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Our top choices for Southold vacation homes
1. The SandPiper
The SandPiperPipes Cove
9.6 out of 10, Exceptional, (57 reviews)
"Place was perfect ! Great location / clean/ everything we needed was there ! Would love to stay there again :)"
Manuela C.
The price is AED 314
AED 846 total
includes taxes & fees
10 Nov - 11 Nov
2. Aqua Vista
Aqua VistaPipes Cove
10.0 out of 10, Exceptional, (52 reviews)
"Great location and nice spot."
Kerri L.
The price is AED 349
AED 890 total
includes taxes & fees
9 Nov - 10 Nov
3. Blue Bay Dream w/ Seasonal Outdoor Jacuzzi, Cabana + Office
Blue Bay Dream w/ Seasonal Outdoor Jacuzzi, Cabana + OfficePipes Cove
10.0 out of 10, Exceptional, (35 reviews)
"We had a great stay!! "
Callie E.
The price is AED 479
AED 1,278 total
includes taxes & fees
3 Nov - 4 Nov
4. Beach Block Hideaway
Beach Block HideawayPipes Cove
10.0 out of 10, Exceptional, (12 reviews)
"Beautiful 2 bedroom close to town. The house is well kept we would rent here again."
Teresa C.
The price is AED 716
AED 1,574 total
includes taxes & fees
3 Nov - 4 Nov
5. American Beech in Greenport - Petite King Room 7
American Beech in Greenport - Petite King Room 7Greenport
9.4 out of 10, Exceptional, (6 reviews)
"Great place! So nice."
Paul F.
The price is AED 731
AED 1,066 total
includes taxes & fees
3 Nov - 4 Nov
6. Northfork Townhouse walk to all
Northfork Townhouse walk to allGreenport
9.4 out of 10, Exceptional, (8 reviews)
"Great property located in a quiet neighborhood within walking distance to all in Greenport. The townhouse was clean and kitchen was well- appointed with off the street parking. Playground up the street was an added bonus with a old school merry-go-round! Would definitely stay again"
Beth R.
7. Beachfront Greenport Villa
Beachfront Greenport VillaGreenport
9.6 out of 10, Exceptional, (15 reviews)
"Beautiful home, great views and host!"
Kate R.
The price is AED 2,663
AED 4,322 total
includes taxes & fees
3 Dec - 4 Dec
8. Renovated Townhouse walk to all
Renovated Townhouse walk to allGreenport
9.6 out of 10, Exceptional, (15 reviews)
"The place was as advertised and in great walking distance to everything in town! "
Liz H.
The price is AED 926
AED 2,073 total
includes taxes & fees
16 Nov - 17 Nov
9. Entire House in Southampton Village, Pool, 2 Fireplaces, Walk Everywhere, Pets!
Entire House in Southampton Village, Pool, 2 Fireplaces, Walk Everywhere, Pets!Southampton
9.2 out of 10, Wonderful, (11 reviews)
"Great house with lots of space. Perfect location! The host is extremely accommodating. Definitely recommend!"
Justin
The price is AED 413
AED 1,970 total
includes taxes & fees
3 Nov - 4 Nov
10. Designer Sag Harbor Home w/ Pool + Fire Pit + Yard
Designer Sag Harbor Home w/ Pool + Fire Pit + YardSag Harbor
10.0 out of 10, Exceptional, (1 review)
"excellent and convenient stay!! located close into town, perfect for the small family group I was traveling with. home was very clean, cozy, had everything we needed! backyard with pool was a dream, beautifully landscaped, plenty of seating, very clean pool, would stay again! thanks for a delightful escape!"
maria m.
The price is AED 1,926
AED 3,984 total
includes taxes & fees
3 Nov - 4 Nov
11. Year round Jacuzzi - Blackberry East Hampton Home
Year round Jacuzzi - Blackberry East Hampton HomeEast Hampton
9.2 out of 10, Wonderful, (7 reviews)
"We had a great time staying here. The home is well worn and there are some fixtures that should be replaced "
Suzanne R.
The price is AED 353
AED 4,828 total
includes taxes & fees
8 Nov - 9 Nov
12. American Beech in Greenport - Deluxe King 6
American Beech in Greenport - Deluxe King 6Greenport
2.0 out of 10, (1 review)
"Not as advertised. Very disappointed "
Jeffrey
13. Jacuzzi year-round - Villa Luz Private Home
Jacuzzi year-round - Villa Luz Private HomeHampon Bays
9.6 out of 10, Exceptional, (27 reviews)
"Overall really great stay! Would definitely stay here again was so peaceful. Had a great weekend!"
Annie B.
The price is AED 349
AED 6,491 total
includes taxes & fees
3 Nov - 4 Nov
14. Breakwater Estate: Heated Saltwater Pool, Sleeps 12
Breakwater Estate: Heated Saltwater Pool, Sleeps 12Mattituck
10.0 out of 10, Exceptional, (39 reviews)
"House has so much character, I rent 7-8 weeks per year and every home is different.This house is the most organized I have ever been in but also the most character.Every room brings you to different place, the furniture is beautiful. Home is spacious.Grounds are larger than most in the Hamptons. Pool is spectacular!"
Frank T.
The price is AED 2,005
AED 4,628 total
includes taxes & fees
10 Nov - 11 Nov
15. Bridgehampton, NY cottage near Sag Harbor, NY. Elegant and modern.
Bridgehampton, NY cottage near Sag Harbor, NY. Elegant and modern.Bridgehampton
10.0 out of 10, Exceptional, (2 reviews)
"The property was great for our Hamptons trip! Very clean and comfortable and communication was great"
Katie B.
The price is AED 1,047
AED 2,052 total
includes taxes & fees
8 Nov - 9 Nov
16. Beachfront Jacuzzi All Year - Black Swan Home
Beachfront Jacuzzi All Year - Black Swan HomeHampton Bays
9.4 out of 10, Exceptional, (21 reviews)
"Views are incredible. Lucky enough to have had great weather before Memorial Day weekend! Our family loved it! Hot tub was wonderful."
Donald J.
The price is AED 453
AED 4,475 total
includes taxes & fees
8 Nov - 9 Nov
17. COLONIAL COMPOUND WITH OVERSIZED LIVING ROOMS, GYM, AND ARCADE ROOM, CLOSE...
COLONIAL COMPOUND WITH OVERSIZED LIVING ROOMS, GYM, AND ARCADE ROOM, CLOSE...Southampton
9.2 out of 10, Wonderful, (29 reviews)
"I loved the area and the home was beautiful and very spacious."
Melissa
The price is AED 7,852
AED 10,190 total
includes taxes & fees
3 Nov - 4 Nov
18. Lovely & Spacious Sag Harbor escape with heated pool
Lovely & Spacious Sag Harbor escape with heated poolSag Harbor
The price is AED 5,620
AED 7,768 total
includes taxes & fees
3 Nov - 4 Nov
19. NEW private studio 1.1 miles to beach in East Lyme
NEW private studio 1.1 miles to beach in East LymeEast Lyme
20. Minutes from the beach, brand new 4 bedroom
Minutes from the beach, brand new 4 bedroomSouthampton
10.0 out of 10, Exceptional, (6 reviews)
"perfect for families"
Okito H.
The price is AED 1,653
AED 3,873 total
includes taxes & fees
3 Nov - 4 Nov
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Southold Hotel Reviews
Hilton Garden Inn Riverhead
10/10 Excellent
