Vacation rentals in Orient

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Top-rated vacation rentals in Orient

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Guest favorite

Condo in Greenport

4.91 out of 5 average rating, 107 reviews

Beachside Waterview 2Br Condo w/ Pool in Greenport

Relax in a pristine 2Br condo with ocean & pool views. Our remodeled apartment is part of high-end development nestled on LI Sound, just minutes from downtown Greenport. Sip a glass of wine while watching sunset, catch some rays on the beach or deep in the pool. 2 bedroom condo with ocean view, beach, and pool (seasonal) Comfortably sleeps 6 Private beach access year-around Pool (seasonal) Functional kitchenette 2 bathrooms, all toiletries Linens and towels are provided Smart TV AC/Heat

Oct 8 – 15

G$65,834 GYD per night

Guest favorite

Home in East Lyme

4.96 out of 5 average rating, 104 reviews

Walk to the beach at Black Point, Niantic, Ct

Black Point beach home (5th house from water) within walking distance of three beaches. Open floor plan with three levels. Ping Pong room on lower level. Living room, dining room, sitting area, and kitchen on mid level. Three bedrooms & 2 full bath on top level. WI-Fi, linens, coffee, water provided. Fenced in back yard with gas grill. Close to casinos, charter fishing, Essex steam train, Mystic Aquarium & Seaport, and Newport (1 Hr). Walk Niantic Bay Boardwalk or Old Black Point.

Mar 26 – Apr 2

G$34,199 GYD per night

Guest favorite

Guest suite in Greenport

4.92 out of 5 average rating, 276 reviews

The Greenport Suite—private entry + near the beach

Welcome to The Greenport Suite! With its separate entrance, secluded outdoor patio space and ideal location, this newly-redesigned private suite in our contemporary Village home is perfect for enjoying a North Fork getaway. We are located just a few short blocks from bay beaches, the harbor, and public transport, while the area's celebrated wineries are a short drive or bike ride away. Come see why Forbes named Greenport one of the 11 prettiest villages in the United States!

Jan 21 – 28

G$50,101 GYD per night

Guest favorite

Home in Greenport

4.98 out of 5 average rating, 165 reviews

Aqua Vista

Newly renovated 2-Family Home! Located right in Greenport Village providing walking distance to all the restaurants, bars, shopping, coffee shops, and Shelter Island Ferry, Long Island Railroad (LIRR), and Hampton Jitney. My place is close to restaurants and dining, the beach, family-friendly activities, nightlife, and public transport. You’ll love my place because of Location!. My place is good for couples, solo adventurers, business travelers, families (with kids).

Jan 4 – 11

G$28,990 GYD per night

Guest favorite

Home in Greenport

4.97 out of 5 average rating, 221 reviews

The Greenport Bungalow

Sweet Modern Bungalow Walking Distance to Town Located in the historic town of Greenport Village - 8 min walk to the beach, center of town, Shelter Island Ferry and LIRR... A newly built sun filled 3 bedroom house with all the amenities you would need when renting a home. Enjoy the large and fenced in back yard after a fun day in this historic Long Island fishing village. Great restaurants, and even better locally produced wine and beer!

Aug 18 – 25

G$119,526 GYD per night

Guest favorite

Guest suite in Old Saybrook

5.0 out of 5 average rating, 37 reviews

Cozy Loft Getaway

The private loft is bright and airy with vaulted ceilings and all brand new furniture and appliances. The kitchen and bathroom were thoughtfully designed and sourced from our design showroom right downstairs! Minutes from local beaches and only blocks from shops and our favorite food spots in town, we hope you enjoy our beautiful and cozy loft as much as we do!

May 6 – 13

G$32,672 GYD per night

Guest favorite

Guest suite in Cutchogue

4.88 out of 5 average rating, 586 reviews

Walk to Vineyards, Beaches, Farms & Town

Private bungalow with a separate entrance in a historical tudor home. Spacious bedroom with king-sized bed, kitchenette and bathroom. Two bikes, cable TV, internet, AC, beach towels, parking, snacks, coffee and water all provided. Walking distance to the beach, restaurants, shops, vineyards, grocery, farms and fish market. Jitney stop is one block away!

Oct 6 – 13

G$35,519 GYD per night

Guest favorite

Home in Greenport

4.98 out of 5 average rating, 143 reviews

Greenport Village walking distance to all

Large spacious home in the heart of wine country. Roomy den for relaxing after the wineries. Screened in patio for al fresco dining and enjoying the spacious yard. Hot tub operational year round! Strong, fast wifi with multiple extenders. Message me with any questions or for special offers on 4/5 day stays or midweek 2/3 night specials.

Jun 11 – 18

G$176,940 GYD per night

Superhost

Apartment in Greenport

4.86 out of 5 average rating, 141 reviews

Quiet Neighborhood and only steps to Town

Walk the 5 min into town with restaurants and bars, shops and cafes or enjoy the quiet neighbourhood and take a stroll down the block to watch the sailboats cruise into Sterling Harbor. This sunny apartment is situated on the second floor of a 1860's house on one of Greenport's prettiest streets. Its the true couples getaway!

Dec 10 – 17

G$57,554 GYD per night

Guest favorite

Home in Greenport

4.98 out of 5 average rating, 164 reviews

Nofo Bungalow-In The Heart of Greenport Village

This historic Greenport home has been completely renovated . The Bungalow is in the heart of Greenport Village on a quiet dead end. The home includes 1500 square feet of open concept living, two bedrooms, and two full baths. The downstairs bedroom features a queen and upstairs bedroom four twins.

