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Check prices for these dates

Next weekend
Aug 15 - Aug 17
In two weeks
Aug 22 - Aug 24
In one month
Sep 5 - Sep 7
In two months
Oct 3 - Oct 5

Browse Select Southbury Vacation Homes

Business or Weekend escape
Enjoy a refreshing swim under the stars at our pool, surrounded by a spacious deck.

Business or Weekend escape

9.2 out of 10, Wonderful, (43)
"Very nice owner with great communication. "
The price is CA $117
CA $202 total
includes taxes & fees
Aug 11 - Aug 12
Business or Weekend escape
Lakehouse, Boat Dock, Kayaks, Fire-Pit, King Bed, 1 Hour & 15 Min from NYC etc!
Enjoy a peaceful lakeside retreat with a barbecue grill and comfortable seating area.

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

9.0 out of 10, Wonderful, (18)
"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!
Cozy 3 bedroom minutes from Yale and the beach
Kitchen features a central island, oven, and white cabinetry with a patterned backsplash.

Cozy 3 bedroom minutes from Yale and the beach

7.0 out of 10, Good, (2)
"The inside was very clean, the back patio/garden area is cute, but the pool was green by day two. Overall we enjoyed our time here"
Cozy 3 bedroom minutes from Yale and the beach
Minutes to Walnut Beach, newly renovated 3 bedroom home
Enjoy a serene beachside retreat with a balcony overlooking the tranquil ocean.

Minutes to Walnut Beach, newly renovated 3 bedroom home

10.0 out of 10, Exceptional, (6)
"Very nice place."
Minutes to Walnut Beach, newly renovated 3 bedroom home
Charming 3-bedroom house with WiFi, AC in serene Fairfield
Enjoy cooking in this well-equipped kitchen with a large window offering a view of the outside.

Charming 3-bedroom house with WiFi, AC in serene Fairfield

9.6 out of 10, Exceptional, (4)
"Thank you for the stay!"
Charming 3-bedroom house with WiFi, AC in serene Fairfield
Historic Connecticut Home w/ Grill & Spacious Yard
Enjoy meals and gatherings in this well-appointed kitchen with a large island, sink, and stainless steel refrigerator.

Historic Connecticut Home w/ Grill & Spacious Yard

10.0 out of 10, Exceptional, (12)
"Very well appointed (Boll & Branch sheets so nice). Great communication from owners. "
Historic Connecticut Home w/ Grill & Spacious Yard
Cozy Lakefront Bungalow w firepit/dock/kayaks
Enjoy the view from the upper balcony, which offers a fire pit and Adirondack chairs in the yard.

Cozy Lakefront Bungalow w firepit/dock/kayaks

10.0 out of 10, Exceptional, (29)
"This is our second time visiting the area and staying at this beautiful home. It's close to many activities for children and adults, easy to access food and services and a beautiful overall area and home. We truly enjoy visiting!"
Cozy Lakefront Bungalow w firepit/dock/kayaks
Tranquil Litchfield Connecticut Retreat".
Relax on the covered porch, surrounded by lush greenery, with a comfortable rocking chair waiting.

Tranquil Litchfield Connecticut Retreat".

9.2 out of 10, Wonderful, (15)
"My friends and stayed for a night. The house is nice and the owners is very communicative. "
The price is CA $310
CA $440 total
includes taxes & fees
Aug 11 - Aug 12
Tranquil Litchfield Connecticut Retreat".
Private Annex/Former Artist Studio
Relax on the deck overlooking a lush garden with a tranquil atmosphere.

Private Annex/Former Artist Studio

10.0 out of 10, Exceptional, (51)
"Great property great location wonderful day"
Private Annex/Former Artist Studio
Charming 2-bedroom house with WiFi, AC in Fairfield
Relax in a stylish living space with a geometric sculpture, potted plant, and modern sofa.

Charming 2-bedroom house with WiFi, AC in Fairfield

8.0 out of 10, Very good, (3)
"Amalfi’s place was as described. It was clean and comfortable and mostly quiet. Amalfi was excellent with communication. Would certainly stay again when visiting family."
The price is CA $205
CA $478 total
includes taxes & fees
Aug 6 - Aug 7
Charming 2-bedroom house with WiFi, AC in Fairfield
The Daydreamer - Walk To Walnut Beach, Restaurant + Shops
Stunning marina views with boats docked, surrounded by beautifully lit buildings.

