Sag Harbor holiday homes

We found 2,511 holiday rentals — enter your dates for availability
Discover a selection of 315 homes, 15 apartments and other holiday rentals in Sag Harbor that are perfect for your trip. Whether you’re travelling with friends, family or just with your pet, holiday homes have the amenities that you expect for your stay, which might include air conditioning and a pool. You'll be sure to find a property to rent for everyone's needs, including places that are non-smoking or accessible.

Holiday rentals with weekly discounts – Sag Harbor

Showing deals for:13 Nov - 20 Nov

Exterior
Private kitchen
Dining Room
Patio
Exceptional
(97 reviews)

Beautiful 3600sq ft Sag Harbor Village Home, Saltwater Pool, Walk to Beach &Town

Sag Harbor

15% off
NZ$14,868
for 7 nights, 1 home
NZ$2,124 per night
includes taxes & fees
Beautiful 3600sq ft Sag Harbor Village Home, Saltwater Pool, Walk to Beach &Town
view from living room towards pool, outdoor dining
aerial view
kitchen with large island and breakfast table
master bedroom with balcony
Exceptional
(7 reviews)

Everything in Hamptons special discount available for weekly and monthly renters

Water Mill

17% off
NZ$98,343
for 7 nights, 1 home
NZ$14,049 per night
includes taxes & fees
Everything in Hamptons special discount available for weekly and monthly renters
Spacious Main Floor Living room
Exterior
Pool
Large Dining/Kitchen Space
Exceptional
(11 reviews)

New Modern Farmhouse Estate Living in the heart of Southold with a pool!!!

Southold

8% off
NZ$16,542
for 7 nights, 1 home
NZ$2,363 per night
includes taxes & fees
New Modern Farmhouse Estate Living in the heart of Southold with a pool!!!
An elegant dining room (to 10 ppl, joins kitchen +8 and outdoor dining  +10,)
Living area
Lower deck With Pool, 9 Loungers, plus 6 pool-chairs. Upper deck dining seats 10
Front entrance, park-like grounds
Exceptional
(26 reviews)

Southampton Pickleball Walk to beach. Kayaks on lake Park-like grounds Pool

Southampton

30% off
NZ$17,189
for 7 nights, 1 home
NZ$2,456 per night
includes taxes & fees
Southampton Pickleball Walk to beach. Kayaks on lake Park-like grounds Pool
Pool
Terrace/patio
Living area
Exterior
Exceptional
(8 reviews)

Stunning fall sunsets, coveted location on Mecox Bay - recently furnished

Water Mill

8% off
NZ$66,192
for 7 nights, 1 home
NZ$9,456 per night
includes taxes & fees
Stunning fall sunsets, coveted location on Mecox Bay - recently furnished
Living area
Pool
Terrace/patio
Dining
Exceptional
(17 reviews)

PRIVATE POOL ~ PERFECT HAMPTONS GETAWAY ~ WBH

East Hampton

8% off
NZ$28,153
for 7 nights, 1 home
NZ$4,022 per night
includes taxes & fees
PRIVATE POOL ~ PERFECT HAMPTONS GETAWAY ~ WBH
Main house dining area with wet bar, 300 bottle wine fridge and ice maker.
Pool area viewed from side with teak loungers and umbrellas
Private kitchen
Covered porch on backside of main house
Exceptional
(6 reviews)

Amagansett Beach Estate with Award Winning Outdoor Amenities

Amagansett

8% off
NZ$57,849
for 7 nights, 1 home
NZ$8,264 per night
includes taxes & fees
Amagansett Beach Estate with Award Winning Outdoor Amenities
Pool
Outdoor dining
Private kitchen
Living area
Exceptional
(13 reviews)

Explore the Hampton in this Shelter Island Getaway. Weekly Bookings

Shelter Island Heights

31% off
NZ$9,997
for 7 nights, 1 home
NZ$1,428 per night
includes taxes & fees
Explore the Hampton in this Shelter Island Getaway. Weekly Bookings
View from entry foyer into double height living room, skylights, leading to pool
Thermador chefs kitchen with expansive island open to dining room & family room
Open entry foyer with wall of windowed doors to Zen Garden
Dining room seating 12 leading to chef's kitchen and doors leading to pool
Exceptional
(6 reviews)

Completely Renovated Home on ~2 Private Acres, Near Beach/Town

Wainscott

8% off
NZ$28,196
for 7 nights, 1 home
NZ$4,028 per night
includes taxes & fees
Completely Renovated Home on ~2 Private Acres, Near Beach/Town
Living room w/ screen porch beyond
Pool
New Kitchen
Den
Exceptional
(46 reviews)

