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

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.

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

1. The Hampton Maid

Hampton Bays

SABINA

6.768.252 ₫

7.732.728 ₫ total

includes taxes & fees

5 Oct - 6 Oct

An outdoor patio with wicker furniture, a fire pit, string lights, and potted plants.

A modern living room with a sofa, coffee table, and a dining area with a bar.

A modern bar area with a round glass table, leather chairs, and a bar counter with stools.

An indoor swimming pool with clear water, surrounded by lounge chairs and a tiled floor.

2. Residence Inn by Marriott New York Long Island East End

Riverhead

Nataliya

4.538.378 ₫

5.185.096 ₫ total

includes taxes & fees

28 Sept - 29 Sept

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

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

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

A dining area with a round table, two chairs, a framed artwork, a vase with flowers, a bottle, and books.

3. The Harbor Front Inn

Greenport

Michael

6.744.913 ₫

8.446.830 ₫ total

includes taxes & fees

4 Oct - 5 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 dining area with wooden paneling, a patterned floor, and a view of outdoor seating through large windows.

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

4. Hyatt Place Long Island East End

Riverhead

Veronica

5.938.428 ₫

6.784.654 ₫ total

includes taxes & fees

7 Oct - 8 Oct

A modern kitchen area with a long counter, various appliances, and a sign that reads "Delight in the day".

A modern living room with a flat-screen TV, a small table, a yellow armchair, a rocking chair, and a mini-fridge stocked with snacks.

A reception area with a wooden reception desk, a green rug, and a wall-mounted abstract art piece.

A hotel with a 'spark by Hilton' sign, a parking lot, and a covered parking area.

5. Spark by Hilton Guilford

Guilford

Stacy

2.743.865 ₫

3.155.445 ₫ total

includes taxes & fees

11 Oct - 12 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 white closet with shelves, a robe hanging on a wooden hanger, and a pair of black straps on a rack.

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

6. Shorewood Inn

Riverhead

KAREN

2.217.186 ₫

2.533.038 ₫ total

includes taxes & fees

4 Oct - 5 Oct

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

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.

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.

7. The Bentley Hotel Southampton

Southampton

Frank

3.760.140 ₫

4.944.260 ₫ total

includes taxes & fees

5 Oct - 6 Oct

A couple in a hot tub with towels and candles, surrounded by mosaic tiles and a plate of food.

An outdoor dining area with tables set for a meal, large windows, and a ceiling fan.

An aerial view of a residential area with multiple houses, a large covered structure, and a parking lot.

A spa and salon interior with wooden flooring, beige sofas, and a Buddha statue.

8. The Inn And Spa At East Wind

Calverton

Kristine

3.489.560 ₫

3.986.823 ₫ total

includes taxes & fees

14 Sept - 15 Sept

Two blue Adirondack chairs and a small white table in a grassy area surrounded by trees.

A train traveling along a river with autumn foliage in the background.

A guesthouse named Pier Blue with a sign, a parking lot, and a building with a red awning.

9. Pier Blue Inn Old Saybrook - Essex

Saybrook Manor

Carolyn

2.212.518 ₫

2.544.448 ₫ total

includes taxes & fees

14 Sept - 15 Sept

A parking lot with a building in the background.

A hotel room with two beds, a desk, a chair, a window with curtains, and two wall-mounted lamps.

A motel with a large parking lot and multiple rooms.

A rectangular swimming pool with a fenced area, surrounded by trees and a concrete deck with white metal loungers.

10. Clinton Motel

Clinton

Selena

2.027.454 ₫

2.331.572 ₫ total

includes taxes & fees

14 Sept - 15 Sept

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 hotel lobby with a sofa, chairs, tables, and a large window.

11. Sag Harbor Inn

Sag Harbor

Loretta

8.401.968 ₫

9.599.248 ₫ total

includes taxes & fees

11 Oct - 12 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 kitchen counter with a coffee maker, thermos, fruits, and breakfast items.

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

12. The Atlantic Hotel

Southampton

Jessa

3.099.665 ₫

4.191.191 ₫ total

includes taxes & fees

1 Oct - 2 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 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.

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

13. Hamlet Inn

Southampton

Thomas

3.294.613 ₫

4.258.433 ₫ total

includes taxes & fees

27 Sept - 28 Sept

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

A breakfast area with a sign that reads 'GOOD MORNING' and another that says 'HOT FOOD'. There are also signs for 'EGG-XACTLY' and 'GO AHEAD. PANCAKE MY DAY.' with a flowchart.

