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Holiday Homes in Southbury

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Featured Holiday Homes in Southbury

Cozy 2 bedroom home located minutes from downtown

9.6 out of 10, Exceptional, (30)
"A very comfortable short stay in a convenient location"
Cozy 2 bedroom home located minutes from downtown

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

9.4 out of 10, Exceptional, (30)
"Stayed here to visit family and it was perfect for what we needed. Would recommend staying here. "
Lakehouse Boat Dock, Kayaks, Fire-Pit, Pool Table, Air Hockey, Hammock, King Bed

Charming 1870 cape cottage in Litchfield

10.0 out of 10, Exceptional, (59)
"My family and I enjoyed our stay and their hospitality!"
Charming 1870 cape cottage in Litchfield

McAngel Haven: 5 mins from Yale

9.6 out of 10, Exceptional, (14)
"My family and I stayed at the property for a wedding in Milford. The house had plenty of space for our group to say, and the bedrooms were comfortable. The three bathrooms were helpful for our group to efficiently get ready for the wedding, and the kitchen was adequately appointed for us to have meals."
The price is NZ$899
includes taxes & fees
15 Oct - 16 Oct
McAngel Haven: 5 mins from Yale

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

8.8 out of 10, Excellent, (23)
"We were very happy with the accommodations. The cottage was neat, clean and well kept, as was the property. All the amenities were as described. We had a great weekend and would highly recommend this lake house."
Lakehouse, Boat Dock, Kayaks, Fire-Pit, King Bed, 1 Hour & 15 Min from NYC etc!

Ranch style living at its best with country garden & patio!

9.6 out of 10, Exceptional, (14)
"the host was really great about getting back to us when we had a question or problem . his home was comfortable and artistic. the location was also easy to get to and the neighborhood was quiet and comvenient to all your needs."
Ranch style living at its best with country garden & patio!

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

10.0 out of 10, Exceptional, (127)
"Fantastic all around!"
Beach Front Arts & Crafts House With Gorgeous Views Of The Sound

Lakeview Estate - Chef's Kitchen - NYC Getaway

9.8 out of 10, Exceptional, (30)
"Happy to have rebooked!!"
Lakeview Estate - Chef's Kitchen - NYC Getaway

Cheerful 4 bedrooms residential house.

9.8 out of 10, Exceptional, (35)
"House was perfect for what we needed. Great proximity to the Amphitheater and Seaside Park. "
Cheerful 4 bedrooms residential house.

Business or Weekend escape

9.2 out of 10, Wonderful, (47)
"We had stayed at Mansoor's a few weeks ago and returned this past weekend. Once again, we found the place spotless, comfortable and well-stocked. We really like this place and expect to return again in the future. "
The price is NZ$252
includes taxes & fees
2 Nov - 3 Nov
Business or Weekend escape

Soothing Carriage House with Hot Tub in charming Stratford

10.0 out of 10, Exceptional, (5)
Soothing Carriage House with Hot Tub in charming Stratford

Candlewood Lakefront 3bd/ 2 bath house w/ 180 degree views!

10.0 out of 10, Exceptional, (47)
"We really enjoyed totally this Candlewood lake house. it has a fantastic view and a large, beautiful lawn with a fire pit. The owner was a pleasure to work with and she even allowed us to check in a few hours early.The house is fully stocked with everything we needed. The views are fabulous, but if you bring your own boat, the property is at the tip of the lake and the water can be a little rough from other boats going by. "
Candlewood Lakefront 3bd/ 2 bath house w/ 180 degree views!

Land’s End – Direct Lake Front on Warner Point, Candlewood Lake, CT

10.0 out of 10, Exceptional, (13)
"Beautiful location and lots of space for a large group. This rental is really about the outdoor space and activities. Would love to return!"
Land’s End – Direct Lake Front on Warner Point, Candlewood Lake, CT

Minutes to Walnut Beach, newly renovated 3 bedroom home

9.8 out of 10, Exceptional, (11)
"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

Charming 2-bedroom house in Bridgeport.Trumbull/Fairfield line with AC, WiFi.

10.0 out of 10, Exceptional, (2)
"Good experience"
Charming 2-bedroom house in Bridgeport.Trumbull/Fairfield line with AC, WiFi.

#37 - Luxury Collection

2.0 star property
8.8 out of 10, Excellent, (3)
"We enjoyed the coziest getaway at this property. Newly renovated, clean and tucked away without being accessible to local attractions. "
#37 - Luxury Collection

NEW Candlewood Lake 3BR 2BA Direct Waterfront Home~ Dock~Fire Pit~Sunset Views!

10.0 out of 10, Exceptional, (13)
"House and property are beautiful. Everything was great!"
NEW Candlewood Lake 3BR 2BA Direct Waterfront Home~ Dock~Fire Pit~Sunset Views!

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

10.0 out of 10, Exceptional, (23)
"Gorgeous views and comfortable stay!"
Candlewood Lake - Family Getaway with direct lake access. 3775 sqft home.

3-bedroom house just walking distance from Yale and Downtown

The price is NZ$714
includes taxes & fees
15 Oct - 16 Oct
3-bedroom house just walking distance from Yale and Downtown

The Connecticut Chalet - On 5 Acres!

9.8 out of 10, Exceptional, (7)
"Highly recommend this property if you're heading to the area!"
The Connecticut Chalet - On 5 Acres!
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

Find out more about Southbury

Find out more about Southbury

Southbury Holiday Homes information

Number of reviews
519
Accommodation
476 Holiday Homes
Lowest Price
NZ$252
Highest Price
NZ$899

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