Quiet Family Friendly Hideaway With Pool And Poolhouse

East Hampton

8% off
NZ$22,731
for 7 nights, 1 home
NZ$3,247 per night
includes taxes & fees
Quiet Family Friendly Hideaway With Pool And Poolhouse
outdoor shower
Dining
living room
kitchen
Exceptional
(60 reviews)

Southampton Village Renovated Sun-filled Charming Home, Heated Salt water Pool

Southampton

8% off
NZ$23,945
for 7 nights, 1 home
NZ$3,421 per night
includes taxes & fees
Southampton Village Renovated Sun-filled Charming Home, Heated Salt water Pool
Living area
Dining
Room
Private kitchen
Exceptional
(18 reviews)

Great Getaway! Exceptional Home. Walking distance to The Christmas Tree Shoppe

Cutchogue

8% off
NZ$8,472
for 7 nights, 1 cottage
NZ$1,210 per night
includes taxes & fees
Great Getaway! Exceptional Home. Walking distance to The Christmas Tree Shoppe
Exterior detail
Living area
Pool
Exceptional
(10 reviews)

Just Posted for Summer 2026! SECLUDED SAG HARBOR COTTAGE w/ HUGE POOL

Sag Harbor

8% off
NZ$24,888
for 7 nights, 1 cottage
NZ$3,555 per night
includes taxes & fees
Just Posted for Summer 2026! SECLUDED SAG HARBOR COTTAGE w/ HUGE POOL
Pool
Terrace/patio
Living area
Living area
Exceptional
(11 reviews)

Large East Hampton house with heated pool and home gym - fully fenced

East Hampton

12% off
NZ$21,412
for 7 nights, 1 home
NZ$3,059 per night
includes taxes & fees
Large East Hampton house with heated pool and home gym - fully fenced
Private kitchen
Private kitchen
Property grounds
Room
Exceptional
(14 reviews)

Steps from Cedar Beach ! Tranquil Retreat in the Heart of Wine Country

Southold

8% off
NZ$7,841
for 7 nights, 1 home
NZ$1,120 per night
includes taxes & fees
Steps from Cedar Beach ! Tranquil Retreat in the Heart of Wine Country
Living area
Private kitchen
Exterior
Living area
Exceptional
(34 reviews)

Totally Renovated Cottage on the North Fork 7 min. walk to the Beach

Cutchogue

7% off
NZ$4,651
for 7 nights, 1 cottage
NZ$664 per night
includes taxes & fees
Totally Renovated Cottage on the North Fork 7 min. walk to the Beach
Bar area pass-through to kitchen, with bar seating.
Living room, looking out toward Accabonac Harbor, water views.
Lovely seating in pool area for morning coffee.
Kitchen with Wolf stove, Sub Zero fridge, pass-through serving area to dining.
Exceptional
(7 reviews)

WATER VIEWS RETREAT, SPRINGS, EAST HAMPTON, POOL, FIRE PIT, 10 MINUTES TO BEACH!

East Hampton

8% off
NZ$27,354
for 7 nights, 1 home
NZ$3,908 per night
includes taxes & fees
WATER VIEWS RETREAT, SPRINGS, EAST HAMPTON, POOL, FIRE PIT, 10 MINUTES TO BEACH!
Queen bedroom leading onto deck.  Ensuite bathroom, walk-in closet and tv.
huge swimming pool and deck surrounded by trees
kitchen leading into open plan living area
living area with gas fire leads onto the deck
Exceptional
(53 reviews)

Large heated pool, games room, private bay beach access, gardens, kid-friendly

East Hampton

8% off
NZ$8,725
for 7 nights, 1 home
NZ$1,246 per night
includes taxes & fees
Large heated pool, games room, private bay beach access, gardens, kid-friendly
Living/dining space
Facade
Front yard closeup
From the bedroom
Exceptional
(22 reviews)

Private Hamptons cottage in ideal Amagansett location

Amagansett

8% off
NZ$9,285
for 7 nights, 1 cottage
NZ$1,326 per night
includes taxes & fees
Private Hamptons cottage in ideal Amagansett location
Interior
Dining
Night time at the pool
Main living room and dining room
Exceptional
(28 reviews)

