Greenwich, Connecticut

Vacation Rentals in Greenwich, Connecticut

Discover 52 vacation rental properties in Greenwich. From 1 to 6 bedrooms. Average $694/night. 100% have pools.

52 verified listings Book securely on VRBO Prices updated March 2026

52 properties available

Twenty - One ! Boutique Stay (2C) in Heart of Downtown

Twenty - One ! Boutique Stay (2C) in Heart of Downtown

1 bed 1 bath
PoolA/CWiFiBalcony
$201/night
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Large sunny quiet unit in very convenient location

Large sunny quiet unit in very convenient location

1 bed 1 bath
PoolA/CWiFiBalcony
$251/night
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The Safe House - High Tech Apt #2 - 3 Beds

The Safe House - High Tech Apt #2 - 3 Beds

2 beds 1 bath
PoolA/CWiFiBalcony
$191/night
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Charming 3 bdr. Close to beach, dining & shopping!

Charming 3 bdr. Close to beach, dining & shopping!

3 beds 1 bath
PoolA/CWiFiBalcony
$196/night
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2 mini-bedrooms apartment with antique bathtub.

2 mini-bedrooms apartment with antique bathtub.

2 beds 1 bath
PoolA/CWiFiBalcony
$221/night
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The Safe House - High Tech Apt #3 - 4 beds

The Safe House - High Tech Apt #3 - 4 beds

2 beds 1 bath
PoolA/CWiFiBalcony
$203/night
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Beautiful downstairs apartment. Walk to town, train, & beach ferry!

Beautiful downstairs apartment. Walk to town, train, & beach ferry!

3 beds 2 baths
PoolA/CWiFiBalcony
$296/night
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Perfect August Rental with Heated Swimming Pool

Perfect August Rental with Heated Swimming Pool

4 beds 4 baths
PoolA/CWiFiBalcony
$1,001/night
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Mansion in Greenwich with private lake and river

Mansion in Greenwich with private lake and river

4 beds 6 baths
PoolA/CWiFiBalcony
$2,770/night
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Beautiful upstairs apt. Walk to town, train, & beach ferry!

Beautiful upstairs apt. Walk to town, train, & beach ferry!

3 beds 2 baths
PoolA/CWiFiBalcony
$314/night
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Spacious 5BR Old Greenwich Village Home - Walk/Bike to Beach, Train to NYC

Spacious 5BR Old Greenwich Village Home - Walk/Bike to Beach, Train to NYC

5 beds 3 baths
PoolA/CWiFiBalcony
$993/night
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Quiet, Sunny, New in Convenient Downtown Greenwich

Quiet, Sunny, New in Convenient Downtown Greenwich

1 bed 1 bath
PoolA/CWiFiBalcony
$168/night
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Modern charming country cottage for long term availability

Modern charming country cottage for long term availability

3 beds 2 baths
PoolA/CWiFiBalcony
$150/night
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Quaint 3br Duplex. Walk to beach, dining, & shopping!

Quaint 3br Duplex. Walk to beach, dining, & shopping!

3 beds 1 bath
PoolA/CWiFiBalcony
$249/night
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Greenwich proper - NYC style, Hotel alternative walk to Greenwich Ave.

Greenwich proper - NYC style, Hotel alternative walk to Greenwich Ave.

2 beds 2 baths
PoolA/CWiFiBalcony
$798/night
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True Downtown Greenwich 1-BR apartment

True Downtown Greenwich 1-BR apartment

1 bed 1 bath
PoolA/CWiFiBalcony
$260/night
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Greenwich Hotel Alternative / Boutique Living - Fully Loaded- Turn Key 1B

Greenwich Hotel Alternative / Boutique Living - Fully Loaded- Turn Key 1B

2 beds 2 baths
PoolA/CWiFiBalcony
$776/night
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Cheerful spacious family home in Old Greenwich - close to beach and town!

Cheerful spacious family home in Old Greenwich - close to beach and town!

5 beds 4 baths
PoolA/CWiFiBalcony
$751/night
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Modern Apartment 5 min from train/beach Greenwich

Modern Apartment 5 min from train/beach Greenwich

2 beds 2 baths
PoolA/CWiFiBalcony
$575/night
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NEW! GREENWICH PICASSO HOUSE/ 5 BDRS, CLOSE TO BEACH, TRAIN, NYC

NEW! GREENWICH PICASSO HOUSE/ 5 BDRS, CLOSE TO BEACH, TRAIN, NYC

5 beds 2 baths
PoolA/CWiFiBalcony
$801/night
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Sun-filled farmhouse for 8, w/gym. 2 acre fenced-in dog friendly property.

Sun-filled farmhouse for 8, w/gym. 2 acre fenced-in dog friendly property.

