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Greenport Holiday Rentals

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Check prices for these dates

In two weeks
24 Oct - 26 Oct
In one month
7 Nov - 9 Nov
In two months
5 Dec - 7 Dec
In three months
2 Jan - 4 Jan

Holiday Rentals in Greenport

Cliffside Resort Condominiums
Beach nearby

Cliffside Resort Condominiums

3.0 star property
9.0 out of 10, Wonderful, (241)
"Great view of the water and nice amenities with the beach and pool."
The price is HK$1,742
HK$2,329 total
includes taxes & fees
2 Nov - 3 Nov
Cliffside Resort Condominiums
NEW VICTORIAN GEM IN GREENPORT
Outdoor pool

NEW VICTORIAN GEM IN GREENPORT

10.0 out of 10, Exceptional, (11)
"We had a great stay! Clean property and well maintained. The hosts were very friendly, helpful and welcoming. Would go back and recommend to others!"
NEW VICTORIAN GEM IN GREENPORT
Windward Shores Ocean Resort
Living area

Windward Shores Ocean Resort

3.0 star property
8.8 out of 10, Excellent, (296)
"Very nice & affordable "
Windward Shores Ocean Resort
Driftwood Resort
Private kitchen

Driftwood Resort

3.5 star property
9.0 out of 10, Wonderful, (235)
"Great place to stay for small family "
The price is HK$1,028
HK$1,428 total
includes taxes & fees
14 Oct - 15 Oct
Driftwood Resort
Historic Inn on a 100 Acre Organic Farm with Lake, Private Pool & Gourmet Food
Outdoor pool

Historic Inn on a 100 Acre Organic Farm with Lake, Private Pool & Gourmet Food

10.0 out of 10, Exceptional, (103)
"Our multigenerational long weekend loved our stay. Fab manager. House so well kitted out. "
Historic Inn on a 100 Acre Organic Farm with Lake, Private Pool & Gourmet Food
Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping
Outdoor pool, a heated pool

Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping

9.8 out of 10, Exceptional, (32)
"Our trip was amazing, the pool was in perfect condition and the house had everything we needed. Would definitely stay here again!!"
Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping
Cozy Bungalow Available Nearby Bridgehampton and Sag Harbor
Outdoor pool, a heated pool

Cozy Bungalow Available Nearby Bridgehampton and Sag Harbor

2.5 star property
9.6 out of 10, Exceptional, (15)
"We had a one-night stay at this location. It was perfect for us from many perspectives and we enjoyed staying there. Very nice place!Thanks! "
The price is HK$1,366
HK$3,143 total
includes taxes & fees
12 Oct - 13 Oct
Cozy Bungalow Available Nearby Bridgehampton and Sag Harbor
Cozy Renovated Cottage with Game Room, WiFi, AC - Mins to Beach & Boardwalk
Outdoor dining

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

2.0 star property
10.0 out of 10, Exceptional, (9)
"This listing was perfect for our stay. Close to the water, beautifully styled, and plenty of items to cook and clean.Thanks so much, Erin!"
The price is HK$1,206
HK$2,570 total
includes taxes & fees
5 Nov - 6 Nov
Cozy Renovated Cottage with Game Room, WiFi, AC - Mins to Beach & Boardwalk
COZY Maple Tree Cabin - Situated on 6 private acres- Enjoy nature
Exterior

COZY Maple Tree Cabin - Situated on 6 private acres- Enjoy nature

10.0 out of 10, Exceptional, (47)
"Amazing property, we loved everything about it, highly recommended, will stay again "
The price is HK$3,113
HK$5,837 total
includes taxes & fees
3 Nov - 4 Nov
COZY Maple Tree Cabin - Situated on 6 private acres- Enjoy nature
Shoreline Oasis
Exterior

Shoreline Oasis

9.2 out of 10, Wonderful, (7)
"A very comfortable, clean, convenient apartment close to the shore and all the natural attractions near Madison and Clinton. We particularly appreciated that the owners quickly replaced the bedroom air conditioner when it broke. Great hosts!"
The price is HK$1,393
HK$2,028 total
includes taxes & fees
11 Oct - 12 Oct
Shoreline Oasis
Rustic Lakeside Cabin at White Gate Farm
Interior

Rustic Lakeside Cabin at White Gate Farm

10.0 out of 10, Exceptional, (120)
"Beautiful cabin on the lake. Will definitely stay again. Easy check-in easy check out. You wont regret staying here!"
Rustic Lakeside Cabin at White Gate Farm
Cozy houseboat escape surrounded by breath taking views across from Rocky Neck!
Terrace/patio

Cozy houseboat escape surrounded by breath taking views across from Rocky Neck!

