50 Best Long Island Apartments on Holiday Lettings - Condos

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407 Vacation rentals

20

Vacation home in Long Island

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 $1,680 / night

$11,760 / week

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from $1,680 / night

11

Vacation home in Long Island

Hamptons / East Hampton

8 20 7 nights min

  • 8 bedrooms
  • Sleeps 20
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
A new construction estate in the exclusive Georgica Pond section of East Hampton brings the fabled tradition of Long Island country houses into the here and now. This gracefully proportioned gambrel home continues the proud lineage of East Hampton estates for the New co …see more

from $5,715 / night

$40,000 / week

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avg. 17 minutes

from $5,715 / night

19

Home rental in Long Island

Fire Island / Ocean Beach

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Private garden
This home is in a unique summer beach community on fire island in New York. The area is accessible by passenger ferry or boat. Motor vehicles are not permitted. This lovely home is a short stroll to the ocean beach. It is close to all local amenities, such as restaur …see more

from $800 / night

$5,600 / week

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from $800 / night

17

Cottage rental in Long Island

Hamptons / Sag Harbor

3 8 2 nights min

  • 3 bedrooms
  • Sleeps 8
  • 2 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
Wonderful Sag Harbor VillageWaterfront Cottage for Rent 3 bedrooms, 4 queen size beds , 1 1/2 baths, A/C, Screaming Water views, multi level Decks, Private Sand beach, with Kayaks and fire pit. All inclusive utilities, Maid service (weekly) and wonderful clear Water …see more

from $900 / night

$6,000 / week

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from $900 / night

21

Home rental in East Hampton

Hamptons / East Hampton

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Child friendly
  • Pet friendly
Green Rock is located in the Northwest Wood section of East Hampton. The property is so well situated you will probably not want to leave it. The moon rises over the water, the sun sets in the back. Turn on the landscape lighting, open a great bottle of wine and enjoy …see more

from $900 / night

$6,300 / week

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from $900 / night

14

Long Island Vacation cottage rental

Long Island / Fire Island

3 6 30 nights min

  • 3 bedrooms
  • Sleeps 6
  • 30 nights min
  • Beach/lakeside relaxation
  • Suitable for children age 5+
  • Car not necessary
Fire Island is a 35mile long barrier island located just off the South Shore of New York's Long Island. It is an island of many diverse communities. The house is located in a community called Lonelyville, one of the oldest on Fire Island. There are no cars permitted on …see more

from $658 / night

$4,600 / week

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from $658 / night

15

East Marion Vacation home rental

North Fork / East Marion

3 6 14 nights min

  • 3 bedrooms
  • Sleeps 6
  • 14 nights min
  • Air conditioning
  • Pet friendly
  • Private garden
Renovated Waterfront Cottage with private beach and spectacular views! The house sits on the edge of the bluff with views of a secluded cove on the sound and has access to an infinity deck where you can relax and enjoy the water views, the sunsets, the landscaped garden …see more

from $470 / night

$3,290 / week

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from $470 / night

18

Vacation cottage in Long Island

Hamptons / Montauk

2 4 30 nights min

  • 2 bedrooms
  • Sleeps 4
  • 30 nights min
  • Child friendly
  • Pet friendly
Two bedroom cottage with vaulted ceilings set on a double lot, last house on a dead end quiet road with a pond and a nature preserve across the road. Lots of outdoor living/dining space. Outdoor shower, gas grill, herb/flower gardens, washer/dryer. 5 minute walk to priv …see more

from $334 / night

$2,334 / week

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from $334 / night

13

Vacation home in Long Island

Hamptons / East Hampton

5 12 30 nights min

  • 5 bedrooms
  • Sleeps 12
  • 30 nights min
  • Child friendly
  • Air conditioning
  • Pet friendly
Furnished 5 bedroom 4 bathroom home on a quiet cul de sac. In-law/nanny suite with private bathroom and living room. Viking/subzero appliances with granite countertops. Spacious deck and Porch on one acre piece of property. Great house for entertaining. Air conditioning …see more

