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Holiday Rentals near Jennings Beach

880 S Benson Rd, Fairfield, Connecticut 06824-6950
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5 km
47 rentals in Fairfield.
Coastal Retreat: Charming 3-Bedroom Fairfield Townhouse nr Beaches & Town Center, holiday rental in Fairfield
Coastal Retreat: Charming 3-Bedroom Fairfield Townhouse nr Beaches & Town Center, holiday rental in Fairfield
Coastal Retreat: Charming 3-Bedroom Fairfield Townhouse nr Beaches & Town Center, holiday rental in Fairfield

Coastal Retreat: Charming 3-Bedroom Fairfield Townhouse nr Beaches & Town Center

Holiday Rental House
2.7 kilometres from Jennings Beach
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Beautiful Fairfield Beach Area home, 5 minute walk to beach, town & train to NYC, holiday rental in Fairfield
Beautiful Fairfield Beach Area home, 5 minute walk to beach, town & train to NYC, holiday rental in Fairfield
Beautiful Fairfield Beach Area home, 5 minute walk to beach, town & train to NYC, holiday rental in Fairfield

Beautiful Fairfield Beach Area home, 5 minute walk to beach, town & train to NYC

Holiday Rental House
0.6 kilometres from Jennings Beach
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Beautiful home on private beach, sleeps 11! Bring your family and friends!, holiday rental in Fairfield
Beautiful home on private beach, sleeps 11! Bring your family and friends!, holiday rental in Fairfield
Beautiful home on private beach, sleeps 11! Bring your family and friends!, holiday rental in Fairfield

Beautiful home on private beach, sleeps 11! Bring your family and friends!

Holiday Rental House
1.6 kilometres from Jennings Beach
6 bedrooms
4 bathrooms
Sleeps 11
Match: Sleeps
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Fairfield Old Post Road-heated pool & Guest Cottage-walk to NYC train and Beach!, holiday rental in Fairfield
Fairfield Old Post Road-heated pool & Guest Cottage-walk to NYC train and Beach!, holiday rental in Fairfield
Fairfield Old Post Road-heated pool & Guest Cottage-walk to NYC train and Beach!, holiday rental in Fairfield

Fairfield Old Post Road-heated pool & Guest Cottage-walk to NYC train and Beach!

Holiday Rental House
1.3 kilometres from Jennings Beach
6 bedrooms
5 bathrooms
Sleeps 14
Match: Sleeps
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Westport "Gold Coast" across from Southport beach, holiday rental in Fairfield
Westport "Gold Coast" across from Southport beach, holiday rental in Fairfield
Westport "Gold Coast" across from Southport beach, holiday rental in Fairfield

Westport "Gold Coast" across from Southport beach

Holiday Rental House
5.1 kilometres from Jennings Beach
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Second floor Beautiful Apartment, holiday rental in Fairfield
Second floor Beautiful Apartment, holiday rental in Fairfield
Second floor Beautiful Apartment, holiday rental in Fairfield

Second floor Beautiful Apartment

Condo/Apartment
2.6 kilometres from Jennings Beach
2 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
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Beach area cape!  Walk to town & beach, holiday rental in Fairfield
Beach area cape!  Walk to town & beach, holiday rental in Fairfield
Beach area cape!  Walk to town & beach, holiday rental in Fairfield

Beach area cape! Walk to town & beach

Holiday Rental House
1.6 kilometres from Jennings Beach
2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Quiet suburban home close to Fairfield beaches and universities, holiday rental in Fairfield
Quiet suburban home close to Fairfield beaches and universities, holiday rental in Fairfield
Quiet suburban home close to Fairfield beaches and universities, holiday rental in Fairfield

Quiet suburban home close to Fairfield beaches and universities

Holiday Rental House
5.8 kilometres from Jennings Beach
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Exceptional August rental one block from beach!, holiday rental in Fairfield
Exceptional August rental one block from beach!, holiday rental in Fairfield
Exceptional August rental one block from beach!, holiday rental in Fairfield

Exceptional August rental one block from beach!

