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3-star hotel Check-in 15:00 · Check-out 10:00

The Cliffside Resort Condominiums

Stay at The Cliffside Resort Condominiums in Greenport, NY. Enjoy 2-bedroom condos, heated outdoor pool, beach access, and nearby vineyards. LGBTQ+ friendly.

61475 N Rd, Greenport, NY 11944, United States View on map
8.8/10
Very Good Based on 249 recent guest reviews
Free Wi-Fi Breakfast Free parking Accessible Outdoor pool
What recent guests emphasize

The Cliffside Resort Condominiums

Comfortable and well-located 2-bedroom condos offering private beach access, ocean views, and proximity to vineyards, ideal for leisurely escapes.

Guests often praise

  • Clean and spacious 2-bedroom condos with well-equipped kitchens and comfortable furnishings.
  • Private beach access and a heated outdoor pool provide relaxing outdoor options.
  • Beautiful views, especially of the Long Island Sound, noted as a highlight from many rooms.
  • Helpful and accommodating management, particularly appreciated during group bookings like weddings.
  • Convenient location near wineries and local attractions for touring visitors.

Worth knowing

  • Condo ownership varies; interior styles and furnishings differ between units.
  • Noise can carry between units due to thin walls; quiet hours start at 9pm to mitigate disturbance.
  • Check-in time is officially late (5pm); early check-in is not always guaranteed or responsive.
  • Bugs can be an issue when spending time on balconies, so bringing insect repellent is recommended.
  • Some guests report inconsistent communication from management regarding access codes and requests.

Best for

  • Families or groups seeking spacious accommodation with 2 bedrooms and multiple bathrooms.
  • Travelers wanting direct private beach access combined with pool amenities.
  • Visitors planning to explore nearby wineries and enjoy local farm-to-table dining experiences.
  • LGBTQ+ friendly travelers looking for a welcoming place on the North Fork peninsula.
  • Guests attending local events like weddings who appreciate group booking support.
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About this property

Welcome to The Cliffside Resort Condominiums

The Cliffside Resort Condominiums offer unpretentious two-bedroom condos located on a largely rural peninsula in Greenport, NY. Some units provide ocean views of the Long Island Sound, complemented by access to a private beach and a heated outdoor pool. The individually owned condos vary in décor and layout, reflecting a range of styles and views, which can influence guest experiences.

The accommodations include kitchens and multiple bathrooms, making the property a practical choice for families or small groups. Guests have noted the cleanliness and comfortable furnishings, though the building's concrete construction means neighboring noise can sometimes be noticeable. Quiet hours from 9pm to 6am help maintain a restful atmosphere.

Located at 61475 N Rd, the resort provides easy access to several nearby wineries such as Kontokosta Winery and Pindar Vineyards, ideal for visitors interested in exploring local vineyards and farm-to-table dining options. The setting appeals to those seeking a relaxed stay with a seaside backdrop while remaining within reach of the Long Island Aquarium and regional attractions.

Check-in officially begins at 3:00 PM with check-out by 10:00 AM, although some guests have reported variability in early check-in availability. The resort is LGBTQ+ friendly, which adds to its inclusive atmosphere. Nearby airports include Long Island MacArthur Airport and Bradley International Airport, reachable by car in roughly one to two and a half hours.

Summary compiled by GoHotelly editors from verified guest reviews, partner descriptions and editorial notes.
Facilities & essentials

What's on-site and what you should know before you arrive

The short version: what's available day-to-day, and the key practical details most travelers search for.

Most popular facilities

Free Wi-Fi
Breakfast
Free parking
Accessible
Outdoor pool
Air-conditioned
Kid-friendly
Kitchen in all rooms
Smoke-free

Not available at this property

Pet-friendly
Restaurant
Airport shuttle
Fitness center
Verified guest reviews

What recent guests are actually saying

Reviews from travelers who stayed here in the last 12 months, grouped to help you spot the pattern quickly.

