Sag Harbor holiday rentals

We found 2,466 holiday rentals — enter your dates for availability
Discover a selection of 306 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:22 Jan - 29 Jan

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

Everything in Hamptons special discount available for weekly and monthly renters

Water Mill

17% off
S$76,046
for 7 nights, 1 home
S$10,864 per night
includes taxes & fees
Everything in Hamptons special discount available for weekly and monthly renters
Private kitchen
Property grounds
Living area
Exterior
Exceptional
(8 reviews)

Beautiful charming 1930s fully renovated cottage walking distance to the beach!

Cutchogue

7% off
S$5,610
for 7 nights, 1 cottage
S$801 per night
includes taxes & fees
Beautiful charming 1930s fully renovated cottage walking distance to the beach!
Private kitchen
Pool area viewed from side with teak loungers and umbrellas
Covered porch on backside of main house
Main house dining area with wet bar, 300 bottle wine fridge and ice maker.
Exceptional
(7 reviews)

Amagansett Beach Estate with Award Winning Outdoor Amenities

Amagansett

8% off
S$18,746
for 7 nights, 1 home
S$2,678 per night
includes taxes & fees
Amagansett Beach Estate with Award Winning Outdoor Amenities
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

28% off
S$13,724
for 7 nights, 1 home
S$1,961 per night
includes taxes & fees
Southampton Pickleball Walk to beach. Kayaks on lake Park-like grounds Pool
Living area
Terrace/patio
Pool
Exterior
Excellent
(10 reviews)

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

Water Mill

8% off
S$51,878
for 7 nights, 1 home
S$7,411 per night
includes taxes & fees
Stunning fall sunsets, coveted location on Mecox Bay - recently furnished
Lovely seating in pool area for morning coffee.
Living room, looking out toward Accabonac Harbor, water views.
Bar area pass-through to kitchen, with bar seating.
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
S$21,471
for 7 nights, 1 home
S$3,067 per night
includes taxes & fees
WATER VIEWS RETREAT, SPRINGS, EAST HAMPTON, POOL, FIRE PIT, 10 MINUTES TO BEACH!
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

7% off
S$22,332
for 7 nights, 1 home
S$3,190 per night
includes taxes & fees
Completely Renovated Home on ~2 Private Acres, Near Beach/Town
Dining
Pool
Private kitchen
Living area
Wonderful
(21 reviews)

PRIVATE POOL ~ PERFECT HAMPTONS GETAWAY ~ WBH

East Hampton

7% off
S$22,068
for 7 nights, 1 home
S$3,153 per night
includes taxes & fees
PRIVATE POOL ~ PERFECT HAMPTONS GETAWAY ~ WBH
Outdoor dining
Living area
Interior
Living area
Exceptional
(15 reviews)

PERFECT GETAWAY East Hampton / Sag Harbor

East Hampton

8% off
S$9,907
for 7 nights, 1 home
S$1,415 per night
includes taxes & fees
PERFECT GETAWAY East Hampton / Sag Harbor
Kitchen walks out to covered porch across length of entire back
Featured as one of most beautiful poolsides
Hydrangeas blooming all summer.these are the August bloomers
Couches on covered porch and outdoor dining table for 8
Exceptional
(7 reviews)

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

Southampton

8% off
S$26,222
for 7 nights, 1 home
S$3,746 per night
includes taxes & fees
IN THE ViILLAGE OF SOUTHAMPTON POOL,TENNIS,PICKLEBALL COURTS BEACH CHAIRS&BIKES
Dining
Property grounds
Exterior
Private kitchen
Exceptional
(5 reviews)

Beautiful 4 bedroom house with tranquil gardens close to bay beaches.

East Hampton

8% off
S$9,505
for 7 nights, 1 home
S$1,358 per night
includes taxes & fees
Beautiful 4 bedroom house with tranquil gardens close to bay beaches.
Outdoor dining
Dining
Living area
Private kitchen
Exceptional
(9 reviews)

Chic Modern Private Designer 1.5 Acre Private Oasis

East Hampton

25% off
S$15,341
for 7 nights, 1 home
S$2,192 per night
includes taxes & fees
Chic Modern Private Designer 1.5 Acre Private Oasis
Dining Room
Private kitchen
Patio
The Harbor
Exceptional
(105 reviews)

