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Greenport Holiday Rentals

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Check prices for these dates

In two weeks
9 Jan - 11 Jan
In two months
20 Feb - 22 Feb
In three months
20 Mar - 22 Mar
In four months
17 Apr - 19 Apr

Our top choices for Greenport holiday rentals

Terrace/patio
American Beech in Greenport - Petite King Room 7

Holiday Home in Greenport

American Beech in Greenport - Petite King Room 7
9.0 out of 10, Wonderful, (4)
"We thoroughly enjoyed our stay!"
United States
Parent From The Heart, Inc. E.
The price is HK$1,547
HK$2,354 total
includes taxes & fees
5 Jan - 6 Jan 2026
American Beech in Greenport - Petite King Room 7
Fridge, microwave, stovetop, dishwasher
The Greenport Beach Cottage: 3 Min Walk to Beach, 1 mile to Town

Cottage in Greenport

The Greenport Beach Cottage: 3 Min Walk to Beach, 1 mile to Town
10.0 out of 10, Exceptional, (1)
"Wonderful house. Immaculate with all the provisions you can hope for. Perfect location and beautifully done!"
United States
Jeannette M.
The price is HK$2,138
HK$4,522 total
includes taxes & fees
8 Jan - 9 Jan 2026
The Greenport Beach Cottage: 3 Min Walk to Beach, 1 mile to Town
Fridge, microwave, oven, stovetop
Northfork Townhouse- walk to all/ newly renovated

Holiday Home in Greenport

Northfork Townhouse- walk to all/ newly renovated
9.6 out of 10, Exceptional, (9)
"What a wonderful spot! We could walk to town, and a beach. We loved our stay in Greenport! "
United States
Laura B.
The price is HK$2,489
HK$5,074 total
includes taxes & fees
29 Dec - 30 Dec
Northfork Townhouse- walk to all/ newly renovated
Fridge, microwave, oven, stovetop
Charming Northfork Townhouse- walk to all

Holiday Home in Greenport

Charming Northfork Townhouse- walk to all
10.0 out of 10, Exceptional, (5)
"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.
The price is HK$3,033
HK$5,785 total
includes taxes & fees
29 Dec - 30 Dec
Charming Northfork Townhouse- walk to all
Property grounds
Beachfront Greenport Villa

Holiday Home in Greenport

Beachfront Greenport Villa
9.6 out of 10, Exceptional, (10)
"We came for a girls trip and this property was perfect, had beautiful views and was close to everything...we very much enjoyed our stay!"
United States
Melissa F.
Beachfront Greenport Villa
Property grounds
American Beech in Greenport - Deluxe King 6

Holiday Home in Greenport

American Beech in Greenport - Deluxe King 6
2.0 out of 10, (1)
"Not as advertised. Very disappointed "
United States
Jeffrey
The price is HK$1,633
HK$2,461 total
includes taxes & fees
29 Dec - 30 Dec
American Beech in Greenport - Deluxe King 6
1 bedroom, free WiFi, bed sheets
Lakefront Boho Tiny House

Mobile Home in East Lyme

Lakefront Boho Tiny House
10.0 out of 10, Exceptional, (3)
"this place was amazing i would come again"
United States
Tatyanna R.
The price is HK$795
HK$1,749 total
includes taxes & fees
21 Jan - 22 Jan 2026
Lakefront Boho Tiny House
Exterior
Cozy Lakefront Tiny House

Mobile Home in East Lyme

Cozy Lakefront Tiny House
10.0 out of 10, Exceptional, (2)
"The bed and pillows were very comfortable. The outside space was very relaxing. Kevin’s place was perfect! We had questions and he replied back right away. We definitely want to go back. "
United States
Rebecca K.
The price is HK$796
HK$1,749 total
includes taxes & fees
21 Jan - 22 Jan 2026
Cozy Lakefront Tiny House
On the beach
The Stern at Soundview · Beach+Ocean+Sunrise

Apartment in Old Lyme

The Stern at Soundview · Beach+Ocean+Sunrise
2.0 star property
10.0 out of 10, Exceptional, (3)
"I had a great experience staying at The Stern! I enjoyed celebrating my weekend there! "
United States
Lylian
The price is HK$591
HK$1,503 total
includes taxes & fees
5 Jan - 6 Jan 2026
The Stern at Soundview · Beach+Ocean+Sunrise
Fridge, microwave, oven, stovetop
Luxurious-Modern feel w/ custom features - AC, short walk to the Beach and parks

