Sag Harbor holiday rentals

We found 2,509 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

kitchen with large island and breakfast table
aerial view
living room
view from living room towards pool, outdoor dining
Exceptional
(7 reviews)

Everything in Hamptons special discount available for weekly and monthly renters

Water Mill

17% off
AU$81,733
for 7 nights, 1 home
AU$11,676 per night
includes taxes & fees
Everything in Hamptons special discount available for weekly and monthly renters
Exterior
Private kitchen
Dining Room
Patio
Exceptional
(97 reviews)

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

Sag Harbor

16% off
AU$11,885
for 7 nights, 1 home
AU$1,698 per night
includes taxes & fees
Beautiful 3600sq ft Sag Harbor Village Home, Saltwater Pool, Walk to Beach &Town
Large Dining/Kitchen Space
Exterior
Pool
Exterior
Exceptional
(11 reviews)

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

Southold

8% off
AU$13,772
for 7 nights, 1 home
AU$1,967 per night
includes taxes & fees
New Modern Farmhouse Estate Living in the heart of Southold with a pool!!!
Front entrance, park-like grounds
Living area
Lower deck With Pool, 9 Loungers, plus 6 pool-chairs. Upper deck dining seats 10
An elegant dining room (to 10 ppl, joins kitchen +8 and outdoor dining  +10,)
Exceptional
(26 reviews)

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

Southampton

30% off
AU$14,346
for 7 nights, 1 home
AU$2,049 per night
includes taxes & fees
Southampton Pickleball Walk to beach. Kayaks on lake Park-like grounds Pool
Exterior
Terrace/patio
Pool
Living area
Exceptional
(8 reviews)

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

Water Mill

8% off
AU$55,013
for 7 nights, 1 home
AU$7,859 per night
includes taxes & fees
Stunning fall sunsets, coveted location on Mecox Bay - recently furnished
Exterior
Dining
Living area
Dining
Exceptional
(10 reviews)

Southampton Village Charmer - South of Highway

Southampton

8% off
AU$30,677
for 7 nights, 1 home
AU$4,382 per night
includes taxes & fees
Southampton Village Charmer - South of Highway
Covered porch on backside of main house
Pool area viewed from side with teak loungers and umbrellas
Main house dining area with wet bar, 300 bottle wine fridge and ice maker.
Main house living room
Exceptional
(6 reviews)

Amagansett Beach Estate with Award Winning Outdoor Amenities

Amagansett

8% off
AU$48,078
for 7 nights, 1 home
AU$6,868 per night
includes taxes & fees
Amagansett Beach Estate with Award Winning Outdoor Amenities
Private kitchen
Pool
Terrace/patio
Dining
Exceptional
(16 reviews)

PRIVATE POOL ~ PERFECT HAMPTONS GETAWAY ~ WBH

East Hampton

8% off
AU$23,294
for 7 nights, 1 home
AU$3,328 per night
includes taxes & fees
PRIVATE POOL ~ PERFECT HAMPTONS GETAWAY ~ WBH
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
Frankel Residence
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
AU$23,330
for 7 nights, 1 home
AU$3,333 per night
includes taxes & fees
Completely Renovated Home on ~2 Private Acres, Near Beach/Town
Living area
Outdoor dining
Pool
Living area
Exceptional
(13 reviews)

Explore the Hampton in this Shelter Island Getaway. Weekly Bookings

Shelter Island Heights

31% off
AU$8,187
for 7 nights, 1 home
AU$1,170 per night
includes taxes & fees
Explore the Hampton in this Shelter Island Getaway. Weekly Bookings
Den
Pool
New Kitchen
Living room w/ screen porch beyond
Exceptional
(46 reviews)

Quiet Family Friendly Hideaway With Pool And Poolhouse

East Hampton

8% off
AU$18,863
for 7 nights, 1 home
AU$2,695 per night
includes taxes & fees
Quiet Family Friendly Hideaway With Pool And Poolhouse
Dine al fresco while watching the boats and sea planes
Outdoor dining
Property grounds
Open both doors for a cool breeze while dining
Exceptional
(16 reviews)

Relax and Enjoy!

Shelter Island Heights

7% off
AU$9,942
for 7 nights, 1 home
AU$1,420 per night
includes taxes & fees
Relax and Enjoy!
living room
Dining
Pool
outdoor shower
Exceptional
(60 reviews)

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

Southampton

8% off
AU$19,852
for 7 nights, 1 home
AU$2,836 per night
includes taxes & fees
Southampton Village Renovated Sun-filled Charming Home, Heated Salt water Pool
Private kitchen
Dining
Living area
Outdoor dining
Exceptional
(18 reviews)

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

Cutchogue

8% off
AU$6,984
for 7 nights, 1 cottage
AU$998 per night
includes taxes & fees
Great Getaway! Exceptional Home. Walking distance to The Christmas Tree Shoppe
Pool
Living area
Exterior detail
Interior
Exceptional
(10 reviews)

