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Southbury Holiday Rentals

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Holiday Rentals in Southbury

New One Bedroom Apartment Centrally Located in Southbury

9.6 out of 10, Exceptional, (5)
"Excellent place in an excellent location. Charles is a wonderful host. Will be staying there again. "
The price is NZ$281
includes taxes & fees
10 July - 11 July
New One Bedroom Apartment Centrally Located in Southbury

Business or Weekend escape

9.6 out of 10, Exceptional, (38)
"Very nice owner with great communication. "
The price is NZ$242
includes taxes & fees
6 July - 7 July
Business or Weekend escape

Luxury Apartments by Hyatus at Pierpont

4.0 star property
9.4 out of 10, Exceptional, (17)
"Phenomenal property. Beautiful room and great amenities. Great communication. "
Luxury Apartments by Hyatus at Pierpont

Charming Historic 2BR Retreat in New Haven – Cozy Stay Near Yale & Downtown!

10.0 out of 10, Exceptional, (5)
"We enjoyed our stay at this property. There was lots of room for us to gather and spend time together. The hosts were super helpful when we had any questions or issues and went out of their way to make our stay enjoyable. The property was close to Yale and the freeway, which made it easy to get around. The house was well appointed with everything we needed and was a great deal for the price. "
Charming Historic 2BR Retreat in New Haven – Cozy Stay Near Yale & Downtown!

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

9.4 out of 10, Exceptional, (19)
"My stay was good only con was the parking. Parking was in the street and hope you come in early to get a space or you will park down the street… there is parking in the back for a fee which was not in the description of the property upon booking."
The price is NZ$675
includes taxes & fees
30 June - 1 July
Luxury Designer 2 bedroom+office/3bed vacation home.

Minutes to Walnut Beach, newly renovated 3 bedroom home

10.0 out of 10, Exceptional, (3)
"This house was perfect for our visit. It was clean and comfortable and provided everything we needed. Walking distance to a restaurant, coffee shop and the best ice cream! Would definitely stay here again. "
Minutes to Walnut Beach, newly renovated 3 bedroom home

Dog-Friendly Oceanfront Getaway - Walk to Dining - Private Beach Access

10.0 out of 10, Exceptional, (6)
"Property manager was very attentive to our needs and replied to all msgs in a very timely fashion. There were a couple things that needed tending to when we arrived and he took care of it immediately. Despite having parking on the street, it was never an issue and often got the spot that was right next to the house. The beach was directly across the street and was clean with friendly neighbors! Although there is a sign stating no dogs or animals allowed on the beach, there were many dogs on the...
The price is NZ$942
includes taxes & fees
5 July - 6 July
Dog-Friendly Oceanfront Getaway - Walk to Dining - Private Beach Access

Spectacular Lake front house

9.6 out of 10, Exceptional, (4)
"This beautiful home offered plenty of space for our family of 6 adults and 2 children to enjoy a week together. "
Spectacular Lake front house

Escape to your private lakeside estate! Family & dog friendly, wildlife viewing!

10.0 out of 10, Exceptional, (121)
"My family and I stayed at the Lake House for the holiday. We can not say enough about the amenities, the house & the owners. We look forward to returning to this magical place for our next family reunion."
Escape to your private lakeside estate! Family & dog friendly, wildlife viewing!

Lakehouse, Boat Dock, Kayaks, Fire-Pit, King Bed, 1 Hour & 15 Min from NYC etc!

9.2 out of 10, Wonderful, (14)
"We really enjoyed our stay. The house is walking distance from the lake and a good break for anyone trying to escape the bustle of NYC. The house was very clean and we felt safe and comfortable here’s the outdoor fire pit was a very nice touch."
Lakehouse, Boat Dock, Kayaks, Fire-Pit, King Bed, 1 Hour & 15 Min from NYC etc!

