Vacation Rentals with Private Pool in North Main Street Historic District, NY: Compare 10+ Sites & Save

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  2. Vacation Rentals with Private Pool
  3.  USA

  4.  New York

  5.  Southampton
  6.  North Main Street Historic District

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426 Best Vacation Rentals with Private Pool in North Main Street Historic District (Starting from $1289)

Villa Emery
Villa Emery
Villa
Water Mill, NY, USA
1.6k from North Main Street Historic District center

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

6 Bedrooms12 Guests
New to Booking
$2070
Average price / night
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Modern Home in Southampton Village w/Gunite Pool
Modern Home in Southampton Village w/Gunite Pool
House
Southampton, NY, 11968, United States
0.1k from North Main Street Historic District center

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

4 Bedrooms8 Guests
9.2

Superb

12 reviews

$2657
Average price / night
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Villa Gavin
Villa Gavin
Villa
North Main Street Historic District, Southampton, New York, USA
3.1k from North Main Street Historic District center

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

3 Bedrooms11 Guests
New to Booking
$1434
Average price / night
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Quintessential Hamptons home with 6 bedrooms (all ensuite bathrooms), open...
Quintessential Hamptons home with 6 bedrooms (all ensuite bathrooms), open...
House
Southampton, NY, 11968, United States
0.1k from North Main Street Historic District center

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

6 Bedrooms12 Guests
9.8

Exceptional

19 reviews

$3115
Average price / night
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Modern and Brand New Southampton Village retreat, private pool, great for...
Modern and Brand New Southampton Village retreat, private pool, great for...
House
Southampton, NY, 11968, United States
0.2k from North Main Street Historic District center

AC, Dryer, Fireplace, Free Parking, Heater, Kitchen, Microwave, No Smoking, Patio

4 Bedrooms8 Guests
New to Booking
$3530
Average price / night
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Southampton Village Luxury Retreat
Southampton Village Luxury Retreat
House
Southampton, NY, 11968, United States
0.2k from North Main Street Historic District center

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

4 Bedrooms10 Guests
10.0

Exceptional

1 reviews

$2464
Average price / night
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Southampton Village Cottage SOH Backyard Paradise 20 x 40 OLYMPIC SIZED POOL!!!
Southampton Village Cottage SOH Backyard Paradise 20 x 40 OLYMPIC SIZED POOL!!!
House
Southampton, NY, 11968, United States
0.3k from North Main Street Historic District center

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

3 Bedrooms7 Guests
New to Booking
$1622
Average price / night
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Tastefully Furnished with Upgraded Amenities, Lush Landscaping, Minutes...
Tastefully Furnished with Upgraded Amenities, Lush Landscaping, Minutes...
House
Southampton, NY, 11968, United States
0.3k from North Main Street Historic District center

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

5 Bedrooms8 Guests
New to Booking
$1613
Average price / night
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Southampton Village Renovated Sun-filled Charming Home, Heated Salt water Pool
Southampton Village Renovated Sun-filled Charming Home, Heated Salt water Pool
House
Southampton, NY, 11968, United States
0.4k from North Main Street Historic District center

AC, Barbecue, Dryer, Extra Bed, Fitness Equipment, Free Parking, Heater, Internet, Kitchen

4 Bedrooms10 Guests
10.0

Exceptional

57 reviews

$1870
Average price / night
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SH Village  - Close to town, beach, and 1st tee U.S. Open Golf
SH Village - Close to town, beach, and 1st tee U.S. Open Golf
House
Southampton, NY, 11968, United States
0.4k from North Main Street Historic District center

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

3 Bedrooms8 Guests
10.0

Exceptional

15 reviews

$2400
Average price / night
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Southampton Village Gem
Southampton Village Gem
House
Southampton, NY, 11968, United States
0.4k from North Main Street Historic District center

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

3 Bedrooms8 Guests
10.0

Exceptional

18 reviews

$1475
Average price / night
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Walk to the Village! Charming modern farmhouse.
Walk to the Village! Charming modern farmhouse.
House
Southampton, NY, 11968, United States
0.4k from North Main Street Historic District center

AC, Balcony, Barbecue, Crib, Dryer, Extra Bed, Fireplace, Free Parking, Heater

3 Bedrooms8 Guests
9.8

Exceptional

28 reviews

$2141
Average price / night
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Elegant Southampton Retreat with Pool, Pool House, and Resort-Style Outdoor...
Elegant Southampton Retreat with Pool, Pool House, and Resort-Style Outdoor...
House
Southampton, NY, 11968, United States
0.5k from North Main Street Historic District center

AC, Balcony, Barbecue, Dryer, Fireplace, Fitness Equipment, Free Parking, Heater, Kitchen

5 Bedrooms12 Guests
New to Booking
$16474
Average price / night
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Perfection in the Heart of Southampton Village;  Walk to Town, Bike to Beaches
Perfection in the Heart of Southampton Village; Walk to Town, Bike to Beaches
House
Southampton, NY, 11968, United States
0.5k from North Main Street Historic District center

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

3 Bedrooms7 Guests
New to Booking
$2121
Average price / night
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Spacious 6-bedroom house in enchanting Southampton with pool & fitness room
Spacious 6-bedroom house in enchanting Southampton with pool & fitness room
House
Southampton, NY, 11968, United States
0.6k from North Main Street Historic District center

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

6 Bedrooms11 Guests
New to Booking
$1599
Average price / night
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Entire House in Southampton Village, Pool, 2 Fireplaces, Walk Everywhere, Pets!
Entire House in Southampton Village, Pool, 2 Fireplaces, Walk Everywhere, Pets!
House
Southampton, NY, 11968, United States
0.6k from North Main Street Historic District center

