Photo by Miriam Marcus

Wainscott Woods holiday rentals

We found 2,039 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:25 Dec - 1 Jan

Patio
Private kitchen
Dining Room
Exterior
Exceptional
(103 reviews)

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

Sag Harbor

16% off
AU$11,926
for 7 nights, 1 home
AU$1,704 per night
includes taxes & fees
Beautiful 3600sq ft Sag Harbor Village Home, Saltwater Pool, Walk to Beach &Town
view from living room towards pool, outdoor dining
aerial view
living room
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$81,121
for 7 nights, 1 home
AU$11,589 per night
includes taxes & fees
Everything in Hamptons special discount available for weekly and monthly renters
Pool
Terrace/patio
Living area
Exterior
Excellent
(10 reviews)

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

Water Mill

8% off
AU$54,601
for 7 nights, 1 home
AU$7,800 per night
includes taxes & fees
Stunning fall sunsets, coveted location on Mecox Bay - recently furnished
Front entrance, park-like grounds
Living area
An elegant dining room (to 10 ppl, joins kitchen +8 and outdoor dining +10,)
park-like grounds
Exceptional
(26 reviews)

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

Southampton

30% off
AU$14,238
for 7 nights, 1 home
AU$2,034 per night
includes taxes & fees
Southampton Pickleball Walk to beach. Kayaks on lake Park-like grounds Pool
Den
Pool
Living room w/ screen porch beyond
Front Porch
Exceptional
(48 reviews)

Quiet Family Friendly Hideaway With Pool And Poolhouse

East Hampton

8% off
AU$18,722
for 7 nights, 1 home
AU$2,675 per night
includes taxes & fees
Quiet Family Friendly Hideaway With Pool And Poolhouse
Interior
Living area
Outdoor dining
Pool
Exceptional
(15 reviews)

PERFECT GETAWAY East Hampton / Sag Harbor

East Hampton

8% off
AU$10,666
for 7 nights, 1 home
AU$1,524 per night
includes taxes & fees
PERFECT GETAWAY East Hampton / Sag Harbor
Exterior detail
Living area
Pool
Interior
Exceptional
(11 reviews)

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

Sag Harbor

8% off
AU$14,549
for 7 nights, 1 cottage
AU$2,078 per night
includes taxes & fees
Secluded Sag Harbor Cottage - HUGE pool and separate bungalow/pool house
Front yard closeup
Facade
Living/dining space
Zepherine Drouhin, c. 1868 French thornless rose cultivar famed for its scent
Exceptional
(23 reviews)

Private Hamptons cottage in ideal Amagansett location

Amagansett

8% off
AU$7,647
for 7 nights, 1 cottage
AU$1,092 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
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
AU$25,866
for 7 nights, 1 home
AU$3,695 per night
includes taxes & fees
IN THE ViILLAGE OF SOUTHAMPTON POOL,TENNIS,PICKLEBALL COURTS BEACH CHAIRS&BIKES
Pool
Dining
living room
kitchen
Exceptional
(60 reviews)

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

Southampton

8% off
AU$19,703
for 7 nights, 1 home
AU$2,815 per night
includes taxes & fees
Southampton Village Renovated Sun-filled Charming Home, Heated Salt water Pool
Room
Dining
Exterior
Living area
Exceptional
(10 reviews)

Southampton Village Charmer - South of Highway

Southampton

8% off
AU$30,448
for 7 nights, 1 home
AU$4,350 per night
includes taxes & fees
Southampton Village Charmer - South of Highway
Dining
Pool
Terrace/patio
Living area
Exceptional
(17 reviews)

PRIVATE POOL ~ PERFECT HAMPTONS GETAWAY ~ WBH

East Hampton

8% off
AU$23,120
for 7 nights, 1 home
AU$3,303 per night
includes taxes & fees
PRIVATE POOL ~ PERFECT HAMPTONS GETAWAY ~ WBH
Terrace/patio
Property grounds
Dining
Private kitchen
Exceptional
(5 reviews)

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

East Hampton

8% off
AU$10,251
for 7 nights, 1 home
AU$1,464 per night
includes taxes & fees
Beautiful 4 bedroom house with tranquil gardens close to bay beaches.
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.
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$22,467
for 7 nights, 1 home
AU$3,210 per night
includes taxes & fees
WATER VIEWS RETREAT, SPRINGS, EAST HAMPTON, POOL, FIRE PIT, 10 MINUTES TO BEACH!
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
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
AU$23,155
for 7 nights, 1 home
AU$3,308 per night
includes taxes & fees
Completely Renovated Home on ~2 Private Acres, Near Beach/Town
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$6,404
for 7 nights, 1 home
AU$915 per night
includes taxes & fees
Steps from Cedar Beach ! Tranquil Retreat in the Heart of Wine Country
Living area
Living area
Room
Interior
Exceptional
(9 reviews)

