An aerial view of a harbor with boats, a ship, and a dock extending into the water.

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Check prices for these dates

In two weeks
2 Oct - 4 Oct
In two months
13 Nov - 15 Nov
In three months
11 Dec - 13 Dec
In four months
8 Jan - 10 Jan

Our top choices for Greenport vacation homes

Sun loungers, beach towels

1. Blue Bay Dream w/ Seasonal Outdoor Jacuzzi, Cabana + Office

Blue Bay Dream w/ Seasonal Outdoor Jacuzzi, Cabana + Office
Pipes Cove
10.0 out of 10, Exceptional, (31 reviews)
"We had a great stay!! "
United States
Callie E.
The price is AED 645
AED 1,563 total
includes taxes & fees
28 Sep - 29 Sep
Blue Bay Dream w/ Seasonal Outdoor Jacuzzi, Cabana + Office
Sun loungers, beach towels

2. Aqua Vista

Aqua Vista
Pipes Cove
10.0 out of 10, Exceptional, (45 reviews)
"Great location and nice spot."
United States
Kerri L.
The price is AED 533
AED 1,125 total
includes taxes & fees
7 Oct - 8 Oct
Aqua Vista
Terrace/patio

3. American Beech in Greenport - Petite King Room 7

American Beech in Greenport - Petite King Room 7
Greenport
9.4 out of 10, Exceptional, (6 reviews)
"Great place! So nice."
United States
Paul F.
The price is AED 804
AED 1,221 total
includes taxes & fees
17 Sep - 18 Sep
American Beech in Greenport - Petite King Room 7
Sun loungers, beach towels

4. The SandPiper

The SandPiper
Pipes Cove
9.6 out of 10, Exceptional, (52 reviews)
"Very wonderful location so close to the train station will come back soon"
United States
Julian V.
The price is AED 645
AED 1,269 total
includes taxes & fees
28 Sep - 29 Sep
The SandPiper
Beach

5. Beach Block Hideaway

Beach Block Hideaway
Pipes Cove
10.0 out of 10, Exceptional, (10 reviews)
"Beautiful 2 bedroom close to town. The house is well kept we would rent here again."
United States
Teresa C.
The price is AED 716
AED 1,536 total
includes taxes & fees
17 Sep - 18 Sep
Beach Block Hideaway
Smart TV, fireplace

6. Renovated Townhouse walk to all

Renovated Townhouse walk to all
Greenport
9.6 out of 10, Exceptional, (14 reviews)
"We had a wonderful girls weekend in Greenport. The house was perfect for the three of us. Loved the location. We didn’t get to use the back area due to the weather, but it looked so inviting. Next time!"
United States
Melissa A.
The price is AED 1,388
AED 2,656 total
includes taxes & fees
5 Oct - 6 Oct
Renovated Townhouse walk to all
Dining

7. Northfork Townhouse walk to all

Northfork Townhouse walk to all
Greenport
9.4 out of 10, Exceptional, (8 reviews)
"Great property located in a quiet neighborhood within walking distance to all in Greenport. The townhouse was clean and kitchen was well- appointed with off the street parking. Playground up the street was an added bonus with a old school merry-go-round! Would definitely stay again"
United States
Beth R.
Northfork Townhouse walk to all
Property grounds

8. Beachfront Greenport Villa

Beachfront Greenport Villa
Greenport
9.8 out of 10, Exceptional, (13 reviews)
"Beautiful home, great views and host!"
United States
Kate R.
Beachfront Greenport Villa
Property grounds

9. American Beech in Greenport - Deluxe King 6

American Beech in Greenport - Deluxe King 6
Greenport
2.0 out of 10, (1 review)
"Not as advertised. Very disappointed "
United States
Jeffrey
The price is AED 915
AED 1,364 total
includes taxes & fees
17 Sep - 18 Sep
American Beech in Greenport - Deluxe King 6
Interior

10. Adorable Cottage, 5 min walk to water & town

Adorable Cottage, 5 min walk to water & town
Westbrook Center
9.2 out of 10, Wonderful, (17 reviews)
"Very nice small place to stay by the beach and close to great coffee shop. "
United States
Donovan V.
The price is AED 608
AED 1,732 total
includes taxes & fees
17 Sep - 18 Sep
Adorable Cottage, 5 min walk to water & town
Coffee/tea maker, fridge, microwave, oven

11. Work and Play Special! Extended Stay Discount

Work and Play Special! Extended Stay Discount
Shelter Island
10.0 out of 10, Exceptional, (59 reviews)
"Beautiful property. Everything so clean and welcoming. Slept so great in the comfortable beds. Pool is awesome. Everyone especially loved the outdoor shower"
United States
Kathleen Andrews K.
The price is AED 2,648
AED 4,893 total
includes taxes & fees
21 Sep - 22 Sep
Work and Play Special! Extended Stay Discount
Beach nearby