9BR Sag Harbor PRIVATE w/ Pool-Tennis- B-ball- HotTub

Sag Harbor

8% off
NZ$24,760
for 7 nights, 1 home
NZ$3,537 per night
includes taxes & fees
9BR Sag Harbor PRIVATE w/ Pool-Tennis- B-ball- HotTub
Ariel view- house on quiet culdesac
Hydrangeas blooming all summer.these are the August bloomers
Featured as one of most beautiful poolsides
Living area on 1st floor with wood burning fireplace
Exceptional
(7 reviews)

IN THE ViILLAGE OF SOUTHAMPTON POOL,TENNIS,PICKLEBALL COURTS BEACH CHAIRS&BIKES

Southampton

8% off
NZ$31,141
for 7 nights, 1 home
NZ$4,449 per night
includes taxes & fees
IN THE ViILLAGE OF SOUTHAMPTON POOL,TENNIS,PICKLEBALL COURTS BEACH CHAIRS&BIKES
Private kitchen
Dining
Living area
Outdoor dining
Exceptional
(9 reviews)

Chic Modern Private Designer 1.5 Acre Private Oasis

East Hampton

26% off
NZ$50,597
for 7 nights, 1 home
NZ$7,228 per night
includes taxes & fees
Chic Modern Private Designer 1.5 Acre Private Oasis
Kitchen
Large pool heated pool
Main living area
Dining area
Exceptional
(20 reviews)

Charming, spacious 3 bedroom, 3 bath East Hampton Springs house

East Hampton

7% off
NZ$8,830
for 7 nights, 1 home
NZ$1,261 per night
includes taxes & fees
Charming, spacious 3 bedroom, 3 bath East Hampton Springs house
Dining
Property grounds
Living area
View of Louse Point beach in Springs - swimming, kayaking, paddleboarding
Exceptional
(95 reviews)

Private and Immaculate East Hampton Home With Heated Pool

East Hampton

8% off
NZ$7,959
for 7 nights, 1 home
NZ$1,137 per night
includes taxes & fees
Private and Immaculate East Hampton Home With Heated Pool
  • Peace of mind

    Our Book with Confidence guarantee gives you 24/7 support
  • More quality time

    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more
  • More for less

    More space, more privacy, more amenities — more value

Why visit Sag Harbor

  • Seaside Serenity: Enjoy picturesque waterfront views and stroll along charming beaches.
  • Historic Exploration: Discover the village’s heritage with its well-preserved historic buildings and districts.
  • Art & Culture: Visit local art galleries and museums that capture Sag Harbor’s rich cultural tapestry.
  • Outdoor Leisure: Unwind in local parks and enjoy the vibrant, family-friendly outdoor scene.
  • Romantic Ambience: Experience captivating sunsets by the marina, perfect for a quiet retreat.

Top attractions in and around Sag Harbor

Sag Harbor, New York, is a charming seaside village perfect for outdoor and romantic getaways. Visitors can explore beautiful beaches, historic buildings, and art museums that reflect the area's rich culture. Whether you're seeking a family-friendly experience or a quiet retreat, Sag Harbor offers a delightful blend of activities and attractions that cater to all travellers. Don't miss the chance to soak in the picturesque surroundings and warm atmosphere that make this destination special.

  • Sag Harbor Marine Park: Located within Sag Harbor, this marina offers an adventurous and outdoor experience with beach vibes, perfect for exploring the local waters and enjoying the scenic coast.
  • East Hampton Main Beach: Approximately 11km from Sag Harbor, this beach provides a classic seaside experience with its inviting beach vibes and golden sands.
  • Foster Memorial Town Beach: Situated 3km from Sag Harbor, this urban park offers a blend of city and family-friendly outdoor vibes, ideal for a relaxed day out.

Things to do recommended for couples

For a romantic getaway in Sag Harbor, explore the charming streets hand-in-hand, enjoy a sunset sail on the bay, or savour a candlelit dinner at a local eatery. Don't miss the scenic views at Long Beach, perfect for a stroll together.

Things to do recommended for families

Families can explore the charming streets of Sag Harbor, visiting the Whaling Museum for a glimpse of maritime history, or enjoy a day at the lovely Havens Beach, perfect for swimming and picnicking. Don’t miss the local shops and eateries for a taste of community life.

Things to do recommended for groups

Groups visiting Sag Harbor can enjoy a scenic boat tour of the picturesque harbour, explore the local art galleries, and indulge in fresh seafood at waterfront eateries. Don't miss the chance to stroll through charming streets filled with historic homes and boutique shops.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

What do I need to keep in mind when booking a vacation in Sag Harbor

Whether you're journeying with a group, as a family, with your pets, or seeking extended stays, be sure to filter using the appropriate criteria. Here are some Vrbo booking pointers for you.

