A waterfall in a forested area with autumn foliage.

Southbury Vacation Rentals

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Check prices for these dates

In two weeks
Nov 20 - Nov 22
In two months
Jan 1 - Jan 3
In three months
Jan 29 - Jan 31
In four months
Feb 26 - Feb 28

Our top choices for Southbury vacation 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, Exceptional, (39 reviews)
"Charles was super responsive and the bed was amazingly comfortable. Also the shower head great water pressure :-)"
United States
Lisbeth
$116 nightly
The price is $131
Dec 1 - Dec 2
Total with taxes and fees
Cozy One Bedroom Apartment Centrally Located in Southbury
A modern kitchen with white cabinets, stainless steel appliances, and a dining table with chairs.

2. 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.
$230 nightly
The price is $262
Dec 6 - Dec 7
Total with taxes and fees
Private Apartment in Southbury 104
A modern kitchen with white cabinets, a black countertop, and a dining area with a table and chairs.

3. 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.
$218 nightly
The price is $248
Nov 30 - Dec 1
Total with taxes and fees
Private Apartment in Southbury 102
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, Exceptional, (7 reviews)
"The apartment was nice, big area, loved this rental."
United States
Marissa G.
$235 nightly
The price is $267
Dec 6 - Dec 7
Total with taxes and fees
Private Apartment in Southbury 101
A modern kitchen with white cabinets, a dining area with a black table and chairs, and a large window with curtains.

5. Private Apartment in Southbury 105

Private Apartment in Southbury 105
Southbury
$230 nightly
The price is $262
Nov 9 - Nov 10
Total with taxes and fees
Private Apartment in Southbury 105
A two-story house with a porch, a front door with a wreath, and a small garden area.

6. Bear Retreat - 2-bedroom house in Waterbury

Bear Retreat - 2-bedroom house in Waterbury
Waterbury
10.0 out of 10, Exceptional, (13 reviews)
"Perfect, spacious area. Super clean. Communication was great. Would definitely book here again."
United States
Radha
$283 nightly
The price is $322
Nov 6 - Nov 7
Total with taxes and fees
Bear Retreat - 2-bedroom house in Waterbury
A modern kitchen with wooden cabinets, a stainless steel refrigerator, a built-in oven, and a large island with bar stools.

7. 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.
$115 nightly
The price is $130
Nov 9 - Nov 10
Total with taxes and fees
Cozy private room in a shared home with a Full-size bed and private bathroom.
A modern kitchen with white cabinets, a microwave, stove, and sink. There is a dining area with a table and chairs.

8. 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.
$122 nightly
The price is $139
Nov 6 - Nov 7
Total with taxes and fees
Cozy 1-king size bedroom house in quiet Waterbury with 75" TV in your bedroom.
Deck: Comfortable outdoor sofa sets for outdoor conversations

9. Serenity Haven: A Modern Retreat

Serenity Haven: A Modern Retreat
Monroe
9.6 out of 10, Exceptional, (5 reviews)
"My stay at the modern retreat in Monroe was perfect. Conveniently located near restaurants, supermarkets, banks Starbucks. Beautiful Wolfe Park is minutes away to enjoy a hike or a bike ride.The hosts were easily accessible with any questions and or concerns.This modern retreat won't disappoint."
United States
Tresha J.
$259 nightly
The price is $295
Nov 9 - Nov 10
Total with taxes and fees
Serenity Haven: A Modern Retreat
A compact room with a kitchenette, a bed, a wall decorated with photos and a mirror, and a 'No Fishing From Bridge' sign.

10. Welcome to Sweet Abby Rose!

Welcome to Sweet Abby Rose!
Brewster
7.4 out of 10, Good, (3 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
$162 nightly
The price is $176
Nov 6 - Nov 7
Total with taxes and fees
Welcome to Sweet Abby Rose!
A bedroom with a bed, a blue sofa, a radiator, a window with blinds, a dreamcatcher, and a framed picture on the wall.

11. 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.
$153 nightly
The price is $174
Nov 30 - Dec 1
Total with taxes and fees
One bedroom in United States of America, New Haven
A spacious living room with large windows, a fireplace, and a view of the outdoors.

