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Orient Holiday Rentals

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50 rentals in Orient.
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Orient Point Waterfront Home with Pool & Spectacular Ocean Sunset Views, holiday rental in Orient

Orient Point Waterfront Home with Pool & Spectacular Ocean Sunset Views

3 bedrooms
2 bathrooms
Sleeps 7
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Magnificent Private Orient Beach Front House, holiday rental in Orient

Magnificent Private Orient Beach Front House

3 bedrooms
3 bathrooms
Sleeps 8
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Orient Point Family Waterfront Home, holiday rental in Orient

Orient Point Family Waterfront Home

5 bedrooms
4 bathrooms
Sleeps 10
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Orient Point Cottage with Private Beach, holiday rental in Orient

Orient Point Cottage with Private Beach

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Dream house vacation on the Long Island Sound, holiday rental in Orient

Dream house vacation on the Long Island Sound

5 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Porch On Front~ Greenport Village 1st floor apartment, Easy Walk To Town/Jitney, holiday rental in Orient

Porch On Front~ Greenport Village 1st floor apartment, Easy Walk To Town/Jitney

2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Historic 1830s Greenport Home, holiday rental in Orient

Historic 1830s Greenport Home

2 bedrooms
3 bathrooms
Sleeps 6
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'The Gate House' on Beach front Estate, holiday rental in Orient

'The Gate House' on Beach front Estate

2 bedrooms
1 bathroom
Sleeps 4
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Lovely North Fork Sea Captain's Home, holiday rental in Orient

Lovely North Fork Sea Captain's Home

4 bedrooms
3 bathrooms
Sleeps 10
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Peaceful Retreat with 100 ft private deep water dock, holiday rental in Orient

Peaceful Retreat with 100 ft private deep water dock

3 bedrooms
2 bathrooms
Sleeps 6
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Rose Cottage by the Bay., holiday rental in Orient

Rose Cottage by the Bay.

2 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
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Waterfront Estate - One of a Kind Vacation House, holiday rental in Orient

Waterfront Estate - One of a Kind Vacation House

4 bedrooms
3 bathrooms
Sleeps 10
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Cottage on Beach front  Estate, holiday rental in Orient

Cottage on Beach front Estate

2 bedrooms
2 bathrooms
Sleeps 4
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Cleves Point Estates Home, Private sandy beach, holiday rental in Orient

Cleves Point Estates Home, Private sandy beach

3 bedrooms
3 bathrooms
Sleeps 12
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Greenport Village home w/ POOL! Steps to Town Center & Bay Beach!, holiday rental in Orient

Greenport Village home w/ POOL! Steps to Town Center & Bay Beach!

3 bedrooms
3 bathrooms
Sleeps 13
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Seaside seclusion, salt water sanctuary! Monthly rental discount  fall/winter., holiday rental in Orient

Seaside seclusion, salt water sanctuary! Monthly rental discount fall/winter.

4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Tranquil, Beachfront Getaway with Dock, Fabulous Sunset Views!, holiday rental in Orient

Tranquil, Beachfront Getaway with Dock, Fabulous Sunset Views!

4 bedrooms
3 bathrooms
Sleeps 8
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Beautiful Secluded Family Home on Shelter Island., holiday rental in Orient

Beautiful Secluded Family Home on Shelter Island.

4 bedrooms
3 bathrooms
Sleeps 8
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Enchanted Cottage, holiday rental in Orient

Enchanted Cottage

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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North Fork House with Private Beach Access, holiday rental in Orient

North Fork House with Private Beach Access

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Entire house, private lane, walk to public beach, close to town, holiday rental in Orient

Entire house, private lane, walk to public beach, close to town

3 bedrooms
3 bathrooms
Sleeps 5
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Waterfront House Located In Private Beach Community., holiday rental in Orient

Waterfront House Located In Private Beach Community.

4 bedrooms
2 bathrooms
Sleeps 8
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Greenport Village home for rent, great for group or extended family, holiday rental in Orient

Greenport Village home for rent, great for group or extended family

4 bedrooms
6 bathrooms
Sleeps 8
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North Fork Dreamstate, holiday rental in Orient

North Fork Dreamstate

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Family friendly home near beach with wonderful deck!, holiday rental in Orient

Family friendly home near beach with wonderful deck!

