Search Guest Houses in Southold from CA $150

  • Plan, book, stay with confidence

    • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Browse Select Southold Guest Houses

House on Chase Creek
View from 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 CA $150
CA $171 total
includes taxes & fees
Jan 6 - Jan 7, 2025
House on Chase Creek
Hampton's Vacation Inn
Apartment, 2 Bedrooms | Private kitchen

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
Property grounds

Aqua by American Beech - Superior King

10.0 out of 10, Exceptional, (4)
"Nice"
The price is CA $215
CA $340 total
includes taxes & fees
Dec 29 - Dec 30
Aqua by American Beech - Superior King
American Beech in Greenport NY - King Suite 1
Interior

American Beech in Greenport NY - King Suite 1

10.0 out of 10, Exceptional, (5)
"Perfect Great place"
The price is CA $229
CA $355 total
includes taxes & fees
Jan 2 - Jan 3, 2025
American Beech in Greenport NY - King Suite 1
American Beech in Greenport - King Suite 3
Property grounds

American Beech in Greenport - King Suite 3

The price is CA $229
CA $355 total
includes taxes & fees
Jan 2 - Jan 3, 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 CA $359
CA $526 total
includes taxes & fees
Jan 2 - Jan 3, 2025
American Beech in Greenport - Two-Bedroom Apartment 8
American Beech in Greenport - Deluxe King Suite 11
Interior

American Beech in Greenport - Deluxe King Suite 11

The price is CA $258
CA $395 total
includes taxes & fees
Jan 2 - Jan 3, 2025
American Beech in Greenport - Deluxe King Suite 11
Aqua by American Beech - Deluxe King
Terrace/patio

Aqua by American Beech - Deluxe King

The price is CA $244
CA $376 total
includes taxes & fees
Dec 29 - Dec 30
Aqua by American Beech - Deluxe King
American Beech - King Suite 2
Interior

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 CA $229
CA $356 total
includes taxes & fees
Jan 2 - Jan 3, 2025
American Beech - King Suite 2
American Beech in Greenport - Deluxe King Suite 12
Interior

American Beech in Greenport - Deluxe King Suite 12

The price is CA $258
CA $395 total
includes taxes & fees
Jan 2 - Jan 3, 2025
American Beech in Greenport - Deluxe King Suite 12
American Beech - Deluxe King Suite 14
Interior

American Beech - Deluxe King Suite 14

10.0 out of 10, Exceptional, (2)
"Right in the heart of Greenport Villiage "
The price is CA $287
CA $432 total
includes taxes & fees
Jan 2 - Jan 3, 2025
American Beech - Deluxe King Suite 14
New and Modern Bridgehampton Accommodations
Outdoor pool, a heated pool

New and Modern Bridgehampton Accommodations

2.0 star property
10.0 out of 10, Exceptional, (8)
"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 CA $281
CA $578 total
includes taxes & fees
Jan 5 - Jan 6, 2025
New and Modern Bridgehampton Accommodations
The North Fork Loft
Interior

The North Fork Loft

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

Aqua by American Beech - Deluxe with 2 Queen

Aqua by American Beech - Deluxe with 2 Queen
Aqua by American Beech - Superior with 2 Queens
Outdoor dining

Aqua by American Beech - Superior with 2 Queens

Aqua by American Beech - Superior with 2 Queens
Victorian Seasons Stirling
Romantic House, 4 Bedrooms, Kitchen, Garden View | Terrace/patio

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.
Don't see what you're looking for?
See all available properties in Southold
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Other property types in Southold

Windward Shores Ocean Resort
View from property

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 CA $182
CA $239 total
includes taxes & fees
Jan 8 - Jan 9, 2025
Windward Shores Ocean Resort
Cliffside Resort Condominiums
Beach nearby

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
Outdoor pool

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.