Southbury Vacation Rentals

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Vacation Rentals in Southbury

Charming Colonial for Events! – Perfect for Family Reunions and Group Getaways!

Bridgeport CT

$1,403 nightly

$1,587 total

Dec 15 - Dec 16

Total with taxes and fees

With a stay at this vacation home in Bridgeport (North End), you'll be within a 15-minute walk of Svihra Park and St. Vincent's Medical Center.

Kitchen

Washer

Peaceful Vintage Home with Private Lake in Redding, CT.

Redding CT

$570 nightly

$646 total

Dec 15 - Dec 16

Total with taxes and fees

Located in Redding, this vacation home is on a lake, a 1-minute drive from Putnam Memorial State Park and 6 minutes from Bethel Plaza Shopping Center.

Kitchen

Washer

Charming Home in Seaside

Bridgeport CT

With a stay at this vacation home in Bridgeport (South End), you'll be steps from University of Bridgeport and Seaside Park.

Washer

Dryer

Private Beautiful Home - Family Friendly - 1 min. Walk to Candlewood Lake

New Fairfield CT

With a stay at this vacation home in New Fairfield, you'll be a 1-minute walk from Candlewood Lake and 13 minutes by foot from Squantz Pond State Park.

Kitchen

Washer

Business or Weekend escape

Stratford CT

$130 nightly

$147 total

Jan 1 - Jan 2, 2026

Total with taxes and fees

Located in Stratford, this vacation home is within a 5-minute drive of Perry House and Stratford Historical Society Capt David Judson House.

Pool

Air conditioning

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

Milford CT

When you stay at this vacation home in Milford, you'll be on the beach, within a 15-minute drive of Yale University and Yale-New Haven Hospital.

Kitchen

Washer

Cozy Lakefront Bungalow w firepit/dock/kayaks

Plymouth CT

Located in Plymouth, this vacation home is on the waterfront, within a 15-minute drive of Black Rock State Park and Rockwell Park.

Hot Tub

Kitchen

Cozy 2 bedroom home located minutes from downtown

New Haven CT

With a stay at this vacation home in New Haven (West New Haven), you'll be within a 5-minute drive of Yale University and Yale-New Haven Hospital.

Kitchen

Washer

Sunny Beach Cottage close to Yale 1.5 hr from NYC

West Haven CT

With a stay at this vacation home in West Haven, you'll be within a 10-minute drive of Yale University and Yale-New Haven Hospital.

Free WiFi

Air conditioning

Silver Sands Beach Getaway

Milford CT

With a stay at this vacation home in Milford, you'll be just steps from Silver Sands State Park and Silver Sands.

Kitchen

Washer

New! Trail-side Haven Retreat! Pet friendly

North Haven CT

With a stay at this vacation home in North Haven, you'll be within a 10-minute drive of Yale University and Yale-New Haven Hospital.

Kitchen

Washer

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

Danbury CT

Located in Danbury, this vacation home is on the waterfront, within a 10-minute drive of Candlewood Lake and Hatters Park.

Hot Tub

Kitchen

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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.