Holiday rentals near Amagansett Square
We found 3,381 holiday rentals — enter your dates for availability
If you want to to stay within easy reach of Amagansett Square, 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, friends or just your furry companion, you'll have the best amenities for spending time at your home away from home, such as Wi-Fi and cable TV. Whatever you're looking for, you'll be sure to find a property to rent to meet everyone's needs, including a place that's non-smoking or offers accessibility.
Holiday rentals with weekly discounts - Amagansett Square
Showing deals for:17 Oct - 24 Oct
Image gallery for Private Waterfront Home: Dock, Kayaks
9.29.2 out of 10 rating
Wonderful
(17 reviews)
Private Waterfront Home: Dock, Kayaks
Southold, New York
7% off
Price is AU$6,438
AU$6,438
AU$920 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$98,587
AU$98,587
AU$14,084 per night
includes taxes & fees
Image gallery for Beautiful home with spectacular views of the ocean.
1010 out of 10 rating
Exceptional
(8 reviews)
Beautiful home with spectacular views of the ocean.
Montauk, NY
8% off
Price is AU$23,579
AU$23,579
AU$3,368 per night
includes taxes & fees
Image gallery for Beachfront Heated Pool Hot Tub Orient Village Modern Dream Home
9.49.4 out of 10 rating
Exceptional
(6 reviews)
Beachfront Heated Pool Hot Tub Orient Village Modern Dream Home
Orient, NY
8% off
Price is AU$24,005
AU$24,005
AU$3,429 per night
includes taxes & fees
Image gallery for East Hampton NEW home with Pool: 5 minutes from town and beaches. Kid friendly
9.89.8 out of 10 rating
Exceptional
(8 reviews)
East Hampton NEW home with Pool: 5 minutes from town and beaches. Kid friendly
East Hampton, NY
8% off
Price is AU$8,996
AU$8,996
AU$1,285 per night
includes taxes & fees
Image gallery for PRIVATE POOL ~ PERFECT HAMPTONS GETAWAY ~ WBH
1010 out of 10 rating
Exceptional
(12 reviews)
PRIVATE POOL ~ PERFECT HAMPTONS GETAWAY ~ WBH
East Hampton, NY
7% off
Price is AU$13,887
AU$13,887
AU$1,984 per night
includes taxes & fees
Image gallery for HEATED POOL waterfront HOT TUB, GYM, Watersports, BOATER DELIGHT luxury modern
9.89.8 out of 10 rating
Exceptional
(9 reviews)
HEATED POOL waterfront HOT TUB, GYM, Watersports, BOATER DELIGHT luxury modern
Southold, NY
8% off
Price is AU$35,016
AU$35,016
AU$5,002 per night
includes taxes & fees
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
8% off
Price is AU$46,485
AU$46,485
AU$6,641 per night
includes taxes & fees
Image gallery for New Fully Remodeled Post Modern Home, Perfect getaway for a family!
1010 out of 10 rating
Exceptional
(14 reviews)
New Fully Remodeled Post Modern Home, Perfect getaway for a family!
Water Mill, NY
8% off
Price is AU$11,293
AU$11,293
AU$1,613 per night
includes taxes & fees
Image gallery for Book your vacation at our EH retreat on the water!
1010 out of 10 rating
Exceptional
(29 reviews)
Book your vacation at our EH retreat on the water!
East Hampton, NY
8% off
Price is AU$21,490
AU$21,490
AU$3,070 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$24,057
AU$24,057
AU$3,437 per night
includes taxes & fees
Image gallery for Traditional Immaculate Updated Home- Heated Pool, Gym, Yard- Close to EH and Sag
1010 out of 10 rating
Exceptional
(8 reviews)
Traditional Immaculate Updated Home- Heated Pool, Gym, Yard- Close to EH and Sag
East Hampton, NY
17% off
Price is AU$21,785
AU$21,785
AU$3,112 per night
includes taxes & fees
Image gallery for Steps from Cedar Beach ! Tranquil Retreat in the Heart of Wine Country
9.89.8 out of 10 rating
Exceptional
(12 reviews)
Steps from Cedar Beach ! Tranquil Retreat in the Heart of Wine Country
Southold, NY
8% off
Price is AU$6,968
AU$6,968
AU$995 per night
includes taxes & fees
Image gallery for Peconic Sound Beach Home: Backyard & Vineyards
9.69.6 out of 10 rating
Exceptional
(9 reviews)
Peconic Sound Beach Home: Backyard & Vineyards
Peconic, New York
7% off
Price is AU$7,570
AU$7,570
AU$1,081 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$18,101
AU$18,101
AU$2,586 per night
includes taxes & fees
Image gallery for Newly Renovated Gem on the Cedar Beach Peninsula!
1010 out of 10 rating
Exceptional
(28 reviews)
Newly Renovated Gem on the Cedar Beach Peninsula!
Southold, NY
8% off
Price is AU$11,434
AU$11,434
AU$1,633 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$12,100
AU$12,100
AU$1,729 per night
includes taxes & fees
Image gallery for Summer in the Hamptons
9.29.2 out of 10 rating
Wonderful
(12 reviews)
Summer in the Hamptons
East Hampton, NY
7% off
Price is AU$8,484
AU$8,484
AU$1,212 per night
includes taxes & fees
Image gallery for Newly renovated Modern East Hampton Home / Pets welcome
9.89.8 out of 10 rating
Exceptional
(7 reviews)
Newly renovated Modern East Hampton Home / Pets welcome
East Hampton, NY
16% off
Price is AU$12,837
AU$12,837
AU$1,834 per night
includes taxes & fees
Image gallery for Newly renovated modern cottage, 5 minutes from town, beaches, and trailheads.
1010 out of 10 rating
Exceptional
(5 reviews)
Newly renovated modern cottage, 5 minutes from town, beaches, and trailheads.
Bridgehampton, NY
8% off
Price is AU$6,251
AU$6,251
AU$893 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$10,272
AU$10,272
AU$1,467 per night
includes taxes & fees
Image gallery for Modern East Hampton Getaway
9.89.8 out of 10 rating
Exceptional
(10 reviews)
Modern East Hampton Getaway
East Hampton, NY
8% off
Price is AU$14,727
AU$14,727
AU$2,104 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
32% off
Price is AU$17,821
AU$17,821
AU$2,546 per night
includes taxes & fees
Image gallery for Huge private house, IG heated pool, fire pit, sleeps 10, 5 bath,Walk to Gurneys!
9.89.8 out of 10 rating
Exceptional
(22 reviews)
Huge private house, IG heated pool, fire pit, sleeps 10, 5 bath,Walk to Gurneys!
Montauk, NY
8% off
Price is AU$14,116
AU$14,116
AU$2,017 per night
includes taxes & fees
Find spaces that suit your style
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Find the best place to stay - Amagansett Square
Newly Renovated, 5BR Private Getaway with Pool
Sleeps 12 · 5 bedrooms · 3+ bathrooms
9.29.2 out of 10
Wonderfulwonderful
7 reviews(7 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