50 Best Southampton Estates on Holiday Lettings - Apartments

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268 Vacation rentals

20

Vacation home in Southampton

Hamptons / Southampton

6 12 1 night min

  • 6 bedrooms
  • Sleeps 12
  • 1 night min
  • Child friendly
  • Pet friendly
Located in Southampton, this 6 bedroom home is 8 km from Agawam Park. Southampton 6 Bed with Pool features a grand entrance, kitchen area with marble counters, stainless steel appliances and French doors with an outside seating area. The living room offers an archway w …see more

from $1,674 / night

$11,718 / week

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avg. 3 hours 8 minutes

from $1,674 / night

(9) Excellent 

28

Vacation home in Hampton Bays

Southampton / Hampton Bays

4 8 2 nights min

  • 4 bedrooms
  • Sleeps 8
  • 2 nights min
  • Beach/lakeside relaxation
  • Nearest beach 5 mi
  • Child friendly
Completely renovated 4 bedroom home on quiet street in Hampton Bays. In town location. Walk to shops and dining. 3.5 miles to Atlantic Ocean and 1.0 miles to Shinnecock Bay. Large property with lovely deck and furniture. Handicap accessible with bedroom and wet room o …see more

from $400 / night

$3,000 / week

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avg. 2 hours 44 minutes

from $400 / night

(1) Very Good 

16

Vacation home in Hampton Bays

Southampton / Hampton Bays

2 4 14 nights min

  • 2 bedrooms
  • Sleeps 4
  • 14 nights min
  • Child friendly
  • Air conditioning
  • Private garden
Swimming, beach fun, and the finest sunsets are a 5 minute stroll away at Penonic bay down the private beach access path. This charming cottage is 650 sq/ft with two bedrooms, living room, kitchen and bathroom with shower. The house sleeps four comfortably (two twin bed …see more

from $295 / night

$2,065 / week

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avg. 3 hours 13 minutes

from $295 / night

28

Southampton Vacation home rental

Hamptons / Southampton

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
***PLEASE INQUIRE FIRST (EMAIL OWNER) BEFORE INSTANT BOOKING!!.. 631 - 365 - 3828 Located east of the canal on the beautiful Peconic Bay, over 100 feet of sandy beach, walk down the shore to for food, drinks and entertainment! Beautiful, crystal clear water, 5000 sq ft …see more

from $3,300 / night

$15,900 - $19,900 / week

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avg. 1 hour 20 minutes

from $3,300 / night

27

Hampton Bays Vacation home rental

Southampton / Hampton Bays

3 12 3 nights min

  • 3 bedrooms
  • Sleeps 12
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Beautiful Hampton Bay Home Getaway -- 2500sqft, 3br (sleeps 12) - 3 full bths & 1 half bth (HUGE Master Suite), sitting rm w/fp, living rm, dining rm, eat in kitchen, billiard room & game room -- Large Backyard w LARGE in-ground heated pool, wood burning fire pit, barbe …see more

from $655 / night

$4,585 / week

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from $655 / night

(4) Excellent 

71

Vacation home in Hampton Bays

Southampton / Hampton Bays

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 11 mi
  • Swimming pool
Immaculate four bedrooms, three full baths sleeps 8-10. Full gym, pool and jacuzzi nestled away in prestigious Red Cedar Ridge. Large deck with BBQ. Fully equipped kitchen. Wi-fi internet and premium channels cable tv. Pool table, basketball and children play ground for …see more

from $800 / night

$6,000 - $6,700 / week

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from $800 / night

10

Vacation home in Southampton

Hamptons / Southampton

3 6 21 nights min

  • 3 bedrooms
  • Sleeps 6
  • 21 nights min
  • Child friendly
  • Air conditioning
  • Pet friendly
It's a 3 bedroom, 2 bath home. 2 Family room, one with a TV and one for reading and watching the sunset over Fish Cove through a large window. The master bedroom with en suite bathroom is located on one side of the house while the guest bedrooms are on the other side, …see more

from $400 / night

$2,800 / week

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from $400 / night

11

Vacation villa in Southampton

Hamptons / Southampton

6 12 14 nights min

  • 6 bedrooms
  • Sleeps 12
  • 14 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Fabulous Bay Front Villa on a private acre in Southampton close to village & Beaches. Beautiful fountain to greet you and your guests to the water front retreat with high end finishes. Vaulted ceilings, Professionally decorated and 6 Bedrooms with 4 1/2 baths with Jette …see more

