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Vacation Rentals near Jennings Beach

880 S Benson Rd, Fairfield, Connecticut 06824-6950
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    All 60 Rentals in Fairfield
    Fairfield In-Town/Beach Area "Story-Book" Cottage with Pool1 / 15
    0.7 miles from Jennings Beach
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Charming Cottage By The Sea on Fairfield Beach1 / 30
    (11)Excellent
    1.0 miles from Jennings Beach
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Elegant Beachfront, beautiful views. Come enjoy!1 / 26
    1.0 miles from Jennings Beach
    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Private Renovated Home Convenient to Sacred Heart & Fairfield Universities1 / 30
    5.2 miles from Jennings Beach
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Fairfield, Connecticut
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Beach house - perfect location next to beach and town!1 / 29
    0.8 miles from Jennings Beach
    4 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    Fairfield, Connecticut
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 5
    Stunning direct waterfront beach house!1 / 28
    (3)Excellent
    1.2 miles from Jennings Beach
    3 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    Fairfield, Connecticut
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 7
    Beautiful Fairfield Beach Area home, 5 minute walk to beach, town & train to NYC1 / 17
    0.3 miles from Jennings Beach
    3 Bedrooms, 1 Bathroom, Sleeps 3 Quick View
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    Fairfield, Connecticut
    Rental Home - 3 Bedrooms, 1 Bathroom, Sleeps 3
    Winter Wonderland1 / 20
    4.8 miles from Jennings Beach
    3 Bedrooms, 3 Bathrooms, Sleeps 2 Quick View
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    Fairfield, Connecticut
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 2
    Summer estate close to NY, NJ, MA w heated pool sleeps 161 / 30
    (18)Excellent
    4.9 miles from Jennings Beach
    6 Bedrooms, 8 Bathrooms, Sleeps 16 Quick View
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    Fairfield, Connecticut
    Rental Home - 6 Bedrooms, 8 Bathrooms, Sleeps 16
    Charming Summer House (newly remodeled). 4 min from the beach1 / 22
    1.3 miles from Jennings Beach
    4 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    Fairfield, Connecticut
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 7
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    4 BR Classic Country House in CT1 / 30
    (10)Excellent
    3.4 miles from Jennings Beach
    4 Bedrooms, 5 Bathrooms, Sleeps 8 Quick View
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    Fairfield, Connecticut
    Rental Home - 4 Bedrooms, 5 Bathrooms, Sleeps 8
    Fabulous Carriage House in Gorgeous Southport, CT1 / 6
    2.1 miles from Jennings Beach
    3 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    Fairfield, Connecticut
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 5
    Steps away from the beach -updated 4bd/2 bath beach house with guest house1 / 30
    0.9 miles from Jennings Beach
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Fairfield, Connecticut
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Steps to Jennings Beach and the South Benson Marina!1 / 30
    0.1 miles from Jennings Beach
    2 Bedrooms, 3 Bathrooms, Sleeps 3 Quick View
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    Fairfield, Connecticut
    Rental Home - 2 Bedrooms, 3 Bathrooms, Sleeps 3
    Spacious Beach AreaHome- Walk to Town, Bike >Beach1 / 30
    0.8 miles from Jennings Beach
    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    Fairfield, Connecticut
    Rental Home - 5 Bedrooms, 5 Bathrooms, Sleeps 10
    Dreamy Beachfront Cottage with NYC views1 / 24
    2.0 miles from Jennings Beach
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Fairfield, Connecticut
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 8
    Lakefront getaway walkable to restaurants and shops1 / 18
    3.2 miles from Jennings Beach
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Waterfront
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    Fairfield, Connecticut
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
    Steps from the beach with water views!1 / 21
    0.8 miles from Jennings Beach
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Fairfield, Connecticut
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 8
    Second floor Beautiful Apartment1 / 7
    1.6 miles from Jennings Beach
    2 Bedrooms, 1 Bathroom, Sleeps 2 Quick View
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    Fairfield, Connecticut
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 2
    Westport "Gold Coast" across from Southport beach1 / 30
    3.1 miles from Jennings Beach
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    Fairfield, Connecticut
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 3
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    SUMMER!! Escape rundown & overpriced Shore/Hamptons w own Private Resort 1hr NYC1 / 23
    (7)Very good
    5.1 miles from Jennings Beach
    7 Bedrooms, 5 Bathrooms, Sleeps 8 Quick View
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    Fairfield, Connecticut
    Rental Home - 7 Bedrooms, 5 Bathrooms, Sleeps 8
    Beach area cape! Walk to town & beach1 / 11
    0.9 miles from Jennings Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Fairfield, Connecticut
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 8
    Beach cottage steps from the sand and surf!!1 / 30
    1.0 miles from Jennings Beach
    4 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Fairfield, Connecticut
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 6
    Amazing Beach House On Fairfield Beach1 / 16
    1.8 miles from Jennings Beach
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Fairfield, Connecticut
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 8
    Summer Getaway in Fairfield (Beach Passes Included!)1 / 30
    1.9 miles from Jennings Beach
    4 Bedrooms, 5 Bathrooms, Sleeps 8 Quick View
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    Fairfield, Connecticut
    Rental Home - 4 Bedrooms, 5 Bathrooms, Sleeps 8
    Quaint House with Patio, situated on a cliff overlooking the woods1 / 10
    3.4 miles from Jennings Beach
    1 Bedroom, 1 Bathroom, Sleeps 8 Quick View
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    Fairfield, Connecticut
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 8
    Newly renovated studio with private pool1 / 19
    4.8 miles from Jennings Beach
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Fairfield, Connecticut
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 4