  • Traveling to Sag Harbor with a group: Consider how many bedrooms you'll require, along with features like a full kitchen or an outdoor area for group get-togethers. Luckily, you can search for all these options—and more—on Vrbo.
  • Traveling to Sag Harbor with young kids: Travelling with young children can present its challenges. It's important to prioritise their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, it's wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Sag Harbor: For many families, a trip wouldn't be the same without their furry companion. If this resonates with you, take a look at Vrbo properties that welcome pets. Most of these pet-friendly accommodations come equipped with feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Sag Harbor: If you're in search of holiday rentals offering discounts for stays of a month or more, you've come to the right spot. By using the appropriate filters, you'll be able to effortlessly discover and save on monthly rentals. Don't forget to include amenities like a parking space, a well-equipped kitchen, or a private pool in your search as well.

Where to stay near Sag Harbor

Discover the charm of Sag Harbor, New York, where picturesque streets meet stunning waterfront views. This quaint village offers a perfect blend of outdoor activities, from relaxing on beautiful beaches to exploring local parks. Stroll through historic districts filled with art galleries and boutique shops, or enjoy a romantic sunset by the marina. Summer in Sag Harbor is vibrant, with lively events and a welcoming atmosphere that makes it an ideal destination for families and luxury seekers alike.

  • Hamptons: Situated 8km from Sag Harbor, the Hamptons offer a charming blend of coastal allure and outdoor adventure. Visitors are drawn here for the pristine beaches and a romantic, outdoor retreat. Enjoy a round of golf at a local course or take in the brisk slopes at a nearby ski field. The area is dotted with scenic landmarks including expansive family beaches and a serene lake, making it a perfect destination for a leisurely day exploring natural beauty and recreational pursuits.
  • East Hampton: Located 10km from Sag Harbor, East Hampton provides a vibrant mix of family-friendly outdoor activities and beachside relaxation. The city is a go-to destination for those seeking a versatile holiday experience. Enjoy a day out at the golf course or relax in one of the recreational areas, with a ski field nearby for those inclined to winter sports. Notable attractions include a welcoming beach and park, ideal for picnics and leisurely strolls along the coast.
  • Bridgehampton: Just 6km from Sag Harbor, Bridgehampton is celebrated for its inviting outdoor ambience and picturesque beach scenes. This city is a haven for those seeking a romantic escape or a refreshing outdoor experience. Engage in a round of golf at one of the local courses or spend time at the recreational areas. The area boasts a lovely beach, complete with a family-friendly atmosphere and a charming park, providing a perfect backdrop for a relaxed and scenic holiday.

Best time to go to Sag Harbor

If you're planning a trip to Sag Harbor, it's a good idea to check both the weather and property rates. The warmest month is August.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
January35.6°F (2.0°C)Light RainMostly SunnyAverage
February35.8°F (2.1°C)Light RainMostly CloudyAverage
March39.7°F (4.3°C)Light RainMostly SunnyAverage
April47.5°F (8.6°C)Light RainMostly SunnyAverage
May55.8°F (13.2°C)Light RainMostly SunnyAverage
June64.9°F (18.3°C)Light RainMostly SunnyModerately High
July73.0°F (22.8°C)Light RainMostly SunnyModerately High
August73.4°F (23.0°C)Light RainMostly SunnyModerately High
September68.2°F (20.1°C)Light RainMostly SunnyAverage
October59.7°F (15.4°C)Light RainMostly SunnyModerately Low
November49.6°F (9.8°C)Light RainMostly SunnyModerately Low
December42.1°F (5.6°C)Light RainMostly CloudyModerately Low

Booking with Vrbo is simple

Looking to save on your next holiday? Consider being flexible with your travel dates, as prices can fluctuate. Moreover, extending your stay often results in significant savings. To discover the ideal Vrbo property that fits your budget, make use of our filters to search by price, location, and type of holiday rental. We're here to help you find the perfect place for your getaway.

Vrbo Trips: Planning made easy

Vrbo’s Trip Board offers a handy area for you to plan new trips, continue from where you last stopped, or manage your travel arrangements. You can easily access the properties you've saved or booked, neatly organised under Potential, Upcoming, or Current Trips. To start making the most of Trip Boards, head over to: https://www.bookabach.co.nz/trips.

**Based on Vrbo properties bookings.

Explore the waterfront setting in Sag Harbor

Enjoy the churches and other features of Sag Harbor. This city's boating, island views and beaches draw many visitors. Whether you're planning a family holiday, a trip with friends or a romantic retreat, HomeAway has a great selection of holiday homes. Many rentals come with a full kitchen and separate dining area, perfect if you need a space for entertaining.

