Top 50 Southbury Vacation Rentals

Houses (93)
Cottages (29)
Apartments (10)
Golf rental (91)
Lake view (58)
Lakefront (41)

Explore a selection of Southbury vacation rentals

Charming Farmhouse On A 160 Acre Beautiful & Private Vineyard...
Guests6
Bedrooms3
Bathroom1
Wonderful 4.7 / 5
$258 avg/night
3 beds
1 Bathroom
Guests 6
6 reviews
Spacious, Private Home
Guests6
Bedrooms3
Bathrooms2
Wonderful 5 / 5
$150 avg/night
3 beds
2 Bathrooms
Guests 6
2 reviews
Chalet Home at Candlewood Lake, Beach, Owner Managed.
Guests6
Bedrooms2
Bathroom1
Wonderful 4.8 / 5
$110 avg/night
2 beds
1 Bathroom
Guests 6
51 reviews
Charming Country House Overlooking Candlewood Lake, Beach
Guests6
Bedrooms3
Bathrooms2
Wonderful 5 / 5
$186 avg/night
3 beds
2 Bathrooms
Guests 6
30 reviews
CANDLE WOOD ISLE LAKE HOUSE EARLY FALL GETAWAY LOW RATES
Guests6
Bedrooms4
Bathroom1
Wonderful 4.8 / 5
$121 avg/night
4 beds
1 Bathroom
Guests 6
5 reviews
Beautiful Candlewood Isle Cottage With Spectacular Lake Views.
Guests5
Bedrooms2
Bathroom1
Wonderful 4.9 / 5
$227 avg/night
2 beds
1 Bathroom
Guests 5
13 reviews
Spacious Restored Barn on 700 acre Estate with Magnficent Views
Guests12
Bedrooms6
Bathrooms6
Wonderful 4.5 / 5
$500 avg/night
6 beds
6 Bathrooms
Guests 12
16 reviews
Kozy Direct Waterfront cottage, One Of A Kind Private Lake Loc, 2...
Guests4
Bedrooms2
Bathroom1
Wonderful 4.8 / 5
$300 avg/night
2 beds
1 Bathroom
Guests 4
35 reviews
Elegant Country Estate Guest House
Guests4
Bedroom1
Bathroom1
Wonderful 4.9 / 5
$100 avg/night
1 bed
1 Bathroom
Guests 4
19 reviews
Adorable Guest Cottage
Guests4
Bedrooms2
Bathroom1
Wonderful 4.8 / 5
$162 avg/night
2 beds
1 Bathroom
Guests 4
16 reviews
Beautiful Cottage and Waterfront Access
Guests4
Bedrooms2
Bathrooms2
Wonderful 5 / 5
$221 avg/night
2 beds
2 Bathrooms
Guests 4
9 reviews
Resort-like Setting 2.5 Miles from Merritt; Will PU at Train
Guests2
Bedroom1
Bathroom1
Wonderful 5 / 5
$130 avg/night
1 bed
1 Bathroom
Guests 2
5 reviews
Westville Comfort Central. New Haven
Guests4
Bedrooms2
Bathrooms2
Wonderful 4.2 / 5
$79 avg/night
2 beds
2 Bathrooms
Guests 4
5 reviews
1770 Colonial 5 Bedrooms 4 1/2 Baths Sleeps 9
Guests9
Bedrooms5
Bathrooms4
Wonderful 5 / 5
$250 avg/night
5 beds
4 Bathrooms
Guests 9
8 reviews
Beautiful Large Estate In The Country, Nearby Skiing, Short Or...
Guests22
Bedrooms6
Bathrooms4
Wonderful 4.9 / 5
$909 avg/night
6 beds
4 Bathrooms
Guests 22
18 reviews
Idyllic Family Retreat on Candlewood Lake Beach
Guests12
Bedrooms5
Bathrooms3
Wonderful 4.8 / 5
$267 avg/night
5 beds
3 Bathrooms
Guests 12
6 reviews
Unique Lakefront Estate, 7 acres, Private Dock, Cedar Sauna, 1 hr...
Guests15
Bedrooms5
Bathrooms5
Wonderful 4.9 / 5
$531 avg/night
5 beds
5 Bathrooms
Guests 15
24 reviews
Charming Lakefront Cabin And Guest Cottage With Spectacular View
Guests10
Bedrooms5
Bathrooms2
Wonderful 5 / 5
$500 avg/night
5 beds
2 Bathrooms
Guests 10
7 reviews
Apartment In Great Location In Seymour, Connecticut, Suburban
Guests7
Bedroom1
Bathroom1
Wonderful 4 / 5
$69 avg/night
1 bed
1 Bathroom
Guests 7
4 reviews
Penthouse Apartment at Yale University
Guests4
Bedrooms2
Bathroom1
Wonderful 5 / 5
$214 avg/night
2 beds
1 Bathroom
Guests 4
17 reviews
Newly Renovated 18th Century Cottage On 4 Acres
Guests5
Bedrooms2
Bathrooms2
Wonderful 4.5 / 5
$183 avg/night
2 beds
2 Bathrooms
Guests 5
2 reviews
The perfect quiet country getaway
Guests2
Bedroom1
Bathroom1
Wonderful 4.9 / 5
$146 avg/night
1 bed
1 Bathroom
Guests 2
25 reviews
Prime Direct Waterfront On Candlewood Lake, Private Dock, Cozy...
Guests6
Bedrooms3
Bathrooms2
Wonderful 4.8 / 5
$220 avg/night
3 beds
2 Bathrooms
Guests 6
10 reviews
Expansive Property with Beautiful Waterfront Setting in Sherman, CT
Guests10
Bedrooms4
Bathrooms3
Wonderful 4.8 / 5
$500 avg/night
4 beds
3 Bathrooms
Guests 10
6 reviews
Your 1796 Connecticut Barn Cottage Awaits!