from $1,000 / night

$7,000 / week

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from $1,000 / night

21

Long Island Vacation cottage rental

Fire Island / Fair Harbor

3 6 6 nights min

  • 3 bedrooms
  • Sleeps 6
  • 6 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.1 mi
  • Child friendly
An ideal spot for a comfortable, peaceful beach vacation. Our charming, renovated cottage is located in Lonelyville, on Fire Island a short drive or train ride from New York City. If you've never visited Fire Island you're in for a treat. Close to the city yet a galaxy …see more

from $850 / night

$5,000 / week

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from $850 / night

24

Home rental in Greenport

North Fork / Greenport

3 8 3 nights min

  • 3 bedrooms
  • Sleeps 8
  • 3 nights min
  • Child friendly
  • Air conditioning
Spend your summer days in Long Island as you relax in 'Jason's Haven,' a 3-bedroom, 1-bathroom vacation rental home that sleeps 6. Nestled within the historical town of Greenport, this home provides a unique New York experience, sans big buildings and bustling sidewalks …see more

from $260 / night

$1,820 / week

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Responds fast!
avg. 37 minutes

from $260 / night

24

Vacation home rental

Long Island / Fire Island

4 12 Min stay varies

  • 4 bedrooms
  • Sleeps 12
  • Min stay varies
  • Child friendly
  • Air conditioning
Discover the hidden treasures of Fire Island from this 4-bedroom, 2-bathroom vacation rental house with sleeping accommodations for 10. The property boasts 2,200 square feet of living space, an expansive mahogany deck and breathtaking views of the Great South Bay. Only …see more

from $500 / night

$3,500 / week

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Responds fast!
avg. 37 minutes

from $500 / night

(4) Excellent 

16

Long Island Vacation apartment rental

Long Island / Huntington

1 4 1 night min

  • 1 bedroom
  • Sleeps 4
  • 1 night min
  • Swimming pool
  • Ask about children
  • Ask about pets
Ground floor of hi ranch includes large LR/kitchen combo and separate BR. Fully furnished with queen sized bed with Simmons beauty rest 12" mattress! There is also a pullout couch, new flooring, etc. You will have key to house & separate apt. to come & go as you please. …see more

from $85 / night

$550 - $900 / week

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Responds fast!
avg. 2 hours 38 minutes

from $85 / night

33

Apartment rental in Ocean Beach

Fire Island / Ocean Beach

3 8 3 nights min

  • 3 bedrooms
  • Sleeps 8
  • 3 nights min
  • Nearest beach 0.2 mi
  • Child friendly
  • Car not necessary
Ocean Beach, Fire Island, NY Summer Rental. Steps from beautiful ocean beaches, shops, restaurants, night life, ferries and all the Capital City of Fire Island has to offer. Weekly Rental Only Please. (Ocean Beach Regulation) Credit Cards, …see more

from $300 / night

$1,200 - $2,850 / week

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avg. 1 hour 29 minutes

from $300 / night

(1)  

24

Vacation home in Long Island

Hamptons / East Hampton

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Immerse yourself in all that East Hampton has to offer at this stunning 4-bedroom, 3-bathroom vacation rental house that comfortably sleeps 10. Situated on 2 acres of fenced land with a playground, lush grass, private hot tub and 50-foot pool with 10 chaise lounge chair …see more

from $560 / night

$3,920 - $22,400 / week

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avg. 37 minutes

from $560 / night

9

Vacation apartment in Long Island

Long Island / Islip

1 4 5 nights min

  • 1 bedroom
  • Sleeps 4
  • 5 nights min
  • Child friendly
  • Pet friendly
We take the hassle out of business travel. Along with all of our convenient amenities, furnished apartments and pet friendly rentals in Islip, NY, The Islip Inn offers a laundry service on hand that can pick up and return your items within 24 hours! Each room in The I …see more

