Photo by Chris Kailher

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Compare 451 Vacation Homes in Southbury with updated reviews, rates, and availability.

Historic Connecticut Home w/ Grill & Spacious Yard

10.0 out of 10, Exceptional, (6)
"Very well appointed (Boll & Branch sheets so nice). Great communication from owners. "
Historic Connecticut Home w/ Grill & Spacious Yard

Lakeside luxury: beautiful, relaxing 4 bedroom home

10.0 out of 10, Exceptional, (19)
"This is a beautiful property. When we arrived, everything was perfect. It is completely stocked, including games for the family, and an unbelievable view of the lake. Communication with the homeowner was wonderful and we definitely plan to come back. We highly recommend this beautiful, clean and well kept home on the lake!."
Lakeside luxury: beautiful, relaxing 4 bedroom home

Charming Direct Waterfront Home w/Panoramic Views and Hot Tub on Candlewood Lake

10.0 out of 10, Exceptional, (106)
"The title says it all really. The house is as well equipped as your home, superbly comfortable, has glorious views East over the lake, has space for everyone and was just a delight to stay in. Lisa is so repsonsive, thoughtful and kind, which just adds to the warmth of feeling and quality of experience. Thank you very much indeed. "
Charming Direct Waterfront Home w/Panoramic Views and Hot Tub on Candlewood Lake

Stylish & Luxurious 3 BDR Home with Play Station

9.4 out of 10, Exceptional, (9)
"We needed a place for our family of 6 to stay while visiting family in the area. This place was exactly what we needed, as advertised, and the owner was quick with communications. We would definitely stay here again!"
Stylish & Luxurious 3 BDR Home with Play Station

Business or Weekend escape

9.4 out of 10, Exceptional, (33)
"We had a wonderful stay here. It was the perfect man cave for a mom and two teenage boys! It was very clean and the host was amazing! He was very very helpful with questions we had and things that we needed in the area. I would definitely stay with him again."
The price is AED 275
AED 496 total
includes taxes & fees
30 Mar - 31 Mar
Business or Weekend escape

Cheerful 4 bedrooms residential house.

9.8 out of 10, Exceptional, (29)
"We had 8 people staying in the house. We were in town for a wedding. The house was well fitted for us. Kitchen had all the dishes we needed. Appliances all worked well. Nice walk to the sound. Neighborhood was kind of iffy but we had no problems. "
Cheerful 4 bedrooms residential house.

Cozy Lakefront Cottage - Hot Tub, Game Room & Lake Views

10.0 out of 10, Exceptional, (1)
"Beautiful view from the upstairs window. I enjoyed the pellet stove on the cold days."
The price is AED 661
AED 1,197 total
includes taxes & fees
10 Apr - 11 Apr
Cozy Lakefront Cottage - Hot Tub, Game Room & Lake Views

Direct Lakefront Living - Floating Dock, Boat Watching, Kayaks, & EV Charger

9.8 out of 10, Exceptional, (28)
"Our family's stay at Helen and Richie's property for the holidays was perfect. Waking up to views of the lake every morning, watching flocks of birds travel on the water and being surrounded by nature was all we could ask for. The house has all amenities provided in the kitchen, bathrooms etc. Location is convenient near shops, grocery, and restaurants in New Fairfield. The hosts were very responsive in communication and I appreciated them providing everything we needed. "
Direct Lakefront Living - Floating Dock, Boat Watching, Kayaks, & EV Charger

Tranquil Litchfield Connecticut Retreat".

9.4 out of 10, Exceptional, (9)
"This is a neat, clean and lovely little place that perfectly suited our needs. It had all the amenities we needed for our short stay. Jose was a gracious host, answering all of my questions promptly - even the one about the mattresses which were incredibly comfortable! "
The price is AED 808
AED 1,141 total
includes taxes & fees
2 Apr - 3 Apr
Tranquil Litchfield Connecticut Retreat".

