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

Holiday Rentals in Southampton

Find the holiday rentals that appeal to you the most

Holiday Rentals for every style

Find the right holiday rental for you in Southampton

The best holiday rentals in Southampton

Check out our pick of great holiday rentals in Southampton

Show hotels on map

Filter by:

Review score

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 9.6
Exceptional - What previous guests thought, 103 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 9.4
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.

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.

A
Alexander
From
Germany
Fantastic historical gem really close to the centre of east hampton with lovely garden and pool. Breakfast ist extraordinary Great place for a long weekend or a week of relaxation
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.

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

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, 16 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, 165 reviews
Check availability
All holiday rentals in Southampton

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

See all

Holiday Rentals with swimming pools 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...

  • 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.

  • 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.

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

  • 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.

  • 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.

  • Aria & Mare Hamptons

    Hampton Bays
    Free cancellation options available
    Scored out of 10, guest rating 9.6
    Exceptional - What previous guests thought, 103 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.

  • 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

See all

  • 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$322.30
    Scored out of 10, guest rating 9.7
    Exceptional - What previous guests thought, 165 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

Research, refine and make plans for your whole trip

Holiday Rentals in New Woodstock

Want to extend your trip or still just browsing? Try New Woodstock, also popular with our guests!

Holiday Rentals in Hampton Bays

Try another destination popular with our guests.

Hotels near Long Island MacArthur Airport

Perfect for a late arrival or early departure.

Holiday Rentals in New York

Discover another destination in the United States.

Holiday Rentals in Las Vegas

Discover another destination in the United States.

When to visit the United States

Events, prices, the weather and more.

Hotels near Mystic Seaport

Search and compare hotels close to Mystic Seaport, a popular destination just outside Southampton.

Holiday Rentals in Montauk

Find more hotels in a city close to Montauk.

Cheap holidays in Southampton

Book the best flights, stays and more – all in one place