Family-Friendly Vacation Rentals in Greenfield Hill Historic District, CT: Compare 10+ Sites & Save

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79 Best Family Vacation Rentals in Greenfield Hill Historic District (Starting from $141)

Sunny Westport Studio Apt. Above Historic Mill
Sunny Westport Studio Apt. Above Historic Mill
Apartment
Westport, CT, USA
4.2k from Greenfield Hill Historic District center

Apartments, Cheap, Accommodations, Parking, Pet-friendly, Lodgings, Beach, Places to stay, Family

1 Bedroom3 Guests
9.5

Superb

4 reviews

$390
Average price / night
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8-bedroom estate with breathtaking infinity pool/outdoor kitchen in Fairfield
8-bedroom estate with breathtaking infinity pool/outdoor kitchen in Fairfield
House
Fairfield, CT, 06824, United States
2.5k from Greenfield Hill Historic District center

AC, Barbecue, Dryer, Fireplace, Fitness Equipment, Free Parking, Heater, Hot Tub, Internet

8 Bedrooms17 Guests
New to Booking
$796
Average price / night
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Sunny Westport 2 BR Retreat above Historic Mill
Sunny Westport 2 BR Retreat above Historic Mill
Apartment
Westport, CT, USA
4.2k from Greenfield Hill Historic District center

Apartments, Cheap, Accommodations, Parking, Pet-friendly, Lodgings, Places to stay, Family

2 Bedrooms5 Guests
9.5

Superb

2 reviews

$393
Average price / night
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Summer estate close to NY, NJ, MA w heated pool sleeps 16+
Summer estate close to NY, NJ, MA w heated pool sleeps 16+
House
Fairfield, CT, 06824, United States
2.6k from Greenfield Hill Historic District center

AC, Arcade, Barbecue, Dryer, Fireplace, Fitness Equipment, Free Parking, Heater, Internet

7 Bedrooms16 Guests
10.0

Exceptional

27 reviews

$3489
Average price / night
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Fairfield Retreat
Fairfield Retreat
House
Fairfield, CT, USA
4.4k from Greenfield Hill Historic District center

Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Places to stay, Family

1 Bedroom9 Guests
New to Booking
$436
Average price / night
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Compo Beach access gated private house in Westport
Compo Beach access gated private house in Westport
House
Westport, CT, 06880, United States
2.8k from Greenfield Hill Historic District center

AC, Arcade, Dryer, Free Parking, Heater, Internet, Laundry, Living Area, No Smoking

3 Bedrooms10 Guests
New to Booking
$714
Average price / night
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Fairfield Cottage -Top Rated Gem, Fire Pit, Near Beach, 90 Min to NYC
Fairfield Cottage -Top Rated Gem, Fire Pit, Near Beach, 90 Min to NYC
House
Fairfield, CT, USA
4.5k from Greenfield Hill Historic District center

Cheap, Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Places to stay

3 Bedrooms8 Guests
9.7

Exceptional

3 reviews

$307
Average price / night
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A private summer compound in Westport, CT - total seclusion yet close to it all
A private summer compound in Westport, CT - total seclusion yet close to it all
House
Westport, CT, 06880, United States
2.9k from Greenfield Hill Historic District center

AC, Arcade, Balcony, Barbecue, Crib, Dryer, Fireplace, Fitness Equipment, Free Parking

6 Bedrooms12 Guests
10.0

Exceptional

5 reviews

$1620
Average price / night
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Cozy Retreat Near Westport
Cozy Retreat Near Westport
House
Fairfield, CT, USA
4.8k from Greenfield Hill Historic District center

View, Security/Safety, Guest Services, Air Conditioner, Parking, Child Friendly

1 Bedroom2 Guests
New to Booking
$180
Average price / night
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Quiet suburban home close to Fairfield beaches and universities
Quiet suburban home close to Fairfield beaches and universities
House
Fairfield, CT, 06825, United States
3.5k from Greenfield Hill Historic District center

AC, Barbecue, Crib, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry

3 Bedrooms7 Guests
10.0

Exceptional

14 reviews

$333
Average price / night
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Modern Westport Studio with Pool Table & Lounge
Modern Westport Studio with Pool Table & Lounge
Apartment
Westport, CT, USA
5.0k from Greenfield Hill Historic District center

