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

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The best holiday rentals in Southampton

Check out our pick of great holiday rentals in Southampton

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Harpoon House

Southampton

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 Southampton)

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, 107 reviews
Price from
US$935
1 night, 2 adults
Check availability

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

Southold (Near Southampton)

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

The Huntting Inn

East Hampton (Near Southampton)

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

The Baker House 1650

East Hampton (Near Southampton)

Boasting a seasonal outdoor pool, a sauna and spa facilities, The Baker House 1650 is situated in East Hampton, 2.2 km from Wiborg Beach and 14 km from Montauk Point Lighthouse.

C
Caspar
From
United Kingdom
Beautiful setting with lovely older style decor. Gorgeous gardens with several heated pools and lovely areas in which to relax.
Scored out of 10, guest rating 8.7
Fabulous - What previous guests thought, 36 reviews
Price from
US$305
1 night, 2 adults
Check availability

Cowgirl Palace

Sag Harbor (Near Southampton)

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

ZEY HOTEL

Greenport (Near Southampton)

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, 257 reviews
Price from
US$400
1 night, 2 adults
Check availability

The Cliffside Resort Condominiums

Greenport (Near Southampton)

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, 249 reviews
Price from
US$223.88
1 night, 2 adults
Check availability

The 1708 House

Southampton

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.

A
Angelina
From
Malaysia
Location is perfect as it is nestled along the main street. We could walk to most places easily. We took the LIRR and took an Uber to 1708; we got Ubers almost immediately. The property is extremely charming and so lovely; it is like stepping back in time. It is a wonderful place to take a break after the hustle and bustle of NYC. We stayed in the cottage and were very happy with the amenities within it. Breakfast is amazing; John is so cheerful and friendly and his food is incredible! Great start to our days. The kitchen is also open to guests so we were able to get drinks and snacks even after hours. That is a great convenience to us as well. I would highly recommend 1708 to anyone visiting Southampton for the first time.
Scored out of 10, guest rating 9.7
Exceptional - What previous guests thought, 166 reviews
Check availability

Sweet Dreams Bed and Breakfast Cutchogue

Cutchogue (Near Southampton)

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 9.8
Exceptional - What previous guests thought, 9 reviews
Check availability
All holiday rentals in Southampton

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

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Highly rated holiday rentals in Southampton and nearby

  • Scored out of 10, guest rating 9.7
    Exceptional - What previous guests thought, 107 reviews

    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.

Enjoy breakfast in Southampton and nearby

  • Boasting air-conditioned accommodation with a private pool, pool view and a balcony, Villa Noyaan - Luxury with pool is situated in Southampton.

  • Located in Southampton, 1.6 km from Flying Point Beach and 32 km from Montauk Point Lighthouse, Villa Qadus - Luxury with pool provides spacious air-conditioned accommodation with a balcony and free...

  • Villa Emery

    Water Mill
    Breakfast options

    Located in Water Mill and only 32 km from Montauk Point Lighthouse, Villa Emery provides accommodation with sea views, free WiFi and free private parking.

  • Villa Gavin

    Southampton
    Breakfast options

    Featuring air-conditioned accommodation with a private pool, Villa Gavin is located in Southampton. This property offers access to a terrace, free private parking and free WiFi.

  • Villa Lalam

    Southampton
    Breakfast options

    Located in Southampton, Villa Lalam provides accommodation with an outdoor pool, a garden and a terrace.

  • Villa Skylar

    Southampton
    Breakfast options
    Scored out of 10, guest rating 10.0
    Exceptional - What previous guests thought, 1 review

    Featuring air-conditioned accommodation with a patio, Villa Skylar is located in Southampton. This villa features a private pool, a garden, barbecue facilities, free WiFi and free private parking.

  • Set in Water Mill, Villa Xmart - Luxury with pool offers accommodation with private pool, free WiFi and free private parking for guests who drive.

  • Villa Perlman

    Southampton
    Breakfast options

    Located in Southampton, Villa Perlman provides accommodation with a pool with a view, a patio and garden views.

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

  • Villa Burak - Luxury with pool

    Bridgehampton
    Free cancellation options available

    Featuring air-conditioned accommodation with a private pool, Villa Burak - Luxury with pool is located in Bridgehampton.

  • Villa Victoria - Cozy Hamptons Villa

    Bridgehampton
    Free cancellation options available

    Located in Bridgehampton, Villa Victoria - Cozy Hamptons Villa provides accommodation with private pool, free WiFi and free private parking for guests who drive. A hot tub is available for guests.

  • Hamptons Hideaway

    Hampton Bays
    Free cancellation options available

    Featuring air-conditioned accommodation with a private pool, Hamptons Hideaway is located in Hampton Bays. The property is non-smoking and is set 2.6 km from Meschutt Beach.

  • Villa Zainip - Luxury with pool

    Sag Harbor
    Free cancellation options available

    Set in Sag Harbor, Villa Zainip - Luxury with pool offers accommodation with private pool, free WiFi and free private parking for guests who drive.

FAQ about holiday rentals in Southampton

Holiday rentals that guests love in Southampton

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  • Harpoon House

    Holiday Rental in Southampton
    Avg. price/night: US$411.17
    Scored out of 10, guest rating 7.2
    Good - What previous guests thought, 41 reviews
    Located right in the downtown of Southampton village great walking to town without driving.
    Guest review by
    John
    Young couple

  • The 1708 House

    Holiday Rental in Southampton
    Avg. price/night: US$404.34
    Scored out of 10, guest rating 9.7
    Exceptional - What previous guests thought, 166 reviews
    we travelled there in winter, such a cosy atmosphere! we were welcomed by Liz who showed us around and told us about the story of the B&B. Southampton is also a cute little village where you can stroll around and even walk to the beach (20min). highly recommend this place!
    Guest review by
    Aurélie
    Family with young children

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