Cutchogue Holiday Rentals, New York: Private House Rentals

A coastal landscape with a sandy beach, calm waters, and a clear sky.

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Our top choices for Cutchogue hotels

A modern outdoor seating area with two wicker chairs and a small table, overlooking a body of water and a wooden deck.

A storefront with a sign reading "THE SHOALS".

A light blue bus with "THE SHOALS" written on the front, parked in a driveway with a house and garden in the background.

A modern hotel room with a bed, a sofa, a coffee table, and a view of the city.

1. The Shoals Suites and Slips

Southold

Masayo

4.583.935 ₫

5.883.169 ₫ total

includes taxes & fees

26 Oct - 27 Oct

A round table with a magazine, a plate with a pastry, a cup, and a vase with flowers.

A bedroom with a bed, a door, and a framed picture on the wall.

A reception desk with a vase of flowers, a sign that says "STAY awhile", and a window with blinds.

A white closet with shelves, a robe hanging on a wooden hanger, and a pair of black straps on a rack.

2. Shorewood Inn

Riverhead

Dennis

2.651.287 ₫

3.028.824 ₫ total

includes taxes & fees

26 Oct - 27 Oct

A spacious room with wicker furniture, large windows, and a view of the sea.

A spacious room with large windows, a wooden bench, yoga mats, and a door leading to a balcony with a view of the sea.

A beach bar with wooden chairs and a small table, overlooking the sea.

A coastal building with a deck extending over the water, featuring large windows and a dining area.

3. Sound View Greenport

Greenport

Christine

4.476.953 ₫

5.852.938 ₫ total

includes taxes & fees

22 Nov - 23 Nov

A modern bathroom with a large mirror, wooden vanity, and a sink. There is a chair and a small table in the adjacent living area, with a sofa and a view of the outdoors.

A modern kitchen with a refrigerator, microwave, and wooden cabinets. There is a dining table with two chairs and a TV mounted on the wall.

A modern outdoor seating area with a white sofa and a table, a sliding glass door, and a number '25' on the wall.

A modern living room with a flat-screen TV, a dining area with a round table and chairs, a sofa with cushions, and a small side table with a lamp.

4. The Bentley Hotel Southampton

Southampton

Armando

3.721.104 ₫

4.251.362 ₫ total

includes taxes & fees

31 Oct - 1 Nov

A lakeside patio with outdoor seating and a view of the water.

A grassy area with trees and a view of a body of water.

A beach with sun loungers and umbrellas, a sandy path, and a view of the water.

5. Silver Sands Motel & Beach Bungalows

Greenport

Gaurav

7.235.480 ₫

8.266.536 ₫ total

includes taxes & fees

1 Nov - 2 Nov

A waterfront property with a large house, multiple boats docked, and lush greenery.

A spacious lobby with multiple seating areas, a kitchen area, and large windows providing natural light.

A swimming pool with clear blue water, surrounded by lounge chairs and umbrellas, with a building in the background.

A spacious hallway with a fireplace, a large window, and a built-in shelving unit.

6. Sag Harbor Inn

Sag Harbor

Terri

5.659.179 ₫

6.465.612 ₫ total

includes taxes & fees

1 Nov - 2 Nov

A modern kitchen with a central island, bar stools, pendant lighting, and a seating area with a sofa and coffee table.

A bedroom with a large bed, a chandelier, and multiple windows.

A modern living room with a stone wall, a flat-screen TV mounted above a door, a dark sofa, and a glass coffee table with a vase of flowers.

A beach with sand and sparse vegetation.

7. The Hampton Maid

Hampton Bays

Joshua

5.465.371 ₫

6.244.186 ₫ total

includes taxes & fees

26 Oct - 27 Oct

A beachside lounge with wicker furniture, a fire pit, and string lights.

A room with a large window overlooking a body of water, featuring two wicker chairs and a table.

A spacious room with a large bed, a round table, and a wicker chair.

A beach with thatched umbrellas and a wooden walkway leading to the water.

8. Aqua by American Beech - Adults Only

Riverhead

Monique

4.995.582 ₫

6.611.678 ₫ total

includes taxes & fees

26 Oct - 27 Oct

A tented area with a pool view, wooden lounge chairs, and a table with a drink and food.

A breakfast buffet with various food items and beverages.

A beach chair with a towel labeled "CANOE PLACE" and a wicker basket with bottles and a container on the sand.

9. Canoe Place Inn and Cottages

Hampton Bays

Corrado

12.274.475 ₫

14.864.970 ₫ total

includes taxes & fees

26 Oct - 27 Oct

A swimming pool with a wooden deck, lounge chairs, and a fence.

A bar area with wooden bar stools and a bookshelf.

A hotel room with a bed, a blue sofa, a wicker chair, a small table with a vase, and a lamp.

10. The Harbor Front Inn

Greenport

Antrii

4.069.957 ₫

5.387.946 ₫ total

includes taxes & fees

22 Nov - 23 Nov

A glass-top table with a vase of flowers, surrounded by white-covered chairs, in a bright indoor setting with plants and a fireplace in the background.