from $150 / night

$1,050 / week

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from $150 / night

(9) Excellent 

18

Vacation cottage in Cutchogue

North Fork / Cutchogue

2 6 14 nights min

  • 2 bedrooms
  • Sleeps 6
  • 14 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.1 mi
  • Child friendly
Cozy Cutchogue Beach Cottage on the North Fork of Long Island. It has 2 bedrooms with queen sized beds and there is a sleeping loft appropriate for children over 9 years old (one queen sized bed and one twin). Deck and backyard with gas grill, outdoor picnic table, fi …see more

from $150 / night

$950 - $2,030 / week

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from $150 / night

13

Vacation home in Great Neck

Long Island / Great Neck

3 6 2 nights min

  • 3 bedrooms
  • Sleeps 6
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Private garden
This house is located in Great Neck, New York, in the most peaceful and quiet place in Long Island. With 3 bedrooms and 4 bathrooms this house is perfect for any one. One bedroom accommodates at least 2 people. If you need another bedroom that would be an additional cos …see more

from $125 / night

$875 / week

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Responds fast!
avg. 3 hours 14 minutes

from $125 / night

(5) Excellent 

14

Home rental in East Marion

North Fork / East Marion

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Child friendly
  • Air conditioning
  • Pet friendly
Contemporary 4 bedroom 3 bath house with private Long Island Sound beach access and community tennis and bocce courts in East Marion. Secluded lot with swing set. 2 adult bikes and 2 kids bikes, beach chairs and toys included. Cook's kitchen, large deck. 10 rooms total, …see more

from $249 / night

$1,500 - $2,900 / week

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from $249 / night

5

Apartment rental in Long Island

Fire Island / Kismet

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Car not necessary
  • Air conditioning
A slice of heaven 3 doors down from the beach. Light, airy, private and perfectly situated. Welcome to our barefoot community where there are no cars and getting around requires walking or biking. Our rental comes with everything you will need for your beach vacation …see more

from $250 / night

$1,750 - $2,100 / week

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from $250 / night

(2) Excellent 

30

Long Island Vacation home rental

Hamptons / Shelter Island

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 1 mi
  • Child friendly
  • Air conditioning
WINTER SPECIAL: Stay for long weekend or Week for $999, plus utils, taxes. Any week, except holidays. Beautifully renovated waterfront cottage from early 1800s. Marble baths, two master suites. Sweeping waterfront lawn. 100 foot dock. Swimming, boating, grill on bac …see more

from $295 / night

$1,295 - $4,999 / week

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from $295 / night

6

Villa rental in Long Island

Long Island / Remsenburg

5 9 5 nights min

  • 5 bedrooms
  • Sleeps 9
  • 5 nights min
  • Child friendly
  • Ask about pets
19th Century house on 3 acres of gardens and fields. Traditional styling has been infused with modern touches and updates. Cook's professional kitchen, central air conditioning, jacuzzi, steam shower, heated swimming pool, internet and multi-room music system. Close …see more

from $1,300 / night

$7,950 / week

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avg. 46 minutes

from $1,300 / night

(1) Very Good 

16

Vacation home in Long Island

Fire Island / Fair Harbor

4 7 3 nights min

  • 4 bedrooms
  • Sleeps 7
  • 3 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.16 mi
  • Child friendly
Fair Harbor is on Fire Island in Suffolk county ny.. Imagine a barefoot community with wooden walkways great sandy beaches, great sunsets, wooden walkways... no cars... Sounds like paradise.. less than 2 hours from New york.. so close yet so far away. Our house is 1 …see more

from $750 / night

$3,800 / week

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from $750 / night

(2) Excellent 

7

Vacation home in Long Island

Hamptons / East Hampton

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Suitable for children age 5+
Enjoy this sophisticated, newly renovated, three-bedroom, three-bath contemporary on one of the premier lanes near Jackson Pollack's house in East Hampton. Twenty-four-hundred square feet with oak flooring throughout. Great light in the beautifully designer decorated d …see more

