The 10 best holiday rentals in Southold, USA | Booking.com
Skip to main content

Holiday Rentals in Southold

Find the holiday rentals that appeal to you the most

Holiday Rentals for every style

Find the right holiday rental for you in Southold

The best holiday rentals in Southold

Check out our pick of great holiday rentals in Southold

Show hotels on map

Filter by:

Review score

Vine & Sand--Southold NY's Newest B&B

Southold

33 km from Splish Splash, Vine & Sand--Southold NY's Newest B&B is a recently renovated property located in Southold and provides air-conditioned rooms with free WiFi and private parking.

Scored out of 10, guest rating 9.4
Superb - What previous guests thought, 6 reviews
Price from
US$355.35
1 night, 2 adults
Check availability

ZEY HOTEL

Greenport (Near Southold)

Set in Greenport, within 42 km of Splish Splash, ZEY HOTEL is an accommodation offering garden views. This bed and breakfast offers free private parking and full-day security.

L
Linda
From
United Kingdom
OMG Mia was fantastic from check in to check out. Nothing was too much trouble, she was the perfect host and whatever she is paid - isn’t enough!! She went above and beyond and made us feel so welcome it was exceptional. Room was superb, so many chill out spaces were a brilliant asset to comfortably sit and read our books due to rainy/cloudy weather. The location is like Mia, second to none!! Some reviews suggest it being dated - I think they themselves are the ones who are dated, as the place is designed and styled to be retro, quirky, individual and stylish, it’s a shame this unique property isn’t given the applause it deserves.
Scored out of 10, guest rating 8.7
Fabulous - What previous guests thought, 260 reviews
Price from
US$400
1 night, 2 adults
Check availability

The Cliffside Resort Condominiums

Greenport (Near Southold)

With beautiful views of the sunsets over Long Island Sound, this Greenport resort features spacious grounds and a private beach. Free Wi-Fi is available in all areas.

A
Alyson
From
United Kingdom
We were only here for one night and the weather was terrible so we didn’t go outdoors to explore as we had planned.
Scored out of 10, guest rating 8.9
Fabulous - What previous guests thought, 251 reviews
Price from
US$223.88
1 night, 2 adults
Check availability

House on Chase Creek

Shelter Island Heights (Near Southold)

Offering garden views, House on Chase Creek in Shelter Island Heights provides accommodation and a terrace.

R
Ralphoo
From
Finland
Stay here, you won't regret it! Beautiful old creaky house oozing charm and history, cosy dark wood abounds, a snug conservatory to play games in, a veranda with a swing, and out front chairs and a hammock on the waters edge. Great host, great house, great stay.
Scored out of 10, guest rating 8.1
Very good - What previous guests thought, 16 reviews
Price from
US$106.80
1 night, 2 adults
Check availability

Cowgirl Palace

Sag Harbor (Near Southold)

Boasting a hot tub, Cowgirl Palace is situated in Sag Harbor. With quiet street views, this accommodation provides a patio and a swimming pool.

J
Jean
From
United States
The atmosphere is very relaxing and quiet. The bed is so comfortable that it's hard to get up! The distance to Sag Harbor is less than 5 minutes so it's very convenient. All in all I give it a 10
Scored out of 10, guest rating 5.9
Passable - What previous guests thought, 15 reviews
Price from
US$300
1 night, 2 adults
Check availability

Harpoon House

Southampton (Near Southold)

Situated within 2.4 km of Gin Beach and 34 km of Montauk Point Lighthouse in Southampton, Harpoon House features accommodation with seating area.

K
Kenia
From
United States
Space and comfortable, clean and very comfortable
Scored out of 10, guest rating 7.2
Good - What previous guests thought, 41 reviews
Price from
US$359.10
1 night, 2 adults
Check availability

Aria & Mare Hamptons

Hampton Bays (Near Southold)

Set in Hampton Bays in the New York region with Meschutt Beach nearby, Aria & Mare Hamptons offers accommodation with free private parking, as well as access to a hot tub.