10.0 out of 10, Exceptional, (14)
"Such a fun, beautiful and unique stay. Would love to stay again!"
The price is HK$1,362
HK$2,344 total
includes taxes & fees
8 Oct - 9 Oct
Cozy houseboat escape surrounded by breath taking views across from Rocky Neck!
Perfect Shoreline Stay – Walk to Beach, Dine, Shop & Play!
Beach

Perfect Shoreline Stay – Walk to Beach, Dine, Shop & Play!

2.0 star property
10.0 out of 10, Exceptional, (7)
"We enjoyed our time in Westbrook! Hosts were more than accomodating and helpful throughout our stay - thank you! House is cute, the perfect size for a small group, and in a good location (walking distance to many shops and restaurants). Private beach access is easy to get to (beach area is small, but it worked!)"
Perfect Shoreline Stay – Walk to Beach, Dine, Shop & Play!
Fairy Tale Guest Cottage in Magic Garden by Pool
Property grounds

Fairy Tale Guest Cottage in Magic Garden by Pool

10.0 out of 10, Exceptional, (75)
"We had an AMAZING stay at Eunyoung and Mark's magical cottage. The property was exactly as described. Eunyoung and Mark are delightful people. Tranquil, quiet, peaceful. "
Fairy Tale Guest Cottage in Magic Garden by Pool
Beautiful Waterfront, Sun, Sky, Hot Tub Open Year Round & Gameroom!
Terrace/patio

Beautiful Waterfront, Sun, Sky, Hot Tub Open Year Round & Gameroom!

9.6 out of 10, Exceptional, (137)
"Perfect property to hangout and stay entertained for hours"
Beautiful Waterfront, Sun, Sky, Hot Tub Open Year Round & Gameroom!
The Stern at Soundview · Beach+Ocean+Sunrise
On the beach

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! "
The price is HK$401
HK$1,286 total
includes taxes & fees
8 Oct - 9 Oct
The Stern at Soundview · Beach+Ocean+Sunrise
Mid-Century Modern Beach House: Private Beach Access, Pool, and Chef’s Kitchen
Smart TV, fireplace, stereo

Mid-Century Modern Beach House: Private Beach Access, Pool, and Chef’s Kitchen

10.0 out of 10, Exceptional, (95)
"We loved our stay - it was nice to be a short walk away from the bay and the pool was great. The home was very clean and comfortable."
Mid-Century Modern Beach House: Private Beach Access, Pool, and Chef’s Kitchen
Large Charming Historic House close to Beaches
Fridge, microwave, oven, dishwasher

Large Charming Historic House close to Beaches

9.8 out of 10, Exceptional, (31)
"Great place and location. There was 8 of us and plenty of space and beds!"
Large Charming Historic House close to Beaches
Iconic Bow House, an Oasis in the Heart of the Niantic Bay Marina
Fridge, microwave, oven, stovetop

Iconic Bow House, an Oasis in the Heart of the Niantic Bay Marina

10.0 out of 10, Exceptional, (5)
"This home was amazing! We stayed here for most of the week so we could participate in USCGA graduation activities. The home had everything we could possibly need (including a diffuser for my curly-haired daughter). The labels in the kitchen made it super easy to find and put things away. We enjoyed chatting at the fire pit and warming up in the hot tub after a very chilly graduation day. Would absolutely stay here again."
Iconic Bow House, an Oasis in the Heart of the Niantic Bay Marina
Freeboard at Soundview · Beach+Ocean+Sunrise
On the beach

Freeboard at Soundview · Beach+Ocean+Sunrise

2.0 star property
9.4 out of 10, Exceptional, (6)
"It was very close to the beach , quiet, parking on property room had everything you would need i enjoyed my stay didnt want to leave so soon wouldve liked at least 1 more day maybe next year thank you. "
The price is HK$401
HK$1,287 total
includes taxes & fees
13 Oct - 14 Oct
Freeboard at Soundview · Beach+Ocean+Sunrise
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 Bentley Hotel Southampton

The Bentley Hotel Southampton

10/10 Excellent
"Clean room!!"
Donna 1-night trip
Posted 1 day ago
The Bentley Hotel Southampton

Find out more about Greenport

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!

Explore a world of travel with Expedia

Explore a world of travel with Expedia

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?

Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping: This holiday home rental outside of Greenport offers an outdoor pool, a patio and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a garden, a selection of games 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.