Top 50 Darien Vacation Rentals

Houses (156)
Apartments (16)
Cottages (12)
Golf rental (92)
Beachfront (32)
Beach view (25)

Explore a selection of Darien vacation rentals

Waterfront Property with Pool 50 minutes from New York City
Guests10
Bedrooms5
Bathrooms4
Wonderful 5 / 5
$1,000 avg/night
5 beds
4 Bathrooms
Guests 10
4 reviews
Comfortable home in Darien
Guests4
Bedrooms3
Bathrooms2
Wonderful 0 / 5
$230 avg/night
3 beds
2 Bathrooms
Guests 4
Historic Westport Two Bedroom two Bath Home
Guests4
Bedrooms2
Bathrooms2
Wonderful 4.8 / 5
$160 avg/night
2 beds
2 Bathrooms
Guests 4
4 reviews
Pretty Stone Home, Quiet Lane in Mid-country Greenwich, Ct Privacy!
Guests6
Bedrooms2
Bathrooms2
Wonderful 5 / 5
$257 avg/night
2 beds
2 Bathrooms
Guests 6
4 reviews
Fabulous Rye Beach Cottage
Guests4
Bedroom1
Bathroom1
Wonderful 4.2 / 5
$143 avg/night
1 bed
1 Bathroom
Guests 4
6 reviews
Perfectly located beach, town, train cottage with beach style...
Guests8
Bedrooms4
Bathrooms2
Wonderful 4.8 / 5
$357 avg/night
4 beds
2 Bathrooms
Guests 8
13 reviews
Gorgeous Quiet Old World Charm White Plains Private Apartment...
Guests3
Bedroom1
Bathroom1
Wonderful 4.9 / 5
$125 avg/night
1 bed
1 Bathroom
Guests 3
13 reviews
Luxury Victorian beach house - steps to 2 private beaches!
Guests8
Bedrooms5
Bathrooms3
Wonderful 5 / 5
$767 avg/night
5 beds
3 Bathrooms
Guests 8
2 reviews
Large Home On 4+ Beautiful Acres Of Privacy In Chappaqua
Guests10
Bedrooms6
Bathrooms2
Wonderful 4.7 / 5
$471 avg/night
6 beds
2 Bathrooms
Guests 10
11 reviews
Stunning New Luxury New England Home
Guests11
Bedrooms5
Bathrooms5
Wonderful 4.4 / 5
$263 avg/night
5 beds
5 Bathrooms
Guests 11
7 reviews
Cozy gardener's cottage on sprawling Fairfield estate
Guests4
Bedrooms2
Bathroom1
Wonderful 5 / 5
$214 avg/night
2 beds
1 Bathroom
Guests 4
7 reviews
Circa 1790 Newly Restored Converted Barn
Guests4
Bedroom1
Bathroom1
Wonderful 4.9 / 5
$208 avg/night
1 bed
1 Bathroom
Guests 4
15 reviews
Adorable Guest Cottage
Guests4
Bedrooms2
Bathroom1
Wonderful 4.8 / 5
$162 avg/night
2 beds
1 Bathroom
Guests 4
16 reviews
3 mins drive to Fairfield Beach, 3 bed, Sleeps 6
Guests6
Bedrooms3
Bathrooms2
Wonderful 0 / 5
$214 avg/night
3 beds
2 Bathrooms
Guests 6
Centrally located. Walk to Greenwich Ave and Greenwich Train...
Guests6
Bedrooms3
Bathrooms2
Wonderful 4.8 / 5
$350 avg/night
3 beds
2 Bathrooms
Guests 6
5 reviews
Waterfront Greenwich House - Amazing Views & Private -5 mins...
Guests10
Bedrooms4
Bathrooms3
Wonderful 5 / 5
$319 avg/night
4 beds
3 Bathrooms
Guests 10
2 reviews
Elegant Beachfront Property!
Guests10
Bedrooms5
Bathrooms3
Wonderful 4 / 5
$536 avg/night
5 beds
3 Bathrooms
Guests 10
2 reviews
GREENWICH FALL GETAWAYS NEAR THE BEACH INCLUDING COLUMBUS DAY...
Guests10
Bedrooms5
Bathrooms3
Wonderful 5 / 5
$700 avg/night
5 beds
3 Bathrooms
Guests 10
3 reviews
Great hotel alternative!!! Brand New!!! 3 Bedroom Home - Heart of...
Guests5
Bedrooms3
Bathrooms3
Wonderful 5 / 5
$750 avg/night
3 beds
3 Bathrooms
Guests 5
1 reviews
Great family home, close to the city, surrounded by nature!
Guests8
Bedrooms5
Bathrooms2
Wonderful 4.6 / 5
$595 avg/night
5 beds
2 Bathrooms
Guests 8
14 reviews
We've still got a few days available at our beautiful bungalow...
Guests4
Studio
Bathroom1
Wonderful 4.9 / 5
$199 avg/night
Studio
1 Bathroom
Guests 4
11 reviews
One of a kind French Retreat-Perfect for Holidays-1Hr from NYC...
Guests10
Bedrooms6
Bathrooms5
Wonderful 5 / 5
$992 avg/night
6 beds
5 Bathrooms
Guests 10
3 reviews
Modern Apartment with water views
Guests2
Bedroom1
Bathroom1
Wonderful 0 / 5
$222 avg/night
1 bed
1 Bathroom
Guests 2
The perfect quiet country getaway
Guests2
Bedroom1
Bathroom1
Wonderful 4.9 / 5
$146 avg/night
1 bed
1 Bathroom
Guests 2
26 reviews
Cloud 9, fashionably chic Beach Bungalow in Saugatuck Shores
