Sag Harbor holiday rentals

We found 2,503 holiday rentals — enter your dates for availability
Discover a selection of 317 homes, 14 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:20 Nov - 27 Nov

living room
aerial view
master bedroom with balcony
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
S$75,037
for 7 nights, 1 home
S$10,720 per night
includes taxes & fees
Everything in Hamptons special discount available for weekly and monthly renters
Patio
Private kitchen
Exterior
The Harbor
Exceptional
(97 reviews)

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

Sag Harbor

16% off
S$10,922
for 7 nights, 1 home
S$1,560 per night
includes taxes & fees
Beautiful 3600sq ft Sag Harbor Village Home, Saltwater Pool, Walk to Beach &Town
Lower deck With Pool, 9 Loungers, plus 6 pool-chairs. Upper deck dining seats 10
Living area
park-like grounds
Front entrance, park-like grounds
Exceptional
(26 reviews)

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

Southampton

28% off
S$13,199
for 7 nights, 1 home
S$1,886 per night
includes taxes & fees
Southampton Pickleball Walk to beach. Kayaks on lake Park-like grounds Pool
Exterior
Terrace/patio
Living area
Pool
Wonderful
(9 reviews)

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

Water Mill

8% off
S$50,554
for 7 nights, 1 home
S$7,222 per night
includes taxes & fees
Stunning fall sunsets, coveted location on Mecox Bay - recently furnished
Outdoor dining
Living area
Interior
Living area
Exceptional
(12 reviews)

PERFECT GETAWAY East Hampton / Sag Harbor

East Hampton

8% off
S$9,834
for 7 nights, 1 home
S$1,405 per night
includes taxes & fees
PERFECT GETAWAY East Hampton / Sag Harbor
Living area
Dining
Exterior
Dining
Exceptional
(10 reviews)

Southampton Village Charmer - South of Highway

Southampton

8% off
S$28,458
for 7 nights, 1 home
S$4,065 per night
includes taxes & fees
Southampton Village Charmer - South of Highway
Private kitchen
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
S$44,201
for 7 nights, 1 home
S$6,314 per night
includes taxes & fees
Amagansett Beach Estate with Award Winning Outdoor Amenities
Pool
Dining
outdoor shower
living room
Exceptional
(60 reviews)

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

Southampton

8% off
S$18,446
for 7 nights, 1 home
S$2,635 per night
includes taxes & fees
Southampton Village Renovated Sun-filled Charming Home, Heated Salt water Pool
Frankel Residence
Thermador chefs kitchen with expansive island open to dining room & family room
Dining room seating 12 leading to chef's kitchen and doors leading to pool
View from entry foyer into double height living room, skylights, leading to pool
Exceptional
(6 reviews)

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

Wainscott

8% off
S$21,355
for 7 nights, 1 home
S$3,051 per night
includes taxes & fees
Completely Renovated Home on ~2 Private Acres, Near Beach/Town
Living area
Pool
Private kitchen
Terrace/patio
Exceptional
(17 reviews)

PRIVATE POOL ~ PERFECT HAMPTONS GETAWAY ~ WBH

East Hampton

8% off
S$21,641
for 7 nights, 1 home
S$3,092 per night
includes taxes & fees
PRIVATE POOL ~ PERFECT HAMPTONS GETAWAY ~ WBH
New Kitchen
Pool
Front Porch
Den
Exceptional
(47 reviews)

Quiet Family Friendly Hideaway With Pool And Poolhouse

East Hampton

8% off
S$17,168
for 7 nights, 1 home
S$2,453 per night
includes taxes & fees
Quiet Family Friendly Hideaway With Pool And Poolhouse
Room
Dining
Living area
Outdoor dining
Exceptional
(18 reviews)

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

Cutchogue

8% off
S$6,501
for 7 nights, 1 cottage
S$929 per night
includes taxes & fees
Great Getaway! Exceptional Home. Walking distance to The Christmas Tree Shoppe
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
S$7,617
for 7 nights, 1 home
S$1,088 per night
includes taxes & fees
Explore the Hampton in this Shelter Island Getaway. Weekly Bookings
Main living room and dining room
Dining
Night time at the pool
Interior
Exceptional
(28 reviews)

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

Sag Harbor

8% off
S$18,970
for 7 nights, 1 home
S$2,710 per night
includes taxes & fees
9BR Sag Harbor PRIVATE w/ Pool-Tennis- B-ball- HotTub
Pool
Living area
Interior
Exceptional
(10 reviews)

