Photo by Miriam Marcus

Wainscott Woods holiday homes

We found 2,074 holiday rentals — enter your dates for availability
Discover a selection of 18 homes and other holiday rentals in Wainscott Woods that are perfect for your trip. Holiday rentals provide the amenities that you need and want for you and your friends, family or even pets, such as a fireplace and garden. 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 – Wainscott Woods

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$14,844
for 7 nights, 1 home
NZ$2,121 per night
includes taxes & fees
Beautiful 3600sq ft Sag Harbor Village Home, Saltwater Pool, Walk to Beach &Town
living room
aerial view
kitchen with large island and breakfast table
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
NZ$98,187
for 7 nights, 1 home
NZ$14,027 per night
includes taxes & fees
Everything in Hamptons special discount available for weekly and monthly renters
Lower deck With Pool, 9 Loungers, plus 6 pool-chairs. Upper deck dining seats 10
Living area
park-like grounds
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
NZ$17,162
for 7 nights, 1 home
NZ$2,452 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
NZ$66,087
for 7 nights, 1 home
NZ$9,441 per night
includes taxes & fees
Stunning fall sunsets, coveted location on Mecox Bay - recently furnished
Terrace/patio
Pool
Living area
Dining
Exceptional
(17 reviews)

PRIVATE POOL ~ PERFECT HAMPTONS GETAWAY ~ WBH

East Hampton

8% off
NZ$28,108
for 7 nights, 1 home
NZ$4,015 per night
includes taxes & fees
PRIVATE POOL ~ PERFECT HAMPTONS GETAWAY ~ WBH
Living area
Dining
Room
Exterior
Exceptional
(10 reviews)

Southampton Village Charmer - South of Highway

Southampton

8% off
NZ$37,024
for 7 nights, 1 home
NZ$5,289 per night
includes taxes & fees
Southampton Village Charmer - South of Highway
Private kitchen
Pool area viewed from side with teak loungers and umbrellas
Covered porch on backside of main house
Main house living room
Exceptional
(6 reviews)

Amagansett Beach Estate with Award Winning Outdoor Amenities

Amagansett

8% off
NZ$57,757
for 7 nights, 1 home
NZ$8,251 per night
includes taxes & fees
Amagansett Beach Estate with Award Winning Outdoor Amenities
Pool
Outdoor dining
Living area
Living area
Exceptional
(13 reviews)

Explore the Hampton in this Shelter Island Getaway. Weekly Bookings

Shelter Island Heights

31% off
NZ$9,981
for 7 nights, 1 home
NZ$1,426 per night
includes taxes & fees
Explore the Hampton in this Shelter Island Getaway. Weekly Bookings
Dining room seating 12 leading to chef's kitchen and doors 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
Frankel Residence
Exceptional
(6 reviews)

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

Wainscott

8% off
NZ$28,151
for 7 nights, 1 home
NZ$4,022 per night
includes taxes & fees
Completely Renovated Home on ~2 Private Acres, Near Beach/Town
Den
Pool
New Kitchen
Front Porch
Exceptional
(46 reviews)

Quiet Family Friendly Hideaway With Pool And Poolhouse

East Hampton

8% off
NZ$22,695
for 7 nights, 1 home
NZ$3,242 per night
includes taxes & fees
Quiet Family Friendly Hideaway With Pool And Poolhouse
outdoor shower
Dining
kitchen
living room
Exceptional
(60 reviews)

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

Southampton

8% off
NZ$23,907
for 7 nights, 1 home
NZ$3,415 per night
includes taxes & fees
Southampton Village Renovated Sun-filled Charming Home, Heated Salt water Pool
Exterior detail
Living area
Interior
Exceptional
(10 reviews)

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

Sag Harbor

8% off
NZ$24,848
for 7 nights, 1 cottage
NZ$3,550 per night
includes taxes & fees
Just Posted for Summer 2026! SECLUDED SAG HARBOR COTTAGE w/ HUGE POOL
Pool
Terrace/patio
Living area
Interior
Exceptional
(11 reviews)

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

East Hampton

12% off
NZ$21,378
for 7 nights, 1 home
NZ$3,054 per night
includes taxes & fees
Large East Hampton house with heated pool and home gym - fully fenced
Dining
Private kitchen
Private kitchen
Room
Exceptional
(14 reviews)

