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Compare 16 Guest Houses in Southold with updated reviews, rates, and availability.

House on Chase Creek
Front of property

House on Chase Creek

2.5 star property
9.4 out of 10, Exceptional, (66)
"The view of the creek is beautiful. Time stops."
The price is SAR 391
SAR 446 total
includes taxes & fees
2 Jan - 3 January 2025
House on Chase Creek
Hampton's Vacation Inn
Front of property

Hampton's Vacation Inn

2.5 star property
9.0 out of 10, Wonderful, (272)
"Very clean and quiet."
Hampton's Vacation Inn
Aqua by American Beech - Superior King
Room

Aqua by American Beech - Superior King

10.0 out of 10, Exceptional, (4)
"Nice"
The price is SAR 560
SAR 879 total
includes taxes & fees
23 Dec - 24 Dec
Aqua by American Beech - Superior King
American Beech in Greenport NY - King Suite 1
Room

American Beech in Greenport NY - King Suite 1

10.0 out of 10, Exceptional, (5)
"Perfect Great place"
The price is SAR 672
SAR 1,030 total
includes taxes & fees
5 Jan - 6 January 2025
American Beech in Greenport NY - King Suite 1
American Beech in Greenport - King Suite 3
Room

American Beech in Greenport - King Suite 3

The price is SAR 672
SAR 1,030 total
includes taxes & fees
5 Jan - 6 January 2025
American Beech in Greenport - King Suite 3
American Beech in Greenport - Two-Bedroom Apartment 8
Interior

American Beech in Greenport - Two-Bedroom Apartment 8

The price is SAR 898
SAR 1,321 total
includes taxes & fees
23 Dec - 24 Dec
American Beech in Greenport - Two-Bedroom Apartment 8
American Beech in Greenport - Deluxe King Suite 11
Room

American Beech in Greenport - Deluxe King Suite 11

The price is SAR 935
SAR 1,364 total
includes taxes & fees
2 Jan - 3 January 2025
American Beech in Greenport - Deluxe King Suite 11
Aqua by American Beech - Deluxe King
Room

Aqua by American Beech - Deluxe King

The price is SAR 635
SAR 976 total
includes taxes & fees
23 Dec - 24 Dec
Aqua by American Beech - Deluxe King
American Beech - King Suite 2
Room

American Beech - King Suite 2

10.0 out of 10, Exceptional, (1)
"Wonderful weekend getaway. American Beech offers a perfect blend of privacy and indulgence. Great communication, cool vibe, and a variety of fun food and drink options."
The price is SAR 672
SAR 1,030 total
includes taxes & fees
5 Jan - 6 January 2025
American Beech - King Suite 2
American Beech in Greenport - Deluxe King Suite 12
Room

American Beech in Greenport - Deluxe King Suite 12

The price is SAR 935
SAR 1,360 total
includes taxes & fees
30 Dec - 31 Dec
American Beech in Greenport - Deluxe King Suite 12
American Beech - Deluxe King Suite 14
Room

American Beech - Deluxe King Suite 14

10.0 out of 10, Exceptional, (2)
"Right in the heart of Greenport Villiage "
The price is SAR 1,048
SAR 1,493 total
includes taxes & fees
2 Jan - 3 January 2025
American Beech - Deluxe King Suite 14
New and Modern Bridgehampton Accommodations
Pool

New and Modern Bridgehampton Accommodations

2.0 star property
10.0 out of 10, Exceptional, (7)
"the perfect weekend getaway! if you are looking for somewhere relaxing to stay nearby beaches & shops in the hamptons this is the place to stay! the property itself was beautiful with many great features to enjoy inside and outside. was very secluded and private as well which we enjoyed. the apartment was clean, and the check-in & out process was seamless. definitely reccomend! "
The price is SAR 733
SAR 1,505 total
includes taxes & fees
5 Jan - 6 January 2025
New and Modern Bridgehampton Accommodations
The North Fork Loft
Pool

The North Fork Loft

The North Fork Loft
Aqua by American Beech - Deluxe with 2 Queen
Room

Aqua by American Beech - Deluxe with 2 Queen

Aqua by American Beech - Deluxe with 2 Queen
Aqua by American Beech - Superior with 2 Queens
Room

Aqua by American Beech - Superior with 2 Queens

Aqua by American Beech - Superior with 2 Queens
Victorian Seasons Stirling
Exterior detail

Victorian Seasons Stirling

3.5 star property
Victorian Seasons Stirling
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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Other property types in Southold

Windward Shores Ocean Resort
Property grounds

Windward Shores Ocean Resort

3.0 star property
8.8 out of 10, Excellent, (264)
"Stayed for the second time at Windward and have no complaints. will book again next time I'm in Montauk!"
The price is SAR 474
SAR 623 total
includes taxes & fees
7 Jan - 8 January 2025
Windward Shores Ocean Resort
Cliffside Resort Condominiums
Room

Cliffside Resort Condominiums

3.0 star property
9.0 out of 10, Wonderful, (207)
"Stove it’s not efficient and refrigerator blocked with the corner of wall"
Cliffside Resort Condominiums
Gorgeous private Hamptons house with pool and volleyball court
Exterior

Gorgeous private Hamptons house with pool and volleyball court

8.4 out of 10, Very Good, (17)
"Enjoyed this house in a great location. It was perfect for attending a family wedding!"
Gorgeous private Hamptons house with pool and volleyball court
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.