from $5,500 / night

$12,000 / week

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from $5,500 / night

28

Vacation home in Southampton

Hamptons / Southampton

4 7 7 nights min

  • 4 bedrooms
  • Sleeps 7
  • 7 nights min
  • Swimming pool
  • Suitable for children age 5+
  • Air conditioning
Welcome to your private Hamptons escape! Featuring 4 bedrooms, 5 bathrooms, and enough space to comfortably sleep up to 7 guests, this immaculate Southampton vacation rental house is sure to provide the perfect spot for families or a close group of friends traveling tog …see more

from $849 / night

$5,943 - $10,500 / week

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avg. 30 minutes

from $849 / night

37

Vacation home in Southampton

Hamptons / Southampton

4 8 5 nights min

  • 4 bedrooms
  • Sleeps 8
  • 5 nights min
  • Nearest beach 2 mi
  • Swimming pool
  • Child friendly
A family place with wrap-around windows and skylights gives you the best of the Hamptons. Big beautify yard and gardens, magical garden-set pool, hot-tub and plenty of room for privacy, makes it a family dream. Backyard. 3 decks. Pool set amongst Maples and hibiscus. …see more

from $975 / night

$6,000 - $8,100 / week

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avg. 3 hours 49 minutes

from $975 / night

14

Hampton Bays Vacation home rental

Southampton / Hampton Bays

6 12 14 nights min

  • 6 bedrooms
  • Sleeps 12
  • 14 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Your own private summer resort. This house has it alll, you won't want to leave! Waterfront dock, jacuzzi, sparkling pool, multiple patios, 2 outdoor grills, and multiple balconies are key outdoor features. State of the art kitchen, large country dining room table, 2 f …see more

from $1,000 / night

$7,000 / week

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from $1,000 / night

14

Vacation private room with shared pool in Southampton

Hamptons / Southampton

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Nearest beach 12 mi
  • Swimming pool
  • Air conditioning
Newly renovated house with nice spacious rooms with comfortable new double beds. Double occupancy room /private bathroom/entrance, queen size bed newly renovated 4 bedroom-3 bathroom home in prime Southampton location. Close to bay, beach and town. Directly across the s …see more

from $200 / night

$1,400 / week

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avg. 37 minutes

from $200 / night

22

Vacation villa in Southampton

Hamptons / Southampton

3 6 30 nights min

  • 3 bedrooms
  • Sleeps 6
  • 30 nights min
  • Child friendly
  • Air conditioning
  • Pet friendly
ONE-OF-A-KIND VILLA NESTLED ALONG THE SHORE OF THE GREAT PECONIC BAY, with 180 degree views. The newly renovated and newly furnished (indoor as well as out) with all white interior consists of an open kitchen, living and dining area which lead to french doors, opening o …see more

from $893 / night

$6,250 / week

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from $893 / night

90

Home rental in Southampton with golf nearby

Hamptons / Southampton

15 30 3 nights min

  • 15 bedrooms
  • Sleeps 30
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
In Real These Are 3 Houses That Can Be Separately Rented also together. House 1 6 Bedrooms 8.5 Bathrooms 12 Sleeps Price Range $1400/N (Wknd) $2100 Damage Deposit $500 Cleaning Fee $450 House 2 Bedroom 3 Bathroom 2.5 Sleeps 6 Price Range $780/N (Wkn …see more

from $3,580 / night

$25,060 / week

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from $3,580 / night

15

Vacation cottage rental

Hamptons / Southampton

4 10 14 nights min

  • 4 bedrooms
  • Sleeps 10
  • 14 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Air conditioning
Getaway to this charming Cottage on the water with spectacular views!! 3 Bedrooms & Baths in the main house with a separate guest cottage with Bedroom, Kitchen & Bathroom. Heated water front Gunite Pool, Hot Tub, Dock plus Kayaks & Bikes. Close to the village of Sout …see more

