Holiday rentals near North Main Street Historic District
We found 1,625 holiday rentals — enter your dates for availability
If you want to to stay within easy reach of North Main Street Historic District, scroll through and discover private holiday rentals to find the perfect home base for your trip. Whether you’re staying in a holiday home with family or friends, you'll find the amenities that you need and want, such as air conditioning and a TV. Whatever you're looking for, you're sure to find a property to rent for everyone's needs, including a place that is accessible or non-smoking.
Holiday rentals with weekly discounts - North Main Street Historic District
Showing deals for:15 Aug - 22 Aug
Image gallery for Stunning House: Tennis & Pool in Southampton Estate section
1010 out of 10 rating
Exceptional
(32 reviews)
Stunning House: Tennis & Pool in Southampton Estate section
Southampton, NY
8% off
Price is AU$78,395
AU$78,395
AU$11,199 per night
includes taxes & fees
Image gallery for Ultimate Hamptons Vacation Mansion
1010 out of 10 rating
Exceptional
(10 reviews)
Ultimate Hamptons Vacation Mansion
Wainscott, NY
17% off
Price is AU$51,008
AU$51,008
AU$7,287 per night
includes taxes & fees
Image gallery for Hamptons Oasis with Heated Pool
9.89.8 out of 10 rating
Exceptional
(7 reviews)
Hamptons Oasis with Heated Pool
Hampton Bays, NY
8% off
Price is AU$19,411
AU$19,411
AU$2,773 per night
includes taxes & fees
Image gallery for NEW LISTING! Chic, Affordably Priced Southampton home, convenient location.
1010 out of 10 rating
Exceptional
(6 reviews)
NEW LISTING! Chic, Affordably Priced Southampton home, convenient location.
Southampton, NY
8% off
Price is AU$15,152
AU$15,152
AU$2,165 per night
includes taxes & fees
Image gallery for Incredible Location, Family and Dog Friendly , minutes to flying point
9.49.4 out of 10 rating
Exceptional
(15 reviews)
Incredible Location, Family and Dog Friendly , minutes to flying point
Water Mill, NY
8% off
Price is AU$25,545
AU$25,545
AU$3,649 per night
includes taxes & fees
Image gallery for Stunning Hamptons Beach Home for Family Vacations By The Ocean
9.89.8 out of 10 rating
Exceptional
(13 reviews)
Stunning Hamptons Beach Home for Family Vacations By The Ocean
Hampton Bays, NY
8% off
Price is AU$15,272
AU$15,272
AU$2,182 per night
includes taxes & fees
Image gallery for Sag Harbor Home: Large Heated Pool, Beach Access, Walking Distance to Town
1010 out of 10 rating
Exceptional
(5 reviews)
Sag Harbor Home: Large Heated Pool, Beach Access, Walking Distance to Town
Sag Harbor, NY
8% off
Price is AU$16,231
AU$16,231
AU$2,319 per night
includes taxes & fees
Image gallery for Ultimate Hamptons Vacation Estate
9.69.6 out of 10 rating
Exceptional
(14 reviews)
Ultimate Hamptons Vacation Estate
Sag Harbor, NY
21% off
Price is AU$47,901
AU$47,901
AU$6,843 per night
includes taxes & fees
Image gallery for 8/6-8/13 special Prime Wainscott Estate South of Highway
1010 out of 10 rating
Exceptional
(7 reviews)
8/6-8/13 special Prime Wainscott Estate South of Highway
Wainscott, NY
9% off
Price is AU$41,484
AU$41,484
AU$5,926 per night
includes taxes & fees
Image gallery for Newly Renovated Pristine Southampton Colonial
9.89.8 out of 10 rating
Exceptional
(11 reviews)
Newly Renovated Pristine Southampton Colonial
Southampton, NY
22% off
Price is AU$17,252
AU$17,252
AU$2,465 per night
includes taxes & fees
Image gallery for Southampton Retreat: Heated Pool, Hot Tub, Beach
9.89.8 out of 10 rating
Exceptional
(6 reviews)
Southampton Retreat: Heated Pool, Hot Tub, Beach
Southampton, NY
7% off
Price is AU$16,343
AU$16,343
AU$2,335 per night
includes taxes & fees
Image gallery for 3bed, 2bath Hamptons Home, Close to Incredible Beaches and Restaurants!
9.69.6 out of 10 rating
Exceptional
(10 reviews)
3bed, 2bath Hamptons Home, Close to Incredible Beaches and Restaurants!