Holiday Home in Waterford

Luxurious-Modern feel w/ custom features - AC, short walk to the Beach and parks
10.0 out of 10, Exceptional, (11)
"We had a nice stay. Kitchen well stocked and house was clean and comfortable."
United States
Elaine A.
The price is HK$742
HK$2,815 total
includes taxes & fees
5 Jan - 6 Jan 2026
Luxurious-Modern feel w/ custom features - AC, short walk to the Beach and parks
Smart TV
1-bedroom cottage with Grove Beach 🏖️ access.

Cottage in Clinton

1-bedroom cottage with Grove Beach 🏖️ access.
9.2 out of 10, Wonderful, (36)
"Very clean rustic cabin. The host was very accommodating. Fresh flowers and fruit were a nice touch from the host"
United States
Deb P.
The price is HK$672
HK$1,456 total
includes taxes & fees
6 Jan - 7 Jan 2026
1-bedroom cottage with Grove Beach 🏖️ access.
Beach
Seabreeze #4: Charming Cottage Footsteps to the Beach

Cottage in Hampton Bays

Seabreeze #4: Charming Cottage Footsteps to the Beach
8.8 out of 10, Excellent, (3)
"Great stay. Would stay again. "
United States
Weston B.
The price is HK$428
HK$3,536 total
includes taxes & fees
25 Jan - 26 Jan 2026
Seabreeze #4: Charming Cottage Footsteps to the Beach
Outdoor pool, a heated pool
NEW Luxury 7BR Water Mill Estate – Salt Pool, Sauna & Cold Plunge, Mins to Beach

Holiday Home in Water Mill

NEW Luxury 7BR Water Mill Estate – Salt Pool, Sauna & Cold Plunge, Mins to Beach
10.0 out of 10, Exceptional, (6)
"Highly recommend everything from start to finish went smoothly and it was a great experience!!"
United States
Stephanie M.
The price is HK$32,604
HK$57,482 total
includes taxes & fees
5 Jan - 6 Jan 2026
NEW Luxury 7BR Water Mill Estate – Salt Pool, Sauna & Cold Plunge, Mins to Beach
Property grounds
Rogers Lake House (87) · CT College+Beach+USCGA

Holiday Home in Old Lyme

Rogers Lake House (87) · CT College+Beach+USCGA
10.0 out of 10, Exceptional, (5)
"My family and I came for an 8 day event from a different state and wanted a clean and comfortable place to stay with our at the time 9 month old daughter. And this place did exactly that. Comfortable and CLEAN. The owner did a great job with details. Even when we had unexpected check out delays the owner showed human empathy. Great place!"
United States
Hemie J.
The price is HK$671
HK$3,131 total
includes taxes & fees
4 Jan - 5 Jan 2026
Rogers Lake House (87) · CT College+Beach+USCGA
Outdoor dining
Cozy Renovated Cottage with Game Room, WiFi, AC - Mins to Beach & Boardwalk

Cottage in Waterford

Cozy Renovated Cottage with Game Room, WiFi, AC - Mins to Beach & Boardwalk
2.0 star property
10.0 out of 10, Exceptional, (14)
"The property was amazing. The house was very clean and the game room was really fun. It was a very cute place and the backyard was perfect for sitting outside in the afternoon. The beds were really soft and comfortable as well."
United States
Jorie M.
The price is HK$1,167
HK$2,516 total
includes taxes & fees
4 Jan - 5 Jan 2026
Cozy Renovated Cottage with Game Room, WiFi, AC - Mins to Beach & Boardwalk
Private kitchen
Charming 2-bedroom house with WiFi, AC in lovely Waterford

Holiday Home in Waterford

Charming 2-bedroom house with WiFi, AC in lovely Waterford
10.0 out of 10, Exceptional, (1)
"The home was very clean and welcoming."
United States
Michelle M.
The price is HK$1,166
HK$2,867 total
includes taxes & fees
25 Jan - 26 Jan 2026
Charming 2-bedroom house with WiFi, AC in lovely Waterford
Fridge, microwave, oven, stovetop
The Bay Cottage · Rocky Neck Park, Beach & Niantic