from $4,500 / night

$10,500 / week

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from $4,500 / night

34

Apartment rental in Hampton Bays

Southampton / Hampton Bays

2 6 2 nights min

  • 2 bedrooms
  • Sleeps 6
  • 2 nights min
  • Beach/lakeside relaxation
  • Nearest beach 5 mi
  • Ask about children
WaterFront Walkout is the Ground Floor of Stunning Private Legal 2 Family with 1500 Sq. Feet, Roomy Open Floor Plan, Laundry Room, AC, Heat & Water Views Galore. The Upper Unit is never Rented and for Owner's Exclusive Use Only. It is Available For Short Stays Year Ro …see more

from $350 / night

$2,500 - $3,900 / week

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from $350 / night

17

Hampton Bays Vacation home rental

Southampton / Hampton Bays

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 2 mi
  • Child friendly
Sunny & Peaceful home within walking distance to the bay and a 15 min bicycle ride to the ocean. With an outdoor fireplace, outdoor shower and spacious backyard the day doesn't have to end. Master bedroom has a queen bed, daybed, and en-suite bathroom. The second bedr …see more

from $650 / night

$3,500 / week

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from $650 / night

15

Southampton Vacation home rental

Hamptons / Southampton

4 8 2 nights min

  • 4 bedrooms
  • Sleeps 8
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Hilltop Hideaway in Southampton, this lovely turn of the century house was recently renovated and appointed with new high end chic furnishings. Spacious 4 bedroom, 3 bathrooms. Central air conditioning throughout. Large living room with fireplace, stainless steel and gr …see more

from $1,200 / night

$8,400 / week

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from $1,200 / night

17

Home rental in Hampton Bays

Southampton / Hampton Bays

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Child friendly
  • Air conditioning
  • Private garden
My wife and I have a quaint country/beach house with new furniture and a fresh coat of paint. We have furnished our home with our love for the ocean and the country. Terra cotta tiles and farm style kitchen table with bench and chairs in the kitchen. Living room w …see more

from $286 / night

$2,000 / week

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from $286 / night

29

Vacation home in Hampton Bays

Southampton / Hampton Bays

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly
Family 2+ children or group adults over 27 years inquire for availability w your specific details.Min 2 nights Jun & Sep, min. 3 nights US Open,Memorial D & July 8-Labor D, min. 4 nights July 4th. No pets & check-in out SAT for short rentals price based 2 guests/bedro …see more

from $679 / night

$3,900 - $7,100 / week

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avg. 3 hours 58 minutes

from $679 / night

24

Southampton Vacation home rental

Hamptons / Southampton

3 6 6 nights min

  • 3 bedrooms
  • Sleeps 6
  • 6 nights min
  • Child friendly
  • Air conditioning
  • Pet friendly
Pack your bags for an unforgettable East Coast escape at this 3-bedroom, 2.5-bathroom Southampton vacation rental house. Boasting 2,500 square-feet of luxurious living space, this home offers sleeping accommodations for up to 6 guests, a covered front porch and a spacio …see more

from $399 / night

$2,793 - $4,749 / week

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avg. 21 minutes

from $399 / night

28

Southampton Vacation home rental

Hamptons / Southampton

6 12 3 nights min

  • 6 bedrooms
  • Sleeps 12
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Newly build home, no expense spared. Beautiful pool and outdoor dining and cooking/BBQ area. The prefect home for entertaining and relaxing. Fully equipped kitchen for cooking and dining, plenty of space for entertaining. Master bedroom is fit for royalty, 4 more beauti …see more

from $2,500 / night

$17,500 / week

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avg. 3 hours 41 minutes

from $2,500 / night

(3) Excellent 

25

Home rental in Hampton Bays with swimming pool

Southampton / Hampton Bays

4 9 Min stay varies

  • 4 bedrooms
  • Sleeps 9
  • Min stay varies
  • Nearest beach 3 mi
  • Swimming pool
  • Child friendly
Summer house that has it all! This 4 BR/3 Bath newly updated property, sits on a 1/2 acre lot with a newly lined in-ground pool with Trex decking surround and features an open concept main living space, entertainment space, high end finishes and tons of privacy. Local R …see more

from $650 / night

$3,500 - $4,200 / week

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avg. 2 hours 41 minutes

from $650 / night

33

Vacation home rental

Southampton / Hampton Bays

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 3 mi
  • Child friendly
Waterview Hampton home located in sought after Shinnecock Hills. 900 ft from Shinnecock bay with mooring rights. Which means you can basically keep your boat in your backyard of Shinnecock bay. 5min from Southampton village and ocean beaches. 5 star restaurants within w …see more