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

Sag Harbor

16% off
S$11,127
for 7 nights, 1 home
S$1,590 per night
includes taxes & fees
Beautiful 3600sq ft Sag Harbor Village Home, Saltwater Pool, Walk to Beach &Town
Private kitchen
seating area rear deck
dining area, expandable table
view of pool
Exceptional
(15 reviews)

Sunsets Sweeping Farmland Views, Great Retreat Minutes from Flying Point Beach

Water Mill

8% off
S$21,791
for 7 nights, 1 home
S$3,113 per night
includes taxes & fees
Sunsets Sweeping Farmland Views, Great Retreat Minutes from Flying Point Beach
Large Dining/Kitchen Space
Exterior
Pool
Exterior
Exceptional
(12 reviews)

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

Southold

7% off
S$11,243
for 7 nights, 1 home
S$1,606 per night
includes taxes & fees
New Modern Farmhouse Estate Living in the heart of Southold with a pool!!!
Dining Room with seating for Ten
Pool
Outdoor dining
Exterior
Exceptional
(29 reviews)

Spacious New 4 Bedroom Home With Pool on 2 Acre Property

Peconic

8% off
S$11,186
for 7 nights, 1 home
S$1,598 per night
includes taxes & fees
Spacious New 4 Bedroom Home With Pool on 2 Acre Property
The front of the house
A view of the house and pool from the creek, looking south
The front walkway
The kitchen is all glass with a spectacular view of the pool and creek
Exceptional
(21 reviews)

Unique Southold waterfront luxury home with heated pool on Long Creek

Southold

7% off
S$5,841
for 7 nights, 1 home
S$834 per night
includes taxes & fees
Unique Southold waterfront luxury home with heated pool on Long Creek
Sunlit living room with wide sliding glass doors that lead out to sundeck.
Swim in the solar heated pool or basque in the sun...
Spacious, stylish, and bright dining room
Fireplace with expansive hearth
Exceptional
(10 reviews)

Chic Village Cape w/sparkling pool! Walk to boutiques & eateries, bike to ocean!

East Hampton

26% off
S$6,208
for 7 nights, 1 home
S$887 per night
includes taxes & fees
Chic Village Cape w/sparkling pool! Walk to boutiques & eateries, bike to ocean!
Living room on main floor with mid-century modern sofa
Brightly lit dining room with 9' ceilings and view of heated swimming pool.
Sunlit living room w/ coffered ceilings, tv, fireplace, & French doors to pool
Three Mile Harbor, glorious sunsets, and waterfront restaurants- 8 minute drive
Exceptional
(19 reviews)

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

East Hampton

26% off
S$7,296
for 7 nights, 1 home
S$1,042 per night
includes taxes & fees
Prime East Hampton Village Location. Heated Pool. Walk To All!
Second eating area
Wrap around deck
Living room
Second living room
Exceptional
(35 reviews)

Our Peaceful, Beach Escape From the City

Sag Harbor

8% off
S$12,239
for 7 nights, 1 home
S$1,748 per night
includes taxes & fees
Our Peaceful, Beach Escape From the City
Private kitchen
Dining
Living area
Room
Exceptional
(18 reviews)

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

Cutchogue

8% off
S$6,575
for 7 nights, 1 cottage
S$939 per night
includes taxes & fees
Great Getaway! Exceptional Home. Walking distance to The Christmas Tree Shoppe
Interior
Living area
Dining
Room
Exceptional
(9 reviews)

Modern Home in East Hampton great for a summer or winter retreat.

East Hampton

7% off
S$6,309
for 7 nights, 1 home
S$901 per night
includes taxes & fees
Modern Home in East Hampton great for a summer or winter retreat.
Living area
Interior
Exterior
Pool
Exceptional
(11 reviews)

Lovely Private Estate In East Hampton

East Hampton

7% off
S$6,651
for 7 nights, 1 home
S$950 per night
includes taxes & fees
Lovely Private Estate In East Hampton
Interior
Terrace/patio
Interior
Dining
Exceptional
(21 reviews)

Entire, new, roomy, village beach house close to beach, park, and town center

Greenport

7% off
S$6,308
for 7 nights, 1 home
S$901 per night
includes taxes & fees
Entire, new, roomy, village beach house close to beach, park, and town center
  • 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)
  • Gardiner's Bay Country Club (6.8 mi / 11 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)

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:

  • Mashomack Preserve (4.5 mi / 7.3 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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