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Sag Harbor, NY vacation rentals
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Best Vacation rentals and Airbnb offers in Sag Harbor, NY

Best Sag Harbor, NY vacation rentals with a balcony

Prime Location! Walk To Beach! Wainscott Family House & Cottage. Pool & Hot Tub! - Sag Harbor, NY
10 29 reviews
Sag Harbor, NY
10/13 – 10/19
$2984/nighttotal: $17904 (6 )

Prime Location! Walk To Beach! Wainscott Family House & Cottage. Pool & Hot Tub!

5 1
apartment , Wainscott
This charming cottage sits in the heart of Wainscott, a quiet, rural area just a short walk from one of the most beautiful Hamptons beaches. It's rated excellent by previous guests, making it a popular choice for families and groups seeking a relaxing getaway. The 3,500 square foot cottage comfortably accommodates up to 14 guests with 5 bedrooms and pull-out couches. Enjoy a fully equipped kitchen, a private pool and jacuzzi, spacious outdoor areas, and a host of other amenities, including a Sonos sound system, three decks, and a fully enclosed courtyard.
Hamptons 9bd Mega Compound W Pool Tennis Bball Nightclub - Sag Harbor, NY
Sag Harbor, NY
10/13 – 10/19
$2174/nighttotal: $13044 (6 )

Hamptons 9bd Mega Compound W Pool Tennis Bball Nightclub

9 1
house , Noyack
This 9-bedroom villa is located in Noyack, 48 miles from Long Island MacArthur Airport.
This spacious residence offers 5010 square feet of living space, accommodating up to 60 guests with amenities including a private pool, hot tub, and a well-equipped kitchen.
Waterfront Home On Beautiful Shelter Island W/large Deep Water Dock - Sag Harbor, NY
9.6 13 reviews
Sag Harbor, NY
10/13 – 10/19
$1349/nighttotal: $8094 (6 )

Waterfront Home On Beautiful Shelter Island W/large Deep Water Dock

5 1
apartment , Shelter Island Heights
This oceanfront Shelter Island Heights home offers stunning views and easy beach access, located within two miles of Havens House, the Shelter Island Historical Society, and Sylvester Manor.
This 4,700-square-foot vacation rental boasts six bedrooms, three bathrooms, sleeps twelve guests, and includes a full kitchen, spa, fireplace, game room, and private parking.
Summer East Hampton Retreat- Heated Pool, Tennis, Hot Tub - Sag Harbor, NY
9.7 7 reviews
Sag Harbor, NY
10/13 – 10/19
$1713/nighttotal: $10278 (6 )

Summer East Hampton Retreat- Heated Pool, Tennis, Hot Tub

5 1
apartment , Wainscott
This Wainscott home is conveniently located just a short drive from both Sag Harbor Village and East Hampton Village, offering easy access to the beaches, restaurants, and cultural attractions of both towns. The property boasts excellent user, location, and cleanliness ratings, making it a popular choice for travelers.
This 5-bedroom, 6-bathroom house provides 4,000 square feet of living space. Guests can enjoy a private pool, hot tub, tennis court, and a variety of other amenities, including a fully equipped kitchen, a Sonos entertainment system, and a gym.

Search Family Vacation Rentals in Sag Harbor, NY

Plan the perfect family beach trip to Sag Harbor, NY with spacious rentals that offer plenty of room to spread out.

Shelter Island Retreat With Pool ...Close To Beach & Pet Friendly - Sag Harbor, NY
10 17 reviews
Sag Harbor, NY
10/13 – 10/19
$1071/nighttotal: $6426 (6 )

Shelter Island Retreat With Pool ...Close To Beach & Pet Friendly

3 1
apartment , Shelter Island Heights
This family-friendly vacation home is located in Shelter Island Heights, just a short distance from Crescent Beach, Sunset Beach, and Shelter Island Country Club. This rental has received excellent reviews from previous guests.
The house has 3 bedrooms and 3 bathrooms, comfortably accommodating up to 7 guests. The home features a private pool, barbecue grills, a garden, a fireplace, and a game room for entertainment.
Sag Harbor Village 3 Bedroom Gem - Sag Harbor, NY
10 5 reviews
Sag Harbor, NY
10/13 – 10/19
$962/nighttotal: $5772 (6 )

