A marina with several boats docked, including a white motorboat and a sailboat with a canopy.

Find Hotels with a Pool in Sag Harbor, NY from CA $212

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Check availability on Sag Harbor Hotels with a Pool

Tonight
Oct 19 - Oct 20
Tomorrow
Oct 20 - Oct 21
This weekend
Oct 23 - Oct 25
Next weekend
Oct 30 - Nov 1

Our top choices for Sag Harbor hotels with a pool

A swimming pool with clear blue water, surrounded by lounge chairs and umbrellas, with a building in the background.
A waterfront property with a large house, multiple boats docked, and lush greenery.
A spacious hallway with a fireplace, a large window, and a built-in shelving unit.
A spacious lobby with multiple seating areas, a kitchen area, and large windows providing natural light.

1. Sag Harbor Inn

Sag Harbor Inn
Sag Harbor
  • Swim into serenity at this charming Sag Harbour retreat with a seasonal outdoor pool and balcony views.
CA $310
CA $354 total
includes taxes & fees
Nov 1 - Nov 2
Sag Harbor Inn
A pool area with umbrellas, potted plants, and a pathway leading to a building.
A spacious living room with a fireplace, comfortable seating, and large windows.
A dining area with tables set for a meal, a fireplace, and a large mirror reflecting the room.
A cozy outdoor seating area with a brick fireplace, cushioned seating, and potted plants.

2. Faraway Sag Harbor

Faraway Sag Harbor
Sag Harbor
  • Dive into summer splendour at a tranquil pool retreat with chic cabanas and luxe loungers.
CA $497
CA $625 total
includes taxes & fees
Nov 19 - Nov 20
Faraway Sag Harbor
A backyard with a swimming pool, wicker lounge chairs, and potted plants.
A garden with hydrangea bushes, a stone wall, and a covered area with plants.
A living room with a green sofa, a small round table with a board game, a blue vase with dried plants, and a white arched cabinet.
A modern living room with a sectional sofa, a chandelier, framed artwork, and a view through a glass door.

3. Designer Sag Harbor Home w/ Pool + Fire Pit + Yard

Designer Sag Harbor Home w/ Pool + Fire Pit + Yard
Sag Harbor
CA $762
CA $1,641 total
includes taxes & fees
Oct 20 - Oct 21
Designer Sag Harbor Home w/ Pool + Fire Pit + Yard
A covered outdoor seating area with wicker furniture and a glass door leading to a pool.
A deck with a wicker sofa and cushions, surrounded by a white fence and trees.
A building with a white exterior, a set of steps leading to a white porch, and a statue of a lion.
A dining area with a wooden table and chairs, a hanging light fixture, a framed picture on the wall, and vertical blinds.

4. Large Room w use of pool/tennis in Spacious home

Large Room w use of pool/tennis in Spacious home
Sag Harbor
  • Enjoy coastal serenity with a refreshing swim in the outdoor pool at this seaside B&B.
CA $808
CA $1,166 total
includes taxes & fees
Oct 20 - Oct 21
Large Room w use of pool/tennis in Spacious home
A swimming pool with lounge chairs and umbrellas, surrounded by a forested area.
A bedroom with two beds, a ceiling fan, a large window, and a view of greenery outside.
An outdoor dining area with a table and chairs, surrounded by tall trees and string lights.
Beach

5. A Room At The Beach

A Room At The Beach
Bridgehampton
  • Soak up sunshine and serene vibes at this Hamptons motel with a stylish outdoor pool.
CA $419
CA $478 total
includes taxes & fees
Oct 21 - Oct 22
A Room At The Beach
A swimming pool with two lounge chairs and a green umbrella.
Two bicycles with wicker baskets labeled "Sophie & Co." parked in front of a building with a dark door and white columns.
A wooden building with a white window and a balcony.
A wooden outdoor seating area with a sofa and a table, surrounded by gravel and greenery, with a house in the background.

6. The Sagaponack

The Sagaponack
Wainscott
  • Take a summer dip in the seasonal outdoor pool with loungers for relaxing in the Hamptons sun.
CA $272
CA $368 total
includes taxes & fees
Nov 19 - Nov 20
The Sagaponack
Property amenity
Front of property - evening/night
Bar (on property)
Terrace/patio

7. Shelter Island House

Shelter Island House
Shelter Island Heights
  • Relaxing seasonal pool oasis beckons at this Shelter Island retreat, where a poolside bar enhances sun-drenched afternoons.
CA $285
CA $325 total
includes taxes & fees
Oct 21 - Oct 22
Shelter Island House
A pool area with lounge chairs and umbrellas, a mural on the wall, and a clear view of the sky.
A modern outdoor seating area with a white sofa and a table, a sliding glass door, and a number '25' on the wall.
A modern lounge area with a pool view, white furniture, and contemporary lighting fixtures.
A hotel room with two beds, a wall art piece with the text "GOOD DREAMS START HERE", and a pink abstract wall design.

