Owner Direct Vacation Rentals in Greenfield Hill Historic District

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177 Greenfield Hill Historic District Vacation Homes From $88

Looking for the ideal vacation rental in Greenfield Hill Historic District? Discover an extensive gallery of private rentals offering space, comfort, and authentic local character. Owner Direct simplifies your search by matching you with verified property options.

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
Check Availability
Fabulous private home on desirable street in Westport.
Fabulous private home on desirable street in Westport.
House
Westport, CT, 06880, United States
2.4k from Greenfield Hill Historic District center

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

4 Bedrooms6 Guests
10.0

Exceptional

1 reviews

$985
Average price / night
Check Availability
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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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, Internet, Kitchen

8 Bedrooms17 Guests
New to Booking
$1153
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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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

28 reviews

$3672
Average price / night
Check Availability
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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4 BR Classic Country House in CT
4 BR Classic Country House in CT
House
Fairfield, CT, 06890, United States
2.7k from Greenfield Hill Historic District center

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

4 Bedrooms8 Guests
10.0

Exceptional

18 reviews

$1809
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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Cozy 1 br apartment with a private entrance and patio in Fairfield
Cozy 1 br apartment with a private entrance and patio in Fairfield
Apartment
Fairfield, CT, 06824, United States
2.8k from Greenfield Hill Historic District center

AC, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Microwave, No Smoking

1 Bedroom2 Guests
10.0

Exceptional

1 reviews

$88
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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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, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry

3 Bedrooms8 Guests
New to Booking
$856
Average price / night
Check Availability
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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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

$357
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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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

$680
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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Southport Charm! Steps away from town!
Southport Charm! Steps away from town!
House
Fairfield, CT, 06890, United States
4.1k from Greenfield Hill Historic District center

AC, Dryer, Heater, Internet, Laundry, No Smoking, Washer

4 Bedrooms6 Guests
New to Booking
$1284
Average price / night
Check Availability
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
Check Availability
Cosima Guest House: Your Fairfield getaway
Cosima Guest House: Your Fairfield getaway
Apartment
Fairfield, CT, 06824, United States
4.2k from Greenfield Hill Historic District center

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

New to Booking
$348
Average price / night
Check Availability
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

79 reviews

$287
Average price / night
Check Availability

Pro Tip:
OwnerDirectVacationRental 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 Vacation Rentals in Greenfield Hill Historic District.

Greenfield Hill Historic District Vacation Rentals on the Map

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Frequently Asked Questions

There are a lot of options in Greenfield Hill Historic District. If you plan on staying in the Greenfield Hill Historic District area, consider making a reservation for a few nights at one of these properties as these have been rated the top Vacation Rentals in Greenfield Hill Historic District

You can explore 177 verified vacation rentals in Greenfield Hill Historic District. Our listings are sourced from a range of trusted providers, giving you access to a wide selection of private homes, apartments, and unique stays—all in one place.

Vacation rental prices in Greenfield Hill Historic District vary depending on the season, property size, and location. Rates typically start from around $88 per night, with higher prices for larger homes or peak travel periods. Comparing available options can help you find a stay that matches both your budget and travel plans.

Most vacation rentals in Greenfield Hill Historic District include fully equipped kitchens, making it easy to prepare meals and enjoy a more flexible stay. This is especially useful for families, longer stays, or travelers who prefer a home-like experience.

Yes, many vacation rentals in Greenfield Hill Historic District welcome pets. Currently, 45 listings allow pets, although specific policies may vary by property. You can filter for pet-friendly options to quickly find suitable accommodations.

For popular travel periods such as holidays or peak seasons, it's recommended to book your vacation rental 60 to 90 days in advance to secure the best options. During quieter times, you may still find good availability closer to your travel dates.

Vacation rentals in Greenfield Hill Historic District often include amenities such as Fireplace/Heating, Child Friendly, and Internet. These features provide added comfort and convenience, making them a popular choice for travelers seeking more space and privacy.

You can use filters to narrow down your search by criteria such as number of bedrooms, guest ratings, or specific amenities like private pools or beachfront access. This makes it easier to find a property that fits your exact needs and preferences.