Town of Southampton Holiday Rentals

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Our top choices for Town of Southampton holiday rentals

Immaculate Waterfront 2 bedroom!

Immaculate Waterfront 2 bedroom!
Hampton Bays
10.0 out of 10, Exceptional, (5 reviews)
"Clean and fully updated home situated on a canal with a partial view of the bay . A perfect location ."
United States
Michael L.
The price is HK$2,542
HK$4,933 total
includes taxes & fees
5 Mar - 6 Mar
Immaculate Waterfront 2 bedroom!

Entire House in Southampton Village, Pool, 2 Fireplaces, Walk Everywhere, Pets!

Entire House in Southampton Village, Pool, 2 Fireplaces, Walk Everywhere, Pets!
Southampton
9.2 out of 10, Wonderful, (11 reviews)
"Great location. Great host. Easy house, pool and private back yard. It's modest but has it all."
United States
Harry V.
The price is HK$4,049
HK$8,245 total
includes taxes & fees
17 Mar - 18 Mar
Entire House in Southampton Village, Pool, 2 Fireplaces, Walk Everywhere, Pets!

Minutes from the beach, brand new 4 bedroom

Minutes from the beach, brand new 4 bedroom
Southampton
10.0 out of 10, Exceptional, (3 reviews)
"perfect for families"
United States
Okito H.
The price is HK$3,520
HK$8,677 total
includes taxes & fees
5 Mar - 6 Mar
Minutes from the beach, brand new 4 bedroom

Hamptons apartment getaway

Hamptons apartment getaway
East Quogue
6.0 out of 10, (3 reviews)
"The room was a lot more spacious than I anticipated and everything was very clean. There was some music playing upstairs but it was quiet by nighttime. Check in and check out was very straightforward. Turning into the driveway was a bit difficult when the highway was crowded but was otherwise easy to find "
United States
Hilary K.
The price is HK$1,173
HK$2,243 total
includes taxes & fees
29 Mar - 30 Mar
Hamptons apartment getaway

Cozy Hamptons Escape 3BR Minutes From Beach!

Cozy Hamptons Escape 3BR Minutes From Beach!
Hampton Bays
9.2 out of 10, Wonderful, (5 reviews)
"Great place. It's exactly like the listing! Would stay again!"
United States
Taylor H.
The price is HK$9,386
HK$12,251 total
includes taxes & fees
5 Mar - 6 Mar
Cozy Hamptons Escape 3BR Minutes From Beach!

NEW Luxury 7BR Southampton Estate – Salt Pool & Sauna, <10min US Open Shinnecock

NEW Luxury 7BR Southampton Estate – Salt Pool & Sauna, <10min US Open Shinnecock
Water Mill
10.0 out of 10, Exceptional, (6 reviews)
"Highly recommend everything from start to finish went smoothly and it was a great experience!!"
United States
Stephanie M.
The price is HK$21,118
HK$42,847 total
includes taxes & fees
5 Mar - 6 Mar
NEW Luxury 7BR Southampton Estate – Salt Pool & Sauna, <10min US Open Shinnecock

5 Bedrooms! 4 Min to the Beach! HEATED POOL!

5 Bedrooms! 4 Min to the Beach! HEATED POOL!
Westhampton Beach
10.0 out of 10, Exceptional, (2 reviews)
"awesome house and awesome host"
United States
Matthew M.
The price is HK$11,227
HK$17,152 total
includes taxes & fees
8 Mar - 9 Mar
5 Bedrooms! 4 Min to the Beach! HEATED POOL!

Spacious 5-bedroom house with water views and 2 houses from the bay.

Spacious 5-bedroom house with water views and 2 houses from the bay.
Sag Harbor
The price is HK$31,285
HK$50,175 total
includes taxes & fees
8 Mar - 9 Mar
Spacious 5-bedroom house with water views and 2 houses from the bay.