A reception desk with a modern design, a nameplate, and a security camera above it.

A coffee station with two coffee machines and a variety of coffee pods and cups.

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

Riverhead

LUIS

4.938.670 ₫

5.642.431 ₫ total

includes taxes & fees

5 Oct - 6 Oct

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

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

A two-story house with a front porch, a staircase, and a large glass window on the upper floor.

15. The Preston House & Hotel

Riverhead

Michael

6.026.737 ₫

6.885.286 ₫ total

includes taxes & fees

5 Oct - 6 Oct

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.

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.

A window with a view of a building and trees, a small table with a lamp, and a curtain partially covering the window.

16. Ocean View Terrace Inn

Hampton Bays

Sally

3.564.420 ₫

5.600.972 ₫ total

includes taxes & fees

13 Sept - 14 Sept

A two-story motel with a symmetrical facade, multiple windows, and a parking lot in front.

A bedroom with a dark wooden dresser, a flat-screen TV, a microwave, and a door leading to another room.

A hotel room with a bed, a small table, a chair, a painting on the wall, and a window with a curtain.

17. Lamplighter Motel - Clinton, Connecticut

Clinton

Steven

1.789.308 ₫

2.057.704 ₫ total

includes taxes & fees

11 Oct - 12 Oct

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

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.

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

18. The Shoals Suites and Slips

Southold

Melissa

5.246.037 ₫

6.643.422 ₫ total

includes taxes & fees

1 Oct - 2 Oct

A patio area with wicker furniture, a stone fire pit, and candles.

A modern dining room with a large table, chairs, a fireplace, and pendant lights.

A modern bar area with a long counter, bar stools, and a television mounted above.

A modern hotel with a covered entrance, large windows, and a well-maintained garden.

19. Hilton Garden Inn Riverhead

Riverhead

Amelia

3.593.657 ₫

4.105.753 ₫ total

includes taxes & fees

7 Oct - 8 Oct

A snow-covered pathway leading to a building with a porch.

A well-maintained garden with a central pathway leading to a house.

20. Southampton Inn

Southampton

Kevin

7.797.900 ₫

9.332.787 ₫ total

includes taxes & fees

4 Oct - 5 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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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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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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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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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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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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Waters Crest Winery

This family-run North Fork winery crafted distinctive Cabernet Franc and Merlot in an intimate setting. Visitors could enjoy personalised tastings with owner Jim Waters and attend enlightening "Wine University" classes.

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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.

See all hotels in Cutchogue

A vineyard with rows of grapevines under a partly cloudy sky.

Top Cutchogue Hotel Reviews

North Fork Resort

10/10 Excellent

"This property is so awesome! Adorable cottages, not very big, but sufficient. We were 2 couples, and we managed. Very quaint an comfortable. Services were provided if asked. They give you everything you need. I may buy in or for sure go back as a guest next year. We loved it, and it's so convenient to town, restaurants, and wineries all around you."

Zey Hotel

10/10 Excellent

"Such an amazing hotel to stay for the weekend"

The Hampton Maid

10/10 Excellent

"Our stay at The Hampton Maid was such a great choice. The entire hotel is absolutely charming—you can tell that every corner and every detail has been thoughtfully designed. The front desk staff was wonderful: so friendly, welcoming, and very clear with all the information. We loved the bungalow-style rooms, each with its own deck and parking, which gives you wonderful privacy between rooms. But what truly stole our hearts was the gorgeous, beautifully kept garden—a true green oasis that brings complete peace and lets you fully disconnect from city stress. The room was spotless, and the restaurant was phenomenal—we had breakfast there, and it was spectacular. On top of that, getting a pass to 7 local beaches for just $5 is an incredible perk. You really couldn't ask for more! It’s one of those places where you haven't even left yet, and you're already planning your return. Can't wait to go back!"

Pier Blue Inn Old Saybrook - Essex

10/10 Excellent

"Welcoming, helpful, friendly, professional front desk staff. My room was impeccably clean and tidy. The property is centrally-located with ease of accessibility to main roads and major highways, yet far enough off Boston Post Road to ensure a quiet, peaceful and restful stay. Overall, an outstanding, no-frills property! I look forward to staying here once again!"

Greenview Inn Riverhead

10/10 Excellent

"Great hotel!"

