Holiday Rentals in Sag Harbor
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5 km
287 rentals in Sag Harbor.
Summer 2025 Now Available! Wolffer Vineyard Close!
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Waterfront, Pool, HotTub, Strong WIFI, Pingpong, Paddleboard, Kayak, Bocce Court
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Modern Luxury w/ Private Pool. 5 min from Beach & Town of Sag Harbor
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Cove View Manor of Sag Harbor
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sunset bikes and kayaks in the village
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Room 1 queen bed on waterfront + bikes and kayaks
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Room3 best waterfront view +bikes+kayaks
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Large Room w use of pool/tennis in Spacious home
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Tucked into the quiet woods of Sag Harbor.
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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COTTAGE IS AVAILABLE FOR MONTHY, WEEKLY, WEEKENDS,Also WINTERS
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Tranquil getaway just steps from Long Pond Trails and Sag Harbor Village.
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Island View Manor-Secluded, Pool Hot, Tub
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Secluded Hamptons Cottage
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SECLUDED SAG HARBOR COTTAGE w/ HUGE POOL
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Great Sag Harbor Cottage on the Water Bay views
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Neoclassical Farmhouse by the sea
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Picturesque Sag Harbor Cottage w/ Salt Water Pool
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Sag Harbor Village-walk to town and beach
Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Sag Harbor secluded retreat
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LOCATED IN HISTORIC SECTION OF SAG HARBOR
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Lovely Sag Harbor Village 3BR, 1.5B Home 4 minute walk to bay beach
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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In Sag Harbor Village. Walk to town, and less than 1/2 mile to Havens Beach.
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Summer House Walk to The Beaches
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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*New Listing* Sag Harbor Beach and Marina
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Halloween / Autumn special - Sag Harbor Gem
Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 12
Match: Sleeps
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Beautiful Cottage in private Sag Harbor community nxt to beach & nature preserve
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Sag Harbor - Stylish and elegant modern house
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
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Sag Harbor Hamptons hideaway
Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Country Home in Sag Harbor Village
Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Remodeled historic Greek Revival house in heart of Sag Harbor.
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Sag Harbor Village Gem
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Modern Beach Cottage in Sag Harbor Village
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Enjoy a lovely summer retreat in Sag Harbor Village, 1 mile to Main Street
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Newly renovated Sag Harbor home with beautiful bay view, Gunite pool & hot tub
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Beautiful newly renovated house with hot tub
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Beautifully renovated historic home in Sag Harbor Village. Walk to Everything.
Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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PVT Sag Harbor Beachfront community - Saline Solar Hted Pool, Community Tennis.
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Stunning Waterfront Home with Pool, Boat Dock, and Acre of Land
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Exquisite Historic Farmhouse
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
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Beautiful Sag Harbor Cottage with direct access to Sag Harbor Cove and a...
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4BR Sag House, Heated Pool with automatic cover, Perfect for families
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Beautiful Bay Point Beach House
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Eclectic and colorful home with a private yard close to town in Sag Harbor.
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
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Gorgeous Four Bedroom Home in Sag Harbor with Pool/water access
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Post Modern on Mature Landscaping, Master Bedroom with Separate...
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Beautiful, new design with tons of natural light, beautiful pool, and great...
Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Spacious Vacation Home On 2nd Private Acres With Community Tennis
Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Coastal-style home with open-floor plan, ample natural light, blocks away...
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Walking distance to Circle Beach
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Sagaponack home with fenced-in Pool. Ideal for young kids.
Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Showing results 1-50 of 287
Frequently Asked Questions about Sag Harbor
- Yes, here are some popular holiday rentals in Sag Harbor that have a pool:
- Enjoy a Thanksgiving Mini Vacation ! Wolffer Vineyard Close!
- Waterfront, Pool, HotTub, Strong WIFI, Pingpong, Paddleboard, Kayak, Bocce Court
- Modern Luxury w/ Private Pool. 5 min from Beach & Town of Sag Harbor
- Yes, here are some popular holiday rentals in Sag Harbor that have internet access:
- Enjoy a Thanksgiving Mini Vacation ! Wolffer Vineyard Close!
- Waterfront, Pool, HotTub, Strong WIFI, Pingpong, Paddleboard, Kayak, Bocce Court
- Modern Luxury w/ Private Pool. 5 min from Beach & Town of Sag Harbor
- The best pet friendly rentals in Sag Harbor are:
- Enjoy a Thanksgiving Mini Vacation ! Wolffer Vineyard Close!
- Waterfront, Pool, HotTub, Strong WIFI, Pingpong, Paddleboard, Kayak, Bocce Court
- Modern Luxury w/ Private Pool. 5 min from Beach & Town of Sag Harbor
- Some of the most popular kid friendly rentals in Sag Harbor are:
- Enjoy a Thanksgiving Mini Vacation ! Wolffer Vineyard Close!
- Waterfront, Pool, HotTub, Strong WIFI, Pingpong, Paddleboard, Kayak, Bocce Court
- Modern Luxury w/ Private Pool. 5 min from Beach & Town of Sag Harbor
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