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House holiday rentals in Orient

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Top-rated house rentals in Orient

Guests agree: These houses are highly rated for location, cleanliness and more.

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Home in Greenport

4.83 out of 5 average rating, 190 reviews

The Greenport Townhouse - Amazing Location & Large Backyard

The house is located on a .35 acre lot with plenty of outdoor dining space and a huge grass area with a firepit & hammock. There are 2 floors. The first floor has an open floor plan with a connecting kitchen, dining room, and living room. The kitchen is well equipped with a dish washer, electric stove/oven, refrigerator, and coffee bar. There is also a bedroom on the 1st floor with 2 full-sized beds. The 2nd floor has 3 bedrooms and a loft/den area. The three bedrooms on this floor have 1 queen bed+futon, 2 full-sized beds, and 2 twin beds (which can be made together to form a king upon request), respectively. All rooms have AC. There are 2 full bathrooms (1 on each floor) and a washer/dryer. Guests have access to the entire house and backyard area. We respect your privacy, but we are accessible if you have questions or need anything throughout your stay. Greenport was voted one of the prettiest towns in America by Forbes magazine. It has a vibrant and relaxing culture, offering access to beaches, wine tasting, and wonderful restaurants. The Shelter Island Ferry and Hampton Jitney stops are nearby. We are just a few short blocks from the Hampton Jitney stop, the LIRR station, and the Shelter Island Ferry. No car necessary - you can walk wherever you need!

2–9 Apr

$936 NZD per night

Guest favourite

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.

21–28 Aug

$1,528 NZD per night

Guest favourite

Home in Lyme

4.97 out of 5 average rating, 190 reviews

“The Answer” Tidal River-Kayaks Fire pit Fireplace

“The Answer” is listed amongst the 15 best Airbnbs in Ct, from Travellers Worldwide 2022 and 2023 and featured in “Only In Your State” titled “This Riverfront House Will Be Your New Favorite” February 2024 Kayaks included This unique glass-front, tidal river retreat, is privately nestled on historic Hamburg Cove. It offers gorgeous year-round, tranquil water and valley views. Extraordinarily and serene. The interior is open/spacious and bathed in light. Wake up to the many sounds of nature.

9–16 May

$618 NZD per night

Guest favourite

Home in East Hampton

4.94 out of 5 average rating, 202 reviews

Private beach Historical House with large property

Entire three-story house. 3 large bedrooms and 3 FULL BATHROOMS on a very private, 2+acre wood lot on the bay in Historical East Hampton with private beach access. Fully renovated in 2018 with modern amenities while preserving the original charm. A/C and heating. Private upper floor with bedroom + sitting area for office and extra sleeping. Modern kitchen with island that opens to living room with fireplace. Walk through the secluded backyard to enjoy the amazing sunsets. Ideal for fishing.

4–11 Feb

$1,534 NZD per night

Guest favourite

Home in East Lyme

4.96 out of 5 average rating, 105 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.

25 Jan – 1 Feb

$309 NZD per night

Home in Greenport

4.94 out of 5 average rating, 136 reviews

Harbor Heights

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).

14–21 Oct

$305 NZD per night

Guest favourite

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!

11–18 Aug

$1,018 NZD per night

Home in Shelter Island

4.89 out of 5 average rating, 106 reviews

Hay Beach Getaway!

Welcome to our family-friendly oasis just two blocks from beautiful beaches! Our house offers an open space living area, an expansive yard, fire pits, and a basement with a playroom and workout area. Enjoy our quiet neighborhood. We provide kid-friendly toys, beach gear, bicycles, and more. Sleeps six, with additional options available for larger parties. Monday-Thursday stays February through June no cleaning fees!!!

15–22 Mar

$1,444 NZD per night

Guest favourite

Home in Sag Harbor

4.97 out of 5 average rating, 260 reviews

Sag Harbor Cottage, Walk to the Beach!

Renovated to perfection, this fully equipped fresh & modern beach cottage has an open-plan living room, dining room & kitchen, all with high ceilings, immaculate finishings, & a sunny lower level TV room. A broad mahogany deck with large outdoor shower & gas BBQ grill runs the full length of the house & overlooks a roomy lawn with great privacy, fire pit and mature landscaping.

27 May – 3 Jun

$1,043 NZD per night

Guest favourite

Home in Greenport

4.98 out of 5 average rating, 144 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.

10–17 May

$1,379 NZD per night

Guest favourite

Home in Old Lyme

4.96 out of 5 average rating, 128 reviews

Modern Farmhouse with Hot Tub in Old Lyme, CT

Originally built in 1856 this farmhouse has been lovingly restored with stylish and modern amenities for a perfect vacation getaway. Nestled in the heart of downtown, historic Old Lyme the property is convenient to shops, restaurants and local shoreline activities including water sports and hiking.