4 bedrooms
2 bathrooms
Sleeps 7
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Greenport Renovated Farm House, holiday rental in Orient

Greenport Renovated Farm House

3 bedrooms
2 bathrooms
Sleeps 6
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The Ultimate Beach House, holiday rental in Orient

The Ultimate Beach House

7 bedrooms
5 bathrooms
Sleeps 15
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Relaxed Village Farmhouse, holiday rental in Orient

Relaxed Village Farmhouse

4 bedrooms
3 bathrooms
Sleeps 8
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Gorgeous, tranquil 9000 Sq Ft home on Dering Harbor, holiday rental in Orient

Gorgeous, tranquil 9000 Sq Ft home on Dering Harbor

6 bedrooms
10 bathrooms
Sleeps 12
Match: Sleeps
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Beautiful, newly-remodeled home w/ a gas fireplace, patio, & firepit - dogs OK!, holiday rental in Orient

Beautiful, newly-remodeled home w/ a gas fireplace, patio, & firepit - dogs OK!

3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Historic Cottage Near Beach!, holiday rental in Orient

Historic Cottage Near Beach!

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Architect Designed Home in Waterfront Village, holiday rental in Orient

Architect Designed Home in Waterfront Village

2 bedrooms
2 bathrooms
Sleeps 4
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'This must be the place', holiday rental in Orient

'This must be the place'

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Greenport Beach House, holiday rental in Orient

Greenport Beach House

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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NEW LIST: Luxury Waterfront Condo-Pool, Beach Access, heart of Greenport Village, holiday rental in Orient

NEW LIST: Luxury Waterfront Condo-Pool, Beach Access, heart of Greenport Village

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Charming 4 Bed/2.5 Bath Cottage In Historic Shelter Island, Walk To Ferry, holiday rental in Orient

Charming 4 Bed/2.5 Bath Cottage In Historic Shelter Island, Walk To Ferry

4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Shingled Chic & Modern Light & Bright, holiday rental in Orient

Shingled Chic & Modern Light & Bright

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Greenport NY Chic Designer Beach House, steps to water, vineyard views, holiday rental in Orient

Greenport NY Chic Designer Beach House, steps to water, vineyard views

3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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New Listing: Rustic Chic Designer Home on Dering Harbor, Private Dock &..., holiday rental in Orient

New Listing: Rustic Chic Designer Home on Dering Harbor, Private Dock &...

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Charming Country House minutes from Greenport, holiday rental in Orient

Charming Country House minutes from Greenport

3 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Charming historic house on Sterling Harbor, waterviews, walk to village, holiday rental in Orient

Charming historic house on Sterling Harbor, waterviews, walk to village

3 bedrooms
3 bathrooms
Sleeps 5
Match: Sleeps
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Chic, Historic fully renovated Greenport Home, holiday rental in Orient

Chic, Historic fully renovated Greenport Home

5 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Picturesque Views Of Gardiners Bay / Shelter Island With Heated Waterfront Pool, holiday rental in Orient

Picturesque Views Of Gardiners Bay / Shelter Island With Heated Waterfront Pool

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Newly Renovated  3 bedroom Northfork ranch with Heated Pool, holiday rental in Orient

Newly Renovated 3 bedroom Northfork ranch with Heated Pool

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Scandinavian modern style meets the North Fork., holiday rental in Orient

Scandinavian modern style meets the North Fork.

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Beach House Amazing Views on the beach with a Heated pool till All Year round, holiday rental in Orient

Beach House Amazing Views on the beach with a Heated pool till All Year round

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Cottage fields of Lavender by the Sea 5min Greenport Shelter Island, holiday rental in Orient

Cottage fields of Lavender by the Sea 5min Greenport Shelter Island

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Beach house Sailors Delight Vineyards, Farm Stands, North Fork Private Beach, holiday rental in Orient

Beach house Sailors Delight Vineyards, Farm Stands, North Fork Private Beach

4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Water Front home Sailors Rest Boat Dock near Greenport walk to sandy beach!, holiday rental in Orient

Water Front home Sailors Rest Boat Dock near Greenport walk to sandy beach!

3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Bright 3 Bdr North Fork Home Close to Beach & Greenport Wineries, Breweries, holiday rental in Orient

Bright 3 Bdr North Fork Home Close to Beach & Greenport Wineries, Breweries

3 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
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