Vacation Rentals with Pool in Greenfield Hill Historic District, CT: Compare 10+ Sites & Save

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  2. Vacation Rentals with Pool
  3.  USA

  4.  Connecticut

  5.  New Haven

  6.  Greenfield Hill Historic District

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22 Best Vacation Rentals with Pool in Greenfield Hill Historic District (Starting from $95)

Luxury Estate Heated Pool - Tennis - Gym - Sauna!
Luxury Estate Heated Pool - Tennis - Gym - Sauna!
House
Fairfield, CT, USA
6.1k from Greenfield Hill Historic District center

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

1 Bedroom17 Guests
New to Booking
$2994
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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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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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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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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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
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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
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Fairfield Old Post Road-heated pool & Guest Cottage-walk to NYC train and Beach!
Fairfield Old Post Road-heated pool & Guest Cottage-walk to NYC train and Beach!
House
Fairfield, CT, 06824, United States
5.2k from Greenfield Hill Historic District center

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

6 Bedrooms14 Guests
10.0

Exceptional

23 reviews

$1792
Average price / night
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Chic, Impeccably Decorated 5000 sq ft Estate, Coveted Greens Farms, 5 bed, 6 bth
Chic, Impeccably Decorated 5000 sq ft Estate, Coveted Greens Farms, 5 bed, 6 bth
House
Westport, CT, 06880, United States
5.3k from Greenfield Hill Historic District center

AC, Arcade, Barbecue, Dryer, Fireplace, Fitness Equipment, Heater, Hot Tub, Internet

5 Bedrooms8 Guests
10.0

Exceptional

3 reviews

$2454
Average price / night
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Westport Summer retreat w/ 40 Ft saltwater pool, 6 bedrooms + guest cottage
Westport Summer retreat w/ 40 Ft saltwater pool, 6 bedrooms + guest cottage
House
Westport, CT, 06880, United States
5.4k from Greenfield Hill Historic District center

AC, Dryer, Fitness Equipment, Heater, Internet, Kitchen, Laundry, No Smoking, Patio

7 Bedrooms14 Guests
New to Booking
$2012
Average price / night
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Newly Renovated Home in Westport CT, Private Pool, Walk to Town, Close to Beach
Newly Renovated Home in Westport CT, Private Pool, Walk to Town, Close to Beach
House
Westport, CT, 06880, United States
5.9k from Greenfield Hill Historic District center

AC, Barbecue, Dryer, Internet, Kitchen, Laundry, Microwave, No Smoking, Pool

3 Bedrooms10 Guests
New to Booking
$1169
Average price / night
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🌟 Fairfield Luxury Estate for Short or Mid Term Stays | 🏊 Pool | 🎾 Tennis | 🧖 Sauna
🌟 Fairfield Luxury Estate for Short or Mid Term Stays | 🏊 Pool | 🎾 Tennis | 🧖 Sauna
House
Fairfield, CT, 06825, United States
6.1k from Greenfield Hill Historic District center

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

7 Bedrooms17 Guests
10.0

Exceptional

1 reviews

$1616
Average price / night
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Fairfield Beach Modern Colonial
Fairfield Beach Modern Colonial
House
Fairfield, CT, 06824, United States
6.2k from Greenfield Hill Historic District center

AC, Barbecue, Crib, Dryer, Fitness Equipment, Free Parking, Heater, Internet, Kitchen

4 Bedrooms7 Guests
10.0

Exceptional

7 reviews

$1756
Average price / night
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Spacious 6-bedroom 5 bathroom Dream House, with salt water pool & stone hot tub.
Spacious 6-bedroom 5 bathroom Dream House, with salt water pool & stone hot tub.
House
Westport, CT, 06880, United States
6.5k from Greenfield Hill Historic District center