Holiday Rental House
1.3 kilometres from Jennings Beach
3 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Gem by the Sound - Beach Front, holiday rental in Fairfield
Gem by the Sound - Beach Front, holiday rental in Fairfield
Gem by the Sound - Beach Front, holiday rental in Fairfield

Gem by the Sound - Beach Front

Holiday Rental House
1.6 kilometres from Jennings Beach
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Modern Beach Area Vacation Home With Pool, holiday rental in Fairfield
Modern Beach Area Vacation Home With Pool, holiday rental in Fairfield
Modern Beach Area Vacation Home With Pool, holiday rental in Fairfield

Modern Beach Area Vacation Home With Pool

Holiday Rental House
1.0 kilometres from Jennings Beach
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Cozy summer house 4 bed & 2 baths - Weekly rental, holiday rental in Fairfield
Cozy summer house 4 bed & 2 baths - Weekly rental, holiday rental in Fairfield
Cozy summer house 4 bed & 2 baths - Weekly rental, holiday rental in Fairfield

Cozy summer house 4 bed & 2 baths - Weekly rental

Holiday Rental House
3.1 kilometres from Jennings Beach
4 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Fabulous Carriage House in Gorgeous Southport, CT, holiday rental in Fairfield
Fabulous Carriage House in Gorgeous Southport, CT, holiday rental in Fairfield
Fabulous Carriage House in Gorgeous Southport, CT, holiday rental in Fairfield

Fabulous Carriage House in Gorgeous Southport, CT

Holiday Rental House
3.4 kilometres from Jennings Beach
3 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Beachfront cottage located in the heart of Fairfield Beach!!, holiday rental in Fairfield
Beachfront cottage located in the heart of Fairfield Beach!!, holiday rental in Fairfield
Beachfront cottage located in the heart of Fairfield Beach!!, holiday rental in Fairfield

Beachfront cottage located in the heart of Fairfield Beach!!

Holiday Rental House
1.6 kilometres from Jennings Beach
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Cozy beach retreat with stunning views of Long Island Sound, holiday rental in Fairfield
Cozy beach retreat with stunning views of Long Island Sound, holiday rental in Fairfield
Cozy beach retreat with stunning views of Long Island Sound, holiday rental in Fairfield

Cozy beach retreat with stunning views of Long Island Sound

Holiday Rental House
1.9 kilometres from Jennings Beach
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Beachy Kind of Life, holiday rental in Fairfield
Beachy Kind of Life, holiday rental in Fairfield
Beachy Kind of Life, holiday rental in Fairfield

Beachy Kind of Life

Condo/Apartment
1.3 kilometres from Jennings Beach
3 bedrooms
3 bathrooms
Sleeps 5
Match: Sleeps
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Steps away from the beach -updated  4bd/2 bath beach house with guest house, holiday rental in Fairfield
Steps away from the beach -updated  4bd/2 bath beach house with guest house, holiday rental in Fairfield
Steps away from the beach -updated  4bd/2 bath beach house with guest house, holiday rental in Fairfield

Steps away from the beach -updated 4bd/2 bath beach house with guest house

Holiday Rental House
1.4 kilometres from Jennings Beach
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Amazing Beach House On Fairfield Beach, holiday rental in Fairfield
Amazing Beach House On Fairfield Beach, holiday rental in Fairfield
Amazing Beach House On Fairfield Beach, holiday rental in Fairfield

Amazing Beach House On Fairfield Beach

Holiday Rental House
2.9 kilometres from Jennings Beach
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Enjoy lovely sunset view surrounded by nature., holiday rental in Fairfield
Enjoy lovely sunset view surrounded by nature., holiday rental in Fairfield
Enjoy lovely sunset view surrounded by nature., holiday rental in Fairfield

Enjoy lovely sunset view surrounded by nature.