Saybrook Point Resort & Marina

10/10 Excellent

"Old Saybrook never disappoints. The rooms have been remodel Edinburgh the last six months but the resort has managed to retain its old world chatm. Eventhough there were three weddings at the property during our visit, the staff were attentive to us and we weren't as re remained their only guests. We will visit again."

Hilton Garden Inn Riverhead

10/10 Excellent

"Bartender was great. I got in late a wanted a beer so she took her time cleaning up so i could relax and have a beer! Great service."

Faraway Sag Harbor

8/10 Good

"Faraway has been renovated Beautifully. The food has improved since Baron's Cove. The pool would benefit improving service and perhaps combining the food / drinks servers and pool attendants. In addition since we have been guests of the older Hotel, Baron's Cove for 16 years it would have been meaningful to have the new staff welcome guests and perhaps give a priority rate or welcome massage etc."

The Shoals Suites and Slips

10/10 Excellent

"Loved everything about our stay!"

More cheap stays in Cutchogue

Pier Blue Inn Old Saybrook - Essex

1430 Boston Post Rd Old Saybrook CT

2.212.518 ₫

2.544.448 ₫ total

14 Sept - 15 Sept

includes taxes & fees

8/10 Very good! (1,001 reviews)

Greenview Inn Riverhead

1433 W Main St Riverhead NY

2.237.024 ₫

2.555.800 ₫ total

5 Oct - 6 Oct

includes taxes & fees

7.4/10 Good! (860 reviews)

Budget Host East End

30 Lake Avenue Riverhead NY

2.307.948 ₫

2.636.831 ₫ total

13 Sept - 14 Sept

includes taxes & fees

The Atlantic Hotel

1655 County Road 39 Southampton NY

3.099.665 ₫

4.191.191 ₫ total

1 Oct - 2 Oct

includes taxes & fees

Holiday Inn Express & Suites Riverhead - Long Island by IHG

1707 Old Country Rd Riverhead NY

4.938.670 ₫

5.642.431 ₫ total

5 Oct - 6 Oct

includes taxes & fees

The Hampton Maid

259 E Montauk Hwy Hampton Bays NY

6.768.252 ₫

7.732.728 ₫ total

5 Oct - 6 Oct

includes taxes & fees

9.2/10 Wonderful! (776 reviews)

Hotels in Cutchogue with star rating

Frequently asked questions

What's the weather like in Cutchogue?

The hottest months are usually August and July, with an average temperature of 21°C, while the coldest months are January and February, with an average of 3°C. Average annual precipitation for Cutchogue is 1452 mm.

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Find hotels in Cutchogue, NY from 2.544.448 ₫

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in Cutchogue

Check prices for these dates

Filter by

Star rating

Guest rating

Our top choices for Cutchogue hotels

1. The Hampton Maid

2. Residence Inn by Marriott New York Long Island East End

3. The Harbor Front Inn

4. Hyatt Place Long Island East End

5. Spark by Hilton Guilford

6. Shorewood Inn

7. The Bentley Hotel Southampton

8. The Inn And Spa At East Wind

9. Pier Blue Inn Old Saybrook - Essex

10. Clinton Motel

11. Sag Harbor Inn

12. The Atlantic Hotel

13. Hamlet Inn

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

15. The Preston House & Hotel

16. Ocean View Terrace Inn

17. Lamplighter Motel - Clinton, Connecticut

18. The Shoals Suites and Slips

19. Hilton Garden Inn Riverhead

20. Southampton Inn

Stay near popular Cutchogue attractions

Bedell Cellars

Peconic Bay Winery

8 Hands Farm

Cutchogue Village Green

Pugliese Vineyards

McCall Wines

Pellegrini Vineyards

Waters Crest Winery

Learn more about Cutchogue

Top Cutchogue Hotel Reviews

North Fork Resort

Zey Hotel

The Hampton Maid

Pier Blue Inn Old Saybrook - Essex

Greenview Inn Riverhead

Saybrook Point Resort & Marina

Hilton Garden Inn Riverhead

Faraway Sag Harbor

The Shoals Suites and Slips

More cheap stays in Cutchogue

Pier Blue Inn Old Saybrook - Essex

Greenview Inn Riverhead

Budget Host East End

The Atlantic Hotel

Holiday Inn Express & Suites Riverhead - Long Island by IHG

The Hampton Maid

Hotels in Cutchogue with star rating

Frequently asked questions

Explore a world of travel with Expedia

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