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

Sag Harbor

8% off
AU$20,618
for 7 nights, 1 cottage
AU$2,945 per night
includes taxes & fees
Just Posted for Summer 2026! SECLUDED SAG HARBOR COTTAGE w/ HUGE POOL
Living area
Terrace/patio
Pool
Living area
Exceptional
(11 reviews)

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

East Hampton

12% off
AU$17,789
for 7 nights, 1 home
AU$2,541 per night
includes taxes & fees
Large East Hampton house with heated pool and home gym - fully fenced
Private kitchen
Private kitchen
Dining
Property grounds
Exceptional
(14 reviews)

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

Southold

8% off
AU$6,453
for 7 nights, 1 home
AU$922 per night
includes taxes & fees
Steps from Cedar Beach ! Tranquil Retreat in the Heart of Wine Country
Lovely seating in pool area for morning coffee.
Living room, looking out toward Accabonac Harbor, water views.
Guest house small private
outdoor seating area.
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
AU$22,637
for 7 nights, 1 home
AU$3,234 per night
includes taxes & fees
WATER VIEWS RETREAT, SPRINGS, EAST HAMPTON, POOL, FIRE PIT, 10 MINUTES TO BEACH!
living area with gas fire leads onto the deck
huge swimming pool and deck surrounded by trees
kitchen backs onto the garden
Queen bedroom leading onto deck.  Ensuite bathroom, walk-in closet and tv.
Exceptional
(53 reviews)

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

East Hampton

8% off
AU$7,195
for 7 nights, 1 home
AU$1,028 per night
includes taxes & fees
Large heated pool, games room, private bay beach access, gardens, kid-friendly
Main living room and dining room
Dining
Interior
Interior
Exceptional
(27 reviews)

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

Sag Harbor

8% off
AU$20,515
for 7 nights, 1 home
AU$2,931 per night
includes taxes & fees
9BR Sag Harbor PRIVATE w/ Pool-Tennis- B-ball- HotTub
Living area
Private kitchen
Living area
Exterior
Exceptional
(34 reviews)

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

Cutchogue

8% off
AU$3,783
for 7 nights, 1 cottage
AU$540 per night
includes taxes & fees
Totally Renovated Cottage on the North Fork 7 min. walk to the Beach
Zepherine Drouhin, c. 1868 French thornless rose cultivar famed for its scent
Facade
From the bedroom
Living/dining space
Exceptional
(22 reviews)

Private Hamptons cottage in ideal Amagansett location

Amagansett

8% off
AU$7,598
for 7 nights, 1 cottage
AU$1,085 per night
includes taxes & fees
Private Hamptons cottage in ideal Amagansett location
Private kitchen
Dining
Living area
Pool
Exceptional
(9 reviews)

Chic Modern Private Designer 1.5 Acre Private Oasis

East Hampton

26% off
AU$42,005
for 7 nights, 1 home
AU$6,001 per night
includes taxes & fees
Chic Modern Private Designer 1.5 Acre Private Oasis
Dining area
Large pool heated pool
Exterior
Main living area
Exceptional
(20 reviews)

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

East Hampton

7% off
AU$7,284
for 7 nights, 1 home
AU$1,041 per night
includes taxes & fees
Charming, spacious 3 bedroom, 3 bath East Hampton Springs house
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    Enjoy full kitchens, laundry, pools, gardens and more
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    More space, more privacy, more amenities — more value

Why visit Sag Harbor

  • Coastal Charm: Sag Harbor offers a peaceful seaside retreat with scenic waterfront views and pristine beaches ideal for romantic escapes or family outings.
  • Historic Ambience: Wander amongst well-preserved historic buildings and quaint seating areas that echo the rich past of this coastal village.
  • Artistic Flair: Immerse yourself in the local arts scene at the museum and nearby galleries, celebrating the creative spirit of the community.
  • Village Vibe: Enjoy the small-town feel with delightful local boutiques and cosy public spaces that enhance your visit.
  • Natural Beauty: Revel in leisurely strolls along the coast, absorbing the serene coastal environment and fresh sea air.

Popular types of accommodation in Sag Harbor

Discover the charm of Sag Harbor, New York, a delightful coastal village steeped in history and character. Enjoy an array of private holiday homes, cosy cottages, and stylish apartments, perfect for your getaway. Explore the scenic waterfront, vibrant arts scene, and local boutiques, all while relishing outdoor seating options that enhance your stay. Whether you seek relaxation or adventure, Sag Harbor's unique attractions promise a memorable holiday experience.

  • Private Holiday Homes: The top choice for visitors, offering spacious and comfortable living spaces ideal for families or groups.
  • Cottages: A charming option, these quaint dwellings provide a cosy atmosphere perfect for a romantic getaway or a peaceful retreat.
  • Apartments: A versatile and convenient choice, ideal for those seeking modern amenities and easy access to local attractions.
  • Condos: These offer a blend of comfort and community, often featuring shared facilities and a sociable environment.
  • Villas: For those desiring luxury, villas provide upscale accommodations with ample space and premium features.**

Top attractions near Sag Harbor

Sag Harbor offers a delightful blend of history and natural beauty, making it a superb destination for cultural and family outings. Enjoy leisurely strolls along the beach, immerse yourself in art at the local museum, and explore its charming historic buildings. Whether seeking a romantic retreat or a fun-filled family holiday, Sag Harbor provides a serene setting to relax and discover its unique coastal allure.