7Mins to Yale I ENTIRE HOUSE I Large fenced yard I King bed I 3BR I Group Gather

10.0 out of 10, Exceptional, (9)
"Is a great location given minutes from Yale. We were able to make a nice meal to celebrate our son’s success. Nice place!"
7Mins to Yale I ENTIRE HOUSE I Large fenced yard I King bed I 3BR I Group Gather

Charming 3BR Hilltop House, Newly Remodeled with Arcade

10.0 out of 10, Exceptional, (19)
"Very nice clean house. Felt like coming home after work"
Charming 3BR Hilltop House, Newly Remodeled with Arcade

BREATHTAKING BUNGALOW-HOME AWAY FROM HOME

10.0 out of 10, Exceptional, (27)
"We loved the location and the space was great for our visit. Very clean and cozy. Would recommend and we would book again if we are ever back in the area. "
BREATHTAKING BUNGALOW-HOME AWAY FROM HOME

Beach Front Arts & Crafts House With Gorgeous Views Of The Sound

10.0 out of 10, Exceptional, (116)
"The Arts and Crafts home was more beautiful than the pictures reflected! We loved all of the details in the woodwork, hidden little corners, tons of space to spread out and wonderful places to gather together. Having recently sold our "family home" we were thrilled to find this home in which to have a mini- family reunion. The kitchen was incredibly well-stocked- from serving platters to garlic powder to paper towels...We had everything we needed. The gas fireplace created a beautiful focal...
Beach Front Arts & Crafts House With Gorgeous Views Of The Sound

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

9.4 out of 10, Exceptional, (10)
"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!

Ocean Front Beach House with Private Beach Access - Newly Renovated!

10.0 out of 10, Exceptional, (14)
"Communication was top notchThe property was very well appointed and perfect for a family gathering The most important part was the accessibility of the bathroom and bedroom for my mom who has mobility issues I was worried about the half step from bedroom to bathroom but I put pick lights on floor to remind her to step upLocation was perfect Especially loved visiting pez!"
Ocean Front Beach House with Private Beach Access - Newly Renovated!

Cottage at Sunny Day- Lakeside, views, kayak, dock

9.8 out of 10, Exceptional, (35)
"This property was very new and clean. It had everything you needed. Every room was comfortable and had its own TV. The open layout of the main floor made for great socializing and eating, and the 180 views of the frozen lake (in February) were beautifully serene. Would definitely come again and maybe next time in the summer! Thanks you for sharing this lovely property."
Cottage at Sunny Day- Lakeside, views, kayak, dock

Waterfront Family Retreat on Candlewood Lake

10.0 out of 10, Exceptional, (41)
"The Hosts were extremely nice and helpful in the entire process. They answered questions and helped me understand the offering so I could book with confidence, The home is spacious and welcoming in design. Generous spaces throughout including a very nice kitchen and a basement gameroom that was very enjoyable. The outside seating areas were outstanding including a wonderful lakefront area to sit and enjoy the views. Book with confidence for a great experience. Dan and Kit "
Waterfront Family Retreat on Candlewood Lake

Litchfield County Four Season Country Paradise

9.6 out of 10, Exceptional, (40)
"Considering that area does not have convenient hotels, this location was perfect for the event we attended. It was nice of them to vacate their home so we could stay - though we wish that would have been communicated. There is no extra room with twin beds - at least not functional. The property is nice. Whomever took the pictures did a great job. It worked for us for the short time we were in the area."
Litchfield County Four Season Country Paradise

Spacious 4-bedroom house with WiFi and AC in awesome Milford

The price is AED 1,300
AED 2,619 total
includes taxes & fees
30 Mar - 31 Mar
Spacious 4-bedroom house with WiFi and AC in awesome Milford

Have a quiet weekend retreat at my recently renovated riverside bungalow

Have a quiet weekend retreat at my recently renovated riverside bungalow
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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Other property types in Southbury

Cozy cute Relaxing home

10.0 out of 10, Exceptional, (1)
"nice quiet area"
The price is AED 514
AED 1,029 total
includes taxes & fees
28 Mar - 29 Mar
Cozy cute Relaxing home

New Haven Village Suites

3.0 star property
7.6 out of 10, Good, (2019)
"It was nice"
The price is AED 334
AED 384 total
includes taxes & fees
8 Apr - 9 Apr
New Haven Village Suites

Business or Weekend escape

9.4 out of 10, Exceptional, (33)
"We had a wonderful stay here. It was the perfect man cave for a mom and two teenage boys! It was very clean and the host was amazing! He was very very helpful with questions we had and things that we needed in the area. I would definitely stay with him again."
The price is AED 275
AED 496 total
includes taxes & fees
30 Mar - 31 Mar
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.