Greenport Holiday Rentals

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Check prices for these dates

In two weeks
1 May - 3 May
In two months
12 Jun - 14 Jun
In three months
10 Jul - 12 Jul
In four months
7 Aug - 9 Aug

Our top choices for Greenport holiday rentals

Free WiFi, bed sheets

North Fork Cottages & RV Resort

North Fork Cottages & RV Resort
3.0 star property
Greenport
8.6 out of 10, Excellent, (11 reviews)
"great place to stay, clean and quiet....loved it"
United States
Darlin
The price is HK$1,457
HK$1,664 total
includes taxes & fees
28 Apr - 29 Apr
North Fork Cottages & RV Resort
Terrace/patio

Cliffside Resort Condominiums

Cliffside Resort Condominiums
3.0 star property
Greenport
9.0 out of 10, Wonderful, (249 reviews)
"Great stay - beautiful place"
United States
Rebecca
The price is HK$1,357
HK$1,890 total
includes taxes & fees
27 Apr - 28 Apr
Cliffside Resort Condominiums
Terrace/patio

American Beech in Greenport - Petite King Room 7

American Beech in Greenport - Petite King Room 7
Greenport
9.2 out of 10, Wonderful, (5 reviews)
"We thoroughly enjoyed our stay!"
United States
Parent From The Heart, Inc. E.
The price is HK$1,323
HK$2,076 total
includes taxes & fees
27 Apr - 28 Apr
American Beech in Greenport - Petite King Room 7
Dining

Northfork Townhouse walk to all

Northfork Townhouse walk to all
Greenport
10.0 out of 10, Exceptional, (5 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.
The price is HK$2,326
HK$4,840 total
includes taxes & fees
19 Apr - 20 Apr
Northfork Townhouse walk to all
Smart TV, fireplace

Renovated Townhouse walk to all

Renovated Townhouse walk to all
Greenport
9.6 out of 10, Exceptional, (10 reviews)
"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$2,503
HK$5,070 total
includes taxes & fees
16 Apr - 17 Apr
Renovated Townhouse walk to all
Smart TV, books

The Greenport Beach Cottage: 3 Min Walk to Beach, 1 mile to Town

The Greenport Beach Cottage: 3 Min Walk to Beach, 1 mile to Town
Greenport
10.0 out of 10, Exceptional, (1 review)
"Wonderful house. Immaculate with all the provisions you can hope for. Perfect location and beautifully done!"
United States
Jeannette M.
The price is HK$2,546
HK$5,370 total
includes taxes & fees
22 Apr - 23 Apr
The Greenport Beach Cottage: 3 Min Walk to Beach, 1 mile to Town
Property grounds

Beachfront Greenport Villa

Beachfront Greenport Villa
Greenport
9.8 out of 10, Exceptional, (11 reviews)
"Super location - just near The beautiful village of Greenport with a sweeping view of the bay, A very happy house - super Clean, and we had everything that we needed. Meghan was a wonderful host, and answered us quickly with any question that we had. I loved the NorthFork and this home was the perfect place to stay!"
United States
Carine J.
The price is HK$4,724
HK$8,314 total
includes taxes & fees
16 Apr - 17 Apr
Beachfront Greenport Villa
Property grounds

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 HK$1,558
HK$2,380 total
includes taxes & fees
16 Apr - 17 Apr
American Beech in Greenport - Deluxe King 6
Interior

Floating Nest on Private River. Serene Views & Ultimate Relaxation

Floating Nest on Private River. Serene Views & Ultimate Relaxation
Old Lyme
The price is HK$1,762
HK$2,941 total
includes taxes & fees
22 Apr - 23 Apr
Floating Nest on Private River. Serene Views & Ultimate Relaxation
Exterior

Cozy Lakefront Tiny House

Cozy Lakefront Tiny House
East Lyme
10.0 out of 10, Exceptional, (3 reviews)
"It was a peaceful and quant "
United States
Patricia M.
The price is HK$1,034
HK$2,084 total
includes taxes & fees
16 Apr - 17 Apr
Cozy Lakefront Tiny House
1 bedroom, free WiFi, bed sheets

Lakefront Boho Tiny House

Lakefront Boho Tiny House
East Lyme
10.0 out of 10, Exceptional, (4 reviews)
"Every thing was amazing "
United States
Annaliaa C.
The price is HK$827
HK$1,815 total
includes taxes & fees
16 Apr - 17 Apr
Lakefront Boho Tiny House
Individually decorated, individually furnished, iron/ironing board