from $469 / night

$3,283 / week

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from $469 / night

11

Vacation cottage rental

Hamptons / Southampton

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Child friendly
Enjoy the best of both worlds! Wake up and take your kayak or stand up paddle board across the street and out in the beautiful N. Sea Harbor & then head into nearby Southampton village for a nice relaxing lunch. Finish the day by soaking in the hot tub with a glass of w …see more

from $400 / night

$2,800 / week

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from $400 / night

16

Home rental in Southampton

Hamptons / Southampton

5 12 14 nights min

  • 5 bedrooms
  • Sleeps 12
  • 14 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Newly Renovated Private Contemporary on 2 Acres of Privacy offers 5 Bedrooms 4 Bathrooms, Heated Pool, Hot Tub and All Weather Tennis Court. Bright and Airy lots of Glass & skylights with Glass doors to beautiful Bluestone patio perfect for Entertaining! Lush gardens …see more

from $1,929 / night

$13,500 / week

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from $1,929 / night

6

Vacation cottage in Southampton

Hamptons / Southampton

2 2 2 nights min

  • 2 bedrooms
  • Sleeps 2
  • 2 nights min
  • Air conditioning
  • Private garden
This private and quiet waterfront cottage is the perfect Hamptons retreat for one or two people. A short drive to the ocean beach or Main Street in the village for strolling and dining. Located near Southampton Village, the cottage is convenient for wine tasting excurs …see more

from $550 / night

$3,850 / week

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from $550 / night

101

Vacation home with swimming pool in Southampton

Hamptons / Southampton

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 1 mi
  • Swimming pool
Your best spot for the greatest game's annual championship. South of the highway and perched on a Shinnecock hill, this two story house with artist's loft is surrounded by decks. This paradise if very private. It has a gated pool and generous parking. Perfect for a fam …see more

from $1,100 / night

$7,000 - $10,000 / week

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avg. 3 hours 49 minutes

from $1,100 / night

17

Vacation home in Southampton

Hamptons / Southampton

4 9 7 nights min

  • 4 bedrooms
  • Sleeps 9
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Mint-renovated and newly decorated Southampton Village home offers a sunny living room, eat-in chef's kitchen and four bedrooms with two baths. Subzero and Wolf appliances, Waterworks fixtures, Cararra marble throughout. Enjoy the summer in our fully-fenced backyard sit …see more

from $1,500 / night

$10,500 / week

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from $1,500 / night

23

Vacation home in Hampton Bays

Southampton / Hampton Bays

4 8 3 nights min

  • 4 bedrooms
  • Sleeps 8
  • 3 nights min
  • Child friendly
  • Air conditioning
  • Ask about pets
Waterfront Home on Shinnecock Bay, on one of the nicest private streets in Hampton Bays, you will have use of the 2 kayaks on the bay, beautiful sunsets, and a mile away from the ocean beaches on Dune Road. We are about 2 miles from town. Great little cafe/market wal …see more

from $995 / night

$5,900 / week

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avg. 1 hour 22 minutes

from $995 / night

19

Vacation villa in Southampton

Hamptons / Southampton

4 9 Min stay varies

  • 4 bedrooms
  • Sleeps 9
  • Min stay varies
  • Ask about children
  • Ask about pets
Please note: Posted rates are for weekend bookings only. For weekday rates, contact a Villa Specialist.   The quintessential Infamous Hamptons showcases the posh, yet understated style characteristic to this legendary holiday destination. In an area of New York renown …see more

from $1,250 / night

$8,750 / week

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avg. 2 minutes

from $1,250 / night

18

Vacation home in Southampton

Hamptons / Southampton

4 8 14 nights min

  • 4 bedrooms
  • Sleeps 8
  • 14 nights min
  • Beach/lakeside relaxation
  • Air conditioning
  • Private garden
THIS SOUTHAMPTON HOME OFFERS PRIVACY, LUXURY ,SERENITY AND IS EXQUISITELY DECORATED ,THIS RENTAL HAS EVERYTHING ONE WOULD ASK FOR AS THE OWNER.I LIVE THERE PART TIME AS WELL AND HAVE GIVEN THE UTMOST ATTENTION TO EVERY DETAIL IN THE HOUSE FOR ONES COMFORTS THIS HOUSE …see more