Holiday Home in East Lyme

The Bay Cottage · Rocky Neck Park, Beach & Niantic
2.0 star property
9.0 out of 10, Wonderful, (4)
"This house suited our needs for a place to stay while attending a nearby family reunion. Communication and check in were great and the house is very comfortable (very nice mattresses, sheets, pillows)."
United States
Sarah G.
The price is HK$912
HK$2,839 total
includes taxes & fees
21 Jan - 22 Jan 2026
The Bay Cottage · Rocky Neck Park, Beach & Niantic
Microwave, oven, stovetop, dishwasher
Entire Vacation Home in Waterford Connecticut

Holiday Home in Waterford

Entire Vacation Home in Waterford Connecticut
2.0 star property
9.0 out of 10, Wonderful, (2)
"Located so perfectly close to everything we wanted to do on vacation. The house was so clean and comfortable. Communication with the owner was A++. The neighbors were even so friendly and waving/smiling. It felt as if we were home. If we come back to that area again we hope this place will be available. "
United States
Jennifer A.
The price is HK$1,477
HK$3,316 total
includes taxes & fees
25 Jan - 26 Jan 2026
Entire Vacation Home in Waterford Connecticut
Fridge, microwave, oven, stovetop
Blackberry: Private home with jacuzzi year-round

Holiday Home in East Hampton

Blackberry: Private home with jacuzzi year-round
9.0 out of 10, Wonderful, (4)
"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 HK$770
HK$7,098 total
includes taxes & fees
4 Jan - 5 Jan 2026
Blackberry: Private home with jacuzzi year-round
Front of property
Canoe Place Waterfront Residences

Condo in Hampton Bays

Canoe Place Waterfront Residences
4.0 star property
10.0 out of 10, Exceptional, (1)
The price is HK$15,513
HK$18,787 total
includes taxes & fees
28 Dec - 29 Dec
Canoe Place Waterfront Residences
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

Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

10/10 Excellent
"Room was clean though a bit rustic. Staff was very nice. No housekeeping but was able to collect all clean towels, etc. in the office. We were here for a funeral. Pier Blue Inn was close to funeral home, Catholic Church, and repast. Nice restaurants so close by! I’m glad I booked this place. Added a second night to avoid Friday night traffic back to our house in Rockland County NY."
Joseph 1-night trip
Posted 5 days ago
Pier Blue Inn Old Saybrook - Essex

Find out more about Greenport

Search for holiday rentals in Greenport on Expedia! You can easily find your home rentals, villas, holiday apartments in Greenport using one of the methods below:

  • View our selection of featured holiday rentals in Greenport
  • Use the map to find apartments and other holiday homes in the Greenport neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Greenport while they last

Look no further and take a look at our great range of rental properties in Greenport!

Frequently asked questions

Can I find a holiday rental in Greenport?

Yes, there are holiday rentals in Greenport close to Greenport Carousel, or you can select a more secluded option if you're looking for a relaxing stay. Nature enthusiasts will enjoy the beaches in Greenport. Make sure you have time to check out the waterfront and festivals during your trip.

What are some of the best holiday rentals that Greenport has to offer?

Cozy Bungalow Available Nearby Bridgehampton and Sag Harbor : This holiday home rental outside of Greenport offers an outdoor pool, a fireplace and a BBQ to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. It offers a patio, a garden and 1 hot tub so that you can immerse yourself in your holiday.

How many holiday rentals are there in Greenport?

With 97 Expedia holiday rentals, you're guaranteed to find just the right place for your Greenport stay.

What can I see and do in Greenport?

Enjoy the outdoors at 67 Steps Beach and Norman E. Klipp Marine Park, or simply take in cultural attractions like Railroad Museum of Long Island and East End Seaport Maritime Museum. While here, Greenport Carousel and Kontokosta Winery are other places worth a visit.

What are holiday rentals like in Greenport?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Greenport. Holiday rentals offer extras such as WiFi and washers and dryers to help you enjoy your stay. If you're concerned about a sanitised environment, a holiday rental can provide a sense of security away from shared hotel lifts and busy front desks while still allowing you the excitement and enjoyment of travel. You'll also find more space in a holiday rental than in a standard hotel, which makes a holiday rental a great choice for small groups.