Activities and attractions in Sag Harbor

Are you searching for top things to see and do while you're in town? Although it can be tempting to stay in your comfortable holiday rental, you'll want to check out everything that Sag Harbor has to offer. Here are some of the top attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • Wolffer Estates Vineyard (3.7 mi / 6 km)
  • LongHouse Reserve (5 mi / 8 km)
  • Duck Walk Vineyards (7.6 mi / 12.3 km)
  • Croteaux Vineyards (8.3 mi / 13.4 km)
  • Kontokosta Winery (8.9 mi / 14.4 km)
  • Raphael Winery (9.1 mi / 14.7 km)

Exploring the natural features in Sag Harbor

Whether you're an active traveller or just want to take in the scenery, Sag Harbor is a great place to get outside. These are a few of the area's most eye-catching sights, all within 30 miles (48.2 km) of the city centre:

  • Elizabeth A. Morton National Wildlife Refuge (4.1 mi / 6.5 km)
  • LongHouse Reserve (5 mi / 8 km)
  • The Hamptons Beaches (5 mi / 8.1 km)
  • Georgica Beach (5.9 mi / 9.6 km)
  • East Hampton Main Beach (6.4 mi / 10.3 km)
  • Sunset Beach (6.5 mi / 10.5 km)

Transport to and around Sag Harbor

The nearest airport is in East Hampton, NY (HTO), located 3.5 mi (5.6 km) from the city centre. If you can't find a flight that's convenient for your trip, you could book a flight to Montauk, NY (MTP), which is 19.8 mi (31.9 km) away.

Frequently asked questions

What is the best area to stay in Sag Harbour when booking a holiday home?
One of the more desired areas to get a Sag Harbour holiday home is North Haven. When you lock in your holiday property with Bookabach, you'll enjoy having the entire place to yourselves. That means you don't have to share it with anybody other than your group.
What is the most popular type of holiday home accommodation in Sag Harbour?
Houses are the most popular kind of holiday home in Sag Harbour, according to our data. Even if you've got something a little different in mind, Bookabach has holiday homes in loads of shapes and sizes. Explore our options to find your perfect pad.
How much does it cost to rent a holiday home in Sag Harbour?
Length of stay, season and property type are some things that can affect the price of a holiday home. Simply click on your dates of travel to find your dream escape. From comfy cabins to expansive luxury villas, all Bookabach holiday homes offer incredible value.
How much does it cost to rent a beach house in Sag Harbour?
The average price for a holiday home near the beach in Sag Harbour depends on when you're travelling and the type and size of property you're searching for. You can find prices quickly and easily on Bookabach by entering your travel dates. Then use the filter tool to choose the number of bedrooms and amenities that you prefer, such as air conditioning, WiFi and a hot tub.
What are popular home amenities in Sag Harbour?
A garden, a barbecue grill and a fireplace are the most popular home amenities in Sag Harbour. Whether you're taking to the road alone, with a partner or a group of family members, Bookabach can help you find a holiday home that matches your tastes with all the conveniences you're looking for.
What are the top attractions for families in Sag Harbour?
There are tons of wonderful things to see and do with the family in Sag Harbour, such as:
  • East Hampton Main Beach
  • Georgica Beach
  • Atlantic Avenue Beach
Can I find two-bedroom holiday homes in Sag Harbour?
Sag Harbour has 31 two-bedroom properties to select from. Book a holiday home with all the comfort and privacy you're looking for at a price that won't break the bank on Bookabach.
Are there holiday homes with WiFi in Sag Harbour?
Sag Harbour has 108 holiday homes with WiFi, so you can stay connected while travelling. Simply check the "WiFi" box in our handy search filter for a list of properties with this feature. From streaming Hollywood blockbusters to sending emails, these Bookabach homes make it a breeze to go online.
How old do you have to be to rent a holiday home in Sag Harbour?
You'll have to check with the Sag Harbour holiday home you'd like on Bookabach as age restrictions differ. However, it's generally 16, 18 or 21.
How long can I rent a holiday home in Sag Harbour for?
The amount of time you can book a Sag Harbour holiday home for varies depending on the property. Simply put in your travel dates to find options that offer extended stays. They come with all you need to make your extended trip more enjoyable like laundries and air conditioning. Some holiday homes may also offer weekly or monthly discounts, so you can stick around for longer for less.

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