Holiday rentals near North Main Street Historic District
We found 1,620 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:14 Nov - 21 Nov
Image gallery for Hamptons Compound w/ Golf, Tennis, Pool, Basketball, Bocce, and much more!
9.69.6 out of 10 rating
Exceptional
(21 reviews)
Hamptons Compound w/ Golf, Tennis, Pool, Basketball, Bocce, and much more!
East Hampton, NY
8% off
Price is AU$47,066
AU$47,066
AU$6,724 per night
includes taxes & fees
Image gallery for Relax in Hampton Bays...
9.89.8 out of 10 rating
Exceptional
(72 reviews)
Relax in Hampton Bays...
Hampton Bays, NY
8% off
Price is AU$6,955
AU$6,955
AU$994 per night
includes taxes & fees
Image gallery for Sag Harbor Sleeps 10 ……5 min drive to town.
1010 out of 10 rating
Exceptional
(21 reviews)
Sag Harbor Sleeps 10 ……5 min drive to town.
Sag Harbor, NY
35% off
Price is AU$19,677
AU$19,677
AU$2,811 per night
includes taxes & fees
Image gallery for Southampton Pickleball Walk to beach. Kayaks on lake Park-like grounds Pool
9.89.8 out of 10 rating
Exceptional
(25 reviews)
Southampton Pickleball Walk to beach. Kayaks on lake Park-like grounds Pool
Southampton, NY
12% off
Price is AU$20,441
AU$20,441
AU$2,920 per night
includes taxes & fees
Image gallery for Just renovated, Amazing oasis, heated pool-spa, between Sag Harbor -Southampton
1010 out of 10 rating
Exceptional
(10 reviews)
Just renovated, Amazing oasis, heated pool-spa, between Sag Harbor -Southampton
Southampton, NY
8% off
Price is AU$18,327
AU$18,327
AU$2,618 per night
includes taxes & fees
Image gallery for Modern Family Retreat with Heated Pool, Playground and Peloton
9.89.8 out of 10 rating
Exceptional
(25 reviews)
Modern Family Retreat with Heated Pool, Playground and Peloton
Hampton Bays, NY
8% off
Price is AU$12,520
AU$12,520
AU$1,789 per night
includes taxes & fees
Image gallery for Heated Pool + Hot Tub - Luxe 7BR Villa
1010 out of 10 rating
Exceptional
(19 reviews)
Heated Pool + Hot Tub - Luxe 7BR Villa
Hampton Bays, NY
9% off
Price is AU$20,263
AU$20,263
AU$2,895 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$99,819
AU$99,819
AU$14,260 per night
includes taxes & fees
Image gallery for Hamptons Oasis with Heated Pool
9.89.8 out of 10 rating
Exceptional
(10 reviews)
Hamptons Oasis with Heated Pool
Hampton Bays, NY
8% off
Price is AU$19,478
AU$19,478
AU$2,783 per night
includes taxes & fees
Image gallery for Cozy Seaside Cottage
1010 out of 10 rating
Exceptional
(37 reviews)
Cozy Seaside Cottage
New Suffolk, NY
11% off
Price is AU$8,283
AU$8,283
AU$1,183 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$25,746
AU$25,746
AU$3,678 per night
includes taxes & fees
Image gallery for Enjoy a lovely summer retreat in Sag Harbor Village, 1 mile to Main Street
1010 out of 10 rating
Exceptional
(8 reviews)
Enjoy a lovely summer retreat in Sag Harbor Village, 1 mile to Main Street
Sag Harbor, NY
8% off
Price is AU$19,686
AU$19,686
AU$2,812 per night
includes taxes & fees
Image gallery for Newly Renovated Modern Home With Beach Access and Pool!
1010 out of 10 rating
Exceptional
(20 reviews)
Newly Renovated Modern Home With Beach Access and Pool!
Laurel, NY
9% off
Price is AU$7,026
AU$7,026
AU$1,004 per night
includes taxes & fees
Image gallery for Poppy's Hampton House: Big Yard, Beach, Renovated
9.89.8 out of 10 rating
Exceptional
(12 reviews)
Poppy's Hampton House: Big Yard, Beach, Renovated
Hampton Bays, NY
7% off
Price is AU$5,947
AU$5,947
AU$850 per night
includes taxes & fees
Image gallery for Mansion Near the Bay. 7 bedrooms! Chef’s kitchen.