A room with a wicker sofa, a small table with a potted plant, and a bed with a wooden ladder.

A beach scene with a sunset, calm sea, and a few people fishing.

A spacious living room with a white sofa, a coffee table, and a fireplace. There are large windows offering a view of the outdoors.

11. Hamlet Inn

Southampton

Eric

3.000.140 ₫

3.877.959 ₫ total

includes taxes & fees

26 Oct - 27 Oct

A two-story house with a balcony, outdoor seating area, and a variety of plants.

A bathroom with a bathtub, green tiled walls, and windows with white blinds.

A bar area with stools, a shelf with glasses, and decorative plants.

A modern bedroom with two beds, a sofa, a coffee table, and a potted plant.

12. Zey Hotel

Greenport

sacha

4.186.242 ₫

4.782.783 ₫ total

includes taxes & fees

26 Oct - 27 Oct

A Holiday Inn Express hotel with a stone facade, multiple windows, and a covered entrance area.

A modern lounge area with white sofas, a round table, and a stone fireplace.

A hotel room with a gray sofa, a blue ottoman, a wooden desk, and a bed with white linens.

A buffet with labeled containers of turkey sausage and cookies.

13. Holiday Inn Express & Suites Riverhead - Long Island by IHG

Riverhead

LUIS

3.307.648 ₫

3.778.986 ₫ total

includes taxes & fees

1 Nov - 2 Nov

A modern house with a deck, outdoor seating, and a fire pit.

A tented accommodation with a bed, television, and a small table with a chair.

A modern kitchen with a stainless steel sink, white cabinets, and a blue-tiled backsplash.

A rustic cabin with a wooden exterior, a front porch, and a staircase leading to the entrance.

14. North Fork Resort

Greenport

Altynai

8.302.713 ₫

9.485.850 ₫ total

includes taxes & fees

26 Oct - 27 Oct

A marina with boats docked, a globe sculpture, wicker furniture, and a bottle of wine on a table.

A modern hotel with a glass facade, a covered entrance, and a sign indicating it is a Hyatt Place.

A modern bar area with a long counter, multiple seating options, and a variety of bottles and glasses on shelves.

A marina with boats docked, a fire feature, and outdoor seating with a bottle and glasses.

15. Hyatt Place Long Island East End

Riverhead

Timothy

3.436.853 ₫

3.926.604 ₫ total

includes taxes & fees

22 Nov - 23 Nov

An outdoor seating area with Adirondack chairs and a table, surrounded by American flags and flowers, with a view of houses and a body of water in the background.

A bedroom with a bed, a desk, a chair, a window with a view of trees and a body of water.

Two Adirondack chairs facing a beach with a clear view of the sea and a distant island.

A house with a dark blue exterior, a white porch railing, and a red door.

16. Ocean View Terrace Inn

Hampton Bays

james

3.097.819 ₫

4.997.649 ₫ total

includes taxes & fees

26 Oct - 27 Oct

A hotel room with a bed, bedside tables, a desk with chairs, a sofa, a window with curtains, and a door leading outside.

A swimming pool with lounge chairs and umbrellas, surrounded by a wooden fence and trees.

A hotel room with a bed, bedside tables, a desk with a chair, and a window with a view of greenery.

A kitchen counter with a coffee maker, thermos, fruits, and breakfast items.

17. The Atlantic Hotel

Southampton

miranda

2.767.571 ₫

3.807.975 ₫ total

includes taxes & fees

28 Oct - 29 Oct

A bedroom with a bed, bedside table, lamp, and a view of the outdoors through a window.

A swimming pool with a white fence, a table with chairs, and a building with a white picket fence in the background.

A covered patio area with outdoor seating, a potted plant, and a well-maintained lawn.

A living room with a wooden entertainment center, a sofa, a coffee table, and a lamp.

18. Southampton Long Island Hotel

Southampton

William

4.108.719 ₫

4.899.970 ₫ total

includes taxes & fees

26 Oct - 27 Oct

A balcony with a view of the sea, a dining table, and a blue house in the background.

19. Cliffside Resort Condominiums

Greenport

William

4.367.646 ₫

7.856.956 ₫ total

includes taxes & fees

12 Nov - 13 Nov

A reception area with a marble counter, wooden walls, and a large vertical sign for The Preston House & Hotel.

A lobby with yellow upholstered chairs, a round wooden table, and a large abstract painting on the wall.

A modern bar area with a mural of a woman in a flowing dress, wooden bar stools, and a seating area with yellow sofas and chairs.

A modern living room with a sofa, a coffee table, and a TV mounted on the wall.

20. The Preston House & Hotel

Riverhead

Fayth

5.905.858 ₫

6.747.442 ₫ total

includes taxes & fees

2 Nov - 3 Nov

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Stay near popular Cutchogue attractions

Bedell Cellars

8.6/10 (4 reviews)

This award-winning Long Island winery served its 2009 Merlot at the 2013 Presidential Inauguration. Sample handcrafted wines in a renovated barn with panoramic vineyard views and artisanal cheese pairings.