The Daydreamer - Walk To Walnut Beach, Restaurant + Shops

9.8 out of 10, Exceptional, (8)
"5 Star stay!"
The Daydreamer - Walk To Walnut Beach, Restaurant + Shops

Tranquil Litchfield Connecticut Retreat".

9.2 out of 10, Wonderful, (14)
"Quick trip"
The price is NZ$528
includes taxes & fees
20 July - 21 July
Tranquil Litchfield Connecticut Retreat".

Chateau Blanc Yale Located Downtown

8.0 out of 10, Very good, (4)
"Getting in and out was a cinch because the property manager is extremely quick to respond. The room was clean, comfortable, and exactly what I booked. 10/10 stay. Would stay here again."
The price is NZ$318
includes taxes & fees
25 July - 26 July
Chateau Blanc Yale Located Downtown

Modern Apartment in Black Rock

2.0 star property
9.6 out of 10, Exceptional, (10)
"The place is in the heart of Black Rock and was exactly as listed. Clean, nice as well as practical as I had to work from here. Great wifi also.I have stayed here for 2 weeks. I am happy to have found this listing. Very convenient, Metro North is nearby quick walk"
Modern Apartment in Black Rock

Cozy Cabin @ Sticks & Stones Farm

8.4 out of 10, Very good, (6)
"Nice clean cabin. Good communication with host."
Cozy Cabin @ Sticks & Stones Farm

Lake Cottage, Kayaks, FirePit, Grill & Deck, 1 hour & 15 Minutes to NYC!

9.4 out of 10, Exceptional, (91)
"This is a beautiful home even if you live in the area and just want to spend the weekend at the lake, it’s a perfect getaway. We love that it was dog friendly. The host was wonderful and very accommodating. The house came stocked with everything that you would need for a perfect stay. "
Lake Cottage, Kayaks, FirePit, Grill & Deck, 1 hour & 15 Minutes to NYC!

Spacious Woodbury Home w/ Pool + Hot Tub!

8.0 out of 10, Very good, (1)
"We rented this place for the first time for a family gathering. The setting was very private and “country-ish”. For the most part everything listed was present at the place and there were enough sleeping options for our crew. Overall - the owners were nice and fairly responsive but there was a level of disappointment to the care of the property and more importantly the preparedness for our arrival. They said the pool and hot tub were cleaned and ready but the pool was still dirty and the hot tub...
Spacious Woodbury Home w/ Pool + Hot Tub!

Stunning Apt W/ Parking and Gym | Downtown at Yale

10.0 out of 10, Exceptional, (41)
"We had a great second stay at Aurun downtown New Haven. The apartment was very clean with very good amenities and protected parking. We will definitely be back."
Stunning Apt W/ Parking and Gym | Downtown at Yale

Beautiful, Spacious, Beachfront Home - Perfect for Entertaining Family & Friends

10.0 out of 10, Exceptional, (48)
"Property was great. Host was very accommodating and great with communicating."
Beautiful, Spacious, Beachfront Home - Perfect for Entertaining Family & Friends

SALTY KISSES COZY BEACH HOUSE /BEACH ACCESS ACROSS STREET WATER VIEW

2.0 star property
10.0 out of 10, Exceptional, (2)
"The house is absolutely perfect. Location, cleanliness, beach amenities, owner communication, etc. I’ve stayed at 30+ VRBO/Aribnb properties over the last decade and this is by far one of my top 2. Denise was so nice and accommodating and even had restaurant & entertainment suggestions. The house, the yard, garage, bikes, beach chairs, umbrella, kayaks, fire pit…it all made our stay so wonderful. We will absolutely be back. "
SALTY KISSES COZY BEACH HOUSE /BEACH ACCESS ACROSS STREET WATER VIEW
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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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?

Business or Weekend escape: This holiday home rental outside of Southbury is equipped with a BBQ, air conditioning and a Smart TV to help you feel comfortable during your stay. Kitchen amenities include a fridge, a microwave and a coffee maker.

How many holiday rentals are there in Southbury?

Expedia has 4 holiday 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 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.