Best price vacation rentals in Southampton, NY, USA • 150 Listings
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Southampton, NY, USA Vacation Rentals | 

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United States New York Fire Island vacation rental compare prices direct by owner 240278
Verified Host
5.0 (78)
Oceanfront Heaven! - 5 BR
Up to 12 guests
EstimatedVerified Host$1,250
Vrbo$1,850
Airbnb$1,250
Average Nightly Rate
United States New York Ocean Bay Park vacation rental compare prices direct by owner 32593838
Verified Host
5.0 (61)
Windows on the Sea ★ Modern Pool & Beach Retreat ★
Up to 12 guests
EstimatedVerified Host$800
Vrbo$1,820
Airbnb$800
Average Nightly Rate
United States Connecticut Milford vacation rental compare prices direct by owner 686868
Verified Host
5.0 (102)
Waterfront!-Hot Tub-The Charles Island Beach House
Up to 12 guests
EstimatedVerified Host$1,300
Airbnb$1,300
Average Nightly Rate
United States Connecticut Milford vacation rental compare prices direct by owner 27242009
Verified Host
0.0 (0)
Whales Tale Fantastic BEACH Home This Summer 2025
Up to 8 guests
EstimatedVerified Host$750
Airbnb$750
Average Nightly Rate
United States New York Greenport vacation rental compare prices direct by owner 195332
5.0 (78)
Greenport Victorian Captains House
Up to 8 guests
Vrbo$960
Airbnb$1,250
Booking.com
Average Nightly Rate
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United States Connecticut Clinton vacation rental compare prices direct by owner 203239
5.0 (34)
The Perfect Family Beachfront Cottage The Viola Cottage
Up to 7 guests
Vrbo$412
Airbnb
Booking.com
Average Nightly Rate
United States New York Sag Harbor vacation rental compare prices direct by owner 493594
5.0 (25)
LUXURY 2.4 ACRS- 5BR, Tennis Court, Pool, Hot Tub
Up to 10 guests
Airbnb$1,100
Vrbo$2,498
Booking.com
Average Nightly Rate

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United States Connecticut Waterford vacation rental compare prices direct by owner 2765510
Property Manager
5.0 (57)
Deluxe Waterford Home w/ Views, Outdoor Bar & More
Up to 9 guests
Vrbo$543
Airbnb$999
Booking.com$712
Property Manager
Average Nightly Rate
United States New York Wading River vacation rental compare prices direct by owner 2929472
5.0 (26)
Luxury Beach Cottage: Wineries, Shopping & The Ham
Up to 4 guests
Vrbo$329
Airbnb$375
Booking.com
Average Nightly Rate

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United States New York Southold vacation rental compare prices direct by owner 6654956
Property Manager
5.0 (2)
2BR The Hamptons | Patio | Garage Parking | W/D
Up to 4 guests
Airbnb$162
Vrbo$168
Property Manager
Booking.com
Average Nightly Rate
United States New York Riverhead vacation rental compare prices direct by owner 10432541
5.0 (43)
Charming North Fork Retreat - 2 mins walk to Beach
Up to 6 guests
Vrbo$406
Airbnb$450
Booking.com
Average Nightly Rate
United States New York East Hampton vacation rental compare prices direct by owner 19645371
5.0 (26)
Newly renovated kitchen/baths, Clean, Cozy, Bright
Up to 8 guests
Airbnb$800
Vrbo$910
Booking.com
Average Nightly Rate
United States New York Southampton vacation rental compare prices direct by owner 23679714
Property Manager
5.0 (2)
Modern 2BR The Hamptons | Fireplace | Patio
Up to 4 guests
Vrbo$284
Airbnb$518
Property Manager
Booking.com
Average Nightly Rate
United States New York Southold vacation rental compare prices direct by owner 24148680
Property Manager
5.0 (1)
Charming 1BR Bayview The Hamptons Dog Friendly
Up to 4 guests
Vrbo$231
Airbnb$248
Property Manager
Booking.com
Average Nightly Rate
United States New York Westhampton Beach vacation rental compare prices direct by owner 26594827
Property Manager
5.0 (1)
Stunning Westhampton Beach Home w/ Private Pool
Up to 11 guests
Airbnb$874
Vrbo$956
Booking.com$1,100
Property Manager
Average Nightly Rate
United States Connecticut Niantic vacation rental compare prices direct by owner 26602122
Property Manager
5.0 (78)
Coastal Getaway w/ Porch, 2 Mi to Niantic Beach!
Up to 4 guests
Vrbo$304
Airbnb$354
Booking.com$377
Property Manager
Average Nightly Rate
United States New York Mattituck vacation rental compare prices direct by owner 26613918
Property Manager
5.0 (8)
Mattituck Home w/ Fireplaces - Near Wineries
Up to 6 guests
Vrbo$470
Airbnb$503
Property Manager
Booking.com
Average Nightly Rate
United States New York Cutchogue vacation rental compare prices direct by owner 27456956
Property Manager
5.0 (1)
The Endless Summer Cottage
Up to 6 guests
Vrbo$273
Property Manager
Airbnb
Booking.com
Average Nightly Rate
United States New York Greenport vacation rental compare prices direct by owner 28047200
Property Manager
5.0 (1)
3BR private home w/ pool, sauna, gym, & work desks
Up to 10 guests
Vrbo$397
Airbnb$574
Property Manager
Booking.com
Average Nightly Rate
United States New York Greenport vacation rental compare prices direct by owner 28738316
Property Manager
5.0 (2)
Modern on 9th
Up to 6 guests
Vrbo$442
Property Manager
Airbnb
Booking.com
Average Nightly Rate
United States Connecticut Stonington vacation rental compare prices direct by owner 29433769
Property Manager
5.0 (16)
Spacious Connecticut Home - Deck, Grill & Fire Pit
Up to 6 guests
Airbnb$805
Vrbo$833
Booking.com$963
Property Manager
Average Nightly Rate
United States New York Hampton Bays vacation rental compare prices direct by owner 29466699
Property Manager
5.0 (1)
5BR renovated home with a pool, grill, & firepit
Up to 10 guests
Airbnb$613
Vrbo$626
Property Manager
Booking.com
Average Nightly Rate
United States New York Sag Harbor vacation rental compare prices direct by owner 32242419
5.0 (3)
The Rosemorran Retreat
Up to 10 guests
Airbnb$1,750
Vrbo$2,780
Booking.com$2,340
Average Nightly Rate
United States New York East Hampton vacation rental compare prices direct by owner 33241288
5.0 (6)
East Hampton Beach Getaway
Up to 6 guests
Booking.com$1,127
Vrbo$1,209
Airbnb
Average Nightly Rate
United States New York Riverhead vacation rental compare prices direct by owner 33311866
Property Manager
5.0 (8)
Waterfront New York Getaway w/ Kayaks
Up to 2 guests
Vrbo$179
Airbnb$208
Property Manager
Booking.com
Average Nightly Rate
  1. United States
  2. New York
  3. Southampton Vacation Rental Price Comparison

Compare Airbnb vs. Booking.com vs. Vrbo prices for vacation rentals in Southampton, NY, USA

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