Sep 4 – 11

G$119,351 GYD per night

Guest favorite

Apartment in Greenport

4.97 out of 5 average rating, 195 reviews

Greenport Village View - Walkable 2BR Stay

Located in the heart of Greenport Village with easy walking access to restaurants, shops, Greenport Brewery, Kontakasta Winery, and much much more! Originally from Greenport, we look forward to hosting you and sharing our local favorites to make your stay memorable.

Apr 5 – 12

G$77,652 GYD per night

Guest favorite

Home in East Marion

4.83 out of 5 average rating, 6 reviews

Private North Fork Cottage- Walk to Beach!

Sunny and peaceful 3 bedroom cottage perfect for exploring all the North Fork has to offer! 7 minute walk to a pebble beach with spectacular sunsets as well as Sepps farm stand, the East Marion jitney stop and a Lavender farm.

Sep 7 – 14

G$66,709 GYD per night

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Orient vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Stay near Orient's top sights

Orient Point Ferry20 locals recommend

Orient Point County Park5 locals recommend

Duryea's Orient Point20 locals recommend

Orient Country Store13 locals recommend

Latham Farms5 locals recommend

Oysterponds Historical Society4 locals recommend

Other great vacation rentals in Orient

Guest favorite

Guest suite in Greenport

5.0 out of 5 average rating, 46 reviews

Private Suite in Greenport Historical District

Jun 20 – 27

G$66,216 GYD per night

Guest favorite

Home in East Marion

4.95 out of 5 average rating, 99 reviews

Quiet, Upscale Retreat by the Beach

Sep 21 – 28

G$91,775 GYD per night

Guest favorite

Home in Greenport

5.0 out of 5 average rating, 35 reviews

Beachfront Greenport Villa

Jan 16 – 23

G$123,866 GYD per night

Superhost

Cottage in Greenport

4.84 out of 5 average rating, 38 reviews

Newly Renovated 2-Bedroom Home on the LI Sound

Oct 7 – 14

G$113,827 GYD per night

Guest favorite

Home in Greenport

5.0 out of 5 average rating, 29 reviews

Historic Stunner in Heart of Village

Dec 24 – 31

G$116,895 GYD per night

Guest favorite

Apartment in Greenport

4.97 out of 5 average rating, 61 reviews

Lovely 2-bedroom apartment in a historic home

Aug 30 – Sep 6

G$89,395 GYD per night

Guest favorite

Home in Greenport

5.0 out of 5 average rating, 70 reviews

Beach House in L.I. Wine Country

Oct 24 – 31

G$99,621 GYD per night

Guest favorite

Home in Greenport

5.0 out of 5 average rating, 10 reviews

The Sandy Shack - Coastal Escape

Sep 1 – 8

G$146,713 GYD per night

Show all

Quick stats about vacation rentals in Orient

Total rentals
30 properties
Rentals with a pool
10 properties have a pool
Pet-friendly rentals
10 properties allow pets
Family-friendly rentals
20 properties are a good fit for families
Total number of reviews
300 reviews
Nightly prices starting at
G$20,848 GYD before taxes and fees

Frequently Asked Questions

Do house rentals in Orient have air conditioning?
Absolutely! We offer over 20 house rentals with air conditioning in Orient. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Orient have wifi?
Absolutely! We offer over 20 house rentals with wifi in Orient. Enjoy a tailored experience with all the comforts you desire.
How much does it cost to stay in house rentals in Orient?
Experience the best of Orient with our house rentals, starting at about $300 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Are there pet-friendly vacation rentals in Orient?
Four-legged friends are welcome in Orient. Choose from more than 10 vacation rentals for guests traveling with pets.
What are the most popular amenities for House Rentals in Orient?
Enhance your stay in our House Rentals with the most popular amenities: over 20 homes with wifi, over 20 homes with air conditioning, over 10 homes with a bbq area, and more. Indulge in the ultimate retreat, tailored to your preferences.
Are there Orient vacation rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 10 vacation homes with pools in Orient, available on Airbnb. Make a splash and soak up the sun in style!
Are there vacation rentals with a dedicated workspace in Orient?
Yes! Work meets play with ease at over 10 vacation rentals in Orient featuring dedicated workspaces. Stay connected and productive in your home away from home.
Do house rentals in Orient have a bbq area?
Absolutely! We offer over 10 house rentals with a bbq area in Orient. Enjoy a tailored experience with all the comforts you desire.

Vacation rentals in Orient

Top-rated vacation rentals in Orient

Vacation rentals for every style

Houses

Hotels

Unique stays

Popular amenities for Orient vacation rentals

Stay near Orient's top sights

Other great vacation rentals in Orient

Guest suite in Greenport

Home in East Marion

Home in Greenport

Cottage in Greenport

Home in Greenport

Apartment in Greenport

Home in Greenport

Home in Greenport

Quick stats about vacation rentals in Orient

Total rentals

Rentals with a pool

Pet-friendly rentals

Family-friendly rentals

Total number of reviews

Nightly prices starting at

Frequently Asked Questions

Do house rentals in Orient have air conditioning?

Do house rentals in Orient have wifi?

How much does it cost to stay in house rentals in Orient?

Are there pet-friendly vacation rentals in Orient?

What are the most popular amenities for House Rentals in Orient?

Are there Orient vacation rentals on Airbnb with pools?

Are there vacation rentals with a dedicated workspace in Orient?

Do house rentals in Orient have a bbq area?

Destinations to explore