Sag Harbor Village 3 Bedroom Gem

3 1
apartment , Sag Harbor
This Sag Harbor Village residence is a historic landmark reimagined, located steps from Sag Harbor's boutiques, dining, and waterfront, with the Sag Harbor Jitney stop a 10-minute walk away.
This 3-bedroom, 2-bathroom apartment accommodates up to 5 guests and features a gourmet eat-in kitchen, a library/dining room, an outdoor patio, and a private backyard, offering a quintessential Sag Harbor village experience.
Designer Retreat In The Village - Sag Lighthouse - Sag Harbor, NY
9.7 136 reviews
Sag Harbor, NY
10/13 – 10/19
$2114/nighttotal: $12684 (6 )

Designer Retreat In The Village - Sag Lighthouse

1 1
apartment , Sag Harbor
This midcentury-style home is located in Sag Harbor's historic district, a short walk from the village center's shops and restaurants. The property has excellent user, location, and cleanliness ratings. This 3-bedroom, 1-bathroom house accommodates up to 6 guests. The house offers a spacious layout, a swimming pool, a fitness center, a garden, and a gourmet kitchen, perfect for enjoying the beautiful Sag Harbor weather.
Summer 2026 Now Available! Grab An Amazing Property In The Heart Of The Hamptons - Sag Harbor, NY
10 90 reviews
Sag Harbor, NY
10/13 – 10/19
$2121/nighttotal: $12726 (6 )

Summer 2026 Now Available! Grab An Amazing Property In The Heart Of The Hamptons

7 1
apartment , Bridgehampton
This 7-bedroom, 5-bathroom luxury home is located just two miles from Bridgehampton village, harbor, and beaches, offering a secluded setting in a private wooded area. It has received excellent user ratings for its amenities and location.
The 4,500-square-foot home can accommodate up to 14 guests and features a gourmet kitchen, a home theater system, a finished basement with games, a gym, and a large DVD collection. Amenities include a heated saltwater pool, a hot tub, an outdoor BBQ grill, a spacious deck with a pergola, a fire pit, and an outdoor TV.

Frequently Asked Questions about vacation rentals in Sag Harbor, NY

  • Which walking or cycling routes are the best in Sag Harbor, NY?

    There are some great walking and cycling routes in Sag Harbor. You can walk or bike along the waterfront, or take a scenic ride through the historic streets. The Long Wharf is a popular spot for walking and enjoying the views, and the Sag Harbor Bike Path is a great way to explore the area on two wheels.
  • What are the best Airbnb and vacation rentals in Sag Harbor, NY?

    Whaling Captain Pierson's Cottage, Sag Harbor Beach House and Whaling Captain Pierson's Apartment Too are the most popular Airbnb and vacation rentals in Sag Harbor, NY among travelers.

  • What sports or outdoor activites can visitors enjoy in and around Sag Harbor, NY?

    Sag Harbor is a great place for outdoor activities. You can go swimming, fishing, kayaking, or paddleboarding in the harbor. There are also several golf courses in the area, and you can even go horseback riding on the beach. If you're looking for a more challenging activity, there's also great hiking and biking in the surrounding area.
  • What are the most popular Airbnbs in Sag Harbor, NY?

    Among the Airbnbs in Sag Harbor, NY, Sag Harbor Beach House, Whaling Captain Pierson's Cottage and Whaling Captain Pierson's Apartment Too are the most popular ones.

  • What other towns or cities can be easily accessed from Sag Harbor, NY?

    Sag Harbor is a great base for exploring the East End of Long Island. You can easily drive to nearby towns like Southampton, East Hampton, and Montauk. If you're looking for a bigger city, you can take a train or bus to New York City, which is about a 2-hour drive from Sag Harbor.
  • What are the best vacation rentals with a pool in Sag Harbor, NY?

  • What amenities are commonly available in vacation rentals in Sag Harbor, NY?

    Vacation rentals in Sag Harbor usually offer a wide range of amenities, including kitchens, laundry facilities, and outdoor spaces like patios or decks. Many rentals also offer amenities like swimming pools, hot tubs, and fireplaces.
  • What are the best rentals for families and kids in Sag Harbor, NY?

  • What time of year is best to rent a vacation rental Sag Harbor, NY?

    The best time to visit Sag Harbor depends on what you're looking for. The summer months are the most popular time to visit, but it can get crowded and expensive. If you're looking for a more relaxed experience, you might consider visiting in the shoulder seasons, like spring or fall.
  • What are the best rentals or Airbnbs with a jacuzzi in Sag Harbor, NY?

