Photo by Chris Kailher

Southbury Vacation Rentals

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
Nov 11 - Nov 12
Tomorrow
Nov 12 - Nov 13
This weekend
Nov 14 - Nov 16
Next weekend
Nov 21 - Nov 23

Vacation Rentals in Southbury

Exterior
New One Bedroom Apartment Centrally Located in Southbury

New One Bedroom Apartment Centrally Located in Southbury

Southbury
9.8 out of 10, Exceptional, (16)
"Excellent stay !!!! Everything was perfect. Communication was phenomenal.!!!!"
United States
daniellle
The price is ￥13,457
￥18,559 total
includes taxes & fees
Nov 23 - Nov 24
New One Bedroom Apartment Centrally Located in Southbury
Interior
Private Apartment in Southbury 101

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 ￥18,104
￥44,676 total
includes taxes & fees
Dec 2 - Dec 3
Private Apartment in Southbury 101
Honeymoon Apartment, 3 Bedrooms, Kitchen | In-room dining
Luxury Furnished Apartments by Hyatus Downtown at Yale

Luxury Furnished Apartments by Hyatus Downtown at Yale

3.5 star property
The Hill
9.6 out of 10, Exceptional, (60)
"Wonderful property- brand new building, nice spacious rooms perfect for family. Instructors for check in and out and everything in between very clear and helpful. "
United States
Zhuo
Luxury Furnished Apartments by Hyatus Downtown at Yale
Pool
Business or Weekend escape

Business or Weekend escape

Stratford
9.2 out of 10, Wonderful, (51)
"Very nice stay and very clean"
United States
Markel W.
The price is ￥12,274
￥21,594 total
includes taxes & fees
Nov 18 - Nov 19
Business or Weekend escape
Outdoor dining
Lakehouse Boat Dock, Kayaks, Fire-Pit, Pool Table, Air Hockey, Hammock, King Bed

Lakehouse Boat Dock, Kayaks, Fire-Pit, Pool Table, Air Hockey, Hammock, King Bed

New Fairfield
9.4 out of 10, Exceptional, (31)
"I stayed here for three nights with my elderly mom. The home is lovely and very comfortable, with lovely linens, updated bathrooms, and luxurious beds. The kitchen is wonderfully equipped for anything you might want to prepare. This would be an excellent spot for a family with children. The hosts were very responsive and gracious. Above all else, the view is absolutely spectacular. I wish i could wake up to it every day. I hope to go back in the fall when the leaves are changing. Highly...
United States
Virginia F.
Lakehouse Boat Dock, Kayaks, Fire-Pit, Pool Table, Air Hockey, Hammock, King Bed
Outdoor dining
Beechmont - Perfect for Family Retreat!

Beechmont - Perfect for Family Retreat!

5.0 star property
Bridgeport
The price is ￥107,621
￥177,461 total
includes taxes & fees
Nov 12 - Nov 13
Beechmont - Perfect for Family Retreat!
Seasonal outdoor pool
Luxury Apartments by Hyatus at Pierpont

Luxury Apartments by Hyatus at Pierpont

4.0 star property
The Hill
9.4 out of 10, Exceptional, (21)
"Great. Would prefer to anyone"
United States
Bryan
Luxury Apartments by Hyatus at Pierpont
Dining
Lakeside/Sleeps20/HotTub/GameRoom/2Acres/Firepit

Lakeside/Sleeps20/HotTub/GameRoom/2Acres/Firepit

Brookfield
9.6 out of 10, Exceptional, (4)
"The host was very kind and welcoming. The home was spacious and the perfect setting for our celebration weekend. Everyone had their own space and we had multiple spaces for group activities. We enjoyed our time and appreciate the hospitality. "
United States
Valerie V.
Lakeside/Sleeps20/HotTub/GameRoom/2Acres/Firepit
55-inch Smart TV with digital channels, TV, streaming services
Charming Colonial for Events! – Perfect for Family Reunions and Group Getaways!

Charming Colonial for Events! – Perfect for Family Reunions and Group Getaways!

Bridgeport
9.6 out of 10, Exceptional, (4)
"Extremely clean and well prepared home stocked with items we may need. Plenty of space for all guests. Comfortable beds. Felt safe with the use of electronic keypad entry and security system. Very well maintained. Historic feel with modern amenities. Great location in regards to where we needed to be. Able to communicate with host who assisted in accommodations. Plenty of parking. Lovely place. "
United States
natalie c.
The price is ￥110,462
￥212,103 total
includes taxes & fees
Nov 13 - Nov 14
Charming Colonial for Events! – Perfect for Family Reunions and Group Getaways!
Property grounds
Luxury Designer 2 bedroom+office/3bed vacation home.

Luxury Designer 2 bedroom+office/3bed vacation home.