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Peconic Bay Winery

This sustainable North Fork winery showcases Long Island's unique terroir through exceptional vintages. Reserve a private picnic among the vines or savour wine paired with fresh oysters in their elegant tasting room.

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8 Hands Farm

This regenerative farm showcases heritage breed animals and sustainable practices. Sample artisanal charcuterie and seasonal farm-to-plate offerings at the on-site store while exploring the pastoral landscape.

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McCall Wines

10.0/10 (1 review)

This sustainable vineyard pairs award-winning Pinot Noir with the rustic charm of a converted potato barn. Sample their acclaimed wines while watching Charolais cattle graze among the vines.

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Old House Museum

Built in 1699, The Old House is one of America's finest examples of English colonial architecture. Step into its meticulously restored interior with period furnishings to experience 17th-century domestic life.

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Pugliese Vineyards

8.0/10 (2 reviews)

This family-owned North Fork winery offers estate-bottled varieties and sparkling champagnes in an intimate setting. Enjoy guided tastings beside a picturesque koi pond while savouring the serene vineyard atmosphere.

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Pellegrini Vineyards

Pellegrini Vineyards crafts award-winning Merlot and Chardonnay in its on-site winemaking facility. Savour premium tastings in the cathedral-like tasting room with vineyard views or explore through self-guided tours.

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Cutchogue Village Green

Step back in time at Cutchogue Village Green, home to the Old House (1649), one of New York State's oldest English-style dwellings. Wander through preserved colonial buildings that illuminate early American life.

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Learn more about Cutchogue

Vineyard-hop through North Fork's wine country, where family-owned tasting rooms offer flights alongside views of grapevines stretching to the horizon. Explore historic Cutchogue Village Green with its 1700s buildings, then head to nearby Peconic Bay beaches for kayaking or sampling just-caught oysters at waterfront seafood shacks.

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Top Cutchogue Hotel Reviews

Zey Hotel

10/10 Excellent

"Had a nice stay. Room was very clean. Amenities were nice. We enjoyed our 40th anniversary."

Hyatt Place Long Island East End

10/10 Excellent

"clean room"

Greenview Inn Riverhead

10/10 Excellent

"Clean rooms parkking easy check in"

Faraway Sag Harbor

8/10 Good

"Beautiful and charming hotel! Unfortunately the restaurant was only serving breakfast and not dinner, since we arrived off- season. However the restaurant was freezing due to the heating system not working so we had to go elsewhere in town for breakfast. Too bad because it was a lovely room with a harbor view. Our biggest disappointment by far was the coffee in the room and in the lobby. Nasty stuff! I have never tasted coffee this bad in any hotel (and we have been to many). First of all at this high- end price point per night, Faraway should be providing at least a Nespresso machine in each room for a decent morning cup of coffee instead of instant coffee packets which went out with Sanka like forty years ago. :( Then we thought that maybe the coffee urns on the bar in the common area would at least provide a half decent cup of coffee. Boy were we wrong! The fact that other filled cups of coffee which were left on the bar still full told us that other guests felt the same about the quality of coffee. Thank goodness for Goldbergs Bagel shop in town! Come on guys. If you want to be recognized as a high end getaway in an extremely wealthy part of Long Island, please find yourselves a better quality coffee source. Its not that hard these days. We speak for all true coffee lovers."

The Bentley Hotel Southampton

10/10 Excellent

"Perfect one day stay. I would stay here again and can recommend it to others."

Pier Blue Inn Old Saybrook - Essex

10/10 Excellent

"I stayed twice and borh rooms were decorated uniquely. The staff and owners were very nice. Good people"

Sag Harbor Inn

10/10 Excellent

"The hotel was beautiful. The room was very spacious and comfortable. The continental breakfast offered many choices, and they had coffee, tea and hot chocolate available 24 hours a day."

The Harbor Front Inn

8/10 Good

"The room was clean and the staff is always wonderful. Parking was a nightmare because of the festival which had nothing to do with the hotel. My only issue is the breakfast , I wish it had a little more so I don’t have to go down the street to get something to eat . Honestly it’s not even an issue we will continue to stay here because it is a very nice hotel"

The Atlantic Hotel

10/10 Excellent

"We were 4 girls and the room was two bedrooms and another bed also so it accommodated all of us. 😊"

More cheap stays in Cutchogue

Pier Blue Inn Old Saybrook - Essex

1430 Boston Post Rd Old Saybrook CT

2.111.468 ₫

2.428.279 ₫ total

15 Nov - 16 Nov

includes taxes & fees

8/10 Very good! (1,002 reviews)

Budget Host East End

30 Lake Avenue Riverhead NY

2.299.849 ₫

2.627.578 ₫ total

26 Oct - 27 Oct

includes taxes & fees