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Holiday Rentals in Southbury

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Our top choices for Southbury holiday rentals

1. Cozy One Bedroom Apartment Centrally Located in Southbury

Cozy One Bedroom Apartment Centrally Located in Southbury
Southbury
10.0 out of 10, Exceptional, (39 reviews)
"Charles was super responsive and the bed was amazingly comfortable. Also the shower head great water pressure :-)"
United States
Lisbeth
The price is €128
includes taxes & fees
2 Nov - 3 Nov
Cozy One Bedroom Apartment Centrally Located in Southbury

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 €202
includes taxes & fees
28 Oct - 29 Oct
Private Apartment in Southbury 102

3. 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 €263
includes taxes & fees
22 Nov - 23 Nov
Private Apartment in Southbury 104

4. 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 €249
includes taxes & fees
17 Nov - 18 Nov
Private Apartment in Southbury 101

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, Exceptional, (6 reviews)
"Beautiful place. Very clean & welcoming "
United States
Chris
The price is €220
includes taxes & fees
28 Oct - 29 Oct
The Perch in the Purchase -- Cozy, unique, and private

6. Private Apartment in Southbury 105

Private Apartment in Southbury 105
Southbury
The price is €254
includes taxes & fees
17 Nov - 18 Nov
Private Apartment in Southbury 105

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 €133
includes taxes & fees
4 Nov - 5 Nov
Private, Quiet, Cozy Studio Guesthouse with 75" TV WiFi etc. In Watertown.

8. Bear Retreat - 2-bedroom house in Waterbury

Bear Retreat - 2-bedroom house in Waterbury
Waterbury
10.0 out of 10, Exceptional, (12 reviews)
"Perfect, spacious area. Super clean. Communication was great. Would definitely book here again."
United States
Radha
The price is €300
includes taxes & fees
1 Nov - 2 Nov
Bear Retreat - 2-bedroom house in Waterbury

9. 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 €128
includes taxes & fees
21 Nov - 22 Nov
Cozy private room in a shared home with a Full-size bed and private bathroom.

10. 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 €135
includes taxes & fees
29 Oct - 30 Oct
Cozy 1-king size bedroom house in quiet Waterbury with 75" TV in your bedroom.

11. Modern Westville Home near Yale and Hospitals

Modern Westville Home near Yale and Hospitals
West New Haven
10.0 out of 10, Exceptional, (5 reviews)
"Very clean and comfortable space. Excellent location and parking was a plus. We have stayed here twice and would definitely recommend to friends or family. "
United States
Thomas B.
The price is €219
includes taxes & fees
2 Nov - 3 Nov
Modern Westville Home near Yale and Hospitals

12. Welcome to Sweet Abby Rose!

Welcome to Sweet Abby Rose!
Brewster
10.0 out of 10, Exceptional, (2 reviews)
"We had a wonderful experience! The RV was very nice and cozy. Everything was clean and well maintained. The property was beautiful. The host was very helpful and accommodating. Definitely plan on coming back!"
United States
Fernanda
The price is €170
includes taxes & fees
30 Oct - 31 Oct
Welcome to Sweet Abby Rose!

13. 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
9.4 out of 10, Exceptional, (19 reviews)
"The accommodations were incredible. The host provided many helpful materials that made the stay very comfortable. The apartment was very cute and had nice amenities for the guests that go above any beyond what a hotel can provide."
United States
Bailey
The price is €213
includes taxes & fees
2 Nov - 3 Nov
Lovely Bohemian Loft Downtwn, Amphitheater,Seaside Park,Metro North,2-10min walk

14. Business or Weekend escape

Business or Weekend escape
Stratford
9.2 out of 10, Wonderful, (60 reviews)
"Definitely clean - good place for an overnight stay."
United States
Kimberly
The price is €140
includes taxes & fees
31 Oct - 1 Nov
Business or Weekend escape

15. 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 €173
includes taxes & fees
23 Nov - 24 Nov
One bedroom in United States of America, New Haven

16. 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 €431
includes taxes & fees
2 Nov - 3 Nov
Luxurious-Modern feel w/ custom features - AC, short walk to Shelton

17. 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 €481
includes taxes & fees
28 Oct - 29 Oct
Watertown Home w/ Yard: 1 Mi to Echo Lake Park!

18. 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 €283
includes taxes & fees
28 Oct - 29 Oct
Once the old Schools house now a newly furnished Apartment

19. 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 €194
includes taxes & fees
17 Nov - 18 Nov
Serene Country Cottage

20. 2 FULL BEDS | NON-SMOKING

2 FULL BEDS | NON-SMOKING
MILFORD
8.8 out of 10, Excellent, (5 reviews)
The price is €70
includes taxes & fees
8 Nov - 9 Nov
2 FULL BEDS | NON-SMOKING
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, apart-hotels, 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 favorite 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 depends 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 €70 per night. Entering your travel dates in the search wizard you might find 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?

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?

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.