A
Alexis
From
Switzerland
We had a great time, the new owners are just amazing and me and my daughter had a great time. Go for it!
Scored out of 10, guest rating 9.6
Exceptional - What previous guests thought, 103 reviews
Price from
US$935
1 night, 2 adults
Check availability

Westbrook Inn Bed and Breakfast

Westbrook (Near Southold)

Situated in Westbrook, 25 km from Goodspeed Opera House, Westbrook Inn Bed and Breakfast features air-conditioned rooms with free WiFi and express check-in and check-out.

C
Codrin
From
France
Wonderful owner, gorgeous proprety, clean room and comfortable sheets and bed. Also, a great delicious breakfast. Strongly recommend.
Scored out of 10, guest rating 9.1
Superb - What previous guests thought, 32 reviews
Price from
US$205.85
1 night, 2 adults
Check availability

The Huntting Inn

East Hampton (Near Southold)

Offering a bar and garden view, The Huntting Inn is located in East Hampton, 2.5 km from Wiborg Beach and 13 km from Montauk Point Lighthouse.

J
Judith
From
United Kingdom
Breakfast was fantastic. A huge bowl of fruit, natural yoghurt (hard to come by in American hotels we found) and nice juices
Scored out of 10, guest rating 9.1
Superb - What previous guests thought, 18 reviews
Price from
US$575
1 night, 2 adults
Check availability

East Hampton Art House Bed and Breakfast

East Hampton (Near Southold)

Offering garden views, East Hampton Art House Bed and Breakfast in East Hampton offers accommodation, a private beach area, a seasonal outdoor swimming pool, a fitness centre, an indoor pool and an...

M
Melanie
From
Australia
The hosts are true artists with their beautiful artwork spread across the property. They are great hosts, very friendly and accommodating. Very relaxed vibe. Amazing home and gardens! I felt like a queen being there. Lovely breakfast with a lot of options to choose from.
Scored out of 10, guest rating 9.7
Exceptional - What previous guests thought, 17 reviews
Price from
US$422
1 night, 2 adults
Check availability
All holiday rentals in Southold

Most booked holiday rentals in Southold and surroundings in the past month

See all

These holiday rentals in Southold and nearby have options with free cancellation

  • Scored out of 10, guest rating 9.8
    Exceptional - What previous guests thought, 72 reviews

    Just 450 metres to the beach, this bed and breakfast is located in Shelter Island Heights. A free breakfast is served each morning.

  • Modern on 9th

    Greenport
    Free cancellation options available

    Featuring air-conditioned accommodation with a patio, Modern on 9th is located in Greenport. The holiday home is 41 km from Splish Splash. The property has a restaurant with an outdoor dining area.

  • West Neck Guesthouse

    Shelter Island Heights
    Free cancellation options available
    Scored out of 10, guest rating 7.8
    Good - What previous guests thought, 21 reviews

    Situated in Shelter Island Heights, West Neck Guesthouse features free bikes and garden. This guest house features free private parking and a housekeeping service. The guest house has family rooms.

  • The Endless Summer Cottage

    Cutchogue
    Free cancellation options available
    Scored out of 10, guest rating 10.0
    Exceptional - What previous guests thought, 1 review

    Featuring air-conditioned accommodation with a patio, The Endless Summer Cottage is located in Cutchogue. The property is non-smoking and is set 2.9 km from Fleet Neck Beach.

  • Cozy Greenport Cottage

    Greenport
    Free cancellation options available
    Scored out of 10, guest rating 9.0
    Superb - What previous guests thought, 1 review

    Featuring a sauna, Cozy Greenport Cottage is set in Greenport. Guests can benefit from a patio and an outdoor fireplace. The property is non-smoking and is located 41 km from Splish Splash.

