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Southbury Vacation Rentals

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Check prices for these dates

In two weeks
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 Jan

Our top choices for Southbury vacation 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, (37 reviews)
"Great place. Had everything we needed and was very clean."
United States
Niki B.
The price is AED 324
AED 446 total
includes taxes & fees
27 Sep - 28 Sep
Cozy One Bedroom Apartment Centrally Located in Southbury
Coffee/tea maker, fridge, microwave, oven

2. Private Apartment in Southbury 103

Private Apartment in Southbury 103
Southbury
9.4 out of 10, Exceptional, (6 reviews)
"It was amazing , clean and awesome and good time"
United States
Michael
The price is AED 529
AED 1,077 total
includes taxes & fees
28 Sep - 29 Sep
Private Apartment in Southbury 103
Interior

3. 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 AED 433
AED 953 total
includes taxes & fees
28 Sep - 29 Sep
Private Apartment in Southbury 101
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, (5 reviews)
"Beautiful place. Very clean & welcoming "
United States
Chris
The price is AED 536
AED 848 total
includes taxes & fees
29 Sep - 30 Sep
The Perch in the Purchase -- Cozy, unique, and private
Interior

5. Private Apartment in Southbury 105

Private Apartment in Southbury 105
Southbury
The price is AED 430
AED 960 total
includes taxes & fees
30 Sep - 1 Oct
Private Apartment in Southbury 105
Coffee/tea maker, fridge, microwave, oven

6. 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 AED 518
AED 1,061 total
includes taxes & fees
14 Oct - 15 Oct
Private Apartment in Southbury 104
Exterior detail

7. Bear Retreat - 2-bedroom house in Waterbury

Bear Retreat - 2-bedroom house in Waterbury
Waterbury
10.0 out of 10, Exceptional, (8 reviews)
"Perfect, spacious area. Super clean. Communication was great. Would definitely book here again."
United States
Radha
The price is AED 477
AED 1,269 total
includes taxes & fees
8 Oct - 9 Oct
Bear Retreat - 2-bedroom house in Waterbury
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
8.4 out of 10, Very good, (12 reviews)
"Great night stay! Wonderful place would definitely recommend! "
United States
Laurie P.
The price is AED 327
AED 449 total
includes taxes & fees
28 Sep - 29 Sep
Private, Quiet, Cozy Studio Guesthouse with 75" TV WiFi etc. In Watertown.
House (3 Bedrooms) | Interior

9. 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 AED 1,003
AED 1,980 total
includes taxes & fees
24 Sep - 25 Sep
Watertown Home w/ Yard: 1 Mi to Echo Lake Park!
Interior

10. 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.
The price is AED 804
AED 1,903 total
includes taxes & fees
24 Sep - 25 Sep
Watertown Home w/ Yard: 1 Mi to Echo Lake Park!
Marina

11. North Cliff House - Private Dock & Sauna

North Cliff House - Private Dock & Sauna
Danbury
10.0 out of 10, Exceptional, (8 reviews)
"Enjoyed the property. Beautiful house. Great location. Reserve, stay and enjoy!"
United States
Ron P.
North Cliff House - Private Dock & Sauna
TV

12. #43- Modern Luxury Log Cabin Retreat - Fire Pit

#43- Modern Luxury Log Cabin Retreat - Fire Pit
Prospect
9.4 out of 10, Exceptional, (3 reviews)
"3.5 rounding up to 4. We had a good stay overall. I travel fairly often and tend to reserve 5 stars for places where every detail of the guest experience feels really thoughtfully considered. This home was comfortable and worked fine for our trip, but it felt a bit more basic compared to some other rentals I’ve stayed in."
United States
Lauren P.
The price is AED 703
AED 1,657 total
includes taxes & fees
24 Sep - 25 Sep
#43- Modern Luxury Log Cabin Retreat - Fire Pit
TV, fireplace, books