    The best vacation rentals or Airbnb with a jacuzzi in Sag Harbor, NY are Walk To The Beach, Sag Harbor Getaway-now Booking Spring/summer/fall 2025 and New Sag Harbor Village Pool - Hot Tub &Beach House.

  • What are the local dishes in Sag Harbor, NY region?

    Sag Harbor is known for its fresh seafood, so be sure to try some of the local catches like lobster, clams, and oysters. You can also find delicious Italian food, as well as classic American dishes like burgers and fries.

Destinations nearby

Best Sag Harbor, NY vacation rentals with parking

Dreamy Cottage - Sag Harbor, NY
Sag Harbor, NY
10/13 – 10/19
$537/nighttotal: $3222 (6 )

Dreamy Cottage

1 1
house , Noyack
This Sag Harbor cottage is located an 11-minute walk from Foster Memorial Beach and a considerable distance from Montauk Point Lighthouse.
This 1-bedroom, 1-bathroom accommodation sleeps up to 3 guests and offers complimentary WiFi, private parking, air conditioning, a full kitchen, and a garden.
Peaceful Cottage - Sag Harbor, NY
10 18 reviews
Sag Harbor, NY
10/13 – 10/19
$344/nighttotal: $2064 (6 )

Peaceful Cottage

1 1
house , Northwest Harbor
This Northwest Harbor cottage, situated midway between East Hampton and Sag Harbor, provides easy access to ocean and bay beaches and nearby hiking trails.
The 1-bedroom, 1-bathroom house features a full kitchen, spacious living room with a smart TV, a queen-size bed, garage parking, laundry facilities, and accommodates up to 2 guests.
Escape To Sag Harbor - Sag Harbor, NY
10 55 reviews
Sag Harbor, NY
10/13 – 10/19
$1307/nighttotal: $7842 (6 )

Escape To Sag Harbor

3 1
apartment , Noyack
This spacious 2400-square-foot house in Sag Harbor, a five-minute drive from downtown and two minutes from Long Beach on the Bay, offers easy access to Sag Harbor's art galleries, restaurants, and museums.
The three-bedroom, four-bathroom rental boasts a private saltwater pool, separate guest house, and ample outdoor space with hammocks and swings, comfortably accommodating up to seven guests and featuring a fully equipped kitchen with a fridge, microwave, and dishwasher.
East Hampton- Beautiful 4 Bedroom Home, Large Heated Pool, Private Backyard - Sag Harbor, NY
10 104 reviews
Sag Harbor, NY
10/13 – 10/19
$2188/nighttotal: $13128 (6 )

East Hampton- Beautiful 4 Bedroom Home, Large Heated Pool, Private Backyard

4 1
apartment , Northwest Harbor
This family-friendly vacation home is located in East Hampton, just 2 miles from the Hamptons Beaches, Three Mile Harbor, and Cedar Point County Park. The house has consistently received excellent ratings for its cleanliness, location, and overall experience.
This 4-bedroom house spans 2800 square feet and can comfortably accommodate up to 9 guests. Enjoy a private pool, a fenced yard, a fully equipped kitchen, a terrace, and a bar, all while taking advantage of the free WiFi and the convenience of housekeeping upon request.

Check Out Vacation Rentals with a Pool in Sag Harbor, NY

Enhance your coastal getaway with a Sag Harbor, NY vacation rental featuring a pool.

Sag Harbor Chic 4 Bedroom Saltwater Pool - Sag Harbor, NY
9.8 36 reviews
Sag Harbor, NY
10/13 – 10/19
$1023/nighttotal: $6138 (6 )

Sag Harbor Chic 4 Bedroom Saltwater Pool

1 1
apartment , Sag Harbor
This Sag Harbor house rental is a short walk from Havens Beach and 1.2 miles from Sag Harbor Village, offering easy access to both.
The four-bedroom, two-bathroom home sleeps eight guests and features a saltwater pool (open mid-May), a spacious half-acre property, and a fully equipped kitchen with dishwasher.
Luxury, Private, Gated Heated Pool, Hot Tub, Fenced In Property! Child Friendly! - Sag Harbor, NY
9.9 134 reviews
Sag Harbor, NY
07/17 – 07/19
$5364/nighttotal: $10728 (2 )

Luxury, Private, Gated Heated Pool, Hot Tub, Fenced In Property! Child Friendly!