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

Southold

8% off
NZ$7,828
for 7 nights, 1 home
NZ$1,118 per night
includes taxes & fees
Steps from Cedar Beach ! Tranquil Retreat in the Heart of Wine Country
Bar area pass-through to kitchen, with bar seating.
Living room, looking out toward Accabonac Harbor, water views.
Kitchen with Wolf stove, Sub Zero fridge, pass-through serving area to dining.
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
NZ$27,311
for 7 nights, 1 home
NZ$3,902 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
kitchen leading into open plan living area
Exceptional
(53 reviews)

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

East Hampton

8% off
NZ$8,711
for 7 nights, 1 home
NZ$1,244 per night
includes taxes & fees
Large heated pool, games room, private bay beach access, gardens, kid-friendly
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$24,720
for 7 nights, 1 home
NZ$3,531 per night
includes taxes & fees
9BR Sag Harbor PRIVATE w/ Pool-Tennis- B-ball- HotTub
Living/dining space
Facade
Zepherine Drouhin, c. 1868 French thornless rose cultivar famed for its scent
Front yard closeup
Exceptional
(22 reviews)

Private Hamptons cottage in ideal Amagansett location

Amagansett

8% off
NZ$9,270
for 7 nights, 1 cottage
NZ$1,324 per night
includes taxes & fees
Private Hamptons cottage in ideal Amagansett location
Kitchen walks out to covered porch across length of entire back
Featured as one of most beautiful poolsides
Living area on 1st floor with wood burning fireplace
Hydrangeas blooming all summer.these are the August bloomers
Exceptional
(7 reviews)

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

Southampton

8% off
NZ$31,091
for 7 nights, 1 home
NZ$4,442 per night
includes taxes & fees
IN THE ViILLAGE OF SOUTHAMPTON POOL,TENNIS,PICKLEBALL COURTS BEACH CHAIRS&BIKES
Pool
Dining
Living area
Outdoor dining
Exceptional
(9 reviews)

Chic Modern Private Designer 1.5 Acre Private Oasis

East Hampton

26% off
NZ$50,516
for 7 nights, 1 home
NZ$7,217 per night
includes taxes & fees
Chic Modern Private Designer 1.5 Acre Private Oasis
Kitchen
Large pool heated pool
Dining area
Main living area
Exceptional
(20 reviews)

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

East Hampton

7% off
NZ$8,815
for 7 nights, 1 home
NZ$1,259 per night
includes taxes & fees
Charming, spacious 3 bedroom, 3 bath East Hampton Springs house
View towards pool from backyard
Property grounds
Interior
Dining
Exceptional
(95 reviews)

Private and Immaculate East Hampton Home With Heated Pool

East Hampton

8% off
NZ$7,946
for 7 nights, 1 home
NZ$1,135 per night
includes taxes & fees
Private and Immaculate East Hampton Home With Heated Pool
Living room on main floor with mid-century modern sofa
Brightly lit dining room with 9' ceilings and view of heated swimming pool.
Three Mile Harbor, glorious sunsets, and waterfront restaurants- 8 minute drive
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
NZ$13,071
for 7 nights, 1 home
NZ$1,867 per night
includes taxes & fees
Prime East Hampton Village Location. Heated Pool. Walk To All!
Exterior
Interior
Living area
Exterior
Exceptional
(11 reviews)

Lovely Private Estate In East Hampton

East Hampton

8% off
NZ$8,521
for 7 nights, 1 home
NZ$1,217 per night
includes taxes & fees
Lovely Private Estate In East Hampton
  • 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

Book a holiday rental for your Wainscott Woods getaway

Learn about the unique charm of Wainscott Woods with a stay in a holiday home rental. This city has something for everyone. If you're looking for accommodation options with space to entertain friends and family, HomeAway has plenty of options to choose from. Many rental homes offer full kitchens and laundry facilities, perfect for big groups.