Apartments, Cheap, Accommodations, Parking, Lodgings, Places to stay

1 Bedroom4 Guests
8.0

Good

4 reviews

$280
Average price / night
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Southport Shoreline Charm: Elegant Coastal Escape
Southport Shoreline Charm: Elegant Coastal Escape
House
Southport, CT, 06890, United States
3.8k from Greenfield Hill Historic District center

AC, Barbecue, Crib, Dryer, Heater, Internet, Kitchen, Laundry, Microwave

3 Bedrooms7 Guests
8.8

Fabulous

5 reviews

$488
Average price / night
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Sunny & Spacious 2BD 1BA WFH Apt-Huge Yard & Patio
Sunny & Spacious 2BD 1BA WFH Apt-Huge Yard & Patio
Apartment
Fairfield, CT, USA
5.3k from Greenfield Hill Historic District center

Apartments, Cheap, Accommodations, Parking, Lodgings, Places to stay, Family

2 Bedrooms5 Guests
10.0

Exceptional

2 reviews

$175
Average price / night
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Private Oasis: Completely Renovated Old Farmhouse With Pool And Guesthouse
Private Oasis: Completely Renovated Old Farmhouse With Pool And Guesthouse
House
Westport, CT, 06880, United States
4.1k from Greenfield Hill Historic District center

AC, Arcade, Balcony, Barbecue, Dryer, Extra Bed, Fireplace, Fitness Equipment, Free Parking

4 Bedrooms8 Guests
10.0

Exceptional

1 reviews

$1176
Average price / night
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Cozy condo with yard and patio. Long-stay discount available
Cozy condo with yard and patio. Long-stay discount available
Apartment
Fairfield, CT, USA
5.3k from Greenfield Hill Historic District center

Apartments, Cheap, Accommodations, Parking, Pet-friendly, Lodgings, Vacation rentals, Places to stay, Family

3 Bedrooms6 Guests
9.3

Superb

4 reviews

$295
Average price / night
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Westport summer 5 bed home on quiet street 6 mins to the beach! Pool!
Westport summer 5 bed home on quiet street 6 mins to the beach! Pool!
House
Westport, CT, 06880, United States
4.1k from Greenfield Hill Historic District center

AC, Arcade, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen

5 Bedrooms10 Guests
New to Booking
$1346
Average price / night
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Spacious&Gracious- 5BR Fam-Friendly near I95&Shops
Spacious&Gracious- 5BR Fam-Friendly near I95&Shops
House
Fairfield, CT, USA
5.4k from Greenfield Hill Historic District center

Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Places to stay

5 Bedrooms12 Guests
5.0

Review score

1 reviews

$1117
Average price / night
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Studio Flat Above Historic Cider Mill
Studio Flat Above Historic Cider Mill
Apartment
Westport, CT, 06880, United States
4.2k from Greenfield Hill Historic District center

AC, Crib, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Microwave

1 Bedroom3 Guests
10.0

Exceptional

77 reviews

$199
Average price / night
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Coastal Retreat Charming 3-Bedroom Fairfield Townhouse near Beaches I Town Center
Coastal Retreat Charming 3-Bedroom Fairfield Townhouse near Beaches I Town Center
Apartment
Fairfield, CT, USA
5.6k from Greenfield Hill Historic District center

Parking, Ocean View, View, Child Friendly, Internet, Air Conditioner, Pet Friendly

3 Bedrooms8 Guests
New to Booking
$495
Average price / night
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2BR Flat above Historic Cider Mill
2BR Flat above Historic Cider Mill
Apartment
Westport, CT, 06880, United States
4.2k from Greenfield Hill Historic District center

AC, Crib, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

2 Bedrooms5 Guests
10.0

Exceptional

23 reviews

$382
Average price / night
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Chic Stay w/ King Bed/Near Beardsley Zoo/Free Parking
Chic Stay w/ King Bed/Near Beardsley Zoo/Free Parking
Apartment
Greenfield Hill Historic District, Fairfield, Connecticut, USA
5.6k from Greenfield Hill Historic District center

Internet, Parking, Kitchen, Air Conditioner, Child Friendly

1 Bedroom5 Guests
9.5

Superb

4 reviews

$141
Average price / night
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Renovated Cape Near beach, with Fire Pit and BBQ, 1 mile to NYC train
Renovated Cape Near beach, with Fire Pit and BBQ, 1 mile to NYC train
House
Fairfield, CT, 06824, United States
4.3k from Greenfield Hill Historic District center

