Greenport West Holiday Rentals, Greenport: Private House Rentals

A coastal landscape with a sandy beach, clear blue water, and a distant lighthouse.

Change your mind
Book hotels with free cancellation
Treat yourself
Sign in to save 10% or more on thousands of hotels
Sign in
Be picky
Search almost a million properties worldwide

Go beyond your typical stay in Greenport West

Pet friendly

Apartment

Pool

Condo

Spa

Hot tub

Cottage

Family friendly

Waterpark

Check prices for these dates

Tonight

Tomorrow

This weekend

Next weekend

Our top choices for Greenport West hotels

Reserve now, pay later

Hotel

Breakfast included

Pet-friendly

Sparkling Pointe

A seaside dining area with tables, chairs, and umbrellas, overlooking a body of water.

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

1. Silver Sands Motel & Beach Bungalows

Greenport

Sol

Rp7.000.585

Rp7.998.213 total

includes taxes & fees

21 Sept - 22 Sept

2. Cliffside Resort Condominiums

Greenport

Christine

Rp5.352.878

Rp7.695.504 total

includes taxes & fees

21 Sept - 22 Sept

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

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

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

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

3. North Fork Resort

Greenport

Lisa

Rp5.693.757

Rp6.505.116 total

includes taxes & fees

7 Sept - 8 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.

4. The Harbor Front Inn

Greenport

John

Rp4.895.426

Rp6.504.060 total

includes taxes & fees

8 Sept - 9 Sept

A cozy living room with a wooden floor, a round dining table, a sofa, and a bookshelf.

A cozy interior with a bar area, seating, and a fireplace.

A spacious room with a wooden bar area, shelves with books and decorative items, a patterned wall, and a large window.

A cozy interior with a wooden bench, a sofa, and a bar area.

5. Oyster Estate

Greenport

Jenny

Rp5.768.185

Rp7.267.625 total

includes taxes & fees

7 Sept - 8 Sept

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 storefront with a sign reading "THE SHOALS".

6. The Shoals Suites and Slips

Southold

Maria

Rp5.153.089

Rp6.330.430 total

includes taxes & fees

1 Sept - 2 Sept

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

A restaurant with a signboard listing its hours of operation.

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

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

7. Zey Hotel

Greenport

shaun

Rp3.588.502

Rp4.099.864 total

includes taxes & fees

30 Aug - 31 Aug

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

A seaside restaurant with outdoor seating, a deck, and a view of the ocean.

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.

8. Sound View Greenport

Greenport

Suzanne

Rp4.444.042

Rp6.596.003 total

includes taxes & fees

15 Sept - 16 Sept

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

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

A building with a red facade, a green tree in front, and a sign reading "OPENSPACE".

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

9. American Beech Hotel

Greenport

kerri

Rp6.570.947

Rp8.215.987 total

includes taxes & fees

8 Sept - 9 Sept

10. Shelter Island House

Shelter Island Heights

Dorothy

Rp5.604.266

Rp6.402.952 total

includes taxes & fees

31 Aug - 1 Sept

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

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

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

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

11. The Menhaden

Greenport

Lisa

Rp8.718.298

Rp10.669.600 total

includes taxes & fees

30 Aug - 31 Aug

A serene landscape with a calm body of water reflecting trees with autumn foliage.

A serene lakeside view with two Adirondack chairs facing a calm lake, surrounded by trees and a clear sky.

A conservatory with a dining table set for four, surrounded by wooden chairs, with a view of trees and a lawn.

A sign for 'House on Chase Creek' with a duck illustration.

12. House on Chase Creek

The Heights

Calvin

Rp4.354.050

Rp4.974.462 total

includes taxes & fees

8 Sept - 9 Sept

A spacious lobby with two sofas, a coffee table, and a flat-screen TV mounted on the wall.

A hotel lobby with a reception desk, two sofas, a coffee table, and a carpeted floor.

A dining area with tables and chairs, a clock on the wall, and a counter with food items.