Activities and attractions in Wainscott Woods

Do you want to discover attractions to visit while you're in town? Venture out of your cosy holiday rental and experience everything that makes Wainscott Woods a fun place to get away to. Here are some of the most popular attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • Wolffer Estates Vineyard (1.5 mi / 2.3 km)
  • LongHouse Reserve (3.4 mi / 5.5 km)
  • Duck Walk Vineyards (6.9 mi / 11.1 km)
  • Shinnecock Hills Golf Course (10.6 mi / 17.1 km)
  • Raphael Winery (12.3 mi / 19.9 km)
  • Pindar Vineyards (12.5 mi / 20 km)

Exploring the natural features in Wainscott Woods

Whether you're an adventurous traveller or just want to take in the scenery, Wainscott Woods is a great place to spend some time outside. These are some of the area's most stunning features, all within 30 miles (48.2 km) of the city centre:

  • Georgica Beach (2.2 mi / 3.6 km)
  • East Hampton Main Beach (3 mi / 4.8 km)
  • The Hamptons Beaches (3.2 mi / 5.2 km)
  • LongHouse Reserve (3.4 mi / 5.5 km)
  • Indian Wells Beach (5.9 mi / 9.5 km)
  • Elizabeth A. Morton National Wildlife Refuge (6.7 mi / 10.7 km)

How to get to and around Wainscott Woods

The nearest airport is in East Hampton, NY (HTO), located 0.7 mi (1.1 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 18.9 mi (30.5 km) away.

Frequently asked questions

What is the most popular type of holiday home accommodation in Wainscott Woods?
The most desirable types of holiday homes in Wainscott Woods are houses. Want something different? Bookabach has a variety of options to match our guests' unique requirements, so you'll see holiday homes in lots of sizes and shapes. The ideal home away from home is waiting for you — find yours today.
How much does it cost to rent a holiday home in Wainscott Woods?
Length of stay, season and property type are among the factors that can determine the price of a holiday home. Simply enter your travel dates to find your perfect fit. From comfy cabins to expansive villas, all Bookabach holiday homes provide amazing value.
How much does it cost to rent a beach house in Wainscott Woods?
When you travel and the size and style of the property will influence how much you'll pay for your beachside escape. Type in your Wainscott Woods travel dates to see your options on Bookabach. Can't live without a private pool? Use the filters to choose the amenities and features you need.
Are there pet-friendly holiday homes in Wainscott Woods?
Yes, there are. You'll have a choice of 20 holiday homes that allow pets in Wainscott Woods. Many of our pet-friendly holiday homes have an area outdoors for your furry pal to play around in, special dog beds, complimentary treats and proximity to parks. Apply the "Pets allowed" filter to find your pawfect digs on Bookabach.
Can I rent a house with a pool in Wainscott Woods?
Add an extra layer of fun to your holiday by staying in one of the 19 houses with a private pool in Wainscott Woods. Use our search filter to find properties with pools on Bookabach, then spend your days splishing and splashing in a swimming pool that's for your exclusive use.
What are popular home amenities in Wainscott Woods?
When it comes to home amenities that guests are looking for in Wainscott Woods, a swimming pool, a fireplace and a firepit are the most popular. With Bookabach holiday homes, you'll discover options to match your taste and style, whether you're going on a trip with friends, family or even pets.
Are there large group holiday homes in Wainscott Woods?
Wainscott Woods has eight holiday properties that can host 10 or more people. These properties come with the space and privacy you need to enjoy good times with family and friends.
Are there holiday homes in Wainscott Woods that welcome kids?
With 20 family-friendly holiday homes to choose from in Wainscott Woods, now is a fantastic time to introduce the kids to the excitement of travel. Just click on our "Properties good for families" filter box to find stays packed with conveniences perfect for travelling families, like dining rooms, swimming pools, entertainment units and bunk beds.
Are there holiday homes with WiFi in Wainscott Woods?
Whether you'd like to keep up with the latest headlines, look over emails or update your social media, there are five holiday homes with WiFi in Wainscott Woods. Check the "WiFi" box when searching on Bookabach and stay connected on your getaway.
How can I find holiday homes with air conditioning in Wainscott Woods?
Select your travel dates and then use the filters to look for holiday homes with ac in Wainscott Woods on Bookabach. With 20 air-conditioned properties available here, you can look forward to a cool and comfy stay.
How old do you have to be to rent a holiday home in Wainscott Woods?
Age restrictions can differ between properties on Bookabach, so double-check the rules of the holiday home in Wainscott Woods you want to book. But usually, it's 16, 18 or 21.
How long can I rent a holiday home in Wainscott Woods for?
The length of time you can book a holiday home in Wainscott Woods varies according to the property. Just enter your preferred travel dates to view a list of options offering extended stays. With tons of amenities such as laundries and air conditioning, as well as some offering weekly or monthly discounted prices, you're sure to find someplace just right to call your home away from home in Wainscott Woods.