50 Best Long Island Apartments on Holiday Lettings - Condos

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371 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 $1,579 / night

$11,053 / week

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avg. 2 hours 30 minutes

from $1,579 / 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

8

Villa rental in Long Island

Long Island / Bayville

3 6 2 nights min

  • 3 bedrooms
  • Sleeps 6
  • 2 nights min
  • Child friendly
This is a luxury, modern, waterfront house with 4500 square ft. There are 10 large rooms. All rooms have wall to wall glass windows overlooking the bay. Brand new house with all brand new appliances. KItchen, 2 living areas, 2 fire place 2, dining room, family room, rec …see more

from $950 / night

$6,650 / week

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from $950 / 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

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

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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avg. 2 hours 35 minutes

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

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

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

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

15

Vacation home in Amagansett

Hamptons / Amagansett

3 6 14 nights min

  • 3 bedrooms
  • Sleeps 6
  • 14 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.2 mi
  • Child friendly
Beach house right on the sand, just a block away from a beautiful, uncrowded Atlantic Ocean beach. Clean and comfortable. Upstairs deck and downstairs patio off eat-in kitchen. Big living room, three bedrooms, two full bathrooms, washer and dryer, outdoor shower, gas gr …see more

from $143 / night

$1,000 / week

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from $143 / night

(9) Excellent 

28

Vacation home in Long Island

Hamptons / 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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from $400 / night

23

Vacation home in Long Island

Hamptons / Amagansett

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 8 mi
  • Swimming pool
  • Child friendly
Great Hamptons style in Amagansett's Bell Estate. Less than two miles to ocean beaches and one mile from the bay, close to town, has every amenity and plenty of style. Overlooks a 60-foot heated gunite pool. Details include marble baths, wide plank Walnut flooring, cath …see more

from $1,200 / night

$8,000 / week

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avg. 3 hours 40 minutes

from $1,200 / 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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avg. 2 hours 30 minutes

from $85 / 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 $100 / night

$600 - $875 / week

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avg. 2 hours 8 minutes

from $100 / night

(1) Excellent 

9

Vacation home in Long Island

Hamptons / Westhampton

3 6 2 nights min

  • 3 bedrooms
  • Sleeps 6
  • 2 nights min
  • Child friendly
  • Air conditioning
  • Pet friendly
Located on the bayside of Dune Road, this property is a beach lovers paradise. Walk across the street to one of the top 15 beaches in the country; fish, swim or boat on the bay just footsteps away; or just lounge on the large deck and enjoy a . sunset. The property fe …see more

from $190 / night

$975 / week

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from $190 / 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

14

Vacation private room with shared pool in Long Island

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 $175 / night

$1,225 / week

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avg. 37 minutes

from $175 / night

29

Vacation apartment in East Quogue

Hamptons / East Quogue

2 6 3 nights min

  • 2 bedrooms
  • Sleeps 6
  • 3 nights min
  • Nearest beach 7 mi
  • Child friendly
  • Pet friendly
This is a very cozy house with lots of trees around. Only 7 minute drive to the beach. The house has Two bedrooms, one queen bed in the master bedroom, a trundle bed in the second bedroom. Also a comfortable sofa bed in the living room. There is plenty of space in the b …see more

from $265 / night

$1,750 / week

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avg. 1 hour 20 minutes

from $265 / night

30

Vacation home in Wading River

Long Island / Wading River

4 8 21 nights min

  • 4 bedrooms
  • Sleeps 8
  • 21 nights min
  • Suitable for children age 5+
  • Air conditioning
  • Pet friendly
Immerse yourself in the tranquility of New York's Long Island area when you stay at this wonderful Wading River vacation rental home, called 'The Stella House,' which is ideally situated just steps from a spectacular private beach! With 4 bedrooms, 2 bathrooms and enoug …see more

from $399 / night

$2,793 - $5,523 / week

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avg. 8 minutes

from $399 / night

16

Vacation cottage in Long Island

Long Island / Baiting Hollow

3 7 2 nights min

  • 3 bedrooms
  • Sleeps 7
  • 2 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
Seasonal rental within a 5 minute walk to private beach, ten minute walk to Giorgio's. 5 minute drive to local horse riding farm and ten minutes drive to local north fork wineries. 10 minute drive to downtown Riverhead, Long Island rail road, outlets and restaurants. …see more

from $150 / night

$800 / week

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from $150 / 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 26 minutes

from $3,300 / 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 - $3,325 / week