Brooklawn - St. Vincent
9.4 out of 10, Exceptional, (22)
"Don’t be worried about the neighborhood. It might be different than what you’re used to but it’s safe and a ton of local places to eat are great! Hosts are great and the space was excellent!!"
United States
Jack R.
The price is ￥19,300
￥60,397 total
includes taxes & fees
Nov 12 - Nov 13
Luxury Designer 2 bedroom+office/3bed vacation home.
Outdoor dining
DIRECT WATERFRONT with awesome views and near Yale

DIRECT WATERFRONT with awesome views and near Yale

West Haven
10.0 out of 10, Exceptional, (2)
"Great place to stay! Easy for an overnight for a family wedding!"
United States
Phoebe T.
The price is ￥42,958
￥70,459 total
includes taxes & fees
Nov 18 - Nov 19
DIRECT WATERFRONT with awesome views and near Yale
Exterior
Charming Studio| Near Yale| Downtown New Haven

Charming Studio| Near Yale| Downtown New Haven

Downtown New Haven
9.0 out of 10, Wonderful, (10)
"Nice location in downtown New Haven. The room itself is nice and convenient. The window near the bed does not close because there is a large tube going through the window with tape around it. On a chilly day/night this is not comfortable and there is nothing one can do since the window does not close. You can also hear everything going on outside because the window does not close. Bedsheets were not clean either. Contacted the host about the window and bedsheets and the host gave me the...
United States
Noel
The price is ￥16,957
￥35,609 total
includes taxes & fees
Nov 20 - Nov 21
Charming Studio| Near Yale| Downtown New Haven
Dining
Peaceful Vintage Home with Private Lake in Redding, CT.

Peaceful Vintage Home with Private Lake in Redding, CT.

2.0 star property
Redding
10.0 out of 10, Exceptional, (2)
"Property was beautiful in a very quiet and peaceful area. Our host Kadriia was so amazing and would respond so quickly to any questions we had and communicated clearly. My wife and our friends had a Halloween themed wedding party for our friends who couldn’t make it to the actual wedding and we couldn’t have had a better time. "
United States
Connor K.
The price is ￥55,231
￥90,671 total
includes taxes & fees
Nov 12 - Nov 13
Peaceful Vintage Home with Private Lake in Redding, CT.
1 bedroom, desk, iron/ironing board, free WiFi
Stylish Sheek Loft Dwntwn, Amphitheater, Park, Metro North, Ferry All 2-10min

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

Downtown Bridgeport
The price is ￥13,041
￥25,123 total
includes taxes & fees
Nov 17 - Nov 18
Stylish Sheek Loft Dwntwn, Amphitheater, Park, Metro North, Ferry All 2-10min
Property grounds
Candlewood Lake - Family Getaway with direct lake access. 3775 sqft home.

Candlewood Lake - Family Getaway with direct lake access. 3775 sqft home.

Danbury
10.0 out of 10, Exceptional, (24)
"Beautiful house with amazing views. Can’t wait to stay again. Great location too! Close to everything (shopping/food/activities) but located on a very quiet dead end. Owners were easy to communicate with and very friendly. "
United States
Mary M.
Candlewood Lake - Family Getaway with direct lake access. 3775 sqft home.
Terrace/patio
Log Cabin On A Lake With Private Dock & Beach! One Hour from NYC! No Pet Fees!

Log Cabin On A Lake With Private Dock & Beach! One Hour from NYC! No Pet Fees!

Holmes
10.0 out of 10, Exceptional, (196)
"A sweet little cabin on a quiet lake was exactly what I was looking for. My overall experience was absolutely wonderful."
United States
Janine H.
Log Cabin On A Lake With Private Dock & Beach! One Hour from NYC! No Pet Fees!
1 bedroom, WiFi, bed sheets
Private Third-Floor Attic Apartment Full Kitchen • King Bed • Backyard Access

Private Third-Floor Attic Apartment Full Kitchen • King Bed • Backyard Access

2.0 star property
West New Haven
9.0 out of 10, Wonderful, (2)
"Great communication and easy check in, would recommend "
United States
Ethan R.
The price is ￥12,274
￥19,830 total
includes taxes & fees
Nov 14 - Nov 15
Private Third-Floor Attic Apartment Full Kitchen • King Bed • Backyard Access
Interior
Cozy ground floor suite ideal for a relaxing stay. Enjoy peace and tranquility.

Cozy ground floor suite ideal for a relaxing stay. Enjoy peace and tranquility.

Waccabuc
4.0 out of 10, (2)
"Clean but minimalist, big empty basement, good for a cheap stay near Caramoor"
United States
Patrick M.
The price is ￥22,583
￥31,647 total
includes taxes & fees
Nov 14 - Nov 15
Cozy ground floor suite ideal for a relaxing stay. Enjoy peace and tranquility.
Outdoor dining
Charming 3 Bedroom Beach Front Cottage

Charming 3 Bedroom Beach Front Cottage

2.0 star property
Milford
10.0 out of 10, Exceptional, (4)
"Stayed here while attending the Soundside Fest. Perfect location to be away from the busy Bridgeport area. The water is right there and it’s the perfect space for a weekend get away."
United States
Sarah W.
Charming 3 Bedroom Beach Front Cottage
Interior
Stunning Apt W/ Parking and Gym | Downtown at Yale

Stunning Apt W/ Parking and Gym | Downtown at Yale

The Hill
10.0 out of 10, Exceptional, (46)
"High quality experience, walking distance to all we needed, clean and spacious. Excellent support and communication from the hosts, would stay again."
United Kingdom
Coco N.
Stunning Apt W/ Parking and Gym | Downtown at Yale
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Southbury Hotel Reviews

Omni New Haven Hotel at Yale

Omni New Haven Hotel at Yale

10/10 Excellent
"Giod"
Esin 1-night trip
Posted 1 day ago
Omni New Haven Hotel at Yale

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 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.