The Daydreamer - Walk To Walnut Beach, Restaurant + Shops

10.0 out of 10, Exceptional, (11)
"5 Star stay!"
The Daydreamer - Walk To Walnut Beach, Restaurant + Shops
Updated ranch Home 4 minutes from the beach on a quiet end street.
Enjoy cooking in this well-equipped kitchen with a microwave, toaster, and oven.

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

8.4 out of 10, Very good, (7)
"It was everything that I expected. Fabian was very attentive and responsive. I would definitely rent again. "
Updated ranch Home 4 minutes from the beach on a quiet end street.
Dog-Friendly Oceanfront Getaway - Walk to Dining - Private Beach Access
Enjoy the ocean view from this room, featuring a sofa, chair, and small table.

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

10.0 out of 10, Exceptional, (5)
The price is CA $522
CA $965 total
includes taxes & fees
Aug 11 - Aug 12
Dog-Friendly Oceanfront Getaway - Walk to Dining - Private Beach Access
Lakeside/Sleeps20/HotTub/GameRoom/2Acres/Firepit
Enjoy a formal dining experience with a view of the surrounding forest from the large windows.

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

10.0 out of 10, Exceptional, (1)
Lakeside/Sleeps20/HotTub/GameRoom/2Acres/Firepit
42 Wood Ave · 5 Minute Walk To Beach! Amazing Backyard Space!
Relax in this stylish living room with a high ceiling, leather sofa, and comfortable armchair.

42 Wood Ave · 5 Minute Walk To Beach! Amazing Backyard Space!

8.6 out of 10, Excellent, (7)
"I rented this place because of the location and convenience to the many things we enjoy about Milford CT. The master bedroom is top-notch as well as the living space downstairs. We hoped to use the outdoor fire place make smores, but due to a medical emergency our trip was cut short. Regardless, we enjoyed our stay at 42 Wood Ave. Thank you, Tiffany, for supplying an awesome rental."
42 Wood Ave · 5 Minute Walk To Beach! Amazing Backyard Space!
Beautiful Renovated Direct Waterfront Candlewood Lake Home~Views~Weekly Discount
Relax by the serene lake with a dock, Adirondack chairs, and a small table.

Beautiful Renovated Direct Waterfront Candlewood Lake Home~Views~Weekly Discount

10.0 out of 10, Exceptional, (25)
"The house was very clean and comfortable with really nice seating inside and out with great views of the lake. Our family really enjoyed"
Beautiful Renovated Direct Waterfront Candlewood Lake Home~Views~Weekly Discount
Escape to your private lakeside estate! Family & dog friendly, wildlife viewing!
Enjoy serene lakeside views from the dock, where a rowboat and canoe await.

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

10.0 out of 10, Exceptional, (122)
"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!
Private hidden gem walking distance to town, restaurants, and shopping!
Relax in a serene backyard oasis with a pool, lounge chairs, and dining area.

Private hidden gem walking distance to town, restaurants, and shopping!

9.8 out of 10, Exceptional, (18)
"Great property!"
Private hidden gem walking distance to town, restaurants, and shopping!
Awesome Lake Home with tons of fun!
Relax in a hot tub surrounded by a wooden deck and a serene wooded area.

Awesome Lake Home with tons of fun!

2.0 star property
10.0 out of 10, Exceptional, (1)
"Great spot "
The price is CA $620
CA $1,062 total
includes taxes & fees
Aug 11 - Aug 12
Awesome Lake Home with tons of fun!
Litchfield County Getaway
Enjoy cooking in this well-equipped kitchen with a central island, oven, and stainless steel range hood.

Litchfield County Getaway

10.0 out of 10, Exceptional, (44)
"Came for the garlic festival and antique shopping. Perfect location and everything was just what we expected. If we come for garlic festival next year this is where I want to stay. "
Litchfield County Getaway
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

Wyndham Southbury

Wyndham Southbury

10/10 Excellent
"The staff was very friendly. Beds were so comfortable. "
John 2-night trip
Posted 13 hours ago
Wyndham Southbury