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avg. 19 minutes

from $275 / 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

37

Vacation home in Long Island

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 26 minutes

from $975 / 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. Credit Cards and Pay Pal Accepted. MINIMUM RENTAL 3 NIGHTS. See Photo inlay …see more

from $250 / night

$1,200 - $3,300 / week

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avg. 1 hour 41 minutes

from $250 / night

24

Long Island Vacation home rental

Hamptons / Montauk

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Private garden
Open floorplan newly renovated close to ocean, bay beaches and montauk downs golf course 1st flr: family TV room 2 bedrooms - 2 sets of bunk beds & queen bed 1 bath w/ soaking tub 2nd flr: Open kitchen/living out to deck, 2 bedrooms - 1 king bed & 1 queen bed 1 bath …see more

from $1,000 / night

$7,000 / week

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from $1,000 / 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 - $7,000 / week

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avg. 8 minutes

from $500 / night

31

Vacation home in Ocean Beach

Fire Island / Ocean Beach

5 13 2 nights min

  • 5 bedrooms
  • Sleeps 13
  • 2 nights min
  • Child friendly
Great five bedroom home steps away from the beach and town of Ocean Beach Book Early and Save! Amazing five bedroom, three bathroom house in Ocean Beach/Corneille Estates. There are two bedrooms downstairs and 2 full bathrooms. Upstairs, there are three more bedroom …see more

from $500 / night

$5,000 - $7,500 / week

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from $500 / night

(7) Excellent 

33

Vacation home in Rocky Point

Long Island / Rocky Point

3 5 3 nights min

  • 3 bedrooms
  • Sleeps 5
  • 3 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.5 mi
  • Child friendly
Quaint 3 bedroom, 1 bath home, with beautiful views of the long island sound, and Connecticut, from the kitchen, dining area, bedroom, and back yard.Heat and Central air conditioning, cable, internet, Netflix,phone. electric stove/oven, toaster, coffee maker,microwave,c …see more

from $275 / night

$1,925 / week

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from $275 / 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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Responds fast!
avg. 3 hours 20 minutes

from $150 / night

(3) Excellent 

17

Home rental in Long Island with tennis court

Hamptons / Quogue

4 8 1 night min

  • 4 bedrooms
  • Sleeps 8
  • 1 night min
  • Beach/lakeside relaxation
  • Nearest beach 4 mi
  • Swimming pool
Will your mom have to sit on the end of your futon with a plate of holiday goose and stuffing balanced on her knee? Will your mother in-law fill your entire kitchen.... with herself... only to find out the roast she bought doesn't fit in your oven? Well it is time to …see more

from $400 / night

$1,500 / week

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from $400 / night

21

Vacation home with swimming pool, golf nearby in Long Island

Long Island / Bellport

3 10 4 nights min

  • 3 bedrooms
  • Sleeps 10
  • 4 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
This house has it all! 3 bedrooms with plenty of space for addition guests to sleep in the den. 2 bathrooms. Big living room, dining room, eat in kitchen. The den boasts a large screen TV with surround sound. Patio with furniture and gas grill. Heated pool! Dish washer …see more

from $400 / night

$3,000 / week

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from $400 / 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

(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 $249 / night

$999 - $4,999 / week

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avg. 2 hours 58 minutes

from $249 / night

22

Vacation home rental

Long Island / Westhampton Beach

4 6 14 nights min

  • 4 bedrooms
  • Sleeps 6
  • 14 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
This beautiful waterview home includes 4 Bedrooms and 2 Bathrooms. It has gorgeous waterviews overlooking large upper and lower decks with large inground pool and outdoor shower with dressing area. Newly renovated kitchen with solid surface counter tops and top of the l …see more

from $1,000 / night

$7,000 / week

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from $1,000 / 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 $250 / night

$1,750 - $2,450 / week

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Responds fast!
avg. 43 minutes

from $250 / night

(2) Excellent 

11

East Marion Vacation cottage rental

North Fork / East Marion

2 5 1 night min

  • 2 bedrooms
  • Sleeps 5
  • 1 night min
  • 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 $295 / night

$2,200 / week

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from $295 / 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