12. 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, Wonderful, (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.
$452 nightly
The price is $515
Nov 6 - Nov 7
Total with taxes and fees
Watertown Home w/ Yard: 1 Mi to Echo Lake Park!
A kitchen with white cabinets, a black refrigerator, a double sink, and a window overlooking a wooded area.

13. 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
$182 nightly
The price is $207
Nov 17 - Nov 18
Total with taxes and fees
Serene Country Cottage
A spacious living room with large windows, a fireplace, and a view of the outdoors.

14. 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
$469 nightly
The price is $539
Nov 6 - Nov 7
Total with taxes and fees
Watertown Home w/ Yard: 1 Mi to Echo Lake Park!
A modern living room with hardwood flooring, a leather sofa, a round coffee table, and a wooden side table. There is a dining area with a table and chairs visible in the background.

15. Luxurious-Modern feel w/ custom features - AC, short walk to Shelton

Luxurious-Modern feel w/ custom features - AC, short walk to Shelton
Shelton
$400 nightly
The price is $455
Nov 8 - Nov 9
Total with taxes and fees
Luxurious-Modern feel w/ custom features - AC, short walk to Shelton
A bedroom with a large arched window, a bed, a bedside table with a lamp, and a small seating area with cushions and a plant.

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
9.4 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
$194 nightly
The price is $221
Nov 6 - Nov 7
Total with taxes and fees
Lovely Bohemian Loft Downtwn, Amphitheater,Seaside Park,Metro North,2-10min walk
A modern apartment with a green sofa, a wooden dining table, and a kitchen in the background.

17. 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.
$214 nightly
The price is $243
Nov 19 - Nov 20
Total with taxes and fees
Modern Westville Home near Yale and Hospitals
A hotel lobby with a reception desk, seating area, and a large window providing a view of the outdoors.

18. 2 FULL BEDS | NON-SMOKING

2 FULL BEDS | NON-SMOKING
MILFORD
8.8 out of 10, Excellent, (5 reviews)
$68 nightly
The price is $79
Nov 22 - Nov 23
Total with taxes and fees
2 FULL BEDS | NON-SMOKING
A row of brick townhouses with wooden front doors, black railings, and a sidewalk.

19. Prime Yale Studio Steps to Sallys Apizza

Prime Yale Studio Steps to Sallys Apizza
Downtown New Haven
10.0 out of 10, Exceptional, (2 reviews)
"Great stay - and it is close to Sally's! We had a nice visit and all was as represented for the property."
United States
Milton W.
$202 nightly
The price is $230
Nov 8 - Nov 9
Total with taxes and fees
Prime Yale Studio Steps to Sallys Apizza
A swimming pool at night with blue lighting.

20. 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
$120 nightly
The price is $137
Nov 8 - Nov 9
Total with taxes and fees
Business or Weekend escape
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

Omni New Haven Hotel at Yale

Omni New Haven Hotel at Yale

8/10 Good
"Great"
Bara 1-night trip
Posted 13 hours ago
Omni New Haven Hotel at Yale

Find out more about Southbury

Everything you need to know about Southbury vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Southbury vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Southbury vacation 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 low season months. For more hustle and bustle, you may prefer to visit Southbury in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $79 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Southbury rentals

At Expedia, we put the best Southbury vacation 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 vacation.

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.

Explore a world of travel with Expedia

Frequently asked questions

Can I find vacation rentals in Southbury?

Yes, we have vacation rentals near top sights in Southbury, or you can choose a more remote 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 vacation rentals that Southbury has to offer?

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

How many vacation rentals are there in Southbury?

Expedia has 3 vacation 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 vacation rentals like in Southbury?

Vacation rentals are private accommodations you can stay in for a few days or a quick weekend in Southbury. Vacation rentals provide amenities such as patios, hot tubs, and fire pits so you'll have all the conveniences of home. If you're concerned about a sanitized environment, a vacation rental can offer a sense of safety away from shared hotel elevators and busy front desks while still allowing you the excitement and enjoyment of travel. You'll also get more space in a vacation rental than in a hotel, which makes a vacation rental an attractive choice for a small group gathering.