  • Harbor Knoll Bed and Breakfast

    Greenport
    Free cancellation options available
    Scored out of 10, guest rating 9.8
    Exceptional - What previous guests thought, 17 reviews

    Featuring pool views, Harbor Knoll Bed and Breakfast provides accommodation with a private beach area, a seasonal outdoor swimming pool and a garden, around 42 km from Splish Splash.

  • Set in Cutchogue, 700 metres from Fisherman Beach and 33 km from Splish Splash, Walk to Beach Long Island Wine Country Home! offers a garden and air conditioning.

  • Charming Greenport Gem 1, 1 Mile to Ferry!

    Greenport
    Free cancellation options available
    Scored out of 10, guest rating 9.8
    Exceptional - What previous guests thought, 4 reviews

    Situated in Greenport, within 27 km of Long Island Railroad, Charming Greenport Gem 1, 1 Mile to Ferry! offers accommodation with air conditioning.

Enjoy breakfast in Southold and nearby

  • Scored out of 10, guest rating 9.8
    Exceptional - What previous guests thought, 14 reviews

    Located in Greenport in the New York region, Bright Apartment - half Mi to Greenport Harbor! has a patio. Providing free WiFi throughout the property, the non-smoking apartment features a spa centre.

  • Scored out of 10, guest rating 10.0
    Exceptional - What previous guests thought, 3 reviews

    Situated in Greenport in the New York region, Quaint DT Greenport Apt - 2 Mi to Shelter Island! features a patio.

  • Scored out of 10, guest rating 9.8
    Exceptional - What previous guests thought, 20 reviews

    Featuring a garden and views of garden, The Stirling House Waterfront Inn Greenport is a bed and breakfast situated in a historic building in Greenport, 42 km from Splish Splash.

  • Scored out of 10, guest rating 9.8
    Exceptional - What previous guests thought, 9 reviews

    Situated in Cutchogue, 25 km from Splish Splash, Sweet Dreams Bed and Breakfast Cutchogue features accommodation with air conditioning and access to a garden.

  • Boasting air-conditioned accommodation with a private pool, Villa Ebrar - Luxury with pool is situated in Sag Harbor. 3 km from Foster Memorial Beach and 32 km from Montauk Point Lighthouse, the...

  • Scored out of 10, guest rating 9.2
    Superb - What previous guests thought, 13 reviews

    Situated 44 km from Splish Splash, Arbor View House Bed and Breakfast offers air-conditioned accommodation with a patio.

Highly rated holiday rentals in Southold and nearby

  • Scored out of 10, guest rating 8.9
    Fabulous - What previous guests thought, 251 reviews

    With beautiful views of the sunsets over Long Island Sound, this Greenport resort features spacious grounds and a private beach. Free Wi-Fi is available in all areas.

    From US$441.95 per night
  • Scored out of 10, guest rating 8.1
    Very good - What previous guests thought, 16 reviews

    Offering garden views, House on Chase Creek in Shelter Island Heights provides accommodation and a terrace.

    From US$247.05 per night

  • ZEY HOTEL

    Greenport
    8.0+ review score
    Scored out of 10, guest rating 8.7
    Fabulous - What previous guests thought, 260 reviews

    Set in Greenport, within 42 km of Splish Splash, ZEY HOTEL is an accommodation offering garden views. This bed and breakfast offers free private parking and full-day security.

    From US$372.13 per night

Research, refine and make plans for your whole trip

Holiday Rentals in the United States

Eager to explore more of the United States? Find hotels up and down the country!

Hotels near Long Island MacArthur Airport

Perfect for a late arrival or early departure.

Hotels near Bradley International Airport

Perfect for a late arrival or early departure.

Hotels in Southold

More great accommodation options for your trip.

When to visit the United States

Events, prices, the weather and more.

Holiday Rentals in Montauk

Find more hotels in a city close to Montauk.

Cheap holidays in Southold

Plan everything you need for your holidays in one place – from flights and stays to tours and activities

Holiday Rentals in Long Island

Extend your search and explore the surrounding area.

Holiday Rentals in New York State

Extend your search and explore the surrounding area.