An indoor swimming pool with a tiled floor, a pool ladder, and a ceiling with a grid pattern.

13. Quality Inn Old Saybrook - Westbrook

Old Saybrook

Theresa

Rp1.792.479

Rp2.061.351 total

includes taxes & fees

20 Sept - 21 Sept

A deck with outdoor seating, overlooking a body of water with a sunset view.

A restaurant with green booths, wooden chairs, and round tables.

A beach with rows of white lounge chairs and umbrellas, a wooden table with a drink, and a person walking along the shore.

14. The Pridwin Hotel

Shelter Island Heights

Anna

Rp9.512.798

Rp11.955.201 total

includes taxes & fees

15 Sept - 16 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 hotel lobby with a sofa, chairs, tables, and a large window.

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

15. Sag Harbor Inn

Sag Harbor

Christopher

Rp6.273.234

Rp7.167.169 total

includes taxes & fees

22 Sept - 23 Sept

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

A hotel room with two beds, a wooden bench, a desk, a mirror, and a patterned carpet.

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

16. Pier Blue Inn Old Saybrook - Essex

Saybrook Manor

Egor

Rp1.469.957

Rp1.690.406 total

includes taxes & fees

27 Aug - 28 Aug

A large hotel with a spacious outdoor patio area, multiple dining tables, and umbrellas.

A pool area with lounge chairs and umbrellas, a swimming pool, and a view of the sea.

An aerial view of a coastal resort with a large pool, multiple buildings, and a well-maintained lawn.

A formal dining room with multiple tables and chairs, large windows with a city view, and a decorative carpet.

17. Water's Edge Resort & Spa

Westbrook Center

Thomas

Rp4.130.765

Rp5.056.067 total

includes taxes & fees

20 Sept - 21 Sept

A bedroom with a bed, two rugs, a nightstand, a lamp, and a wall clock.

18. The Scranton Seahorse Inn

Madison Center

Krishna

Rp6.645.375

Rp7.376.366 total

includes taxes & fees

31 Aug - 1 Sept

A living room with a stone fireplace, grey sofas, and a coffee table.

A bedroom with a large bed, a nightstand, a dresser, and a robe rack.

A modern lobby with a round gold table, a large framed floral painting, and a wooden desk.

A dining room with a wooden table, six chairs, and a large window with curtains.

19. The Captain Stannard

Westbrook Center

Joseph

Rp4.145.278

Rp4.601.259 total

includes taxes & fees

27 Aug - 28 Aug

A parking lot with a building in the background.

A motel with a large parking lot and multiple rooms.

A hotel room with a large bed, two bedside tables, a desk with chairs, a TV, and a small table with flowers.

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

20. Clinton Motel

Clinton

Selena

Rp1.400.117

Rp1.610.135 total

includes taxes & fees

2 Sept - 3 Sept

View all properties

Save an average of 15% on thousands of hotels when you're signed in

Stay near popular Greenport West attractions

Kontokosta Winery

9.2/10 (48 reviews)

You can enjoy a tasting or tour at Kontokosta Winery during your travels to Greenport West. Wander the beautiful beaches in this family-friendly area.

See properties

East End Seaport Maritime Museum

9.0/10 (9 reviews)

You can spend time studying the exhibits at East End Seaport Maritime Museum in Greenport. Stroll along this family-friendly area's waterfront or simply enjoy its wineries.

See properties

Railroad Museum of Long Island

9.0/10 (7 reviews)

You can spend time exploring the galleries in Railroad Museum of Long Island during your travels in Greenport. Stroll along this family-friendly area's waterfront or simply enjoy its wineries.

See properties

Learn more about Greenport West

Explore attractions like Kontokosta Winery and 67 Steps Beach as you discover things to see and do in Greenport West.

See all hotels in Greenport West

Top Greenport West Hotel Reviews

The Chequit

10/10 Excellent

"pretty and clean!"