4 beds 3 baths
PoolA/CWiFiBalcony
$1,001/night
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Back Country Estate w/ Pool, Sleeps 8 - Fully loaded, Pet Friendly Greenwich CT

Back Country Estate w/ Pool, Sleeps 8 - Fully loaded, Pet Friendly Greenwich CT

5 beds 4 baths
PoolA/CWiFiBalcony
$1,284/night
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Beautiful modern beach house with newly build swimming pool- 1 hour from NYC

Beautiful modern beach house with newly build swimming pool- 1 hour from NYC

5 beds 3 baths
PoolA/CWiFiBalcony
$900/night
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4-BR Downtown Greenwich Gem steps from Greenwich Av and train station

4-BR Downtown Greenwich Gem steps from Greenwich Av and train station

4 beds 2 baths
PoolA/CWiFiBalcony
$701/night
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ALL AUGUST & SOME JULY AVAILABLE 5-BDRM SHORE HOME PETS OK BEACH PASSES INCLUDED

ALL AUGUST & SOME JULY AVAILABLE 5-BDRM SHORE HOME PETS OK BEACH PASSES INCLUDED

5 beds 3 baths
PoolA/CWiFiBalcony
$923/night
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Twenty - One ! Boutique Stay in Heart of Downtown

Twenty - One ! Boutique Stay in Heart of Downtown

1 bed 1 bath
PoolA/CWiFiBalcony
$201/night
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Summer retreat with salt water pool on tranquil woods.

Summer retreat with salt water pool on tranquil woods.

4 beds 2 baths
PoolA/CWiFiBalcony
$826/night
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Greenwich Proper Brand New Home - 5 minutes to town and train - Must See!!!

Greenwich Proper Brand New Home - 5 minutes to town and train - Must See!!!

4 beds 2 baths
PoolA/CWiFiBalcony
$803/night
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Round Hill Road Estate Home with 5 open acres

Round Hill Road Estate Home with 5 open acres

6 beds 6 baths
PoolA/CWiFiBalcony
$751/night
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California cozy cottage/studio in the middle of the Greenwich

California cozy cottage/studio in the middle of the Greenwich

1 bed 1 bath
PoolA/CWiFiBalcony
$126/night
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Heart of Greenwich - Sun Drenched and Relaxing

Heart of Greenwich - Sun Drenched and Relaxing

3 beds 2 baths
PoolA/CWiFiBalcony
$424/night
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NEW! GREENWICH HOUSE WITH NYC FLAIR/CLOSE TO BEACH & NYC

NEW! GREENWICH HOUSE WITH NYC FLAIR/CLOSE TO BEACH & NYC

5 beds 2 baths
PoolA/CWiFiBalcony
$801/night
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Old Greenwich Gem

Old Greenwich Gem

4 beds 3 baths
PoolA/CWiFiBalcony
$585/night
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Private suite. Convenient to Capital Theater and HPN airport. Free parking.

Private suite. Convenient to Capital Theater and HPN airport. Free parking.

1 bed
PoolA/CWiFiBalcony
$130/night
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Peaceful Colonial on Private Road in Greenwich, CT

Peaceful Colonial on Private Road in Greenwich, CT

4 beds 3 baths
PoolA/CWiFiBalcony
$801/night
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Greenwich, CT Hotel Alternative Completely Renovated High End Townhouse

Greenwich, CT Hotel Alternative Completely Renovated High End Townhouse

2 beds 2 baths
PoolA/CWiFiBalcony
$526/night
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Greenwich/ Hotel Alternative/ Great Location/ Sleeps 6

Greenwich/ Hotel Alternative/ Great Location/ Sleeps 6

2 beds 2 baths
PoolA/CWiFiBalcony
$532/night
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Greenwich Home with Pool

Greenwich Home with Pool

4 beds 4 baths
PoolA/CWiFiBalcony
$1,501/night
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Brand New - Boutique Living, Hotel Alternative

Brand New - Boutique Living, Hotel Alternative

3 beds 3 baths
PoolA/CWiFiBalcony
$475/night
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Stunning waterfront house with dock, walk to shops, restaurants, beach, train.

Stunning waterfront house with dock, walk to shops, restaurants, beach, train.

4 beds 3 baths
PoolA/CWiFiBalcony
$500/night
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2nd Floor, 1 Br / 1 Ba With Sofa Bed In The Living Room

2nd Floor, 1 Br / 1 Ba With Sofa Bed In The Living Room

1 bed 1 bath
PoolA/CWiFiBalcony
$130/night
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Greenwich Cove Beach House

Greenwich Cove Beach House

3 beds 1 bath
PoolA/CWiFiBalcony
$500/night
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Old Greenwich Summer Perfection near Beach and Town!

Old Greenwich Summer Perfection near Beach and Town!

4 beds 4 baths
PoolA/CWiFiBalcony
$977/night
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Waterfront Old Greenwich House, Ct

Waterfront Old Greenwich House, Ct

4 beds 3 baths
PoolA/CWiFiBalcony
$892/night
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Cozy luxury home w private beach

Cozy luxury home w private beach

4 beds 2 baths
PoolA/CWiFiBalcony
$599/night
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Greenwich Beach Old House

Greenwich Beach Old House

5 beds 3 baths
PoolA/CWiFiBalcony
$1,001/night
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Old Greenwich home just a mile from Tod's Point Beach

Old Greenwich home just a mile from Tod's Point Beach

4 beds 2 baths
PoolA/CWiFiBalcony
$1,001/night
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Modern house in Old Greenwich, 250 ft from an amazing dock on the water

Modern house in Old Greenwich, 250 ft from an amazing dock on the water

5 beds 3 baths
PoolA/CWiFiBalcony
$596/night
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More destinations in Connecticut

New Haven (158) Stonington (135) Milford (100) Mystic (93) Stamford (84) Old Saybrook (82) Westbrook (74) Old Lyme (71) Fairfield (57) Madison (56) Westport (55) Branford (53) Norwich (52) Groton (51) Bridgeport (47) East Lyme (43) Clinton (42) Hartford (40) Guilford (38) New Fairfield (37)