Holiday Rental House
2.3 kilometres from Jennings Beach
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Southport Charm! Steps away from town!, holiday rental in Fairfield
Southport Charm! Steps away from town!, holiday rental in Fairfield
Southport Charm! Steps away from town!, holiday rental in Fairfield

Southport Charm! Steps away from town!

Holiday Rental House
4.8 kilometres from Jennings Beach
4 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Coastal Haven - Cozy Cottage for Family Vacation, holiday rental in Fairfield
Coastal Haven - Cozy Cottage for Family Vacation, holiday rental in Fairfield
Coastal Haven - Cozy Cottage for Family Vacation, holiday rental in Fairfield

Coastal Haven - Cozy Cottage for Family Vacation

Holiday Rental House
2.9 kilometres from Jennings Beach
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Charming Cottage By The Sea on Fairfield Beach, holiday rental in Fairfield
Charming Cottage By The Sea on Fairfield Beach, holiday rental in Fairfield
Charming Cottage By The Sea on Fairfield Beach, holiday rental in Fairfield

Charming Cottage By The Sea on Fairfield Beach

Holiday Rental House
1.6 kilometres from Jennings Beach
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Spectacular direct waterfront with rooftop hot tub 360 degree views., holiday rental in Fairfield
Spectacular direct waterfront with rooftop hot tub 360 degree views., holiday rental in Fairfield
Spectacular direct waterfront with rooftop hot tub 360 degree views., holiday rental in Fairfield

Spectacular direct waterfront with rooftop hot tub 360 degree views.

Holiday Rental House
3.2 kilometres from Jennings Beach
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Steps from the beach with water views!, holiday rental in Fairfield
Steps from the beach with water views!, holiday rental in Fairfield
Steps from the beach with water views!, holiday rental in Fairfield

Steps from the beach with water views!

Holiday Rental House
1.4 kilometres from Jennings Beach
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Charming Summer House (newly remodeled).  4 min from the beach, holiday rental in Fairfield
Charming Summer House (newly remodeled).  4 min from the beach, holiday rental in Fairfield
Charming Summer House (newly remodeled).  4 min from the beach, holiday rental in Fairfield

Charming Summer House (newly remodeled). 4 min from the beach

Holiday Rental House
2.3 kilometres from Jennings Beach
4 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
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Summer Rental:  4 Car Garage 1/4 mile to town of Fairfeild Center, holiday rental in Fairfield
Summer Rental:  4 Car Garage 1/4 mile to town of Fairfeild Center, holiday rental in Fairfield
Summer Rental:  4 Car Garage 1/4 mile to town of Fairfeild Center, holiday rental in Fairfield

Summer Rental: 4 Car Garage 1/4 mile to town of Fairfeild Center

Holiday Rental House
1.4 kilometres from Jennings Beach
4 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
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Waterfront, holiday rental in Fairfield
Waterfront, holiday rental in Fairfield
Waterfront, holiday rental in Fairfield

Waterfront

Holiday Rental House
3.2 kilometres from Jennings Beach
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Stunning direct waterfront beach house!, holiday rental in Fairfield
Stunning direct waterfront beach house!, holiday rental in Fairfield
Stunning direct waterfront beach house!, holiday rental in Fairfield

Stunning direct waterfront beach house!

Holiday Rental House
1.9 kilometres from Jennings Beach
3 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
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Beach house - perfect location next to beach and town!, holiday rental in Fairfield
Beach house - perfect location next to beach and town!, holiday rental in Fairfield
Beach house - perfect location next to beach and town!, holiday rental in Fairfield

Beach house - perfect location next to beach and town!