Guests4
Bedrooms3
Bathrooms2
Wonderful 5 / 5
$550 avg/night
3 beds
2 Bathrooms
Guests 4
3 reviews
Stunning New Construction
Guests4
Bedrooms2
Bathrooms2
Wonderful 5 / 5
$400 avg/night
2 beds
2 Bathrooms
Guests 4
2 reviews
Circa 1735 Fully Restored Farm House
Guests6
Bedrooms2
Bathrooms2
Wonderful 4.7 / 5
$225 avg/night
2 beds
2 Bathrooms
Guests 6
11 reviews
Private apartment in South Huntington.
Guests2
Bedroom1
Bathroom1
Wonderful 5 / 5
$110 avg/night
1 bed
1 Bathroom
Guests 2
2 reviews
Studio Apartment 2 miles from Fairfield, CT Beach
Guests6
Bedroom1
Bathroom1
Wonderful 4.9 / 5
$101 avg/night
1 bed
1 Bathroom
Guests 6
33 reviews
Bright Stylish Chic 4BR 4BA Home 1 Hour to NYC Close to Greenwich...
Guests10
Bedrooms4
Bathrooms4
Wonderful 5 / 5
$359 avg/night
4 beds
4 Bathrooms
Guests 10
25 reviews
Greenwich, CT Hotel Alternative Completely Renovated High End...
Guests4
Bedrooms2
Bathrooms2
Wonderful 5 / 5
$327 avg/night
2 beds
2 Bathrooms
Guests 4
1 reviews
Downtown "Blue Nest" Apartment
Guests4
Bedroom1
Bathroom1
Wonderful 5 / 5
$93 avg/night
1 bed
1 Bathroom
Guests 4
4 reviews
2BR Northport House w/3 Private Decks!
Guests4
Bedrooms2
Bathrooms2
Wonderful 4.2 / 5
$175 avg/night
2 beds
2 Bathrooms
Guests 4
19 reviews
APPLE PICKING!! TRACTOR RIDES! and Fall Foliage next door Private...
Guests24
Bedrooms8
Bathrooms6
Wonderful 5 / 5
$645 avg/night
8 beds
6 Bathrooms
Guests 24
5 reviews
Private bedroom with beautiful bathroom
Guests4
Bedroom1
Bathroom1
Wonderful 5 / 5
$93 avg/night
1 bed
1 Bathroom
Guests 4
2 reviews
Fantastic Waterview Home in Quaint Beach Village - NYC - 23 Miles!
Guests8
Bedrooms4
Bathroom1
Wonderful 4.4 / 5
$300 avg/night
4 beds
1 Bathroom
Guests 8
13 reviews
Beach cottage steps from the beach!!
Guests6
Bedrooms4
Bathrooms2
Wonderful 4 / 5
$286 avg/night
4 beds
2 Bathrooms
Guests 6
1 reviews
Greenwich Tudor Home & Gardens near New York City
Guests9
Bedrooms3
Bathrooms2
Wonderful 5 / 5
$334 avg/night
3 beds
2 Bathrooms
Guests 9
3 reviews
Quaint 3br Duplex. Close To Beach, Restaurants And Shopping!
Guests5
Bedrooms3
Bathroom1
Wonderful 4.8 / 5
$232 avg/night
3 beds
1 Bathroom
Guests 5
11 reviews
Rowayton House Close To Town
Guests5
Bedrooms3
Bathrooms2
Wonderful 5 / 5
$367 avg/night
3 beds
2 Bathrooms
Guests 5
1 reviews
Spacious, comfortable home for relaxed weekends in the fall.
Guests8
Bedrooms4
Bathrooms3
Wonderful 5 / 5
$600 avg/night
4 beds
3 Bathrooms
Guests 8
3 reviews
Beautiful Waterfront Home With Fabulous Views In Rye NY...
Guests9
Bedrooms5
Bathrooms4
Wonderful 4 / 5
$700 avg/night
5 beds
4 Bathrooms
Guests 9
3 reviews
European luxury with Pool and Privacy in Westport
Guests6
Bedrooms3
Bathrooms2
Wonderful 4.8 / 5
$483 avg/night
3 beds
2 Bathrooms
Guests 6
12 reviews
Available October 2017 for Long or Short Term Rental
Guests8
Bedrooms4
Bathrooms4
Wonderful 5 / 5
$203 avg/night
4 beds
4 Bathrooms
Guests 8
2 reviews
Weston's Best Summer Home
Guests10
Bedrooms5
Bathrooms4
Wonderful 5 / 5
$3,311 avg/night
5 beds
4 Bathrooms
Guests 10
1 reviews
Westport "Gold Coast" across from Southport beach
Guests3
Bedroom1
Bathroom1
Wonderful 4.8 / 5
$217 avg/night
1 bed
1 Bathroom
Guests 3
16 reviews
Directly on Water. Classic Beach House.
Guests10
Bedrooms5
Bathrooms3
Wonderful 5 / 5
$750 avg/night
5 beds
3 Bathrooms
Guests 10
2 reviews
Westport, CT - Walk To The Beach - NYC Getaway
Guests8
Bedrooms4
Bathrooms2
Wonderful 4.8 / 5
$272 avg/night
4 beds
2 Bathrooms
Guests 8
5 reviews
Greenwich Farm House in a Country Setting with a pool.
Guests7
Bedrooms3
Bathrooms2
Wonderful 4.9 / 5
$600 avg/night
3 beds
2 Bathrooms
Guests 7
8 reviews
1/2 block to Compo Beach on Long Island Sound!
Guests8
Bedrooms4
Bathrooms4
Wonderful 0 / 5
$885 avg/night
4 beds
4 Bathrooms
Guests 8