Windward Shores Ocean Resort

Windward Shores Ocean Resort
3.0 star property
Napeague
8.8 out of 10, Excellent, (310 reviews)
"Amazing stay! Place was perfect and staff was so friendly."
United States
Heather
The price is HK$1,161
HK$1,540 total
includes taxes & fees
20 Apr - 21 Apr
Windward Shores Ocean Resort
Beach nearby

The Stern at Soundview · Beach+Ocean+Sunrise

The Stern at Soundview · Beach+Ocean+Sunrise
Old Lyme
10.0 out of 10, Exceptional, (3 reviews)
"I had a great experience staying at The Stern! I enjoyed celebrating my weekend there! "
United States
Lylian
The price is HK$1,060
HK$2,109 total
includes taxes & fees
4 May - 5 May
The Stern at Soundview · Beach+Ocean+Sunrise
Interior

Cozy Renovated Cottage with Game Room, WiFi, AC - Mins to Beach & Boardwalk

Cozy Renovated Cottage with Game Room, WiFi, AC - Mins to Beach & Boardwalk
Waterford
10.0 out of 10, Exceptional, (21 reviews)
"The home was exactly as described and well appointed, yet charming and cozy. Great location near Niantic, Stonington and Mystic. Perfect for a sister’s birthday getaway. "
United States
Dianne B.
The price is HK$1,214
HK$2,587 total
includes taxes & fees
22 Apr - 23 Apr
Cozy Renovated Cottage with Game Room, WiFi, AC - Mins to Beach & Boardwalk
Private kitchen

Charming 2-bedroom house with WiFi, AC in lovely Waterford

Charming 2-bedroom house with WiFi, AC in lovely Waterford
Waterford
10.0 out of 10, Exceptional, (1 review)
"The home was very clean and welcoming."
United States
Michelle M.
The price is HK$1,175
HK$2,888 total
includes taxes & fees
23 Apr - 24 Apr
Charming 2-bedroom house with WiFi, AC in lovely Waterford
Individually decorated, individually furnished, free WiFi, bed sheets

Driftwood Resort

Driftwood Resort
3.5 star property
Montauk
9.0 out of 10, Wonderful, (236 reviews)
"Great place to stay for small family "
United States
DongHo
The price is HK$1,395
HK$1,849 total
includes taxes & fees
4 May - 5 May
Driftwood Resort
1 bedroom, desk, iron/ironing board, travel cot

1-bedroom cottage with Grove Beach 🏖️ access.

1-bedroom cottage with Grove Beach 🏖️ access.
Clinton
9.6 out of 10, Exceptional, (40 reviews)
"Many local restaurants near by. Christy's for breakfast was very good. "
United States
Benjamin H.
The price is HK$649
HK$1,434 total
includes taxes & fees
23 Apr - 24 Apr
1-bedroom cottage with Grove Beach 🏖️ access.
TV

#35 - Beautiful 3 BR Beach Haven

#35 - Beautiful 3 BR Beach Haven
Old Lyme
The price is HK$1,458
HK$3,440 total
includes taxes & fees
21 Apr - 22 Apr
#35 - Beautiful 3 BR Beach Haven
Microwave, oven, stovetop, dishwasher

Entire Vacation Home in Waterford Connecticut

Entire Vacation Home in Waterford Connecticut
Waterford
8.8 out of 10, Excellent, (3 reviews)
"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$1,488
HK$3,340 total
includes taxes & fees
23 Apr - 24 Apr
Entire Vacation Home in Waterford Connecticut
Smart TV, fireplace, books

Luxurious-Modern feel w/ custom features - AC, short walk to the Beach and parks

Luxurious-Modern feel w/ custom features - AC, short walk to the Beach and parks
Waterford
10.0 out of 10, Exceptional, (11 reviews)
"Beautiful home, we enjoyed our stay. Clean, modern and had everything there we needed. Host was very attentive to our needs and was quick to respond. Looking forward to spend another long weekend there. Highly recommend!"
United States
Brenda W.
The price is HK$1,656
HK$3,986 total
includes taxes & fees
12 May - 13 May
Luxurious-Modern feel w/ custom features - AC, short walk to the Beach and parks
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

The Sagaponack

The Sagaponack

10/10 Excellent
"Convenient "
Nancy 2-night trip
Posted 18 hours ago
The Sagaponack

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
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  • 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?

NOFO ESCAPE relax-swim-enjoy. Bachelorettes-Weddings-Family vacation: This highly rated holiday home rental in Greenport is located near skiing, and has an outdoor pool, a patio and a BBQ to put you at ease in your new surroundings. It has 6 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Make the most of garden in this rental home to help you unwind.

How many holiday rentals are there in Greenport?

With 93 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.