Holiday Rental House
1.3 kilometres from Jennings Beach
4 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Amazing Direct Beachfront Home close to golf, tennis, restaurants and shopping, holiday rental in Fairfield
Amazing Direct Beachfront Home close to golf, tennis, restaurants and shopping, holiday rental in Fairfield
Amazing Direct Beachfront Home close to golf, tennis, restaurants and shopping, holiday rental in Fairfield

Amazing Direct Beachfront Home close to golf, tennis, restaurants and shopping

Holiday Rental House
3.4 kilometres from Jennings Beach
4 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Beach cottage steps from the sand and surf!!, holiday rental in Fairfield
Beach cottage steps from the sand and surf!!, holiday rental in Fairfield
Beach cottage steps from the sand and surf!!, holiday rental in Fairfield

Beach cottage steps from the sand and surf!!

Holiday Rental House
1.6 kilometres from Jennings Beach
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Dreamy Beachfront Cottage with NYC views, holiday rental in Fairfield
Dreamy Beachfront Cottage with NYC views, holiday rental in Fairfield
Dreamy Beachfront Cottage with NYC views, holiday rental in Fairfield

Dreamy Beachfront Cottage with NYC views

Holiday Rental House
3.2 kilometres from Jennings Beach
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Fairfield Beach House, holiday rental in Fairfield
Fairfield Beach House, holiday rental in Fairfield
Fairfield Beach House, holiday rental in Fairfield

Fairfield Beach House

Holiday Rental House
1.3 kilometres from Jennings Beach
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Steps to the Sand & Surf!, holiday rental in Fairfield
Steps to the Sand & Surf!, holiday rental in Fairfield
Steps to the Sand & Surf!, holiday rental in Fairfield

Steps to the Sand & Surf!

Holiday Rental House
1.4 kilometres from Jennings Beach
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Sun and Fun on the beach!!, holiday rental in Fairfield
Sun and Fun on the beach!!, holiday rental in Fairfield
Sun and Fun on the beach!!, holiday rental in Fairfield

Sun and Fun on the beach!!

Holiday Rental House
1.6 kilometres from Jennings Beach
4 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Koi de sac, holiday rental in Fairfield
Koi de sac, holiday rental in Fairfield
Koi de sac, holiday rental in Fairfield

Koi de sac

Holiday Rental House
4.8 kilometres from Jennings Beach
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Fairchild Luxury Retreat: A 5-Bedroom Vacation Home with Endless Entertainment, holiday rental in Fairfield
Fairchild Luxury Retreat: A 5-Bedroom Vacation Home with Endless Entertainment, holiday rental in Fairfield
Fairchild Luxury Retreat: A 5-Bedroom Vacation Home with Endless Entertainment, holiday rental in Fairfield

Fairchild Luxury Retreat: A 5-Bedroom Vacation Home with Endless Entertainment

Holiday Rental House
3.4 kilometres from Jennings Beach
5 bedrooms
2 bathrooms
Sleeps 12
Match: Sleeps
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Elegant Beachfront, beautiful views. Come enjoy!, holiday rental in Fairfield
Elegant Beachfront, beautiful views. Come enjoy!, holiday rental in Fairfield
Elegant Beachfront, beautiful views. Come enjoy!, holiday rental in Fairfield

Elegant Beachfront, beautiful views. Come enjoy!

Holiday Rental House
1.6 kilometres from Jennings Beach
5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Fairfield Beach Modern Colonial, holiday rental in Fairfield
Fairfield Beach Modern Colonial, holiday rental in Fairfield
Fairfield Beach Modern Colonial, holiday rental in Fairfield

Fairfield Beach Modern Colonial

Holiday Rental House
0.6 kilometres from Jennings Beach
4 bedrooms
4 bathrooms
Sleeps 7
Match: Sleeps
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Summer Getaway in Fairfield (Beach Passes Included!), holiday rental in Fairfield
Summer Getaway in Fairfield (Beach Passes Included!), holiday rental in Fairfield
Summer Getaway in Fairfield (Beach Passes Included!), holiday rental in Fairfield

Summer Getaway in Fairfield (Beach Passes Included!)

