At the tip of famously glitzy and elegant Long Island lies your beachside vacation home in Sag Harbor, New York. Surrounded by duney beaches, luxury resorts, and charming farms and wineries, the island's 17th century whaling history is still palpable in its atmosphere today.

Top 15 Recommended vacation rentals in Sag Harbor
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Popular Rental Amenities in Sag Harbor
Many vacationers spend more time comparing vacation rentals including pools. Many of the properties offer access to a pool. Additionally, properties with pools in Sag Harbor have an average price of $1,575 a night. Most of the available vacation rentals with pools are hotel room. If you would also like to be close to the water, one-third of the vacation rentals providing a pool are located within 2 miles of the waterfront.
Waterfront Vacation Rentals in Sag Harbor

Learn about America's greats
It won't surprise you to know that America's best known painter was inspired by this area of Long Island and even had a studio here. Jackson Pollock and his wife, fellow artist Lee Krasner lived in nearby Springs, creating some of their most important work here.
Peggy Guggenheim has since transformed their house and studio into a museum where you can learn more about the lives and work of these seminal American painters.
Discovering the hidden secrets of Long Island
Why not explore the Sunken Forest in South Shore? The 300-year-old forest is wound with trails and provides both shade in summer and flame-colored visuals in fall. The beach to the south of the forest is rugged yet still accessible, and normally less busy than others in the area.
Another outpost worth exploring is the Shinnecock reservation, near Southampton. The tribe run a living history museum dedicated to Native American life and hold special events like craft fairs, children's programs, and dance performances.
Information about vacation rentals in Sag Harbor
🏡 Vacation rentals available | 465 rentals |
---|---|
🌙 Nightly prices starting at | $196 |
⭐ Popular amenities | Pool, Pets allowed and Air conditioning |
🐾 Pet friendly homes | 155 homes |
🏊 Vacation rentals with pools | 280 homes |
Frequently Asked Questions
What is the average nightly price for a vacation home in Sag Harbor?
The average accommodation in Sag Harbor is priced at $196 per night. Nightly prices for house rentals are $1,551 on average. Cottages in Sag Harbor cost on average $932 per night.
How many vacation rentals are available for booking in Sag Harbor?
There are 465 vacation rentals in Sag Harbor to choose from and book for your next trip.
What amenities are most popular for vacation rentals in Sag Harbor?
The most popular amenities for vacation rentals in Sag Harbor include accommodations with: Pets allowed, Pool, and Air conditioning.
How many vacation rentals with a pool are there in Sag Harbor?
Sag Harbor offers 280 Hotel room and Apartment rental options on offer to rent.
Are dogs allowed in vacation homes in Sag Harbor?
Finding a vacation rental in Sag Harbor that allows pets is possible, with 155 pet-friendly available.
What's the best time to travel to Sag Harbor?
If choosing a vacation home in Sag Harbor, consider that rainy season is typically in January or February, with June often being the driest.
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