Secluded Sag Harbor Cottage - HUGE pool and separate bungalow/pool house

Sag Harbor

8% off
S$13,359
for 7 nights, 1 cottage
S$1,908 per night
includes taxes & fees
Secluded Sag Harbor Cottage - HUGE pool and separate bungalow/pool house
Interior
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
S$11,330
for 7 nights, 1 home
S$1,619 per night
includes taxes & fees
Large East Hampton house with heated pool and home gym - fully fenced
Private kitchen
Private kitchen
Dining
Room
Exceptional
(14 reviews)

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

Southold

8% off
S$6,006
for 7 nights, 1 home
S$858 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
S$3,556
for 7 nights, 1 cottage
S$508 per night
includes taxes & fees
Totally Renovated Cottage on the North Fork 7 min. walk to the Beach
Interior
Living area
Interior
Grill + outdoor dining / furniture to dine al fresco!
Exceptional
(42 reviews)

Family and dog-friendly getaway near amazing wineries, beaches and restaurants!

Southold

7% off
S$8,477
for 7 nights, 1 home
S$1,211 per night
includes taxes & fees
Family and dog-friendly getaway near amazing wineries, beaches and restaurants!
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.
Guest house small private
outdoor seating area.
Exceptional
(7 reviews)

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

East Hampton

8% off
S$21,031
for 7 nights, 1 home
S$3,004 per night
includes taxes & fees
WATER VIEWS RETREAT, SPRINGS, EAST HAMPTON, POOL, FIRE PIT, 10 MINUTES TO BEACH!
Main living area
Large pool heated pool
Exterior
Dining area
Exceptional
(20 reviews)

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

East Hampton

7% off
S$6,781
for 7 nights, 1 home
S$969 per night
includes taxes & fees
Charming, spacious 3 bedroom, 3 bath East Hampton Springs house
Living area
Dining
Pool
Outdoor dining
Exceptional
(9 reviews)

Chic Modern Private Designer 1.5 Acre Private Oasis

East Hampton

26% off
S$38,774
for 7 nights, 1 home
S$5,539 per night
includes taxes & fees
Chic Modern Private Designer 1.5 Acre Private Oasis
Second level sunny bedroom with queen bed and views of the pool.
Brightly lit dining room with 9' ceilings and view of heated swimming pool.
Living room on main floor with mid-century modern sofa
Sunlit living room w/ coffered ceilings, tv, fireplace, & French doors to pool
Exceptional
(18 reviews)

Prime East Hampton Village Location. Heated Pool. Walk To All!

East Hampton

15% off
S$11,027
for 7 nights, 1 home
S$1,575 per night
includes taxes & fees
Prime East Hampton Village Location. Heated Pool. Walk To All!
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
S$7,124
for 7 nights, 1 cottage
S$1,018 per night
includes taxes & fees
Private Hamptons cottage in ideal Amagansett location
  • 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

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)
  • Kontokosta Winery (8.9 mi / 14.4 km)
  • Raphael Winery (9.1 mi / 14.7 km)
  • Pindar Vineyards (9.3 mi / 14.9 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:

  • Havens Beach (0.5 mi / 0.8 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 rental?
One of the more desired areas to get a Sag Harbour holiday home is North Haven. When you lock in your holiday property with Vrbo, 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 rental accommodation in Sag Harbour?
Houses are the most popular kind of holiday rental in Sag Harbour, according to our data. Even if you've got something a little different in mind, Vrbo 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 rental 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 Vrbo holiday rentals 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 Vrbo 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 rental amenities in Sag Harbour?
A garden, a barbecue grill and a fireplace are the most popular rental amenities in Sag Harbour. Whether you're taking to the road alone, with a partner or a group of family members, Vrbo can help you find a holiday rental 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 rentals 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 Vrbo.
Are there holiday rentals with WiFi in Sag Harbour?
Sag Harbour has 108 holiday rentals 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 Vrbo homes make it a breeze to go online.
How old do you have to be to rent a holiday rental in Sag Harbour?
You'll have to check with the Sag Harbour holiday rental you'd like on Vrbo as age restrictions differ. However, it's generally 16, 18 or 21.
How long can I rent a holiday rental 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 rentals may also offer weekly or monthly discounts, so you can stick around for longer for less.

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