Guests7
Bedrooms2
Bathrooms2
Wonderful 5 / 5
$135 avg/night
2 beds
2 Bathrooms
Guests 7
4 reviews
Scenic Lakefront Retreat
Guests8
Bedrooms3
Bathrooms2
Wonderful 5 / 5
$283 avg/night
3 beds
2 Bathrooms
Guests 8
14 reviews
Direct Candlewood Lake Front in a sought after location.
Guests9
Bedrooms4
Bathrooms3
Wonderful 4.8 / 5
$529 avg/night
4 beds
3 Bathrooms
Guests 9
16 reviews
Candlewood Lake - Sprawling Waterfront Getaway. Sleeps 10
Guests10
Bedrooms4
Bathrooms2
Wonderful 4.9 / 5
$500 avg/night
4 beds
2 Bathrooms
Guests 10
7 reviews
Apartment In Great Location
Guests5
Bedroom1
Bathroom1
Wonderful 5 / 5
$79 avg/night
1 bed
1 Bathroom
Guests 5
1 reviews
Elegant Country Estate with Equestrian Farm
Guests14
Bedrooms6
Bathrooms5
Wonderful 4.9 / 5
$579 avg/night
6 beds
5 Bathrooms
Guests 14
24 reviews
Elegant Country Estate with Equestrian Farm
Guests14
Bedrooms6
Bathrooms4
Wonderful 4.9 / 5
$579 avg/night
6 beds
4 Bathrooms
Guests 14
24 reviews
House on Lake Waramaug
Guests7
Bedrooms3
Bathrooms2
Wonderful 4.3 / 5
$280 avg/night
3 beds
2 Bathrooms
Guests 7
7 reviews
Adorable 2 Bedroom Lake Cottage- Very Quiet and Private!
Guests5
Bedrooms2
Bathroom1
Wonderful 4.9 / 5
$160 avg/night
2 beds
1 Bathroom
Guests 5
19 reviews
APPLE PICKING!! TRACTOR RIDES! and Fall Foliage next door Private...
Guests24
Bedrooms8
Bathrooms6
Wonderful 4.3 / 5
$645 avg/night
8 beds
6 Bathrooms
Guests 24
6 reviews
Private bedroom with beautiful bathroom
Guests4
Bedroom1
Bathroom1
Wonderful 5 / 5
$93 avg/night
1 bed
1 Bathroom
Guests 4
2 reviews
Litchfield County Farmhouse with a Modern Twist: only 2 hours from...
Guests6
Bedrooms3
Bathrooms3
Wonderful 4.8 / 5
$228 avg/night
3 beds
3 Bathrooms
Guests 6
9 reviews
Breeze Way In The Village - Sunny, Spacious, Converted Artist's...
Guests4
Bedrooms2
Bathroom1
Wonderful 4.9 / 5
$180 avg/night
2 beds
1 Bathroom
Guests 4
9 reviews
Charming Cabin 90 Minutes from NYC!!
Guests8
Bedrooms4
Bathroom1
Wonderful 4.3 / 5
$237 avg/night
4 beds
1 Bathroom
Guests 8
3 reviews
4 Bedroom House With Pool And Lake View
Guests10
Bedrooms5
Bathrooms3
Wonderful 4.6 / 5
$371 avg/night
5 beds
3 Bathrooms
Guests 10
7 reviews
Guest Cottage on Country Estate- Newly renovated
Guests6
Bedrooms2
Bathroom1
Wonderful 4.3 / 5
$119 avg/night
2 beds
1 Bathroom
Guests 6
4 reviews
Beautiful Waterfront Lakefront House for Rent - 3 Bedrooms, 2 Baths
Guests6
Bedrooms3
Bathrooms2
Wonderful 4.3 / 5
$225 avg/night
3 beds
2 Bathrooms
Guests 6
3 reviews
Lakefront Cottage on Quiet Lake, private dock, private beach area...
Guests6
Bedrooms2
Bathroom1
Wonderful 4.9 / 5
$200 avg/night
2 beds
1 Bathroom
Guests 6
14 reviews
Peaceful Lakefront Retreat on Candlewood Lake in Beautiful...
Guests8
Bedrooms4
Bathrooms3
Wonderful 5 / 5
$400 avg/night
4 beds
3 Bathrooms
Guests 8
3 reviews
Spacious, beautifully appointed Colonial
Guests10
Bedrooms4
Bathrooms3
Wonderful 5 / 5
$425 avg/night
4 beds
3 Bathrooms
Guests 10
6 reviews
Candlewood Lake Waterfront
Guests9
Bedrooms4
Bathrooms2
Wonderful 5 / 5
$600 avg/night
4 beds
2 Bathrooms
Guests 9
7 reviews
Beautiful Candlewood Isle Rental- Great Family Gathering Spot
Guests8
Bedrooms3
Bathrooms2
Wonderful 4.9 / 5
$229 avg/night
3 beds
2 Bathrooms
Guests 8
16 reviews
Lovely Cottage, Completely Remodeled Two Bedroom One Bath Can...
Guests6
Bedrooms2
Bathroom1
Wonderful 4.9 / 5
$189 avg/night
2 beds
1 Bathroom
Guests 6
18 reviews
Private Water Front Property
Guests10
Bedrooms4
Bathrooms2
Wonderful 5 / 5
$357 avg/night
4 beds
2 Bathrooms
Guests 10
3 reviews
Unique Woodland Retreat w/ 5 Bedrooms & 50 Private Acres
Guests12
Bedrooms5
Bathrooms4
Wonderful 4.7 / 5
$417 avg/night
5 beds
4 Bathrooms
Guests 12
6 reviews
Romantic Hideaway, Private With Lovely Views Overlooking Pool And...
Guests2
Bedroom1
Bathroom1
Wonderful 5 / 5
$197 avg/night
1 bed
1 Bathroom
Guests 2
2 reviews

