Holiday rentals near North Main Street Historic District
We found 1,636 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:3 Oct - 10 Oct
Image gallery for Hamptons Compound w/ Golf, Tennis, Pool, Basketball, Bocce, and much more!
9.69.6 out of 10 rating
Exceptional
(20 reviews)
Hamptons Compound w/ Golf, Tennis, Pool, Basketball, Bocce, and much more!
East Hampton, NY
17% off
Price is AU$41,388
AU$41,388
AU$5,913 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
13% off
Price is AU$23,646
AU$23,646
AU$3,378 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$12,248
AU$12,248
AU$1,750 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
(9 reviews)
Just renovated, Amazing oasis, heated pool-spa, between Sag Harbor -Southampton
Southampton, NY
8% off
Price is AU$17,818
AU$17,818
AU$2,545 per night
includes taxes & fees
Image gallery for Relax in Hampton Bays...
9.89.8 out of 10 rating
Exceptional
(70 reviews)
Relax in Hampton Bays...
Hampton Bays, NY
8% off
Price is AU$6,446
AU$6,446
AU$921 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$19,384
AU$19,384
AU$2,769 per night
includes taxes & fees
Image gallery for Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping
1010 out of 10 rating
Exceptional
(25 reviews)
Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping
Southampton, NY
7% off
Price is AU$13,113
AU$13,113
AU$1,873 per night
includes taxes & fees
Image gallery for WALK TO BEACH - HAMPTONS WITHOUT THE HASSLE
1010 out of 10 rating
Exceptional
(5 reviews)
WALK TO BEACH - HAMPTONS WITHOUT THE HASSLE
Hampton Bays, NY
8% off
Price is AU$8,864
AU$8,864
AU$1,266 per night
includes taxes & fees
Image gallery for Heated Pool + Hot Tub - Luxe 7BR Villa
1010 out of 10 rating
Exceptional
(18 reviews)
Heated Pool + Hot Tub - Luxe 7BR Villa
Hampton Bays, NY
9% off
Price is AU$28,142
AU$28,142
AU$4,020 per night
includes taxes & fees
Image gallery for Luxury Home with Private Tennis, Basketball, Pool & Jacuzzi
9.69.6 out of 10 rating
Exceptional
(9 reviews)
Luxury Home with Private Tennis, Basketball, Pool & Jacuzzi
Southampton, NY
8% off
Price is AU$10,140
AU$10,140
AU$1,449 per night
includes taxes & fees
Image gallery for Southampton Luxury Waterfront Villa Rental
9.29.2 out of 10 rating
Wonderful
(18 reviews)
Southampton Luxury Waterfront Villa Rental
Southampton, NY
33% off
Price is AU$17,379
AU$17,379
AU$2,483 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$98,535
AU$98,535
AU$14,076 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$25,268
AU$25,268
AU$3,610 per night
includes taxes & fees
Image gallery for Poppy's Hampton House: Big Yard, Beach, Renovated
9.89.8 out of 10 rating
Exceptional
(11 reviews)
Poppy's Hampton House: Big Yard, Beach, Renovated
Hampton Bays, New York
7% off
Price is AU$7,864
AU$7,864
AU$1,123 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$19,163
AU$19,163
AU$2,738 per night
includes taxes & fees
Image gallery for Close to everything! Steps to water and beach, hiking, kayaking, sailing.
1010 out of 10 rating
Exceptional
(5 reviews)
Close to everything! Steps to water and beach, hiking, kayaking, sailing.
Sag Harbor, NY
8% off
Price is AU$12,444
AU$12,444
AU$1,778 per night
includes taxes & fees
Image gallery for Waterfront, Pool, HotTub, Strong WIFI, Pingpong, Paddleboard, Kayak, Bocce Court
1010 out of 10 rating
Exceptional
(93 reviews)
Waterfront, Pool, HotTub, Strong WIFI, Pingpong, Paddleboard, Kayak, Bocce Court
Sag Harbor, NY
8% off
Price is AU$15,468
AU$15,468
AU$2,210 per night
includes taxes & fees
Image gallery for 125+Acre Nature Preserve Enveloped Sag Harbor Home, 5 BED, 5.5 BATH, POOL
1010 out of 10 rating
Exceptional
(9 reviews)
125+Acre Nature Preserve Enveloped Sag Harbor Home, 5 BED, 5.5 BATH, POOL
East Hampton, NY
7% off
Price is AU$16,410
AU$16,410
AU$2,344 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$10,204
AU$10,204
AU$1,458 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$19,064
AU$19,064
AU$2,723 per night
includes taxes & fees
Image gallery for Swim in a sea of hydrangeas on this peaceful, bucolic property.
9.89.8 out of 10 rating
Exceptional
(20 reviews)
Swim in a sea of hydrangeas on this peaceful, bucolic property.
Water Mill, NY
8% off
Price is AU$22,910
AU$22,910
AU$3,273 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$19,629
AU$19,629
AU$2,804 per night
includes taxes & fees
Image gallery for Luxury, private, gated heated pool, hot tub, fenced in property! Child friendly!
1010 out of 10 rating
Exceptional
(30 reviews)
Luxury, private, gated heated pool, hot tub, fenced in property! Child friendly!
East Hampton, NY
8% off
Price is AU$48,000
AU$48,000
AU$6,857 per night
includes taxes & fees
Image gallery for Heated pool/5 min walk to Beach/Beautiful Sag Harbor Village /Restaurant/Museum
1010 out of 10 rating
Exceptional
(45 reviews)
Heated pool/5 min walk to Beach/Beautiful Sag Harbor Village /Restaurant/Museum
Sag Harbor, NY
8% off
Price is AU$26,576
AU$26,576
AU$3,797 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
9.89.8 out of 10
Exceptionalexceptional
24 reviews(24 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
55 reviews(55 reviews)
Fairy Tale Guest Cottage in Magic Garden by Pool
Sleeps 2 · 1 bedroom · 1 bathroom
1010 out of 10
Exceptionalexceptional
67 reviews(67 reviews)
Designer home in a prime location - Close to wineries and Ocean Beaches
Sleeps 10 · 5 bedrooms · 4 bathrooms
1010 out of 10
Exceptionalexceptional
49 reviews(49 reviews)
Charming Waterfront Cottage with Sunset Views!
Sleeps 7 · 4 bedrooms · 1+ bathroom
1010 out of 10
Exceptionalexceptional
1 review(1 review)
Architects' Own Perfect Hideaway With Pool
Sleeps 4 · 3 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
11 reviews(11 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