Southold Station holiday rentals
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 AU$8,906
AU$8,906
AU$1,272 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 AU$5,336
AU$5,336
AU$762 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 AU$7,475
AU$7,475
AU$1,068 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$9,080
AU$9,080
AU$1,297 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$24,043
AU$24,043
AU$3,435 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$13,772
AU$13,772
AU$1,967 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
16% off
Price is AU$42,645
AU$42,645
AU$6,092 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$11,312
AU$11,312
AU$1,616 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$6,432
AU$6,432
AU$919 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$23,945
AU$23,945
AU$3,421 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$7,050
AU$7,050
AU$1,007 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$8,802
AU$8,802
AU$1,257 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$12,403
AU$12,403
AU$1,772 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$18,043
AU$18,043
AU$2,578 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$12,639
AU$12,639
AU$1,806 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 AU$19,195
AU$19,195
AU$2,742 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$8,898
AU$8,898
AU$1,271 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$8,579
AU$8,579
AU$1,226 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$30,872
AU$30,872
AU$4,410 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$13,001
AU$13,001
AU$1,857 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$10,268
AU$10,268
AU$1,467 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$6,233
AU$6,233
AU$890 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$17,599
AU$17,599
AU$2,514 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 AU$10,821
AU$10,821
AU$1,546 per night
includes taxes & fees
Find spaces that suit your style
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Find the best place to stay - Southold Station
Showing deals for: 6 Oct - 9 Oct
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)
The current price is AU$13,595
AU$13,595
for 3 nights, 1 home
AU$4,532 per night
includes taxes & fees
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)
The current price is AU$5,302
AU$5,302
for 3 nights, 1 home
AU$1,767 per night
includes taxes & fees
Fairy Tale Guest Cottage in Magic Garden by Pool
Sleeps 2 · 1 bedroom · 1 bathroom
1010 out of 10
Exceptionalexceptional
68 reviews(68 reviews)
The current price is AU$2,312
AU$2,312
for 3 nights, 1 cottage
AU$771 per night
includes taxes & fees
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)
The current price is AU$8,065
AU$8,065
for 3 nights, 1 home
AU$2,688 per night
includes taxes & fees
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)
The current price is AU$1,610
AU$1,610
for 3 nights, 1 home
AU$537 per night
includes taxes & fees
Architects' Own Perfect Hideaway With Pool
Sleeps 4 · 3 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
12 reviews(12 reviews)
The current price is AU$3,567
AU$3,567
for 3 nights, 1 home
AU$1,189 per night
includes taxes & fees
Top rated rentals - Southold Station
Lovely place right on a lake
1010 out of 10
Exceptionalexceptional
78 reviews(78 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