The 10 best holiday rentals in Southold, USA | Booking.com
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Holiday Rentals in Southold

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The best holiday rentals in Southold

Check out our pick of great holiday rentals in Southold

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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 9.2
Superb - What previous guests thought, 5 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.

A
Anna
From
United States
Such a wonderful experience staying at Zey hotel for the weekend. A true GEM that just opened its doors on Main Street, with everything Greenpoint has to offer in close proximity. We fell completely in love with our suite. Not only did it resemble an actual apartment, but the contemporary decoration and amenities made it even more enjoyable. Clean, cozy and with our very own porch, it was hard to leave the hotel!!! Mia, the manager was AWESOME! Definitely enhanced our experience with her kindness and assertiveness. Looking forward to going back to Greenport and staying at Zey. Would recommend without a doubt!
Scored out of 10, guest rating 8.7
Fabulous - What previous guests thought, 255 reviews
Price from
US$325
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 8.8
Fabulous - What previous guests thought, 246 reviews
Price from
US$223.88
1 night, 2 adults
Check availability

The 1708 House

Southampton (Near Southold)

Offering inner courtyard views, The 1708 House is an accommodation set in Southampton, 2.2 km from Gin Beach and 34 km from Montauk Point Lighthouse.

J
Jorge
From
Canada
It was really great, the blew our expectations.
Scored out of 10, guest rating 9.7
Exceptional - What previous guests thought, 165 reviews
Price from
US$445
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 7.3
Good - What previous guests thought, 40 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.

G
Gustavo
From
United States
The experience at Aria & Mare Hamptons was outstanding. The room was clean and cozy, the owners and Trevor were really kind and helpful, and the location was just perfect to go to the nearby beach and towns. Trevor even sent us a link he prepared with recommendations of attractions and restaurants that was really helpful to decide what to do during our visit.
Scored out of 10, guest rating 9.7
Exceptional - What previous guests thought, 109 reviews
Price from
US$357.50
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, 33 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.

A
Amanpreet
From
India
The location is very good n everything is walking distance even the beaches , market , etc . Montauk is also 20 minutes drive . Also the property is very clean n the chef Paul is very attentive n understanding n can alter his dishes to ur palate. Shiela n Linda at the front disk were really helpful.
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

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Enjoy breakfast in Southold and nearby

  • Scored out of 10, guest rating 9.8
    Exceptional - What previous guests thought, 71 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
    Breakfast options

    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.

  • Scored out of 10, guest rating 7.9
    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.

  • 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.

  • 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.

  • Scored out of 10, guest rating 9.8
    Exceptional - What previous guests thought, 18 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.

  • 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.

Highly rated holiday rentals in Southold and nearby

  • Scored out of 10, guest rating 8.8
    Fabulous - What previous guests thought, 246 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

  • ZEY HOTEL

    Greenport
    8.0+ review score
    Scored out of 10, guest rating 8.7
    Fabulous - What previous guests thought, 255 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
  • 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 9.9
    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.

  • Scored out of 10, guest rating 9.2
    Superb - What previous guests thought, 14 reviews

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

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

  • 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.

  • Villa Ebrar - Luxury with pool

    Sag Harbor
    Free cancellation options available

    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...

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