Compare Southold Guest House Rentals
Earn Orbucks instantly: $1 Orbuck = $1 USD, good toward hotels
Save 10% or more on select hotels with Insider Prices
Book on the app to instantly earn 5% on 350,000+ hotels
Featured Guest Houses in Southold
Hampton's Vacation Inn
177 West Montauk Highway Hampton Bays NY
Guests of Hampton's Vacation Inn enjoy free WiFi in public areas, an outdoor tennis court, and a seasonal outdoor pool. A stay here includes free parking. Helpful staff is there to provide front-desk service during limited hours, as well as offer insight about the area. If you like to take your furry friend along on your adventures, this pet-friendly property offers food and water bowls. Additional amenities include express check-out, a garden, and a picnic area.
Pool
Pet friendly
House on Chase Creek
3 Locust Avenue Shelter Island Heights NY
$185 nightly
The price is $211 total per night
$211 total
Dec 1 - Dec 2
Total with taxes and fees
Guests staying at House on Chase Creek enjoy free WiFi in public areas, a terrace, and a garden. Free parking is available if you drive. The 24-hour front desk has staff standing by to help with luggage storage, and answer any questions about the accommodations.
Parking included
Free WiFi
Victorian Seasons Stirling
857 NY-25 Greenport NY
Guests of Victorian Seasons Stirling enjoy free WiFi in public areas, a meeting room, and a library. Free parking is available if you drive. Other amenities at this beach guesthouse include a terrace, laundry facilities, and a garden.
Parking included
Free WiFi
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.
Hotel Options in Southold
The Shoals Suites and Slips
61600 Main Rd Southold NY
$174 nightly
The price is $199 total per night from Dec 28 to Dec 29
$199 total
Dec 28 - Dec 29
Total with taxes and fees
9.4/10 Exceptional! (221 reviews)
Quality Inn Old Saybrook - Westbrook
100 Essex Rd Old Saybrook CT
$101 nightly
The price is $116 total per night from Dec 2 to Dec 3
$116 total
Dec 2 - Dec 3
Total with taxes and fees
7.6/10 Good! (1,009 reviews)
Sound View Greenport
58775 County Rd 48 Greenport NY
$203 nightly
The price is $232 total per night from Nov 30 to Dec 1
$232 total
Nov 30 - Dec 1
Total with taxes and fees
8.4/10 Very Good! (593 reviews)
Southold Guest Houses essential information
Accommodation | 5 Guest Houses |
|---|---|
Lowest Price | $116 |
Highest Price | $232 |
Popular accommodation | Hampton's Vacation Inn, House on Chase Creek, Victorian Seasons Stirling |