25 Mar – 1 Apr

$814 NZD per night

Guest favourite

Home in Greenport

4.98 out of 5 average rating, 165 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.

4–11 Sep

$1,020 NZD per night

Holiday rentals for every style

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Popular amenities for Orient house rentals

Free parking on premises

Air conditioning

House rentals with a pool

Guest favourite

Home in East Hampton

4.92 out of 5 average rating, 128 reviews

Heated pool, games room, near beach, kid-friendly

23–30 Oct

$1,260 NZD per night

Guest favourite

Home in East Hampton

4.87 out of 5 average rating, 188 reviews

Heated Saltwater Pool, Walk to Beach, Dog Friendly

11–18 Nov

$457 NZD per night

Guest favourite

Home in East Hampton

4.93 out of 5 average rating, 141 reviews

1800 Historical East Hampton Home, 1 Mile to Town!

8–15 Oct

$1,625 NZD per night

Guest favourite

Home in East Hampton

4.97 out of 5 average rating, 116 reviews

Explore the Water & Woods at a Relaxing Retreat

10–17 Oct

$1,729 NZD per night

Home in Sag Harbor

4.82 out of 5 average rating, 132 reviews

New! Sag Harbor Village Pool, Hot Tub &Beach House

3–10 Nov

$1,370 NZD per night

Guest favourite

Home in New London

4.89 out of 5 average rating, 132 reviews

OASIS @ OCEAN BEACH PARK: 6 QUEEN BEDS

14–21 Feb

$1,961 NZD per night

Guest favourite

Home in Watermill

4.88 out of 5 average rating, 128 reviews

Modern House close to the beach

19–26 Dec

$1,945 NZD per night

Guest favourite

Home in Hampton Bays

4.98 out of 5 average rating, 112 reviews

Beach House Feel - newly renovated backyard Oasis

9–16 Sep

$1,419 NZD per night

Weekly house rentals

Guest favourite

Home in Old Lyme

4.94 out of 5 average rating, 257 reviews

Modern Luxurious CT Country Home

28 Oct – 4 Nov

$837 NZD per night

Guest favourite

Home in Old Lyme

4.96 out of 5 average rating, 125 reviews

Cozy Beach Cottage with short walk to the beach

23–30 Jan

$643 NZD per night

Guest favourite

Home in East Marion

4.83 out of 5 average rating, 6 reviews

Private North Fork Cottage- Walk to Beach!

18–25 Nov

$479 NZD per night

Guest favourite

Home in East Marion

4.95 out of 5 average rating, 99 reviews

Quiet, Upscale Retreat by the Beach

22–29 Dec

$836 NZD per night

Guest favourite

Home in Greenport

4.96 out of 5 average rating, 28 reviews

Walk to town, Greenport Village - Harbor Views

31 May – 7 Jun

$791 NZD per night

Guest favourite

Home in Greenport

4.98 out of 5 average rating, 85 reviews

Designer's Dream - Charming Boathouse

7–14 Dec

$776 NZD per night

Guest favourite

Home in Greenport

5.0 out of 5 average rating, 30 reviews

Historic Stunner in Heart of Village

29 Sep – 6 Oct

$979 NZD per night

Guest favourite

Home in East Marion

4.87 out of 5 average rating, 15 reviews

Waterfront NoFo Cottage w/ public beach access

16–23 May

$735 NZD per night

Private house rentals

Guest favourite

Home in Greenport

5.0 out of 5 average rating, 19 reviews

The Corwin House

20–27 May

$1,765 NZD per night

Guest favourite

Home in Greenport

4.91 out of 5 average rating, 22 reviews

Greenport Getaway - North Fork Rental

25 May – 1 Jun

$1,546 NZD per night

Guest favourite

Home in Greenport

4.95 out of 5 average rating, 20 reviews

Walk to Beach or to Town …

16–23 Nov

$729 NZD per night

Guest favourite

Home in East Marion

5.0 out of 5 average rating, 16 reviews

Bright, Newer Home Close to Beach & Greenport Town

24–31 Aug

$1,472 NZD per night

Home in Greenport

5.0 out of 5 average rating, 10 reviews

The Saltbox: Outdoor Dining, Fire Pit, Soaking Tub

24 Sep – 1 Oct

$1,065 NZD per night

Guest favourite

Home in Greenport

5.0 out of 5 average rating, 16 reviews

Relaxation in Greenport

12–19 Mar

$1,349 NZD per night

Guest favourite

Home in Greenport

4.96 out of 5 average rating, 25 reviews

Water front 3 bedrooms 2 bathrooms beach house

22–29 Sep

$1,941 NZD per night

Guest favourite

Home in Greenport

4.97 out of 5 average rating, 38 reviews

Freshly renovated farmhouse

17–24 Oct

$1,209 NZD per night

Quick stats about house rentals in Orient

Total rentals
20 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
200 reviews
Nightly prices starting at
$510 NZD before taxes and fees

Destinations to explore