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 modern living room with a blue sofa, light blue armchairs, a dining table, and a kitchen in the background.

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

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

1. The Shoals Suites and Slips

Southold

Masayo

฿6,217

฿7,940 total

includes taxes & fees

1 Nov - 2 Nov

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

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

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

A breakfast bar with cereal, coffee, and fresh milk.

2. Shorewood Inn

Riverhead

Dennis

฿3,439

฿3,928 total

includes taxes & fees

18 Oct - 19 Oct

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

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

A beach scene with a wooden structure, two wooden chairs, a campfire, and string lights.

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

3. Sound View Greenport

Greenport

Irene

฿6,003

฿7,815 total

includes taxes & fees

16 Nov - 17 Nov

A modern lounge area with a pool view, white furniture, and contemporary lighting fixtures.

A hotel room with two beds, a wall art piece with the text "GOOD DREAMS START HERE", and a pink abstract wall design.

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 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.

4. The Bentley Hotel Southampton

Southampton

Doug

฿4,793

฿5,476 total

includes taxes & fees

16 Nov - 17 Nov

A rooftop terrace with lounge chairs, a wooden table, and a view of the landscape.

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

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

A neatly arranged hotel room with a bed, two bedside tables with lamps, a window with curtains, and two framed artworks on the wall.

5. The Harbor Front Inn

Greenport

Antrii

฿5,999

฿7,811 total

includes taxes & fees

2 Nov - 3 Nov

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

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.

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

6. Sag Harbor Inn

Sag Harbor

Terri

฿7,340

฿8,386 total

includes taxes & fees

1 Nov - 2 Nov

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

A room with a bed, two wicker chairs with checkered cushions, a small round table with a vase of flowers, and a view of a lake through a window with a bamboo blind.

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

7. Silver Sands Motel & Beach Bungalows

Greenport

Keith

฿9,384

฿10,721 total

includes taxes & fees

1 Nov - 2 Nov

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

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

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

A dining area with wooden paneling, a patterned floor, and a view of outdoor seating through large windows.

8. Hyatt Place Long Island East End

Riverhead

Timothy

฿4,256

฿4,863 total

includes taxes & fees

3 Nov - 4 Nov

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

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

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

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

9. Zey Hotel

Greenport

Renee

฿6,108

฿6,979 total

includes taxes & fees

20 Oct - 21 Oct

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 two-story house with a windmill on the roof, a balcony, and three Adirondack chairs in the front yard.

10. The Hampton Maid

Hampton Bays

Joshua

฿7,088

฿8,098 total

includes taxes & fees

26 Oct - 27 Oct

11. Shelter Island House

Shelter Island Heights

Dorothy

฿6,745

฿7,706 total

includes taxes & fees

19 Oct - 20 Oct

A modern building entrance with a black and white striped awning, a staircase leading inside, and two bicycles parked outside.

A modern living room with a grey sofa, black and white patterned rug, and a coffee table.

A modern reception area with a staircase, a framed artwork, and a reception desk with "THE MENHADEN" signage.

A modern bar area with black bar stools, a counter with a variety of bottles, and hanging green plants in wire baskets.

12. The Menhaden

Greenport

Daniel

฿11,580

฿14,571 total

includes taxes & fees

15 Nov - 16 Nov

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 modern bathroom with a large bathtub, a seating area with a sofa and chairs, a dining table, and a view of the water.

13. Aqua by American Beech - Adults Only

Riverhead

Monique

฿7,229

฿9,436 total

includes taxes & fees

18 Oct - 19 Oct

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

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

A breakfast buffet area with various food stations, including yogurt, eggs, and hot water.

A self-service snack and beverage area with shelves stocked with various snacks and a refrigerated section with bottled water and juices.

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

Riverhead

LUIS

฿4,406

฿5,034 total

includes taxes & fees

25 Oct - 26 Oct

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

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

A living room area with a sofa, a dining table, and a separate queen bedroom.

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

15. Southampton Long Island Hotel

Southampton

William

฿5,329

฿6,355 total

includes taxes & fees

18 Oct - 19 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 hotel room with a bed, bedside tables, a desk with a chair, and a window with a view of greenery.

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

16. The Atlantic Hotel

Southampton

Chris

฿3,589

฿4,939 total

includes taxes & fees

28 Oct - 29 Oct

17. Cliffside Resort Condominiums

Greenport

William

฿5,665

฿10,190 total

includes taxes & fees

12 Nov - 13 Nov

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

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

A modern living room with a sofa, a dining table, and a kitchen area in the background.

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

18. North Fork Resort

Greenport

Harold

฿10,768

฿12,303 total

includes taxes & fees

18 Oct - 19 Oct

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

A house with a covered porch, a garden with various plants and flowers, and a 'OPEN' sign on the window.

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

19. Hamlet Inn

Southampton

Eric

฿5,336

฿6,897 total

includes taxes & fees

15 Nov - 16 Nov

A pathway flanked by lush greenery and bamboo, leading to a building with a wooden exterior.

A reception desk with a white backdrop, surrounded by various plants and a modern pendant light.

A modern lounge area with a curved sofa, round coffee tables, and a large potted plant.

An outdoor dining area with tables and chairs, string lights, and hanging lanterns.

20. American Beech Hotel

Greenport

Mary

฿8,406

฿10,944 total

includes taxes & fees

19 Oct - 20 Oct

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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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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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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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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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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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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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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

Greenview Inn Riverhead

10/10 Excellent

"Inn is in a rural areas, along scenic country nestled in nature-immersed Riverhead town.Close to Riverheads amazing stores and popular eatery s They offer a more personal, relaxed atmosphere, often featuring a cozy bed rather than a corporate polish.. Great for a short business trip or as a overnite . Unique Inn atmosphere."

Hyatt Place Long Island East End

8/10 Good

"Front desk staff provider typical Long Island hospitality… Just rude! You should send your people to the South for training for six months to get that chip off their shoulder."

The Atlantic Hotel

10/10 Excellent

"This is actually a really great place to stay if you want something reasonable in the Hamptons. The rooms are clean and spacious and the grounds of the hotel are beautiful. I highly recommend!!!"

Hampton Bays Hotel on Main

8/10 Good

"✅ was very good! perfect for 1-2 nights!! Tksss so much"

The Harbor Front Inn

10/10 Excellent

"Beautiful view and quiet"

Zey Hotel

10/10 Excellent

"The staff particularly James were over the top accommodating!!"

Shorewood Inn

10/10 Excellent

"Clean, affordable, helpful staff, good parking. We will stay again when we are in the area."

Sound View Greenport

10/10 Excellent

"The breakfast could have had a better choice."

The Bentley Hotel Southampton

10/10 Excellent

"Booked a 1bedroom king suite and it was fabulous! Tons of room; full size refrigerator; comfy mattress and suite was so clean. Second time here and returning in 2 months. Staff very pleasant and accommodating, especially the manager, Leah."

More cheap stays in Cutchogue

Pier Blue Inn Old Saybrook - Essex

1430 Boston Post Rd Old Saybrook CT

฿2,582

฿2,969 total

19 Oct - 20 Oct

includes taxes & fees