AC, Balcony, Barbecue, Crib, Dryer, Fireplace, Free Parking, Heater, Internet

3 Bedrooms10 Guests
10.0

Exceptional

11 reviews

$485
Average price / night
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Charming Newly Renovated 2-bedroom apartment in Fairfield
Charming Newly Renovated 2-bedroom apartment in Fairfield
Apartment
Fairfield, CT, 06825, United States
4.4k from Greenfield Hill Historic District center

Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area, No Smoking

2 Bedrooms4 Guests
New to Booking
$193
Average price / night
Check Availability
Cozy Cottage with Fire Pit, near Beach, 1 mile to NYC train
Cozy Cottage with Fire Pit, near Beach, 1 mile to NYC train
House
Fairfield, CT, 06824, United States
4.5k from Greenfield Hill Historic District center

AC, Balcony, Barbecue, Crib, Dryer, Fireplace, Free Parking, Heater, Internet

3 Bedrooms8 Guests
10.0

Exceptional

30 reviews

$499
Average price / night
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2 Beautiful Homes, 1 Stunning Retreat: Pool HotTub Pizza Oven + Near Beach & NYC
2 Beautiful Homes, 1 Stunning Retreat: Pool HotTub Pizza Oven + Near Beach & NYC
House
Fairfield, CT, 06824, United States
4.9k from Greenfield Hill Historic District center

AC, Barbecue, Crib, Dryer, Fireplace, Free Parking, Heater, Hot Tub, Internet

6 Bedrooms14 Guests
10.0

Exceptional

4 reviews

$2664
Average price / night
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6-bedroom house with fitness room and pool in Westport
6-bedroom house with fitness room and pool in Westport
House
Westport, CT, 06880, United States
4.9k from Greenfield Hill Historic District center

AC, Arcade, Barbecue, Dryer, Fireplace, Fitness Equipment, Free Parking, Heater, Internet

7 Bedrooms14 Guests
New to Booking
$2365
Average price / night
Check Availability
Fairfield Historic Street. Private Heated Pool. Walk to Town Restaurants & Beach
Fairfield Historic Street. Private Heated Pool. Walk to Town Restaurants & Beach
House
Fairfield, CT, 06824, United States
4.9k from Greenfield Hill Historic District center

AC, Barbecue, Dryer, Fireplace, Free Parking, Heater, Hot Tub, Internet, Kitchen

4 Bedrooms8 Guests
9.6

Exceptional

5 reviews

$1642
Average price / night
Check Availability

Pro Tip:
VacationByOwnerRentals aggregates the best inventory from leading travel sites, including Booking.com, Agoda.com, Expedia.com, Vrbo.com, and Airbnb.com. Use our Advanced Filters to compare verified homes, villas, cabins, condos, cottages, vacation rentals, hotels, and eco-friendly stays. Our goal is to help you find the absolute best Family Vacation Rentals in Greenfield Hill Historic District.

Where to stay in Greenfield Hill Historic District? Best neighborhoods & areas

Greenfield Hill Historic District Family Vacation Rentals on the Map

Frequently Asked Questions

You can explore 79 verified family-friendly vacation rentals in Greenfield Hill Historic District. These include spacious homes, villas, and condos designed to accommodate families of different sizes.

Prices for family-friendly rentals in Greenfield Hill Historic District vary depending on the season, number of bedrooms, and included amenities. Rates typically start from around $141 per night, with larger homes and peak travel periods often costing more.

Many family-friendly rentals in Greenfield Hill Historic District offer baby-friendly items such as high chairs, cribs, or pack-and-play options. Availability can vary, so it’s helpful to check the listing details before booking.

Yes, some rentals in Greenfield Hill Historic District are well suited for multi-generational stays, offering multiple bedrooms, separate living areas, and enough space for larger groups to stay comfortably together.

For busy travel periods such as school holidays or summer breaks, booking 90 to 120 days in advance is recommended to secure the best options. Availability may be more flexible during quieter times of the year.

Family-friendly rentals in Greenfield Hill Historic District often include amenities such as Child Friendly, Fireplace/Heating, and View. These features help make stays more convenient and enjoyable for both adults and children.

You can use search filters to find rentals that offer features like game rooms, playgrounds, or entertainment areas. Checking property descriptions can also help you identify homes that are well suited for families with children.