from $370 / night

$750 - $5,900 / week

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from $370 / night

(4) Excellent 

15

Vacation cottage in Sag Harbor

Hamptons / Sag Harbor

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Beach/lakeside relaxation
  • Nearest beach 3 mi
  • Swimming pool
Beech Tree Cottage is a charming two-bedroom, one-bath guest cottage conveniently located in the historic district of Sag Harbor, NY - a 5-minute walk along the waterfront to Main Street and the center of the village. The beach is a short drive or bike ride away. The ow …see more

from $500 / night

$3,500 / week

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Responds fast!
avg. 2 hours 56 minutes

from $500 / night

29

Vacation home in Long Island

Hamptons / Sag Harbor

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly
  • Air conditioning
The New York coast awaits at this Sag Harbor 4-bedroom, 3-bathroom vacation rental house with additional sleeping arrangements with 2 sofa beds in the den - the perfect destination for up to 10 guests! This home boasts one of the best locations with walking access to pr …see more

from $850 / night

$5,950 / week

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Responds fast!
avg. 37 minutes

from $850 / night

28

Vacation home in Long Island

Hamptons / Sag Harbor

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Designed to impress, ‘Sag Summer’ is a beautiful 4-bedroom, 3.5-bathroom vacation rental house that will serve as your next ideal retreat in Sag Harbor. This modern farmhouse-inspired home sleeps up to 8 travelers and boasts 2 master bedrooms and a custom sports pool. D …see more

from $525 / night

$3,675 / week

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Responds fast!
avg. 37 minutes

from $525 / night

(9) Excellent 

28

Vacation home in Long Island

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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Responds fast!
avg. 2 hours 36 minutes

from $400 / night

(3) Very Good 

9

Vacation apartment in Bellmore

Long Island / Bellmore

1 4 2 nights min

  • 1 bedroom
  • Sleeps 4
  • 2 nights min
  • Beach/lakeside relaxation
  • Nearest beach 10 mi
  • Ask about children
Enjoy Long Island's pristine beaches, listen to an outdoor waterfront concert at Nikon theater venue,or relax in the back yard of this decorator furnished one bedroom/one full bath apartment situated on a canal. Spectacular sunsets. 45 min by train to NYC and 30 min fro …see more

from $150 / night

$875 / week

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Responds fast!
avg. 47 minutes

from $150 / night

(5) Good 

14

Vacation home with golf nearby in Long Island

Long Island / Baiting Hollow

2 4 4 nights min

  • 2 bedrooms
  • Sleeps 4
  • 4 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.2 mi
  • Child friendly
Charming cottage in the woods just steps from the peaceful Long Island Sound. This cottage has two bedrooms and sleeps 4. One of the twin beds is on a our porch in a common area but it is indoors. See photo. New Kitchen counters and cabinets. Built in 1950, this cottage …see more

from $175 / night

$1,050 / week

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Responds fast!
avg. 27 minutes

from $175 / night

(3) Excellent 

19

Vacation home in Long Island

Long Island / Westhampton Beach

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Child friendly
Located on the bay side of Dune Road on a scenic peninsula and surrounded by water, this contemporary is a beach lovers paradise. It's a short walk to the great Westhampton Beach, one of the top 15 ocean beaches in the country; a 5 minute drive to the village; or you ca …see more

from $190 / night

$975 - $3,500 / week

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from $190 / night

24

Home rental in Long Island

Long Island / Rocky Point

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly
  • Air conditioning
Take in the crisp salty air from this beautiful vacation rental house, situated just steps from the Long Island Sound. This 3-bedroom, 2-bathroom home, called 'McFords on the Sound,' accommodates up to 8 and features bright and homey decor, an open floor plan, and large …see more