8. The Bentley Hotel Southampton

The Bentley Hotel Southampton
Southampton
  • Dive into the pristine oasis of the seasonal outdoor pool, complete with umbrellas and loungers for ultimate relaxation.
CA $185
CA $212 total
includes taxes & fees
Oct 26 - Oct 27
The Bentley Hotel Southampton
A swimming pool with a wooden deck, lounge chairs, and a fence.
A balcony with a view of a dock and a boat, a table with a basket of pastries, and a chair.
A hotel room with a bed, a blue sofa, a wicker chair, a small table with a vase, and a lamp.
A rooftop terrace with lounge chairs, a wooden table, and a view of the landscape.

9. The Harbor Front Inn

The Harbor Front Inn
Greenport
  • Dive into pool paradise at this oceanside retreat with sun loungers for ultimate relaxation.
CA $253
CA $330 total
includes taxes & fees
Nov 2 - Nov 3
The Harbor Front Inn
A modern building with a pool, featuring a dining area with tables and chairs, and a glass entrance.
A modern hotel room with a bed, bedside table, and a view of the garden.
A bar setting with a bartender and a customer. The bar has shelves with various bottles and glasses. There is a cushioned bench in the foreground.
A bar area with shelves stocked with various bottles and glasses.

10. Topping Rose House

Topping Rose House
Bridgehampton
  • Serene outdoor pool creates luxurious oasis in the Hamptons; perfect for unwinding after coastal adventures.
CA $823
CA $945 total
includes taxes & fees
Oct 27 - Oct 28
Topping Rose House
View all properties

Choose what matters most at hotels with a pool in Sag Harbor

Breakfast included
4 stars
Hot tub
5 stars
Spa

Top Sag Harbor Hotel Reviews

The Atlantic Hotel

The Atlantic Hotel

10/10 Excellent
"We were 4 girls and the room was two bedrooms and another bed also so it accommodated all of us. 😊"
Grace 1-night trip
Posted 5 hours ago
The Atlantic Hotel
Sound View Greenport

Sound View Greenport

8/10 Good
"This was our third stay at Soundview. We stay there because all of the rooms face the sound and the natural view can’t be beat. The rooms are lodgy but spacious and depending on your room, there are public/private balconies."
Danielle 1-night trip
Posted 1 day ago
Sound View Greenport
Beachcomber Resort at Montauk

Beachcomber Resort at Montauk

10/10 Excellent
"Great place in Montauk. Beautiful view and room was spacious."
fred 4-night trip
Posted 3 days ago
Beachcomber Resort at Montauk

Frequently asked questions

What are the best hotels in Sag Harbor with outdoor pools?
The Sag Harbor Inn is a charming 3.5-star hotel that features an inviting outdoor pool, superb for families looking to relax and enjoy the sun. Guests have praised the hotel for its comfortable and clean rooms, making it an ideal choice for parents traveling with children.In addition to the pool, the Sag Harbor Inn offers complimentary continental breakfast, which is a great way to start the day without the hassle of dining out. Families appreciate the free WiFi and the availability of cribs at no extra charge, ensuring convenience during their stay. With a traveller review rating of 9.4, it's clear that visitors find the service to be fantastic and the location beautiful—a superb blend of comfort and accessibility.
How much does a hotel with outdoor pool in Sag Harbor cost?
Enjoy staying in a hotel in Sag Harbor with an outdoor pool. You can find a great deal from CA $212 on Expedia. If you're leaning toward a little luxury, prices can rise, and may vary depending on the location, season, and hotel amenities. Be sure to book in advance to enjoy more options and potentially better rates, especially if you're planning a trip during weekends or around public holidays.
Are there hotels with outdoor pools that are close to Havens Beach?
The Sag Harbor Inn is a charming 3.5-star hotel that offers an inviting outdoor pool, superb for families looking to enjoy a refreshing dip after a day at the beach. With a traveller rating of 9.4, guests consistently praise the comfortable and clean rooms, as well as the beautiful location that is just a short distance from Havens Beach.Families will appreciate the convenience of free continental breakfast and WiFi, along with complimentary toiletries and cribs for younger travellers. The self-parking option adds to the ease of your stay, making it a straightforward experience for those traveling with children.In addition to the outdoor pool, the hotel's fantastic service and great coffee further enhance the family-friendly atmosphere, ensuring that your stay in Sag Harbor is both relaxing and enjoyable.
Is it cheaper to book flights and a hotel in Sag Harbor as a package?
Booking a hotel and flight package on Expedia can be cheaper than booking flights and hotels separately. Bundling can lead to significant savings, especially for international travel or when booking well in advance. However, savings vary depending on factors like destination, travel dates, and availability, so it's wise to compare options. With access to over 300,000 hotels worldwide, Expedia makes it easy to build the perfect travel package.
Can I cancel my hotel reservation on Expedia?
Expedia has plenty of refundable hotels. In many cases, you need to cancel your booking 24-48 hours ahead of your arrival date. Remember to check your booking confirmation for the exact cancellation policy. For maximum flexibility, use Expedia's "Fully refundable property" filter during your search to find the right hotel with an outdoor pool in Sag Harbor for you.
How can I save on a hotel in Sag Harbor with Expedia?
Before booking your Sag Harbor hotel, remember to join One Key™, Expedia's free travel rewards program. Just sign up and sign in to access instant discounts with Member Prices as well as member-only perks. Booking your hotel in advance will typically help you save, but there are last-minute deals to explore too.

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