9.89.8 out of 10 rating
Exceptional
(53 reviews)
Mansion Near the Bay. 7 bedrooms! Chef’s kitchen.
Southampton, NY
8% off
Price is AU$16,653
AU$16,653
AU$2,379 per night
includes taxes & fees
Image gallery for Hampton Bays luxury retreat with heated pool, steps from the Beach! Pet friendly
1010 out of 10 rating
Exceptional
(8 reviews)
Hampton Bays luxury retreat with heated pool, steps from the Beach! Pet friendly
Hampton Bays, NY
17% off
Price is AU$17,911
AU$17,911
AU$2,559 per night
includes taxes & fees
Image gallery for Pool/5 min walk to Beach/Restaurants/Museums- Village House w/backyard
1010 out of 10 rating
Exceptional
(6 reviews)
Pool/5 min walk to Beach/Restaurants/Museums- Village House w/backyard
Sag Harbor, NY
8% off
Price is AU$41,823
AU$41,823
AU$5,975 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$10,233
AU$10,233
AU$1,462 per night
includes taxes & fees
Image gallery for Stunning Private Sunny Modern Southampton home-5 beds Last minute discounts
9.89.8 out of 10 rating
Exceptional
(19 reviews)
Stunning Private Sunny Modern Southampton home-5 beds Last minute discounts
Southampton, NY
8% off
Price is AU$11,027
AU$11,027
AU$1,575 per night
includes taxes & fees
Image gallery for Sag Harbor Modern Home, Heated Salt Water Pool, Walk to Beach, Walk to Village
1010 out of 10 rating
Exceptional
(37 reviews)
Sag Harbor Modern Home, Heated Salt Water Pool, Walk to Beach, Walk to Village
Sag Harbor, NY
8% off
Price is AU$18,428
AU$18,428
AU$2,633 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
8% off
Price is AU$20,157
AU$20,157
AU$2,880 per night
includes taxes & fees
Image gallery for Beautiful and Spacious Vacation Home in Sag Harbor!
1010 out of 10 rating
Exceptional
(36 reviews)
Beautiful and Spacious Vacation Home in Sag Harbor!
Sag Harbor, NY
7% off
Price is AU$13,754
AU$13,754
AU$1,965 per night
includes taxes & fees
Image gallery for A Quiet Place in the Hamptons
9.89.8 out of 10 rating
Exceptional
(36 reviews)
A Quiet Place in the Hamptons
East Quogue, NY
8% off
Price is AU$13,363
AU$13,363
AU$1,909 per night
includes taxes & fees
Image gallery for Hampton Bays Oasis
1010 out of 10 rating
Exceptional
(15 reviews)
Hampton Bays Oasis
Hampton Bays, NY
8% off
Price is AU$8,648
AU$8,648
AU$1,235 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
Fairy Tale Guest Cottage in Magic Garden by Pool
Sleeps 2 · 1 bedroom · 1 bathroom
1010 out of 10
Exceptionalexceptional
71 reviews(71 reviews)
Charming Waterfront Cottage with Sunset Views!
Sleeps 7 · 4 bedrooms · 1+ bathroom
9.49.4 out of 10
Exceptionalexceptional
3 reviews(3 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
57 reviews(57 reviews)
Designer home in a prime location - Close to wineries and Ocean Beaches
Sleeps 10 · 5 bedrooms · 4 bathrooms
1010 out of 10
Exceptionalexceptional
50 reviews(50 reviews)
Stunning Hampton Holiday Family Fantasy for your Team
Sleeps 10 · 5 bedrooms · 6+ bathrooms
9.89.8 out of 10
Exceptionalexceptional
69 reviews(69 reviews)
New and Modern Bridgehampton Accommodations
Sleeps 4 · 1 bedroom · 1 bathroom
9.49.4 out of 10
Exceptionalexceptional
10 reviews(10 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