from $1,786 / night

$12,500 / week

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from $1,786 / night

(2) Excellent 

32

Vacation home rental

Hamptons / Southampton

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Experience the exquisite relaxation of upper Long Island, New York by staying at this luxurious 4-bedroom, 4-bathroom Southampton vacation rental home, which sleeps 8! With incredible upscale amenities, an alluring private pool, wraparound deck with bay views, exclusive …see more

from $749 / night

$5,243 - $11,900 / week

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avg. 8 minutes

from $749 / night

7

Home rental in Southampton

Hamptons / Southampton

5 16 7 nights min

  • 5 bedrooms
  • Sleeps 16
  • 7 nights min
  • Suitable for children age 5+
  • Air conditioning
  • Ask about pets
You can rent this weekly, bi-weekly or full summer season. Summer 2015 weekly rentals start at $7000/week for any weeks in June, $8750/week for any weeks in July and $9200/week for any weeks in August. You can rent for as little as a week in the summer season or monthly …see more

from $1,286 / night

$9,000 / week

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from $1,286 / night

20

Southampton Vacation home rental

Hamptons / Southampton

10 22 Min stay varies

  • 10 bedrooms
  • Sleeps 22
  • Min stay varies
  • Child friendly
  • Pet friendly
This estate features the most exquisite blend of old world charm and new. Originally dating back to the year 1882, this fabulous farmhouse underwent a meticulous renovation and expansion. The end result : A luxurious 7 Bedroom, 6.5 bath Main house, and 3 Bedroom, 2 Bath …see more

from $2,950 / night

$20,650 / week

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avg. 3 hours 32 minutes

from $2,950 / night

27

Vacation home in Southampton

Hamptons / Southampton

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly
  • Air conditioning
Plan your next Hamptons family vacation at this modern 3-bedroom, 2-bathroom vacation rental house within walking distance of the Smithtown Bay! This spacious 1,700-square-foot farmhouse offers 8 lucky guests a beautifully furnished interior with whitewashed wood beams, …see more

from $380 / night

$2,660 - $5,705 / week

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avg. 21 minutes

from $380 / night

46

Vacation home in Hampton Bays

Southampton / Hampton Bays

4 10 14 nights min

  • 4 bedrooms
  • Sleeps 10
  • 14 nights min
  • Swimming pool
  • Ask about children
  • Car not necessary
Large swimming pool (43' x 22' free form) with changing colors LED lights and water fall, a 10 people outdoor spa jacuzzi tub. Complete and well equipped outdoor kitchen, walking distance to the bay and 5 minutes drive to town or the OCEAN. Big and clean house in the w …see more

from $685 / night

$4,795 / week

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from $685 / night

24

Vacation cottage in Southampton

Hamptons / Southampton

3 8 3 nights min

  • 3 bedrooms
  • Sleeps 8
  • 3 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
This 3 bedroom waterfront cottage is a perfect family getaway. Located in a small beach community between Southampton and Sag Harbor, it is surrounded by water - from the dining room you look right out onto a serene lake, from the first floor you can see both lake and t …see more

from $945 / night

$6,615 / week

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avg. 2 hours 9 minutes

from $945 / night

(6) Excellent 

20

Vacation home rental

Hamptons / Southampton

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 12 mi
  • Swimming pool
  • Ask about children
This well-appointed and maintained 2,200 sq.ft., 4 bedroom, 3 bath Contemporary has a bright sunlit breakfast area directly off the gourmet kitchen, Situated on a sprawling manicured acre with a 20x40 sparkling swimming pool and directly across the street from the fasci …see more

from $650 / night

$4,500 - $7,000 / week

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avg. 37 minutes

from $650 / night

24

Vacation townhouse in Southampton

Hamptons / Southampton

4 8 30 nights min

  • 4 bedrooms
  • Sleeps 8
  • 30 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Bishops Pond is a new high-end condo development in Southampton Village. The clubhouse offers a pool, fitness center, billiards, outdoor tennis court, and more. This beautiful and comfortable second floor level home located on the far south east corner of the developme …see more

from $184 / night

$1,284 / week

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from $184 / night