12. Insta-worthy Couples Retreat: Perfect for romantic getaway!

Insta-worthy Couples Retreat: Perfect for romantic getaway!
Old Lyme
9.4 out of 10, Exceptional, (60 reviews)
"A beautiful little beach cottage that was just what the doctor ordered. A great place to unwind and take in the sea air."
United States
Emily M.
Insta-worthy Couples Retreat: Perfect for romantic getaway!
Dining

13. BlackBerry Private home with jacuzzi yearlong

BlackBerry Private home with jacuzzi yearlong
East Hampton
9.2 out of 10, Wonderful, (7 reviews)
"We had a great time staying here. The home is well worn and there are some fixtures that should be replaced "
United States
Suzanne R.
The price is AED 801
AED 5,341 total
includes taxes & fees
20 Sep - 21 Sep
BlackBerry Private home with jacuzzi yearlong
Beach

14. Beachside Bliss w/ Game Room, Gym & Golf Green

Beachside Bliss w/ Game Room, Gym & Golf Green
Westbrook
10.0 out of 10, Exceptional, (2 reviews)
"Perfect house for 6 guests. Loved that it was close to the beach."
United States
Shannon G.
The price is AED 945
AED 2,432 total
includes taxes & fees
23 Sep - 24 Sep
Beachside Bliss w/ Game Room, Gym & Golf Green
Outdoor pool, a heated pool

15. Designer Sag Harbor Home w/ Pool + Fire Pit + Yard

Designer Sag Harbor Home w/ Pool + Fire Pit + Yard
Sag Harbor
10.0 out of 10, Exceptional, (1 review)
"excellent and convenient stay!! located close into town, perfect for the small family group I was traveling with. home was very clean, cozy, had everything we needed! backyard with pool was a dream, beautifully landscaped, plenty of seating, very clean pool, would stay again! thanks for a delightful escape!"
United States
maria m.
Designer Sag Harbor Home w/ Pool + Fire Pit + Yard
Smart TV, fireplace, books, offices

16. Great Hammcock Getaway, cozy home, hot tub, fire pit, beaches nearby.

Great Hammcock Getaway, cozy home, hot tub, fire pit, beaches nearby.
Old Saybrook
10.0 out of 10, Exceptional, (13 reviews)
"Very clean & comfortable home, great host & location! "
United States
Becky W.
Great Hammcock Getaway, cozy home, hot tub, fire pit, beaches nearby.
Property grounds

17. Bridgehampton, NY cottage near Sag Harbor, NY. Elegant and modern.

Bridgehampton, NY cottage near Sag Harbor, NY. Elegant and modern.
Bridgehampton
10.0 out of 10, Exceptional, (1 review)
"We thoroughly enjoyed our stay. The property was exactly as described, very well maintained, comfortable, and welcoming. The location is ideal for exploring the Hamptons, with convenient access to Sag Harbor, East Hampton, and Bridgehampton. We would definitely recommend this property to others visiting the area."
United States
Robert R.
The price is AED 1,221
AED 2,386 total
includes taxes & fees
1 Oct - 2 Oct
Bridgehampton, NY cottage near Sag Harbor, NY. Elegant and modern.
Interior

18. Authentic 1795 Historic Homestead w/ Private Grounds for Gatherings and Retreats

Authentic 1795 Historic Homestead w/ Private Grounds for Gatherings and Retreats
Saybrook Manor
9.8 out of 10, Exceptional, (140 reviews)
"This house comfortably sleeps a lot of guests and has a well equipped kitchen. Everything was very clean. The hosts were very easy to communicate with and very helpful."
United States
Alexis L.
The price is AED 1,058
AED 2,067 total
includes taxes & fees
21 Sep - 22 Sep
Authentic 1795 Historic Homestead w/ Private Grounds for Gatherings and Retreats
Interior

19. Perfection in Sag Harbor : 5 Bedrooms with saltwater pool - walk to Beach

Perfection in Sag Harbor : 5 Bedrooms with saltwater pool - walk to Beach
Sag Harbor
10.0 out of 10, Exceptional, (5 reviews)
"Beautiful home !"
United States
Nadja B.
The price is AED 2,755
AED 5,036 total
includes taxes & fees
17 Sep - 18 Sep
Perfection in Sag Harbor : 5 Bedrooms with saltwater pool - walk to Beach
Private kitchen

20. Spacious & Modern 5-bedroom in Sag Harbor, walk to bay

Spacious & Modern 5-bedroom in Sag Harbor, walk to bay
Sag Harbor
The price is AED 4,793
AED 6,777 total
includes taxes & fees
17 Sep - 18 Sep
Spacious & Modern 5-bedroom in Sag Harbor, walk to bay
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Greenport Hotel Reviews

Water's Edge Resort & Spa

Water's Edge Resort & Spa

10/10 Excellent
"It was the perfect getaway- close to home. The property was beautiful, clean and peaceful. The beach could have been cleaner, but overall we loved our stay. The food served in their variety of restaurants was delicious. We will definitely return."
Jennifer 3-night trip
Posted 7 hours ago
Water's Edge Resort & Spa