Southold Station holiday homes
We found 3,804 holiday rentals — enter your dates for availability
Choose the right private holiday rental within close proximity to Southold Station. Holiday homes provide the best amenities for your stay with friends, family or just your pet, such as parking and a hot tub. At the end of the day, you'll find a property to rent to meet everyone's needs, including a place that is accessible or non-smoking.
Holiday rentals with weekly discounts - Southold Station
Showing deals for:10 Oct - 17 Oct
Image gallery for Spacious home near Aquarium & heart of wine country Shopping & close to Hamptons
1010 out of 10 rating
Exceptional
(12 reviews)
Spacious home near Aquarium & heart of wine country Shopping & close to Hamptons
Riverhead, NY
8% off
Price is NZ$9,596
NZ$9,596
NZ$1,371 per night
includes taxes & fees
Image gallery for Peconic River Boatel
1010 out of 10 rating
Exceptional
(14 reviews)
Peconic River Boatel
Riverhead, NY
8% off
Price is NZ$5,784
NZ$5,784
NZ$826 per night
includes taxes & fees
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 NZ$8,312
NZ$8,312
NZ$1,187 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 NZ$9,780
NZ$9,780
NZ$1,397 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 NZ$27,351
NZ$27,351
NZ$3,907 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 NZ$15,607
NZ$15,607
NZ$2,230 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
15% off
Price is NZ$48,523
NZ$48,523
NZ$6,932 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
7% off
Price is NZ$12,692
NZ$12,692
NZ$1,813 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 NZ$6,964
NZ$6,964
NZ$995 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 NZ$27,236
NZ$27,236
NZ$3,891 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 NZ$7,818
NZ$7,818
NZ$1,117 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
7% off
Price is NZ$13,834
NZ$13,834
NZ$1,976 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 NZ$9,513
NZ$9,513
NZ$1,359 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
7% off
Price is NZ$20,491
NZ$20,491
NZ$2,927 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 NZ$14,086
NZ$14,086
NZ$2,012 per night
includes taxes & fees
Image gallery for Hamptons Oasis with Heated Pool
9.89.8 out of 10 rating
Exceptional
(8 reviews)
Hamptons Oasis with Heated Pool
Hampton Bays, NY
8% off
Price is NZ$21,809
NZ$21,809
NZ$3,116 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 NZ$9,586
NZ$9,586
NZ$1,369 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 NZ$35,157
NZ$35,157
NZ$5,022 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 NZ$9,249
NZ$9,249
NZ$1,321 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 NZ$14,470
NZ$14,470
NZ$2,067 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 NZ$11,037
NZ$11,037
NZ$1,577 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 NZ$6,754
NZ$6,754
NZ$965 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 NZ$19,981
NZ$19,981
NZ$2,854 per night
includes taxes & fees
Image gallery for Respite Ranch: Private Pool, Hot Tub, BBQ Grill
9.89.8 out of 10 rating
Exceptional
(7 reviews)
Respite Ranch: Private Pool, Hot Tub, BBQ Grill
Mattituck, New York
7% off
Price is NZ$12,231
NZ$12,231
NZ$1,747 per night
includes taxes & fees
Find spaces that suit your style
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Find the best place to stay - Southold Station
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
68 reviews(68 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)
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)
Architects' Own Perfect Hideaway With Pool
Sleeps 4 · 3 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
12 reviews(12 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