Holiday Rental House
3.2 kilometres from Jennings Beach
4 bedrooms
5 bathrooms
Sleeps 8
Match: Sleeps
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"Sea-Duced" by the Beach! Four-Bedroom Fairfield Beach Home Near Downtown, holiday rental in Fairfield
"Sea-Duced" by the Beach! Four-Bedroom Fairfield Beach Home Near Downtown, holiday rental in Fairfield
"Sea-Duced" by the Beach! Four-Bedroom Fairfield Beach Home Near Downtown, holiday rental in Fairfield

"Sea-Duced" by the Beach! Four-Bedroom Fairfield Beach Home Near Downtown

Holiday Rental House
1.3 kilometres from Jennings Beach
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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4 BR Classic Country House in CT, holiday rental in Fairfield
4 BR Classic Country House in CT, holiday rental in Fairfield
4 BR Classic Country House in CT, holiday rental in Fairfield

4 BR Classic Country House in CT

Holiday Rental House
5.6 kilometres from Jennings Beach
4 bedrooms
5 bathrooms
Sleeps 8
Match: Sleeps
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ELEGANT NEW 4 BEDROOM WATERFRONT HOUSE- SUMMER DREAM - ACADEMIC YR AVAILABLE, holiday rental in Fairfield
ELEGANT NEW 4 BEDROOM WATERFRONT HOUSE- SUMMER DREAM - ACADEMIC YR AVAILABLE, holiday rental in Fairfield
ELEGANT NEW 4 BEDROOM WATERFRONT HOUSE- SUMMER DREAM - ACADEMIC YR AVAILABLE, holiday rental in Fairfield

ELEGANT NEW 4 BEDROOM WATERFRONT HOUSE- SUMMER DREAM - ACADEMIC YR AVAILABLE

Holiday Rental House
1.6 kilometres from Jennings Beach
4 bedrooms
5 bathrooms
Sleeps 8
Match: Sleeps
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Fairfield CT, Historic District w/Heated Pool;Walk to Town/Restaurants, holiday rental in Fairfield
Fairfield CT, Historic District w/Heated Pool;Walk to Town/Restaurants, holiday rental in Fairfield
Fairfield CT, Historic District w/Heated Pool;Walk to Town/Restaurants, holiday rental in Fairfield

Fairfield CT, Historic District w/Heated Pool;Walk to Town/Restaurants

Holiday Rental House
1.4 kilometres from Jennings Beach
4 bedrooms
5 bathrooms
Sleeps 8
Match: Sleeps
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Connecticut Estate - Now available July 9-23rd 2023, holiday rental in Fairfield
Connecticut Estate - Now available July 9-23rd 2023, holiday rental in Fairfield
Connecticut Estate - Now available July 9-23rd 2023, holiday rental in Fairfield

Connecticut Estate - Now available July 9-23rd 2023

Holiday Rental House
6.8 kilometres from Jennings Beach
5 bedrooms
5 bathrooms
Sleeps 8
Match: Sleeps
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Summer estate close to NY, NJ, MA w heated pool sleeps 16, holiday rental in Fairfield
Summer estate close to NY, NJ, MA w heated pool sleeps 16, holiday rental in Fairfield
Summer estate close to NY, NJ, MA w heated pool sleeps 16, holiday rental in Fairfield

Summer estate close to NY, NJ, MA w heated pool sleeps 16

Holiday Rental House
8.0 kilometres from Jennings Beach
7 bedrooms
9 bathrooms
Sleeps 16
Match: Sleeps
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Luxury Beachfront living with amazing views, holiday rental in Fairfield
Luxury Beachfront living with amazing views, holiday rental in Fairfield
Luxury Beachfront living with amazing views, holiday rental in Fairfield

Luxury Beachfront living with amazing views

Holiday Rental House
3.1 kilometres from Jennings Beach
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Showing results 1-47 of 47
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