Photo by Miriam Marcus

Wainscott Woods holiday rentals

We found 2,082 holiday rentals — enter your dates for availability
Discover a selection of 19 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:6 Nov - 13 Nov

living room
aerial view
view from living room towards pool, outdoor dining
kitchen with large island and breakfast table
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
Patio
Private kitchen
Dining Room
The Harbor
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
park-like grounds
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
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
Living area
Terrace/patio
Living area
Exterior
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
Covered porch on backside of main house
Pool area viewed from side with teak loungers and umbrellas
Private kitchen
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
Exterior
Dining
Room
Living area
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
Terrace/patio
Pool
Dining
Living area
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
Open entry foyer with wall of windowed doors to Zen Garden
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
Pool
Outdoor dining
Living area
Private kitchen
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
New Kitchen
Pool
Living room w/ screen porch beyond
Den
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
Pool
Dining
living room
kitchen
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
Pool
Living area
Exterior detail
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
Interior
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
Dining
Private kitchen
Private kitchen
Room
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.
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
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!
kitchen leading into open plan living area
huge swimming pool and deck surrounded by trees
Queen bedroom leading onto deck.  Ensuite bathroom, walk-in closet and tv.
kitchen backs onto the garden
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
Interior
Dining
Night time at the pool
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/dining space
Facade
From the bedroom
Front yard closeup
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
Pool
Dining
Living area
Private kitchen
Exceptional
(8 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
Main living area
Large pool heated pool
Kitchen
Exterior
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
Interior
Property grounds
Dining
Living area
Exceptional
(95 reviews)

Private and Immaculate East Hampton Home With Heated Pool

East Hampton

8% off
AU$6,553
for 7 nights, 1 home
AU$936 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
Second level sunny bedroom with queen bed and views of the pool.
Exceptional
(18 reviews)

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

East Hampton

15% off
AU$10,438
for 7 nights, 1 home
AU$1,491 per night
includes taxes & fees
Prime East Hampton Village Location. Heated Pool. Walk To All!
primary bedroom #1main floor
seating area rear deck
dining area, expandable table
Private kitchen
Exceptional
(15 reviews)

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

Water Mill

8% off
AU$23,544
for 7 nights, 1 home
AU$3,363 per night
includes taxes & fees
Sunsets Sweeping Farmland Views, Great Retreat Minutes from Flying Point Beach
Living area
Interior
Pool
Exterior
Exceptional
(10 reviews)

Lovely Private Estate In East Hampton

East Hampton

8% off
AU$7,036
for 7 nights, 1 home
AU$1,005 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)
  • Croteaux Vineyards (11.8 mi / 18.9 km)
  • Raphael Winery (12.3 mi / 19.9 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:

  • The Hamptons Beaches (3.2 mi / 5.2 km)
  • Georgica Beach (2.2 mi / 3.6 km)
  • East Hampton Main Beach (3 mi / 4.8 km)
  • LongHouse Reserve (3.4 mi / 5.5 km)
  • Indian Wells Beach (5.9 mi / 9.5 km)
  • Amagansett Square (5.9 mi / 9.5 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? Stayz 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 Stayz 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 Stayz. 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 Stayz.
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 Stayz, 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 Stayz 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 Stayz 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 Stayz. 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 Stayz, 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.

More holiday ideas