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Vacation rentals in Orient

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Top-rated vacation rentals in Orient

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Home in Greenport

4.92 out of 5 average rating, 121 reviews

Beautiful Cottage Home W/ Beach & Dock Access

Beautiful, spacious beach side home situated within a block of a private beach. This cozy home is walking distance to Kontokosta Winery, Island's End Golf & Country Club, Lavender By the Bay and a five minute drive to the Village of Greenport. Replete with natural light and an open backyard perfect for outdoor dining and barbecues, this home is perfect for your stay in Greenport. Netflix/Hulu/Disney+ / ESPN+ / HBO MAX. Please note, 4 Bikes/1 Paddle Board/1 Kayak & Life Jackets provided May-Sept.

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.

Home in East Marion

4.95 out of 5 average rating, 99 reviews

Quiet, Upscale Retreat by the Beach

We're on a quiet, tree-lined street, a lovely bike ride or walk from a pebble beach, with crystal clear water and stunning sunsets. Our house is the ideal base to explore the North Fork, where bucolic farmland abuts magnificent beaches. We're 5 minutes by car or 15 by bike to the charming seaside villages of Greenport and Orient. Our house is fully stocked, newly renovated and the spacious backyard borders 10 acres of lovely forest preserve. No large groups of unrelated adults.

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!

Home in Greenport

4.94 out of 5 average rating, 136 reviews

Blue Bay Dream - Apt #2

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).

Home in Greenport

4.97 out of 5 average rating, 220 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!

Home in Orient

4.8 out of 5 average rating, 55 reviews

Corner 3BR Home - Private Beach!

We offer boat cruises around the east end of long island, reach out for more information 1,100 Square Foot house with 400 square foot deck in the backyard, along with am outdoor sofa lounge (fire pit in the fall and winter) lounge under a shaded pergola and an outdoor hot shower. House is part of community with rights to a private beach with a private barbecue/recreation area only a few minutes walk away. 14nt.min

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!

Guest suite in Cutchogue

4.88 out of 5 average rating, 584 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!

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.

Apartment in Greenport

4.86 out of 5 average rating, 141 reviews

Only Steps from Restaurants and Beach

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!

Home in Greenport

4.98 out of 5 average rating, 163 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.

Vacation rentals for every style

Get the amount of space that is right for you

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Unique stays

Spaces that are more than just a place to sleep

Popular amenities for Orient vacation rentals

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 suite in Greenport

5.0 out of 5 average rating, 45 reviews

Private Suite in Greenport Historical District

Home in Greenport

5.0 out of 5 average rating, 29 reviews

Historic Stunner in Heart of Village

Home in Greenport

5.0 out of 5 average rating, 10 reviews

The Sandy Shack - Coastal Escape

Home in Greenport

5.0 out of 5 average rating, 69 reviews

Beach House in L.I. Wine Country

Home in Greenport

5.0 out of 5 average rating, 35 reviews

Beachfront Greenport Villa

Home in East Marion

4.87 out of 5 average rating, 15 reviews

Waterfront NoFo Cottage w/ public beach access

Cottage in Greenport

4.84 out of 5 average rating, 38 reviews

Newly Renovated 2-Bedroom Home on the LI Sound

Home in Greenport

5.0 out of 5 average rating, 18 reviews

Walk to Beach or to Town …

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
$100 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 air conditioning, over 10 homes with a bbq area, over 20 homes with wifi, 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.

Destinations to explore