13. The Little Lake Cabin with hot tub

The Little Lake Cabin with hot tub
New Fairfield
10.0 out of 10, Exceptional, (4 reviews)
"Great location and lots to do despite it raining for half our stay! My dog enjoyed the yard and walks around the neighborhood. My son loved kayaking and having his first ever s’more. Honestly I wished we had booked a longer trip! "
United States
Lyndsey F.
The price is AED 1,137
AED 2,077 total
includes taxes & fees
30 Sep - 1 Oct
The Little Lake Cabin with hot tub
TV

14. 191 Seymour, Ave. Derby · Spacious Renovated 3 bedroom near GriffinHospital

191 Seymour, Ave. Derby · Spacious Renovated 3 bedroom near GriffinHospital
Derby
8.6 out of 10, Excellent, (8 reviews)
"Great stay! Perfect location for my needs. Clean and inviting rental. Modern and well kept. Will stay again. "
United States
Bary B.
The price is AED 666
AED 1,125 total
includes taxes & fees
24 Sep - 25 Sep
191 Seymour, Ave. Derby · Spacious Renovated 3 bedroom near GriffinHospital
Interior

15. 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, (17 reviews)
"Very clean & cozy with everything we needed!"
United States
Joe K.
The price is AED 790
AED 1,011 total
includes taxes & fees
27 Sep - 28 Sep
The Overlook near South Farms in Litchfield County is Hospitality, integrated.
Interior

16. Welcome to Dove Haven — a peaceful and stylish retreat in the heart of Westville. Relax in the private hot tub, enjoy cozy sun-filled spaces, and walk to charming cafés, top restaurants, and beautiful Edgewood Park. Minutes from Yale and downtown.

Welcome to Dove Haven — a peaceful and stylish retreat in the heart of Westville. Relax in the private hot tub, enjoy cozy sun-filled spaces, and walk to charming cafés, top restaurants, and beautiful Edgewood Park. Minutes from Yale and downtown.
West New Haven
10.0 out of 10, Exceptional, (16 reviews)
"Beautiful house, convenient location, great amenities, responsive host."
United States
Niels G.
The price is AED 1,833
AED 3,823 total
includes taxes & fees
24 Sep - 25 Sep
Welcome to Dove Haven — a peaceful and stylish retreat in the heart of Westville. Relax in the private hot tub, enjoy cozy sun-filled spaces, and walk to charming cafés, top restaurants, and beautiful Edgewood Park. Minutes from Yale and downtown.
Coffee/tea maker, fridge, oven, stovetop

17. 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 AED 464
AED 787 total
includes taxes & fees
28 Sep - 29 Sep
Serene Country Cottage
Front of property

18. Beechmont - Perfect for Family Retreat!

Beechmont - Perfect for Family Retreat!
5.0 star property
North End
The price is AED 3,667
AED 5,502 total
includes taxes & fees
24 Sep - 25 Sep
Beechmont - Perfect for Family Retreat!
Dining

19. Spacious 2 Bedroom apartment close to Yale Bowl

Spacious 2 Bedroom apartment close to Yale Bowl
West New Haven
9.6 out of 10, Exceptional, (79 reviews)
"Clean, thoughtful, safe. Great stay"
United States
Daniel S.
The price is AED 419
AED 777 total
includes taxes & fees
28 Sep - 29 Sep
Spacious 2 Bedroom apartment close to Yale Bowl
Exterior

20. Angelica’s safe haven @ west haven

Angelica’s safe haven @ west haven
West Haven
10.0 out of 10, Exceptional, (8 reviews)
"We had a great stay. Comfortable home with a large living room. Beds were great. "
United States
Jason V.
The price is AED 551
AED 1,253 total
includes taxes & fees
29 Sep - 30 Sep
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

Courtyard by Marriott Waterbury Downtown

Courtyard by Marriott Waterbury Downtown

8/10 Good
"The room was clean and very up-to-date decor-wise."
Karen 1-night trip
Posted 14 hours ago
Courtyard by Marriott Waterbury Downtown

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?

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 Lake Quassapaug 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.