The Pridwin Hotel

8/10 Good

"lovely place. Had an issue with my AC and there was nobody around to fix it"

Sound View Greenport

8/10 Good

"The staff was very helpful and nice"

The Bentley Hotel Southampton

8/10 Good

"nice room for the price in season"

Cliffside Resort Condominiums

10/10 Excellent

"Perfect"

Saybrook Point Resort & Marina

10/10 Excellent

"The hotel did not disappoint. Staff was amazing. Loved the mini golf course and the pool and restaurant."

Pier Blue Inn Old Saybrook - Essex

10/10 Excellent

"Absolute gem really cool giant picnic table in the middle of the room, which is great for kids are just getting work done. The staff is absolutely wonderful. The view is gorgeous. If you stay on the backside of the hotel cannot recommend this place enough. What a surprise incredible bargain."

Budget Host East End

8/10 Good

"We came for the pool and enjoyed every minute of a few relaxing days poolside. Lush green grounds provided some shady picnic tables when it was time to get out of the sun. If you are looking for an inexpensive stay not far from the Hamptons or North Fork this is your place. Staff, especially, front desk, very nice, friendly and informative. Rooms had a mini fridge and comfy bed. A/C worked great. Try to get a poolside room. Hotel includes continental breakfast on weekends. Multiple excellent restaurant options nearby on Main Street. We would recommend Olga's for breakfast, offers outdoor/indoor seating. For dinner there is Cliff's Rendezvous steak house. Call and go when they offer their steak special night. Jerry and the Mermaid for seafood, also has outdoor/indoor seating by the water. There is Tweed's where you can try Buffalo. And a few hidden gems with great water views and outdoor seating -Turkuaz (Turkish food ) and Country Farm Kitchen. There is Atlantis Aquarium nearby, that also offers boat tours of the Peconic by day and booze cruises weekend eves. Suffolk Theatre offers well known artists in concert on the weekends. There are at least 4 breweries a short drive away and homemade ice cream at Snowflake and homemade chocolate at North Fork Chocolate & Eatery. Polish Town is nearby if you want Polish food try the Birchwood Restaurant or groceries from the town's deli's."

North Fork Resort

10/10 Excellent

"THERE WAS ONLY ONE THING. THE LAST MORNING THERE WAS NO HOT H2O HOWEVER THE PROBLEM WAS FIXED."

More cheap stays in Greenport West

Pier Blue Inn Old Saybrook - Essex

1430 Boston Post Rd Old Saybrook CT

Rp1.469.957

Rp1.690.406 total

27 Aug - 28 Aug

includes taxes & fees

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

Sleep Inn & Suites Niantic North

5 King Arthur Dr Niantic CT

Rp1.656.914

Rp1.905.451 total

15 Sept - 16 Sept

includes taxes & fees

Budget Host East End

30 Lake Avenue Riverhead NY

Rp2.215.125

Rp2.530.779 total

27 Aug - 28 Aug

includes taxes & fees

The Bentley Hotel Southampton

161 Hills Station Rd Southampton NY

Rp2.994.849

Rp3.864.640 total

7 Sept - 8 Sept

includes taxes & fees

9.6/10 Exceptional! (567 reviews)

Hampton's Vacation Inn

177 West Montauk Highway Hampton Bays NY

Rp3.588.908

Rp4.100.393 total

31 Aug - 1 Sept

includes taxes & fees

The Atlantic Hotel

1655 County Road 39 Southampton NY

Rp3.492.809

Rp4.433.559 total

8 Sept - 9 Sept

includes taxes & fees

7.2/10 Good! (1,009 reviews)

Frequently asked questions

What's the best place for a stay in Greenport West?

Based on our traveller data, North Fork Resort is one of the top choices for your stay. This cottage offers free parking and private patios. Other good options for your stay include Cliffside Resort Condominiums and Silver Sands Motel & Beach Bungalows. See all available top hotels, or vacation rentals in Greenport West.

If I need to cancel my hotel reservation in Greenport West, will I receive a refund?

