Over 1,000 homes

Home in Water Mill
Designer's Own, w Pool, 5 min. to Ocean & Village
5 beds
Oct. 14 – 19
$696 CAD per night
Superhost
Home in Southampton
Dream Home with a wonderful heated pool in SH
7 beds
Oct. 11 – 17
$613 CAD per night
Superhost
Cottage in Southampton
Secluded Southampton Cottage - w/ Pool & Spa
4 beds
Oct. 24 – 29
$580 CAD per night, originally $1,480 CAD
Superhost
Home in Sagaponack
Amazing Home close to Everything -
7 beds
Oct. 28 – Nov. 2
$485 CAD per night
Superhost
Home in Westhampton Beach
Luxury Hamptons Home with Heated Saltwater Pool
4 beds
Oct. 9 – 14
$585 CAD per night, originally $763 CAD
Superhost
Home in Water Mill
Pristine 5 bedroom Home - South of the Highway
5 beds
Oct. 14 – 19
$790 CAD per night, originally $2,113 CAD
Superhost
Home in East Hampton
Designer East Hampton Farmhouse
4 beds
Oct. 11 – 16
$1,108 CAD per night, originally $1,766 CAD
Superhost
Home in Southampton
Serene 3 Bed 2.5 Bath House w/Heated SaltwaterPool
4 beds
Oct. 16 – 21
$391 CAD per night, originally $1,488 CAD
Superhost
Home in Southampton
Bright, Open, and Elegant Southampton Retreat
6 beds
Dec. 5 – 12
$579 CAD per night
Superhost
Home in East Hampton
Marvelous 4 Bed East Hampton home w Heated Pool
4 beds
Oct. 10 – 15
$532 CAD per night, originally $1,238 CAD
Superhost
Home in East Hampton
Mid-Century Hamptons Luxury — 2 min to town!
5 beds
Oct. 31 – Nov. 5
$1,111 CAD per night
Superhost
Home in Sag Harbor
Sag Harbor Wonder, 3 bedroom 2 Bath & Heated Pool
4 beds
Oct. 19 – 24
$931 CAD per night
Superhost
Home in Water Mill
Astounding Watermill 5 Bedroom home with Pool
6 beds
Oct. 9 – 14
$454 CAD per night, originally $742 CAD
Superhost
Home in East Hampton
Light-filled, modern home near Bay & Ocean
5 beds
Oct. 16 – 21
$696 CAD per night, originally $833 CAD
Home in Southampton
Unique Southampton Colonial w/ Gunite Pool & Spa
4 beds
Oct. 11 – 16
$993 CAD per night, originally $1,341 CAD
Home in East Hampton
Bright Modern Home With Stunning Yard & Pool
4 beds
Oct. 23 – 28
$1,062 CAD per night
Superhost
Home in Amagansett
Bright Amagansett getaway w/ private pool & tennis
5 beds
Oct. 20 – 26
$900 CAD per night, originally $3,635 CAD
Superhost
Apartment in Sag Harbor
PRIVATE BASEMENT APARTMENT WITH POOL IN SAG HARBOR
1 king bed
Oct. 16 – 21
$376 CAD per night
Superhost
Home in East Hampton
Cheerful East Hampton home with heated Pool
5 beds
Oct. 12 – 17
$876 CAD per night, originally $3,309 CAD
Superhost
Home in Southampton
Stunning 3 bed 2 bath home W heated Pool
4 beds
Oct. 17 – 22
$555 CAD per night
Superhost
Home in East Hampton
Fantastic East Hampton Village home with Pool
6 beds
Oct. 11 – 16
$688 CAD per night, originally $1,826 CAD
Superhost
Home in East Hampton
Chic 5-Bed in Hamptons w/Gunite Pool+Car for Beach
7 beds
Oct. 18 – 24
$991 CAD per night, originally $1,150 CAD
Superhost
Home in Southampton
BRAND NEW MEGA HOME 6BED 5BATH WITH POOL & JACUZZI
10 beds
Oct. 18 – 23
$906 CAD per night, originally $1,044 CAD
Superhost
Home in East Hampton
Luxury 4-bedroom in East Hampton [w/private beach]
7 beds
Nov. 11 – 18
$626 CAD per night