6 1
apartment , Wainscott
This six-bedroom house is located in Wainscott, East Hampton, less than half a mile from Montauk Highway and a short distance from the beach. The property has excellent user, location, and cleanliness ratings.
This spacious home has a floor area of 2600 square feet and can accommodate up to 13 guests. The home offers a range of amenities, including a heated pool, hot tub, tennis court, fitness center, and a well-equipped kitchen, making it perfect for families and groups.
Sag Harbor Island View Drive House With Pool - Sag Harbor, NY
9.9 14 reviews
Sag Harbor, NY
10/13 – 10/19
$1476/nighttotal: $8856 (6 )

Sag Harbor Island View Drive House With Pool

1 1
apartment , Noyack
This Sag Harbor, Noyac Bay house rental is conveniently located near Long Beach and Main Street, offering easy access to local shops and restaurants.
The five-bedroom, three-bathroom home includes a heated Gunite pool, Jacuzzi, and a private apartment, accommodating up to ten guests and offering stunning Noyac Bay views from its third-floor deck.
Charming Sag Harbor Home W/ Heated Pool - Sag Harbor, NY
10 14 reviews
Sag Harbor, NY
10/13 – 10/19
$1409/nighttotal: $8454 (6 )

Charming Sag Harbor Home W/ Heated Pool

1 1
apartment , Noyack
This Sag Harbor rental is located on a quiet cul-de-sac, a short walk from Sag Harbor village shops and restaurants, and a short drive to Sag Harbor beaches.
The newly renovated 4-bedroom, 2.5-bathroom house features a private pool, accommodates up to 10 guests, and offers stylish mid-century modern and antique furnishings.

Browse Waterfront Vacation Rentals in Sag Harbor, NY

These seaside vacation rentals in Sag Harbor, NY provide an excellent base for exploring the coast. Browse top local properties and plan your beach-town trip.

Whaling Captain Pierson's Cottage - Sag Harbor, NY
9.9 253 reviews
Sag Harbor, NY
10/13 – 10/19
$479/nighttotal: $2874 (6 )

Whaling Captain Pierson's Cottage

1 1
cottage , Sag Harbor
Waterfront House With Dock And Private Beach - Sag Harbor, NY
10 22 reviews
Sag Harbor, NY
10/13 – 10/19
$1040/nighttotal: $6240 (6 )

Waterfront House With Dock And Private Beach

3 1
apartment , Shelter Island
Designer Sag Harbor Home W/ Pool + Fire Pit + Yard - Sag Harbor, NY
9.8 17 reviews
Sag Harbor, NY
10/13 – 10/19
$857/nighttotal: $5142 (6 )

Designer Sag Harbor Home W/ Pool + Fire Pit + Yard

1 1
apartment , Noyack
Cove View Manor Of Sag Harbor - Sag Harbor, NY
10 72 reviews
Sag Harbor, NY
10/13 – 10/19
$1785/nighttotal: $10710 (6 )

Cove View Manor Of Sag Harbor

3 1
apartment , Noyack

Compare Luxury Vacation Rentals in Sag Harbor, NY

Refined interiors and prime locations make these luxury waterfront vacation rentals in Sag Harbor, NY the ideal choice for your stay.

Hamptons Hills Escape - Sag Harbor, NY
9.9 163 reviews
Sag Harbor, NY
07/17 – 07/19
$466/nighttotal: $932 (2 )

Hamptons Hills Escape

1 1
apartment , Noyack

Discover Vacation Rentals with Saunas in Sag Harbor, NY

Relax in style with an on-site sauna at these premium Sag Harbor, NY vacation rentals near the water.

Villa Kimaal - Luxury With Pool - Sag Harbor, NY
Sag Harbor, NY
10/13 – 10/19
$7678/nighttotal: $46068 (6 )

Villa Kimaal - Luxury With Pool

5 1
house , Noyack
Villa Nostro Palazzo - Sag Harbor, NY
Sag Harbor, NY
10/13 – 10/19
$1946/nighttotal: $11676 (6 )

Villa Nostro Palazzo

7 1
house , Wainscott
Sag Harbor Summer House - Sag Harbor, NY
10 1 review
Sag Harbor, NY
10/13 – 10/19
$1683/nighttotal: $10098 (6 )

Sag Harbor Summer House

1 1
apartment , Noyack
Modern Resort-style Retreat In The Heart Of East Hampton Seamless... - Sag Harbor, NY
Sag Harbor, NY
10/13 – 10/19
$873/nighttotal: $5238 (6 )

Modern Resort-style Retreat In The Heart Of East Hampton Seamless...

4 1
apartment , Northwest Harbor
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