Yes, you'll find most room reservations are refundable provided that you cancel before the hotel's cancellation deadline, which in most cases is within 24 or 48 hours of your arrival date. If your reservation is non-refundable, it may still be possible to cancel it and be given a refund within a 24-hour period of your booking. Filter your search by fully refundable to find flexible hotel deals in Greenport West.

What's the best dog-friendly place to stay in Greenport West?

Hotel Moraine is a top dog-friendly hotel, and offers a private beach along with LED TVs for its human guests. See more pet-friendly hotel accommodations in Greenport West.

What's the best accommodation option for a beach holiday in Greenport West?

Silver Sands Motel & Beach Bungalows is a top beachfront hotel with 3 restaurants and a full-service spa, and it's located close to Sunset Beach . Hotel Moraine is another good choice for your stay near the beach. See more stays near the beach in Greenport West.

What's the best place to stay if I'm looking to play golf in Greenport West?

Harbor Knoll Bed & Breakfast is a top B&B that has an adjacent golf course and features private pools. You can tee off at Island's End Golf and Country Club during your trip. See more golf hotels in Greenport West.

What are some hotels with pools in Greenport West?

Hotel Moraine is a top hotel with a seasonal outdoor pool, a private beach and free breakfast. View all hotels with pools in Greenport West.

What is the best spa hotel in Greenport West?

Silver Sands Motel & Beach Bungalows is a top spa hotel featuring 3 restaurants and a private beach. Spend an afternoon at The Salt Marsh Wellness Sanctuary where you'll find facials, body scrubs, and Swedish massages and more. See all spa hotels in Greenport West.

What's it like staying in Greenport West?

Visitors will definitely enjoy all that Greenport West has to offer. In Greenport West, there are 61 hotels and other accommodation options to choose from. Find out more about Greenport West.

What should I see while I'm in Greenport West?

Favourite places to visit include Kontokosta Winery, 67 Steps Beach and Safe Harbor Stirling. A couple of additional sights to add to your itinerary are Island's End Golf and Country Club and Norman E. Klipp Marine Park. Take a look at what more there is to see and do in Expedia's Greenport West guide.

What's the weather like in Greenport West?

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 Greenport West is 1452 mm.

Explore a world of travel with Expedia

More ways to book

Book Hotels in Greenport West on Expedia.com

Find hotels in Greenport West, NY from Rp1.406.161

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in Greenport West

Check prices for these dates

Filter by

Star rating

Guest rating

Our top choices for Greenport West hotels

1. Silver Sands Motel & Beach Bungalows

2. Cliffside Resort Condominiums

3. North Fork Resort

4. The Harbor Front Inn

5. Oyster Estate

6. The Shoals Suites and Slips

7. Zey Hotel

8. Sound View Greenport

9. American Beech Hotel

10. Shelter Island House

11. The Menhaden

12. House on Chase Creek

13. Quality Inn Old Saybrook - Westbrook

14. The Pridwin Hotel

15. Sag Harbor Inn

16. Pier Blue Inn Old Saybrook - Essex

17. Water's Edge Resort & Spa

18. The Scranton Seahorse Inn

19. The Captain Stannard

20. Clinton Motel

Stay near popular Greenport West attractions

Kontokosta Winery

East End Seaport Maritime Museum

Railroad Museum of Long Island

Learn more about Greenport West

Top Greenport West Hotel Reviews

The Chequit

The Pridwin Hotel

Sound View Greenport

The Bentley Hotel Southampton

Cliffside Resort Condominiums

Saybrook Point Resort & Marina

Pier Blue Inn Old Saybrook - Essex

Budget Host East End

North Fork Resort

More cheap stays in Greenport West

Pier Blue Inn Old Saybrook - Essex

Sleep Inn & Suites Niantic North

Budget Host East End

The Bentley Hotel Southampton

Hampton's Vacation Inn

The Atlantic Hotel

Frequently asked questions

Explore a world of travel with Expedia

Go further with the Expedia app