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Compare 458 Vacation Homes in Southbury with updated reviews, rates, and availability.

Business or Weekend escape

9.6 out of 10, Exceptional, (37)
"Very nice owner with great communication. "
The price is AED 248
AED 464 total
includes taxes & fees
9 Jun - 10 Jun
Business or Weekend escape

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

10.0 out of 10, Exceptional, (41)
"Had an amazing stay. House was stocked with all of the essentials. Fantastic location. Would definitely stay again!"
Candlewood Lakefront 3bd/ 2 bath house w/ 180 degree views!

Charming Connecticut Retreat Near Museums & Hiking

8.0 out of 10, Very Good, (3)
"We loved this place. It's an older house but the owner had done a wonderful job with restoration and upkeep. The yard was perfect for our large dog and the kitchen was cozy and inviting. We really enjoyed our stay and would definitely return on another trip to do it all over again."
Charming Connecticut Retreat Near Museums & Hiking

Lakeside luxury: beautiful, relaxing 4 bedroom home

10.0 out of 10, Exceptional, (22)
"This property was perfect for our weekend trip to celebrate my nieces family/birthday weekend at Fairfield"
Lakeside luxury: beautiful, relaxing 4 bedroom home

Connecticut Retreat: Steps to Historic Downtown!

9.6 out of 10, Exceptional, (13)
"Everything was as described and updated we enjoyed our stay. "
Connecticut Retreat: Steps to Historic Downtown!

Charming 2-bedroom house with WiFi, AC in Fairfield

The price is AED 545
AED 1,277 total
includes taxes & fees
9 Jun - 10 Jun
Charming 2-bedroom house with WiFi, AC in Fairfield

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

9.8 out of 10, Exceptional, (28)
"We stayed for 3 weeks it was lovely!"
Direct Lakefront Living - Floating Dock, Boat Watching, Kayaks, & EV Charger

The Daydreamer - Walk To Walnut Beach, Restaurant + Shops

9.8 out of 10, Exceptional, (7)
"5 Star stay!"
The price is AED 529
AED 1,359 total
includes taxes & fees
16 Jun - 17 Jun
The Daydreamer - Walk To Walnut Beach, Restaurant + Shops

Bright Milford Beach House w/ Outdoor Shower

9.2 out of 10, Wonderful, (10)
"We had the best time! It was clean, good location, and the owner was wonderful! We even got to go the beach in December! We would definitely rent this place again!!"
Bright Milford Beach House w/ Outdoor Shower

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

9.8 out of 10, Exceptional, (38)
"Great place magnificent views. It’s a very peaceful place"
Cottage at Sunny Day- Lakeside, views, kayak, dock

Peaceful Oasis in Naugatuck - Charming 3-Bedroom Home with serene backyard.

10.0 out of 10, Exceptional, (1)
"What a great location to travel to graduations. Tidy, comfortable house. Will keep this location in case we’re in the area again. Take care"
Peaceful Oasis in Naugatuck - Charming 3-Bedroom Home with serene backyard.

Updated ranch Home 4 minutes from the beach on a quiet end street.

8.4 out of 10, Very Good, (7)
"A nice long weekend beach getaway with family. House had everything we needed, was very clean and neat and everyone had their own space too. Our host was very responsive when I messaged him. Lots of places to shop and eat and the beach is super close! Thank you for a great place to stay for a really nice long weekend with my family. We will be back!"
Updated ranch Home 4 minutes from the beach on a quiet end street.

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

10.0 out of 10, Exceptional, (118)
"Had a quick work trip and wish we stayed longer! "
Beach Front Arts & Crafts House With Gorgeous Views Of The Sound

Lake house cozy to relax with a family. 6 bedroom very spacious house.

10.0 out of 10, Exceptional, (1)
"Perfect setting for our family as we celebrated a college graduation locally. Great location. Home has many amenities and you cannot beat lake living! Trying to think about a reason we can return. ;-)"
Lake house cozy to relax with a family. 6 bedroom very spacious house.

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

9.4 out of 10, Exceptional, (23)
"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

NEW Candlewood Lake 4BR 2BA Direct Waterfront Home Dock~Fire Pit~Winter Special!

10.0 out of 10, Exceptional, (5)
"We had a wonderful vacation with our grandchildren and family. The children lived in the water if not kayaking or water boards they were fishing!! Rainy days puzzles were our entertainment the summer house provided everything one wanted or needed. It was a very delightful vacation"
NEW Candlewood Lake 4BR 2BA Direct Waterfront Home Dock~Fire Pit~Winter Special!

Modern 3 Bed House in Black Rock

2.0 star property
"Home was as advertised "
Modern 3 Bed House in Black Rock

NEW-Another Fun Downtown Location 1st floor

2.0 star property
9.8 out of 10, Exceptional, (17)
"This was our second stay at this VRBO and hope to stay again on return trips to the area."
NEW-Another Fun Downtown Location 1st floor

Swiss Chalet amidst sixteen acres in Litchfield Hills surrounded by land trust

10.0 out of 10, Exceptional, (9)
"We really enjoyed being able to stay at such a beautiful home. Between the animals and the hot tub view - the serenity will be hard to match elsewhere!"
Swiss Chalet amidst sixteen acres in Litchfield Hills surrounded by land trust

Bright Escape, Top-Rated Design, Fire pit, Near Beach, 90 minutes to NYC

10.0 out of 10, Exceptional, (5)
"And the bed was confortable"
The price is AED 1,102
AED 2,355 total
includes taxes & fees
16 Jun - 17 Jun
Bright Escape, Top-Rated Design, Fire pit, Near Beach, 90 minutes to NYC
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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