Hampton Bays, NY
8% off
Price is AU$7,920
AU$7,920
AU$1,131 per night
includes taxes & fees
Image gallery for Classic Southampton Home: 5BR, Pool, Jacuzzi
9.69.6 out of 10 rating
Exceptional
(28 reviews)
Classic Southampton Home: 5BR, Pool, Jacuzzi
Southampton, New York
7% off
Price is AU$17,854
AU$17,854
AU$2,551 per night
includes taxes & fees
Image gallery for Everything in Hamptons special discount available for weekly and monthly renters
1010 out of 10 rating
Exceptional
(7 reviews)
Everything in Hamptons special discount available for weekly and monthly renters
Water Mill, NY
8% off
Price is AU$100,902
AU$100,902
AU$14,415 per night
includes taxes & fees
Image gallery for Yellowstone In The Hamptons ~ 18-Acre Estate Surrounded By A Nature Preserve
1010 out of 10 rating
Exceptional
(17 reviews)
Yellowstone In The Hamptons ~ 18-Acre Estate Surrounded By A Nature Preserve
Water Mill, NY
17% off
Price is AU$37,838
AU$37,838
AU$5,405 per night
includes taxes & fees
Image gallery for Life is a breeze by the bay
1010 out of 10 rating
Exceptional
(6 reviews)
Life is a breeze by the bay
Hampton Bays, NY
8% off
Price is AU$11,493
AU$11,493
AU$1,642 per night
includes taxes & fees
Image gallery for Family Friendly Home W/ Pool On Pvt Cul-du-sac, Cls To Beach
9.89.8 out of 10 rating
Exceptional
(41 reviews)
Family Friendly Home W/ Pool On Pvt Cul-du-sac, Cls To Beach
Wainscott, NY
8% off
Price is AU$14,601
AU$14,601
AU$2,086 per night
includes taxes & fees
Image gallery for Spacious Contemporary Home with Pool and Tennis
8.48.4 out of 10 rating
Very good
(10 reviews)
Spacious Contemporary Home with Pool and Tennis
Sag Harbor, NY
37% off
Price is AU$19,522
AU$19,522
AU$2,789 per night
includes taxes & fees
Image gallery for New and Modern Bridgehampton Accommodations
1010 out of 10 rating
Exceptional
(7 reviews)
New and Modern Bridgehampton Accommodations
Bridgehampton, NY
8% off
Price is AU$11,106
AU$11,106
AU$1,587 per night
includes taxes & fees
Image gallery for Perfect Hamptons house near the water for a casual weekend out east
9.29.2 out of 10 rating
Wonderful
(7 reviews)
Perfect Hamptons house near the water for a casual weekend out east
Hampton Bays, NY
8% off
Price is AU$10,842
AU$10,842
AU$1,549 per night
includes taxes & fees
Image gallery for Fairy Tale Guest Cottage in Magic Garden by Pool
1010 out of 10 rating
Exceptional
(65 reviews)
Fairy Tale Guest Cottage in Magic Garden by Pool
Bridgehampton, NY
8% off
Price is AU$6,876
AU$6,876
AU$982 per night
includes taxes & fees
Image gallery for Southampton Serenity Walk to beach. Kayaks on lake Park-like grounds Pool Tennis
9.89.8 out of 10 rating
Exceptional
(25 reviews)
Southampton Serenity Walk to beach. Kayaks on lake Park-like grounds Pool Tennis
Southampton, NY
13% off
Price is AU$20,389
AU$20,389
AU$2,913 per night
includes taxes & fees
Image gallery for Brand New Cozy 3-bedroom house in quaint Hampton Bays with AC, WiFi
1010 out of 10 rating
Exceptional
(19 reviews)
Brand New Cozy 3-bedroom house in quaint Hampton Bays with AC, WiFi
Hampton Bays, NY
8% off
Price is AU$7,707
AU$7,707
AU$1,101 per night
includes taxes & fees
Image gallery for Cozy Bungalow Available Nearby Bridgehampton and Sag Harbor
9.89.8 out of 10 rating
Exceptional
(7 reviews)
Cozy Bungalow Available Nearby Bridgehampton and Sag Harbor
Bridgehampton, NY
8% off
Price is AU$15,059
AU$15,059
AU$2,151 per night
includes taxes & fees
Find spaces that suit your style
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Find the best place to stay - North Main Street Historic District
9BR Sag Harbor PRIVATE w/ Pool-Tennis- B-ball- HotTub
Sleeps 28 · 9 bedrooms · 9+ bathrooms
1010 out of 10
Exceptionalexceptional
23 reviews(23 reviews)
Modern Luxury w/ Private Pool. 5 min from Beach & Town of Sag Harbor
Sleeps 10 · 5 bedrooms · 3+ bathrooms
9.69.6 out of 10
Exceptionalexceptional
53 reviews(53 reviews)
Architects' Own Perfect Hideaway With Pool
Sleeps 4 · 3 bedrooms · 2 bathrooms
9.89.8 out of 10
Exceptionalexceptional
6 reviews(6 reviews)
Beach 4 miles Town 2 miles Chef Gym Pelotons Heated Pool hot tub firepits
Sleeps 20 · 7 bedrooms · 5 bathrooms
1010 out of 10
Exceptionalexceptional
4 reviews(4 reviews)
Location and views! Located directly on Shinnecock Bay!
Sleeps 6 · 2 bedrooms · 1 bathroom
9.09.0 out of 10
Wonderfulwonderful
24 reviews(24 reviews)
Stunning Hampton Holiday Family Fantasy for your Team
Sleeps 10 · 5 bedrooms · 6+ bathrooms
9.89.8 out of 10
Exceptionalexceptional
68 reviews(68 reviews)
Peace of mindOur Book with Confidence Guarantee gives you 24/7 support
More quality timeFrom booking to staying, the whole process is simple and enjoyable
All the privacy of homeEnjoy full kitchens, laundry, pools, gardens and more
More for lessMore space, more privacy, more amenities — more value