  • East Hampton Main Beach: Enjoy beach vibes on this sandy haven located 11km from Sag Harbor, where the sound of the waves and golden sunsets set a perfect scene for relaxation.
  • Home Sweet Home Museum: Immerse yourself in culture at this historic building 10km away, where the echoes of the past blend with local heritage and architectural charm.
  • Amagansett Square: Experience urban energy at this modern square 13km from Sag Harbor, offering a vibrant scene and contemporary city ambience.

Things to do recommended for couples

Explore Sag Harbor's seaside charm with leisurely walks along picturesque harbours, cosy beach picnics, and intimate dining experiences in quaint local eateries. Embrace the romantic ambience that sets a perfect backdrop for your couple's retreat.

Things to do recommended for families

Families visiting Sag Harbor can enjoy a day at the picturesque Sag Harbor Beach, perfect for sandcastle building and swimming. Additionally, the Children's Museum of the East End offers engaging exhibits and activities, ensuring a delightful experience for kids of all ages.

Things to do recommended for groups

Groups visiting Sag Harbor can indulge in wine tasting at local vineyards, explore the charming waterfront shops, and enjoy a scenic sailing tour around the picturesque bay. Don’t miss the chance to savour fresh seafood at renowned local restaurants for an authentic culinary experience.

*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

If you're travelling with a group, family, or pets, or if you're seeking longer stays, be sure to apply the appropriate filters to suit your needs. Here are some helpful booking tips for Stayz.

  • Traveling to Sag Harbor with a group: Think about how many bedrooms you'll require, as well as amenities like a fully equipped kitchen or outdoor space for group gatherings. Thankfully, you can easily filter for all these options, and more, on Stayz.
  • Traveling to Sag Harbor with young kids: Travelling with young children can present its own set of challenges. It's essential to prioritise their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, considering your closeness to family-friendly attractions can enhance your experience.
  • Taking your pets with you to Sag Harbor: For many, a family holiday isn't truly complete without their furry companion by their side. If this resonates with you, take a look at Stayz properties that welcome pets. Most of these pet-friendly accommodations offer 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 can effortlessly discover and save on monthly rentals. Don’t forget to include features like a parking space, a well-equipped kitchen, or a private pool in your search as well.

Where to stay near Sag Harbor

Sag Harbor invites travellers to experience its charming village vibe with scenic outdoor attractions and beautiful beaches perfect for a romantic getaway or family holiday. Enjoy leisurely excursions around the historic seating areas and relax in areas that reflect the unique weather and coastal beauty of the Sag Harbor area. This destination offers a luxury and serene retreat in a picturesque setting.

  • Hamptons: Just 8km from Sag Harbor, the Hamptons invites travellers to indulge in a delightful blend of beachside charm and outdoor pursuits. The area is renowned for its romantic ambience, where visitors can enjoy the serenity of expansive beaches and lakes. The local attractions showcase a mix of family-friendly beaches and natural water bodies, while the nearby golf course and ski facilities offer options for both leisurely and adventurous outings. This destination is perfect for those seeking a balanced experience of relaxation and active exploration.
  • East Hampton: Located 10km from Sag Harbor, East Hampton is a vibrant city celebrated for its family-friendly and outdoorsy vibe. Visitors are drawn to its beautiful beaches and recreational areas, with a welcoming park setting that invites picnics and leisurely strolls. The nearby golf course and ski field provide engaging opportunities for sport and leisure, making East Hampton an excellent choice for a well-rounded holiday experience. Its scenic charm and accessible outdoor activities enhance its appeal for families and nature lovers alike.
  • Bridgehampton: Only 6km from Sag Harbor, Bridgehampton offers a delightful mix of outdoor and beachside attractions. Known for its romantic and relaxing setting, this city features a picturesque backdrop of family beaches and parks. The local golf courses and recreational areas add to the charm of the destination, providing ample opportunities for both active pursuits and quiet moments by the sea. Bridgehampton is an ideal stop for travellers seeking a blend of natural beauty and leisurely adventures.

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. Peak season runs from June to August, while off-peak times, like October to December tend to have fewer bookings and better deals.

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

Booking with Stayz is a breeze

Are you hoping to save on your next adventure? Being flexible with your travel dates can help, as prices tend to vary. Additionally, opting for a longer stay often leads to significant savings. To discover the ideal Stayz property that fits your budget, utilise our filters to sort by price, location, and type of holiday rental.

Stayz Trips: Planning as easy as it gets

Stayz's innovative Trip Board offers you a dedicated area to plan new journeys, pick up from where you last paused, or review and arrange your travel plans. Properties that you have previously saved or booked can now be located under Potential, Upcoming, or Current Trips. To access Trip Boards, please visit: https://www.stayz.com.au/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 Stayz, 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, Stayz 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 Stayz 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 Stayz 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, Stayz 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 Stayz.
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 Stayz 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 Stayz 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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