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

3 Bedrooms6 Guests
9.2

Superb

11 reviews

$1289
Average price / night
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New Southampton Village Gem. 6 bedroom, 6 + bath and 5 minutes drive to beach.
New Southampton Village Gem. 6 bedroom, 6 + bath and 5 minutes drive to beach.
House
Southampton, NY, 11968, United States
0.7k from North Main Street Historic District center

AC, Arcade, Barbecue, Dryer, Fitness Equipment, Free Parking, Internet, Kitchen, Laundry

6 Bedrooms8 Guests
New to Booking
$4346
Average price / night
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Beautiful Southampton Village home, new reno, Heated pool!
Beautiful Southampton Village home, new reno, Heated pool!
House
Southampton, NY, 11968, United States
0.8k from North Main Street Historic District center

AC, Barbecue, Crib, Dryer, Extra Bed, Free Parking, Heater, Internet, Kitchen

4 Bedrooms12 Guests
10.0

Exceptional

36 reviews

$2223
Average price / night
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Southampton Village Classic- Close to 2026 US Open
Southampton Village Classic- Close to 2026 US Open
House
Southampton, NY, 11968, United States
0.8k from North Main Street Historic District center

AC, Barbecue, Dryer, Heater, Internet, Laundry, No Smoking, Outdoor Grill, Pool

6 Bedrooms11 Guests
New to Booking
$2107
Average price / night
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Full Gym with Full Tile Steam Room, Roofed Cabana, Short Distance to...
Full Gym with Full Tile Steam Room, Roofed Cabana, Short Distance to...
House
Southampton, NY, 11968, United States
0.9k from North Main Street Historic District center

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

7 Bedrooms10 Guests
New to Booking
$5971
Average price / night
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Southampton Historic Farmhouse Retreat Meets Modern Luxury on Expansive...
Southampton Historic Farmhouse Retreat Meets Modern Luxury on Expansive...
House
Southampton, NY, 11968, United States
0.9k from North Main Street Historic District center

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

5 Bedrooms10 Guests
New to Booking
$8798
Average price / night
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Private Southampton 4BR Retreat w/ Heated Pool
Private Southampton 4BR Retreat w/ Heated Pool
House
Southampton, NY, 11968, United States
0.9k from North Main Street Historic District center

AC, Balcony, Dryer, Fireplace, Heater, Internet, Kitchen, Microwave, No Smoking

4 Bedrooms8 Guests
New to Booking
$7702
Average price / night
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Southampton Home - Farm Views and Close Proximity to Village
Southampton Home - Farm Views and Close Proximity to Village
House
Southampton, NY, 11968, United States
0.9k from North Main Street Historic District center

AC, Balcony, Barbecue, Dryer, Fitness Equipment, Free Parking, Internet, Kitchen, Laundry

5 Bedrooms10 Guests
10.0

Exceptional

5 reviews

$2255
Average price / night
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Luxurious Southampton Retreat with Private Pool and Pool House, Great for...
Luxurious Southampton Retreat with Private Pool and Pool House, Great for...
House
Southampton, NY, 11968, United States
1.0k from North Main Street Historic District center

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

6 Bedrooms12 Guests
New to Booking
$3447
Average price / night
Check Availability
Summer Rental with Private Heated Pool &Tennis Near Beach & Village
Summer Rental with Private Heated Pool &Tennis Near Beach & Village
House
Southampton, NY, 11968, United States
1.0k from North Main Street Historic District center

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

4 Bedrooms13 Guests
9.8

Exceptional

49 reviews

$2154
Average price / night
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Steps away from Southampton Village Main Street
Steps away from Southampton Village Main Street
House
Southampton, NY, 11968, United States
1.0k from North Main Street Historic District center

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

3 Bedrooms6 Guests
10.0

Exceptional

1 reviews

$3855
Average price / night
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Southampton Village 5 minute walk to Main Steet 10 minute walk to Coopers Beach
Southampton Village 5 minute walk to Main Steet 10 minute walk to Coopers Beach
House
Southampton, NY, 11968, United States
1.0k from North Main Street Historic District center

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

7 Bedrooms14 Guests
10.0

Exceptional

1 reviews

$3851
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 Private Pool in North Main Street Historic District.

Where to stay in North Main Street Historic District? Best neighborhoods & areas

North Main Street Historic District Vacation Rentals with Private Pool on the Map

Frequently Asked Questions

You can explore 426 verified vacation rentals with a private pool in North Main Street Historic District. These include standalone villas and private homes where the pool is reserved exclusively for your group.

Prices for rentals with a private pool in North Main Street Historic District vary depending on the property size, location, and travel season. Rates typically start from around $1289 per night, with higher prices for larger homes, prime locations, or peak travel periods.

Yes, properties listed with private pools are intended for the exclusive use of guests staying at that home. You can review listing photos and descriptions to better understand the layout and level of privacy offered.

Yes, some vacation rentals with private pools in North Main Street Historic District also welcome pets. Currently, 22 listings allow pets, although policies may vary. It’s a good idea to review any rules related to pets and outdoor areas before booking.

Private pool properties are often in high demand, especially during holidays and warmer months, so booking 90 to 120 days in advance is recommended. During quieter periods, you may still find availability closer to your travel dates.

Vacation rentals with private pools in North Main Street Historic District often include additional features such as Pool, Private Pool, and Balcony/Terrace. These amenities enhance comfort and create a more relaxing, self-contained stay.

Some family-friendly vacation rentals in North Main Street Historic District include safety features such as pool fences, covers, or screened enclosures. It’s recommended to check the property details to confirm whether a specific rental meets your safety preferences.