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

5 Bedrooms13 Guests
New to Booking
$2109
Average price / night
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Newly renovated 6BR, Pool, Spa, ScreenPorch, 2 private acres, Heart of Westport.
Newly renovated 6BR, Pool, Spa, ScreenPorch, 2 private acres, Heart of Westport.
House
Westport, CT, 06880, United States
6.6k from Greenfield Hill Historic District center

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

6 Bedrooms12 Guests
New to Booking
$1437
Average price / night
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Newly renovated summer home in Westport CT private pool & spa, near beach & town
Newly renovated summer home in Westport CT private pool & spa, near beach & town
House
Westport, CT, 06880, United States
6.8k from Greenfield Hill Historic District center

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

6 Bedrooms12 Guests
New to Booking
$1470
Average price / night
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A private room for any traveler
A private room for any traveler
House
Weston, CT, 06883, United States
7.0k from Greenfield Hill Historic District center

AC, Free Parking, Heater, Internet, No Smoking, Outdoor Space, Patio, Pool

1 Bedroom1 Guest
6.0

Review score

4 reviews

$95
Average price / night
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Modern 4 bed 4.5 bath w hot tub & heated pool close to beach
Modern 4 bed 4.5 bath w hot tub & heated pool close to beach
House
Weston, CT, 06883, United States
7.7k from Greenfield Hill Historic District center

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

5 Bedrooms8 Guests
9.8

Exceptional

6 reviews

$1292
Average price / night
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Westport Compo Beach Summer rental with Water Views & infinity Pool
Westport Compo Beach Summer rental with Water Views & infinity Pool
House
Westport, CT, 06880, United States
8.4k from Greenfield Hill Historic District center

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

5 Bedrooms10 Guests
New to Booking
$2754
Average price / night
Check Availability
Spacious 4-bedroom house with AC in tranquil Norwalk. Year round hot tub.  Pool
Spacious 4-bedroom house with AC in tranquil Norwalk. Year round hot tub. Pool
House
Norwalk, CT, 06851, United States
8.7k from Greenfield Hill Historic District center

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

4 Bedrooms10 Guests
New to Booking
$603
Average price / night
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Luxury 3-Acre Estate: Private Pool, Basketball Court & Designer Interiors
Luxury 3-Acre Estate: Private Pool, Basketball Court & Designer Interiors
House
Weston, CT, 06883, United States
9.8k from Greenfield Hill Historic District center

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

4 Bedrooms8 Guests
New to Booking
$1150
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 Vacation Rentals with Pool in Greenfield Hill Historic District.

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

Greenfield Hill Historic District Vacation Rentals with Pool on the Map

Frequently Asked Questions

You can explore 22 verified vacation rentals with a pool in Greenfield Hill Historic District. These include a wide range of private homes, villas, and condos that offer on-site swimming facilities for a more relaxing stay.

Prices for vacation rentals with a pool in Greenfield Hill Historic District vary depending on the season, property size, and whether the pool is private or shared. Rates typically start from around $95 per night, with private pool homes and peak travel periods often costing more.

Many rentals in Greenfield Hill Historic District offer private pools for exclusive use, while others provide access to shared or community pools. You can use filters to specifically find properties with private pools if that is your preference.

Yes, some vacation rentals with pools in Greenfield Hill Historic District welcome pets. Currently, 9 listings allow pets, although policies may vary by property. It’s a good idea to review any rules related to pets around pool areas before booking.

Properties with pools are often in high demand, especially during warmer months and holidays, so booking 90 to 120 days in advance is recommended for the best selection. During off-peak seasons, you may still find availability closer to your travel dates.

Vacation rentals with pools in Greenfield Hill Historic District often include additional outdoor features such as Pool, Fireplace/Heating, and Kitchen. These amenities enhance comfort and make it easier to enjoy outdoor living during your stay.

Some vacation rentals in Greenfield Hill Historic District offer heated pools, which can be especially useful during cooler months. In certain cases, pool heating may be available for an additional fee, so it’s best to check the property details before booking.