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

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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.

I
Ivano
From
Italy
Super clean and very well curated! Karen is magic and makes you feel like being home. Fantastic, we’ll come back for sure!
Scored out of 10, guest rating 9.6
Exceptional - What previous guests thought, 101 reviews
Price from
US$935
1 night, 2 adults
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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 9.4
Superb - What previous guests thought, 6 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.

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
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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
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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, 14 reviews
Price from
US$300
1 night, 2 adults
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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.

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
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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 8.9
Fabulous - What previous guests thought, 249 reviews
Price from
US$223.88
1 night, 2 adults
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House on Chase Creek

Shelter Island Heights (Near Southampton)

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, 15 reviews
Price from
US$106.80
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.

M
Michel
From
Netherlands
It’s the perfect location to wind down after long flight. Beautiful location, great room, brilliant staff. But that doesn’t do it justice. To feel at home to just help yourself to a glass of wine in the afternoon, the attention of the staff, John cooking you the perfect breakfast (but eggs Benedict 😄)… it’s the total lack of pretence which makes it great. I stay in way to many hotels per year for work but this is the only one which stood out in the last year. Just Awesome
Scored out of 10, guest rating 9.7
Exceptional - What previous guests thought, 166 reviews
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Most booked holiday rentals in Southampton and surroundings in the past month

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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
    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.

Highly rated holiday rentals in Southampton and nearby

  • Scored out of 10, guest rating 9.6
    Exceptional - What previous guests thought, 101 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.

Holiday Rentals with swimming pools in Southampton and nearby

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

  • 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.

  • 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.

  • 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$345.74
    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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