Darien, CT, USA Vacation Rentals

Waterfront Property with Pool 50 minutes from New York City

Comfortable home in Darien

Historic Westport Two Bedroom two Bath Home

Pretty Stone Home, Quiet Lane in Mid-country Greenwich, Ct Privacy!

Fabulous Rye Beach Cottage

Perfectly located beach, town, train cottage with beach style...

Gorgeous Quiet Old World Charm White Plains Private Apartment...

Luxury Victorian beach house - steps to 2 private beaches!

Large Home On 4+ Beautiful Acres Of Privacy In Chappaqua

Stunning New Luxury New England Home

Cozy gardener's cottage on sprawling Fairfield estate

Circa 1790 Newly Restored Converted Barn

Adorable Guest Cottage

3 mins drive to Fairfield Beach, 3 bed, Sleeps 6

Centrally located. Walk to Greenwich Ave and Greenwich Train...

Waterfront Greenwich House - Amazing Views & Private -5 mins...

Elegant Beachfront Property!

GREENWICH FALL GETAWAYS NEAR THE BEACH INCLUDING COLUMBUS DAY...

Great hotel alternative!!! Brand New!!! 3 Bedroom Home - Heart of...

Great family home, close to the city, surrounded by nature!

We've still got a few days available at our beautiful bungalow...

One of a kind French Retreat-Perfect for Holidays-1Hr from NYC...

Modern Apartment with water views

The perfect quiet country getaway

Cloud 9, fashionably chic Beach Bungalow in Saugatuck Shores

Stunning New Construction

Circa 1735 Fully Restored Farm House

Private apartment in South Huntington.

Studio Apartment 2 miles from Fairfield, CT Beach

Bright Stylish Chic 4BR 4BA Home 1 Hour to NYC Close to Greenwich...

Greenwich, CT Hotel Alternative Completely Renovated High End...

Downtown "Blue Nest" Apartment

2BR Northport House w/3 Private Decks!

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

Private bedroom with beautiful bathroom

Fantastic Waterview Home in Quaint Beach Village - NYC - 23 Miles!

Beach cottage steps from the beach!!

Greenwich Tudor Home & Gardens near New York City

Quaint 3br Duplex. Close To Beach, Restaurants And Shopping!

Rowayton House Close To Town

Spacious, comfortable home for relaxed weekends in the fall.

Beautiful Waterfront Home With Fabulous Views In Rye NY...

European luxury with Pool and Privacy in Westport

Available October 2017 for Long or Short Term Rental

Weston's Best Summer Home

Westport "Gold Coast" across from Southport beach

Directly on Water. Classic Beach House.

Westport, CT - Walk To The Beach - NYC Getaway

Greenwich Farm House in a Country Setting with a pool.

1/2 block to Compo Beach on Long Island Sound!