Holiday Homes in Orient

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Find holiday rentals that suit your style

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Apartments
Apartments
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Aparthotels

Check prices for these dates

Next weekend
13 Nov - 15 Nov
In two weeks
20 Nov - 22 Nov
In one month
4 Dec - 6 Dec
In two months
1 Jan - 3 Jan

Our top choices for Orient holiday homes

A covered patio with outdoor furniture, a door, and a view of a residential area.

1. The SandPiper

The SandPiper
Pipes Cove
9.6 out of 10, Exceptional, (57 reviews)
"Place was perfect ! Great location / clean/ everything we needed was there ! Would love to stay there again :)"
United States
Manuela C.
The price is AU$333
includes taxes & fees
10 Nov - 11 Nov
The SandPiper
A metal compass sign with the words "AQUA VISTA GREENPORT" on a building's exterior wall.

2. Aqua Vista

Aqua Vista
Pipes Cove
10.0 out of 10, Exceptional, (52 reviews)
"Great location and nice spot."
United States
Kerri L.
The price is AU$348
includes taxes & fees
9 Nov - 10 Nov
Aqua Vista
A porch with a white railing, a small blue house decoration, and a 'Gone' sign.

3. 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, (35 reviews)
"We had a great stay!! "
United States
Callie E.
The price is AU$490
includes taxes & fees
5 Nov - 6 Nov
Blue Bay Dream w/ Seasonal Outdoor Jacuzzi, Cabana + Office
A small, single-story house with a gabled roof, a front door, and a number "401" on the door.

4. Beach Block Hideaway

Beach Block Hideaway
Pipes Cove
10.0 out of 10, Exceptional, (12 reviews)
"Beautiful 2 bedroom close to town. The house is well kept we would rent here again."
United States
Teresa C.
The price is AU$602
includes taxes & fees
12 Nov - 13 Nov
Beach Block Hideaway
A patio area with wicker chairs and a table, surrounded by gravel and plants.

5. 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 AU$412
includes taxes & fees
23 Nov - 24 Nov
American Beech in Greenport - Petite King Room 7
A cozy living room with a sofa, a coffee table, and a dining area with chairs.

6. NEW private studio 1.1 miles to beach in East Lyme

NEW private studio 1.1 miles to beach in East Lyme
East Lyme
The price is AU$196
includes taxes & fees
28 Nov - 29 Nov
NEW private studio 1.1 miles to beach in East Lyme
A dining area with a round table, six chairs, and a chandelier.

7. Year round Jacuzzi - Blackberry East Hampton Home

Year round Jacuzzi - Blackberry East Hampton Home
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 AU$1,884
includes taxes & fees
8 Nov - 9 Nov
Year round Jacuzzi - Blackberry East Hampton Home
A modern dining area with a wooden table, white chairs, and a chandelier.

8. 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.
The price is AU$772
includes taxes & fees
10 Nov - 11 Nov
Northfork Townhouse walk to all
A living room with a fireplace, a television mounted above it, a dining area with a table and chairs, and a staircase with wooden railings.

9. Renovated Townhouse walk to all

Renovated Townhouse walk to all
Greenport
9.6 out of 10, Exceptional, (15 reviews)
"The place was as advertised and in great walking distance to everything in town! "
United States
Liz H.
The price is AU$738
includes taxes & fees
1 Dec - 2 Dec
Renovated Townhouse walk to all
A living room with a fireplace, a grey armchair, and a large window.

10. 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, (13 reviews)
"We had a nice stay. Kitchen well stocked and house was clean and comfortable."
United States
Elaine A.
The price is AU$593
includes taxes & fees
9 Nov - 10 Nov
Luxurious-Modern feel w/ custom features - AC, short walk to the Beach and parks
A dining area with a glass table, two chairs, and a bottle of champagne. There are framed paintings on the walls and a refrigerator in the background.

11. Cozy 2-bedroom vacation home《 free WiFi & parking 》New London, Connecticut, USA

Cozy 2-bedroom vacation home《 free WiFi & parking 》New London, Connecticut, USA
New London
8.0 out of 10, Very good, (31 reviews)
"Good location, great price, communication always great with the host. Accommodations were clean, decorative and comfortable. Heat and air, family friendly, and neat. Will return and recommend to friends and family!"
United States
Alicia W.
The price is AU$328
includes taxes & fees
11 Nov - 12 Nov
Cozy 2-bedroom vacation home《 free WiFi & parking 》New London, Connecticut, USA
A wooden deck with lounge chairs and a potted plant, overlooking a beach and ocean.

