartment in United States of America, New Haven

Apartment in 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 HK$739
HK$1,611 total
includes taxes & fees
28 Dec - 29 Dec
One bedroom apartment in United States of America, New Haven
Pool
Business or Weekend escape

Holiday Home in Stratford

9.2 out of 10, Wonderful, (51)
"Clean room, easy check-in, parking available on-site "
United States
Cindy
The price is HK$662
HK$1,140 total
includes taxes & fees
1 Jan - 2 Jan 2026
Business or Weekend escape
Outdoor dining
Top Rated Gem, Fire Pit, Near Beach, Fairfield U, 90 min to NYC

Holiday Home in Fairfield

10.0 out of 10, Exceptional, (22)
"Great family home. Location is perfect, close to everything yet private and quiet. "
United States
Margaret W.
The price is HK$1,596
HK$3,927 total
includes taxes & fees
8 Dec - 9 Dec
Top Rated Gem, Fire Pit, Near Beach, Fairfield U, 90 min to NYC
2 bedrooms, iron/ironing board, travel cot, WiFi
Renovated 2BR Retreat / Modern Comforts Included

Apartment in 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 HK$824
HK$2,177 total
includes taxes & fees
14 Dec - 15 Dec
Renovated 2BR Retreat / Modern Comforts Included
Fridge, microwave, oven, stovetop
Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.

Apartment in Cheshire

9.2 out of 10, Wonderful, (11)
"Needed a place to sleep for a couple of nights and this worked for us."
United States
James (Jim) L.
The price is HK$659
HK$1,271 total
includes taxes & fees
6 Dec - 7 Dec
Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.
Cookware/dishes/utensils
Urban Oasis 3BR Parking Washer & Dryer Yale East Rock

Apartment in 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 HK$739
HK$2,082 total
includes taxes & fees
8 Dec - 9 Dec
Urban Oasis 3BR Parking Washer & Dryer Yale East Rock
Fridge, microwave, oven, stovetop
#26 Beautifully Renovated 2 BR Home

Holiday Home in 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 HK$750
HK$1,664 total
includes taxes & fees
10 Dec - 11 Dec
#26 Beautifully Renovated 2 BR Home
Interior
Charming & Private 1-bed & 1 ba ,sleeps 2, on 1st floor of a 5 bed 3ba House,

Holiday Home in 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 HK$934
HK$1,532 total
includes taxes & fees
8 Dec - 9 Dec
Charming & Private 1-bed & 1 ba ,sleeps 2, on 1st floor of a 5 bed 3ba House,
Interior
Private, Quiet, Cozy Studio Guesthouse with 75" TV WiFi etc. In Watertown.

Apartment in Watertown

9.0 out of 10, Wonderful, (8)
"Great night stay! Wonderful place would definitely recommend! "
United States
Laurie P.
The price is HK$693
HK$952 total
includes taxes & fees
8 Dec - 9 Dec
Private, Quiet, Cozy Studio Guesthouse with 75" TV WiFi etc. In Watertown.
TV
Studio City Stay in the heart of Downtown New Haven, commutable and walkable to Yale and Yale hospital.

Apartment in Dwight

8.0 out of 10, Very good, (2)
"The studio apartment is in a very convenient location. It is a lovely walk to Yale. Many restaurants just outside the door. My friends, who joined me for a meal, found parking easily. It was a plus having use of a parking pass for Dwight Street. We never had a problem getting a parking spot. We also loved being able to bring our two small pups with us. The bottle of wine was a thoughtful touch. "
United States
ELIZABETH M S M.
The price is HK$899
HK$1,602 total
includes taxes & fees
5 Dec - 6 Dec
Studio City Stay in the heart of Downtown New Haven, commutable and walkable to Yale and Yale hospital.
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

Homewood Suites by Hilton Orange New Haven

Homewood Suites by Hilton Orange New Haven

10/10 Excellent
"Great property, clean rooms. Pool was awesome, staff was amazing! "
Frederick 1-night trip
Posted 1 day ago
Homewood Suites by Hilton Orange New Haven

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?

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.