Southbury, CT, USA Vacation Rentals

Charming Farmhouse On A 160 Acre Beautiful & Private Vineyard...

Spacious, Private Home

Chalet Home at Candlewood Lake, Beach, Owner Managed.

Charming Country House Overlooking Candlewood Lake, Beach

CANDLE WOOD ISLE LAKE HOUSE EARLY FALL GETAWAY LOW RATES

Beautiful Candlewood Isle Cottage With Spectacular Lake Views.

Spacious Restored Barn on 700 acre Estate with Magnficent Views

Kozy Direct Waterfront cottage, One Of A Kind Private Lake Loc, 2...

Elegant Country Estate Guest House

Adorable Guest Cottage

Beautiful Cottage and Waterfront Access

Resort-like Setting 2.5 Miles from Merritt; Will PU at Train

Westville Comfort Central. New Haven

1770 Colonial 5 Bedrooms 4 1/2 Baths Sleeps 9

Beautiful Large Estate In The Country, Nearby Skiing, Short Or...

Idyllic Family Retreat on Candlewood Lake Beach

Unique Lakefront Estate, 7 acres, Private Dock, Cedar Sauna, 1 hr...

Charming Lakefront Cabin And Guest Cottage With Spectacular View

Apartment In Great Location In Seymour, Connecticut, Suburban

Penthouse Apartment at Yale University

Newly Renovated 18th Century Cottage On 4 Acres

The perfect quiet country getaway

Prime Direct Waterfront On Candlewood Lake, Private Dock, Cozy...

Expansive Property with Beautiful Waterfront Setting in Sherman, CT

Your 1796 Connecticut Barn Cottage Awaits!

Scenic Lakefront Retreat

Direct Candlewood Lake Front in a sought after location.

Candlewood Lake - Sprawling Waterfront Getaway. Sleeps 10

Apartment In Great Location

Elegant Country Estate with Equestrian Farm

Elegant Country Estate with Equestrian Farm

House on Lake Waramaug

Adorable 2 Bedroom Lake Cottage- Very Quiet and Private!

APPLE PICKING!! TRACTOR RIDES! and Fall Foliage next door Private...

Private bedroom with beautiful bathroom

Litchfield County Farmhouse with a Modern Twist: only 2 hours from...

Breeze Way In The Village - Sunny, Spacious, Converted Artist's...

Charming Cabin 90 Minutes from NYC!!

4 Bedroom House With Pool And Lake View

Guest Cottage on Country Estate- Newly renovated

Beautiful Waterfront Lakefront House for Rent - 3 Bedrooms, 2 Baths

Lakefront Cottage on Quiet Lake, private dock, private beach area...

Peaceful Lakefront Retreat on Candlewood Lake in Beautiful...

Spacious, beautifully appointed Colonial

Candlewood Lake Waterfront

Beautiful Candlewood Isle Rental- Great Family Gathering Spot

Lovely Cottage, Completely Remodeled Two Bedroom One Bath Can...

Private Water Front Property

Unique Woodland Retreat w/ 5 Bedrooms & 50 Private Acres

Romantic Hideaway, Private With Lovely Views Overlooking Pool And...