MT
M T Apr 18, 2026
10

Came here with my husband and 3yr old. Check in was simple and our condo was so clean. From what I understand, each condo on the resort is individually owned but are all rented out by the same management company. So what your room looks like will be totally different then the condo next to you. I loved that the beach is located right behind the resort and it’s private. Walls are thin but there are quiet hours from 9pm-6am, so it worked out great for us. I was able to get an early check in (10am!) instead of the stated time, 5pm, which I felt was super late, especially with a young child. Our view of the LI Sound was spectacular from our room. Overall we had a great time and hope to be back next year.

JR
Jenn Reynolds Apr 01, 2026
8.0

These condos are in the most perfect spot to spend a few days touring local wineries. Very clean, all amenities provided (extra bath towels, bed linens, plenty of kitchen necessities). The grounds are beautiful and access to the private beach with chairs was a huge plus. We did have some issues with check-in: 5pm guarantee check-in is a little late. We asked several times to have early access but never heard from management. Then we were never sent code for check-in until we called at 5:05 pm. A bit of a frustrating process. Overall, would stay again.

MZ
Mike Z Mar 12, 2026
8.0

Great location and affordable for North Fork price. Plenty of space for a couple in 2 bedroom unit. Because it was mid week in early September, we were lucky to have few neighbors around. Otherwise it could be much more noisy, simply having your neighbor going downstairs wakes you up at night as if someone is walking up right next to you in your room. Renting concrete unit directly from Condo management is recommended since you would get exactly what you want. Water edge units have best water views. Getting a good deal from Booking or Expedia may mean getting units closer to the road noise with partial water views. Beach is very picturesque, just don’t count much on swimming here: many small and medium size rocks under the water surface makes it treacherous to enter.

M!
Mathuaerknedam ! Mar 09, 2026
10

I've stayed in three units. They've been similar but different, and all have been a good experience. The views vary greatly.

LMD
Lisa Marie Dantino Mar 02, 2026
10

Great spot ! Our condo was very clean , cute and super comfortable. It was more those needed . Loved the pool and private beach too . Family wedding nearby but would stay here again .

HS
Heather S Feb 11, 2026
10

We used Cliffside for our wedding room block, and they were great to work with—super helpful and even assisted with distributing our welcome bags. It’s an affordable but high-quality option for out-of-town guests, right on the water with beautiful views and a pool. All of our guests had a great stay!

AH
Anne-Marie Hodne Jan 27, 2026
10

Stayed here in November for a family wedding nearby. Even though we couldn't enjoy the beach the view is absolutely breathtaking! We had a two bedroom and it was amazing with a little kitchen. It was decorated beautifully and roomy for us to get together and hangout with other family staying there! I would love to come in the summer and enjoy all this place has to offer!!

TL
Twi Light Jan 22, 2026
10

So perfect, right on the beach. Just one night there is enough to recharge you. I think it’s the salty air. Bring bug spray if you want to hang out on your balcony. 2 bathrooms are a huge plus. Kids loved it.

Location & neighborhood

Where you'll find The Cliffside Resort Condominiums

Greenport, New York, USA

Largely rural peninsula known for vineyards, farmstands, locavore dining & the Long Island Aquarium.

  • Greenport 48 min Walk
  • Southold 1 hr 18 Walk
  • Bradley International Airport 2 hr 37 Car
  • Long Island MacArthur Airport 1 hr 4 Car · 2 hr 31 Transit
  • Tweed New Haven Airport 2 hr 19 Car
Things to do nearby

Worth the walk or a quick ride

Curated spots travelers usually pair with a stay in New York. Distances are rough real-world times, not straight-line.

Kontokosta Winery 532 reviews

Kontokosta Winery

825 North Rd, Greenport, NY 11944, United States

3.8 · Winery
Sparkling Pointe Vineyards & Winery 333 reviews

Sparkling Pointe Vineyards & Winery

39750 County Rd 48, Southold, NY 11971, United States

4.5 · Winery
Pindar Vineyards 413 reviews

Pindar Vineyards

37645 NY-25, Peconic, NY 11958, United States

4.5 · Vineyard
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