    Fairfield beach area cozy retreat1 / 13
    1.7 miles from Jennings Beach
    4 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    Fairfield, Connecticut
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 7
    Sun and Fun on the beach!!1 / 30
    1.0 miles from Jennings Beach
    4 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    Fairfield, Connecticut
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 7
    Amazing Direct Beachfront Home close to golf, tennis, restaurants and shopping1 / 30
    2.1 miles from Jennings Beach
    4 Bedrooms, 3 Bathrooms, Sleeps 4 Quick View
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    Fairfield, Connecticut
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 4
    Fairfield beach and downtown combo1 / 30
    0.6 miles from Jennings Beach
    2 Bedrooms, 1 Bathroom, Sleeps 2 Quick View
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    Fairfield, Connecticut
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 2
    Cozy getaway in Fairfield - EXPERTLY SANITIZED1 / 30
    (7)Very good
    1.9 miles from Jennings Beach
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Fairfield, Connecticut
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Fairfield Beach House1 / 18
    0.8 miles from Jennings Beach
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Fairfield, Connecticut
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 10
    Steps to the Sand & Surf!1 / 30
    0.9 miles from Jennings Beach
    4 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Fairfield, Connecticut
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 6
    Beachfront cottage located in the heart of Fairfield Beach!!1 / 30
    1.0 miles from Jennings Beach
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Fairfield, Connecticut
    Rental Home - 3 Bedrooms, 1 Bathroom, Sleeps 6
    "Sea-Duced" by the Beach! Four-Bedroom Fairfield Beach Home Near Downtown1 / 29
    0.8 miles from Jennings Beach
    4 Bedrooms, 4 Bathrooms, Sleeps 4 Quick View
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    Fairfield, Connecticut
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 4
    Fairfield Old Post Road with pool - walk to NYC train and Beach1 / 25
    (5)Excellent
    0.7 miles from Jennings Beach
    5 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    Fairfield, Connecticut
    Rental Home - 5 Bedrooms, 4 Bathrooms, Sleeps 12
    ELEGANT NEW 4 BEDROOM WATERFRONT HOUSE- SUMMER DREAM - ACADEMIC YR AVAILABLE1 / 30
    1.0 miles from Jennings Beach
    4 Bedrooms, 5 Bathrooms, Sleeps 8 Quick View
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    Fairfield, Connecticut
    Rental Home - 4 Bedrooms, 5 Bathrooms, Sleeps 8
    Summer Rental: 4 Car Garage 1/4 mile to town of Fairfeild Center1 / 30
    0.8 miles from Jennings Beach
    4 Bedrooms, 3 Bathrooms, Sleeps 4 Quick View
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    Fairfield, Connecticut
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 4
    Spectacular direct waterfront with rooftop hot tub 360 degree views.1 / 30
    (2)Very good
    2.0 miles from Jennings Beach
    3 Bedrooms, 2 Bathrooms, Sleeps 30 Quick View
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    Fairfield, Connecticut
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 30
    Connecticut Estate - Now available July 9-23rd 20231 / 30
    4.1 miles from Jennings Beach
    5 Bedrooms, 5 Bathrooms, Sleeps 8 Quick View
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    Fairfield, Connecticut
    Rental Home - 5 Bedrooms, 5 Bathrooms, Sleeps 8
    Rarely available "Seaesta House" Beachfront Home1 / 25
    2.0 miles from Jennings Beach
    4 Bedrooms, 3 Bathrooms, Sleeps 4 Quick View
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    Fairfield, Connecticut
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 4
    Beautiful Connecticut Abode, close to park & beach1 / 26
    4.3 miles from Jennings Beach
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Fairfield, Connecticut
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    Fairchild Luxury Retreat: A 5-Bedroom Vacation Home with Endless Entertainment1 / 30
    (5)Excellent
    2.0 miles from Jennings Beach
    5 Bedrooms, 2 Bathrooms, Sleeps 12 Quick View
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    Fairfield, Connecticut
    Rental Home - 5 Bedrooms, 2 Bathrooms, Sleeps 12
    Beautiful home on private beach, sleeps 11! Bring your family and friends!1 / 30
    1.0 miles from Jennings Beach
    6 Bedrooms, 4 Bathrooms, Sleeps 11 Quick View
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    Fairfield, Connecticut
    Rental Home - 6 Bedrooms, 4 Bathrooms, Sleeps 11
    Beach House1 / 11
    0.6 miles from Jennings Beach
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Fairfield, Connecticut
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Fairfield Beach Modern Colonial1 / 27
    0.3 miles from Jennings Beach
    4 Bedrooms, 4 Bathrooms, Sleeps 7 Quick View
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    Fairfield, Connecticut
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 7
    Exceptional August rental one block from beach!1 / 19
    0.8 miles from Jennings Beach
    3 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Washer
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
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    Location Information
    Fairfield, Connecticut
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 5
    Fairfield Old Post Road-heated pool & Guest Cottage-walk to NYC train and Beach!1 / 34
    0.7 miles from Jennings Beach
    6 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
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    Amenities & Details
    • Patio
    • Washer
    • Balcony
    • Grill
    • Terrace
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Location, Location, Location. *Completely renovated Spring 2023* Covered in ivy, this beautiful 6 bedroom/5 bath English Tudor on the historic Old Post Road is only 1 block to downtown Fairfield with great restaurants, theatre, concerts, shopping and a Metro North station (1 hour to NYC). Or walk...
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    Location Information
    Fairfield, Connecticut
    Rental Home - 6 Bedrooms, 5 Bathrooms, Sleeps 14
    Gem by the Sound - Beach Front1 / 30
    (18)Excellent
    1.0 miles from Jennings Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Amenities & Details
    • Terrace
    • Air Conditioning
    • Wi-Fi
    • Washer
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
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    Location Information
    Fairfield, Connecticut
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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