Sag Harbor Water View w Dock 1.5ml from town

Sag Harbor Water View w Dock 1.5ml from town
Bay Point
The price is HK$10,559
HK$17,863 total
includes taxes & fees
10 Mar - 11 Mar
Sag Harbor Water View w Dock 1.5ml from town

Floating Nest on Private River. Serene Views & Ultimate Relaxation

Floating Nest on Private River. Serene Views & Ultimate Relaxation
Old Lyme
The price is HK$1,760
HK$2,937 total
includes taxes & fees
21 Mar - 22 Mar
Floating Nest on Private River. Serene Views & Ultimate Relaxation

Montauk Manor

Montauk Manor
3.5 star property
Montauk
9.2 out of 10, Wonderful, (1,299 reviews)
"Nice pool, great restaurant "
United States
April
The price is HK$1,183
HK$1,504 total
includes taxes & fees
30 Mar - 31 Mar
Montauk Manor

Windward Shores Ocean Resort

Windward Shores Ocean Resort
3.0 star property
Napeague
8.8 out of 10, Excellent, (309 reviews)
"Quiet place, went off season, cooked all meals in the room, good home base to explore the area."
United States
Jerry
The price is HK$1,116
HK$1,488 total
includes taxes & fees
5 Mar - 6 Mar
Windward Shores Ocean Resort

The Stern at Soundview · Beach+Ocean+Sunrise

The Stern at Soundview · Beach+Ocean+Sunrise
Old Lyme
10.0 out of 10, Exceptional, (3 reviews)
"I had a great experience staying at The Stern! I enjoyed celebrating my weekend there! "
United States
Lylian
The price is HK$785
HK$1,738 total
includes taxes & fees
4 Mar - 5 Mar
The Stern at Soundview · Beach+Ocean+Sunrise

South Shore Studio in Mastic

South Shore Studio in Mastic
Mastic
10.0 out of 10, Exceptional, (3 reviews)
"Great stay! Super comfy and clean😊"
United States
ERIN
The price is HK$1,056
HK$1,743 total
includes taxes & fees
4 Mar - 5 Mar
South Shore Studio in Mastic

1-bedroom cottage with Grove Beach 🏖️ access.

1-bedroom cottage with Grove Beach 🏖️ access.
Clinton
9.6 out of 10, Exceptional, (37 reviews)
"Many local restaurants near by. Christy's for breakfast was very good. "
United States
Benjamin H.
The price is HK$626
HK$1,408 total
includes taxes & fees
11 Mar - 12 Mar
1-bedroom cottage with Grove Beach 🏖️ access.

3 Story Beach Waterview, 3 KING bed, golf putting green!

3 Story Beach Waterview, 3 KING bed, golf putting green!
Shirley
10.0 out of 10, Exceptional, (22 reviews)
"The house was beautiful and the owner was incredibly easy to work with! Will be trying to stay here every year! "
United States
Red F.
The price is HK$1,400
HK$4,772 total
includes taxes & fees
4 Mar - 5 Mar
3 Story Beach Waterview, 3 KING bed, golf putting green!

Cozy king suite with kitchen and dining area.

Cozy king suite with kitchen and dining area.
Coram
9.6 out of 10, Exceptional, (7 reviews)
"Very clean and well kept property. Easy communication with ow er/manager"
United States
Tasia P.
The price is HK$1,369
HK$2,082 total
includes taxes & fees
12 Mar - 13 Mar
Cozy king suite with kitchen and dining area.

Spacious one Bedroom Apt with private entrance

Spacious one Bedroom Apt with private entrance
Centereach
7.8 out of 10, Good, (10 reviews)
"The host was extremely attentive to any questions or needs. Excellent and immediate communication. Good, quiet location between Islip airport and Port Jefferson. The size of the unit was very adequate for two people. Bathroom was clean and adequately stocked with towels and wash cloths.The reason for 2 stars is we thought the apartment was not very clean from floor to ceiling. This apartment has huge potential to be very cute. In my option, it needs an entire over haul."
United States
Russell R.
The price is HK$880
HK$2,685 total
includes taxes & fees
11 Mar - 12 Mar
Spacious one Bedroom Apt with private entrance

Montauk Oceanside Suites

Montauk Oceanside Suites
3.0 star property
Downtown Montauk
8.6 out of 10, Excellent, (420 reviews)
"Great spot- walkable and nice accommodations! "
United States
Lesley
The price is HK$1,064
HK$1,301 total
includes taxes & fees
5 Mar - 6 Mar
Montauk Oceanside Suites

Modern Vacation home. Close to The Hamptons

Modern Vacation home. Close to The Hamptons
Shirley
10.0 out of 10, Exceptional, (4 reviews)
"5/5 I enjoyed my stay , very clean and spacious. "
United States
Quywana F.
The price is HK$1,828
HK$3,849 total
includes taxes & fees
4 Mar - 5 Mar
Modern Vacation home. Close to The Hamptons
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Town of Southampton Hotel Reviews