from $275 / night

$1,925 / week

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Responds fast!
avg. 37 minutes

from $275 / night

27

Long Island Vacation apartment rental

Long Island / East Patchogue

1 2 3 nights min

  • 1 bedroom
  • Sleeps 2
  • 3 nights min
  • Air conditioning
  • Private garden
Gorgeous 2nd Floor Private entrance apartment with its own deck over looking the Great South Bay - Large bedroom - Bath & Living spaces , Kitchen w/washer dryer. All emendates, central heat & ac- w/internet , direct tv , private parking on 5 acres estate, 10 min to Vil …see more

from $145 / night

$950 / week

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from $145 / night

(1) Excellent 

19

Long Island Vacation home rental

Hamptons / East Hampton

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
located only 5 minutes from shops and eateries and 5 minutes to the beach. With a serene setting surrounded by mature trees, this home is a haven for ultimate relaxation and leisure. Enjoy poolside luxury by 20X40 pool in very private yard. Low Allergen Environmentchil …see more

from $500 / night

$3,500 / week

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from $500 / night

4

Long Island Vacation home rental

Hamptons / Bridgehampton

2 4 90 nights min

  • 2 bedrooms
  • Sleeps 4
  • 90 nights min
  • Child friendly
  • Air conditioning
  • Ask about pets
Lovely Hamptons Cottage. 2BR with w/d on site and plenty of off street parking. Lovely ponds and peaceful environment. Central to accessing all of the Hamptons. Internet, Cable TV, Wifi, contemporary design. New furniture. Full kitchen. Outdoor patio. Lovely lands …see more

from $429 / night

$3,000 / week

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from $429 / night

(4) Excellent 

11

East Marion Vacation cottage rental

North Fork / East Marion

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Private garden
Welcome to the Victorian Seasons guest cottages, nestled between wildlife preserves and protected land. Victorian Seasons is a significantly important historic site that dates back to 1855. It is on the historic corridor in the heart of East Marion on the beautiful Nort …see more

from $400 / night

$475 - $2,300 / week

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from $400 / night

(1) Excellent 

21

Vacation home in East Marion

North Fork / East Marion

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
  • Child friendly
  • Air conditioning
This is a one-bedroom efficiency apartment with a kitchen and bistro dining area, located in the heart of East Marion on the beautiful North Fork. It is part of the main farmhouse that dates to the late 1800's with a separate entrance that once belonged to the Stars fa …see more

from $175 / night

$1,100 / week

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Responds fast!
avg. 1 hour 54 minutes

from $175 / night

15

Long Island Vacation home rental

Hamptons / East Hampton

2 4 30 nights min

  • 2 bedrooms
  • Sleeps 4
  • 30 nights min
  • Child friendly
  • Air conditioning
  • Private garden
It is in a very green and charming location best for walking and bicycle and canoeing. 5 minutes driving to town near the best restaurant and shopping stores and parking and near the ocean and bays in less than 5 minutes drive. very safe and secure area for families wit …see more

from $200 / night

$1,400 / week

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from $200 / night

(1) Excellent 

16

Vacation farmhouse in East Marion

North Fork / East Marion

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Child friendly
Victorian Seasons is a unique historic property. All work is of excellent craftsmanship and is historically accurate in restorations. This one bedroom apartment features a kitchen with stove/oven, refrigerator and necessary utensils. The bathroom is new and designed to …see more

from $350 / night

$2,000 / week

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from $350 / night

5

Vacation home in Long Island

Hamptons / Bridgehampton

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • Child friendly
  • Ask about pets
Beautiful sundenched hamptons property recently renovated quiet and private yet centrally located to all ocean and bay beaches, shopping and transportation. Bike to beaches, towns of Bridgehampton and Sag Harbor. Vineyards and farm stands just up the street. Dead end s …see more

from $1,950 / night

$13,500 / week

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from $1,950 / night