12. Beachfront Greenport Villa

Beachfront Greenport Villa
Greenport
9.6 out of 10, Exceptional, (15 reviews)
"Beautiful home, great views and host!"
United States
Kate R.
The price is AU$1,181
includes taxes & fees
10 Nov - 11 Nov
Beachfront Greenport Villa
A spacious, well-lit room with a high ceiling, large windows, and a cozy seating area with a sofa and chairs.

13. 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 AU$776
includes taxes & fees
16 Nov - 17 Nov
Authentic 1795 Historic Homestead w/ Private Grounds for Gatherings and Retreats
A greenhouse with a checkered floor, a table with a lamp, and a potted plant.

14. 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 AU$459
includes taxes & fees
5 Nov - 6 Nov
American Beech in Greenport - Deluxe King 6
A modern kitchen with a granite island, stainless steel appliances, and a bar area with bar stools.

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

Beachside Bliss w/ Game Room, Gym & Golf Green
Westbrook
10.0 out of 10, Exceptional, (4 reviews)
"Very lovely home! We very much enjoyed our stay and hope to be back again!"
United States
Morgan M.
The price is AU$801
includes taxes & fees
10 Nov - 11 Nov
Beachside Bliss w/ Game Room, Gym & Golf Green
A modern kitchen with white cabinetry, a central island, stainless steel appliances, and pendant lighting.

16. Spacious house in East Hampton with heated pool + WFH

Spacious house in East Hampton with heated pool + WFH
East Hampton
10.0 out of 10, Exceptional, (2 reviews)
"Great clean beautiful property."
United States
ANGELA S.
The price is AU$1,952
includes taxes & fees
1 Dec - 2 Dec
Spacious house in East Hampton with heated pool + WFH
Vaulted living room with statement chandelier and cozy sectional

17. 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.
The price is AU$1,532
includes taxes & fees
5 Nov - 6 Nov
Designer Sag Harbor Home w/ Pool + Fire Pit + Yard
A room with a large window, a wooden bookshelf, a stone wall, and a white sofa.

18. Entire House in Southampton Village, Pool, 2 Fireplaces, Walk Everywhere, Pets!

Entire House in Southampton Village, Pool, 2 Fireplaces, Walk Everywhere, Pets!
Southampton
9.2 out of 10, Wonderful, (11 reviews)
"Great house with lots of space. Perfect location! The host is extremely accommodating. Definitely recommend!"
United States
Justin
Entire House in Southampton Village, Pool, 2 Fireplaces, Walk Everywhere, Pets!
A wooden deck with a round table and chairs overlooking a lake, surrounded by lush greenery.

19. Lakeside Bliss

Lakeside Bliss
East Lyme
9.6 out of 10, Exceptional, (32 reviews)
"Lovely house - excellently equipped and fun decor. The owner was gracious and flexible and the location is beautiful. "
United States
Brenda M.
The price is AU$733
includes taxes & fees
17 Nov - 18 Nov
Lakeside Bliss
A modern living room with a wooden accent wall, a flat-screen TV, a fireplace, and a dining area with a chair and table.

20. 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, (2 reviews)
"The property was great for our Hamptons trip! Very clean and comfortable and communication was great"
United States
Katie B.
The price is AU$766
includes taxes & fees
8 Nov - 9 Nov
Bridgehampton, NY cottage near Sag Harbor, NY. Elegant and modern.
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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Learn more about Orient

Nestled on the North Fork, this charming hamlet offers pristine beaches and vineyards with spectacular Long Island Sound views. Explore the historic Orient Point Lighthouse or catch the ferry to adventure, stopping at farm stands for local oysters along the way.

See all hotels in Orient
An aerial view of a coastal area with a sandy beach, a small settlement, and a clear blue sea.

Top reviews in Orient

A spacious hallway with a fireplace, a large window, and a built-in shelving unit.
Sag Harbor Inn

Sag Harbor Inn

Sag Harbor Inn
Sag Harbor

10/10 Excellent

Great location, room was spacious with great outlook and breakfast was perfect!
Australia
Jennifer
Reviewed May 30, 2026
Sag Harbor Inn