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

East Hampton

7% off
AU$7,731
for 7 nights, 1 home
AU$1,104 per night
includes taxes & fees
Modern Home in East Hampton great for a summer or winter retreat.
Kitchen
Large pool heated pool
Dining area
Main living area
Exceptional
(21 reviews)

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

East Hampton

7% off
AU$7,230
for 7 nights, 1 home
AU$1,033 per night
includes taxes & fees
Charming, spacious 3 bedroom, 3 bath East Hampton Springs house
Living area
Dining
Outdoor dining
Private kitchen
Exceptional
(9 reviews)

Chic Modern Private Designer 1.5 Acre Private Oasis

East Hampton

26% off
AU$41,691
for 7 nights, 1 home
AU$5,956 per night
includes taxes & fees
Chic Modern Private Designer 1.5 Acre Private Oasis
Living area
Terrace/patio
Interior
Living area
Exceptional
(12 reviews)

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

East Hampton

12% off
AU$13,265
for 7 nights, 1 home
AU$1,895 per night
includes taxes & fees
Large East Hampton house with heated pool and home gym - fully fenced
Room
Private kitchen
Living area
Terrace/patio
Exceptional
(10 reviews)

Springs Chic, Steps from private Gardiners Bay beach!

East Hampton

8% off
AU$8,105
for 7 nights, 1 home
AU$1,158 per night
includes taxes & fees
Springs Chic, Steps from private Gardiners Bay beach!
Living room on main floor with mid-century modern sofa
Brightly lit dining room with 9' ceilings and view of heated swimming pool.
Second level sunny bedroom with queen bed and views of the pool.
Three Mile Harbor, glorious sunsets, and waterfront restaurants- 8 minute drive
Exceptional
(18 reviews)

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

East Hampton

16% off
AU$12,137
for 7 nights, 1 home
AU$1,734 per night
includes taxes & fees
Prime East Hampton Village Location. Heated Pool. Walk To All!
Primary bedroom with stylish, new, mid-century modern furnishings and pool view
Dine in style overlooking the pool and grounds
Lounge by the pool in total privacy
New, professional grade, stainless steel appliances including Bertazzoni range
Exceptional
(32 reviews)

Stylish East Hampton Village Retreat- Heated Pool and Sauna, Steps to Village

East Hampton

16% off
AU$9,557
for 7 nights, 1 home
AU$1,365 per night
includes taxes & fees
Stylish East Hampton Village Retreat- Heated Pool and Sauna, Steps to Village
Exterior
Wrap around deck
Living room
Second living room
Exceptional
(34 reviews)

Our Peaceful, Beach Escape From the City

Sag Harbor

8% off
AU$11,576
for 7 nights, 1 home
AU$1,654 per night
includes taxes & fees
Our Peaceful, Beach Escape From the City

  • 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)
  • Havens Beach (3.8 mi / 6.1 km)
  • Indian Wells Beach (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 best area to stay in Wainscott Woods when booking a holiday rental?
When considering a holiday rental in Wainscott Woods, New York, the surrounding areas offer some excellent options. One particularly appealing neighbourhood is Wainscott itself, which boasts a charming blend of tranquillity and proximity to beautiful beaches. In Wainscott, you can enjoy the stunning scenery at nearby beaches like Wainscott Beach, superb for sunbathing and enjoying the coastal atmosphere. Additionally, the area is close to the iconic LongHouse Reserve, a lovely sculpture garden that showcases contemporary art amidst lush landscapes.Another great option is East Hampton, just a short drive away. This vibrant area is known for its upscale shops, fine dining, and lively arts scene. The East Hampton Village is a delightful place to explore, with attractions such as the East Hampton Historical Society and the famous Main Beach, which is superb for a sunny day out.In terms of holiday rentals, both Wainscott and East Hampton offer a variety of properties, ranging from quaint cottages to more luxurious homes, providing ample choices to suit different tastes and budgets.
What are the top attractions in Wainscott Woods?
In Wainscott Woods, visitors can enjoy a tranquil retreat characterised by its scenic beauty and proximity to the Hamptons. One of the standout attractions is the nearby Wainscott Beach, which offers a serene stretch of sand superb for sunbathing and swimming. The area is also close to the charming town of East Hampton, where travellers can explore boutique shops, art galleries, and fine dining options.Nature enthusiasts can visit the nearby Long Pond Greenbelt, which features scenic trails for hiking and birdwatching. Additionally, the famous Montauk Point Lighthouse is just a short drive away, providing stunning coastal views and a glimpse into maritime history.
Are all fees included in the Wainscott Woods holiday homes prices shown on Stayz?
Stayz provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
Are there any Wainscott Woods holiday homes with parking?
Stayz offers a wide selection of holiday homes in Wainscott Woods with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Are there any discounts for Wainscott Woods holiday homes?
You can find great discounts on holiday homes in Wainscott Woods on Stayz, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for last-minute bookings, and early-bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Can I change or cancel my Wainscott Woods holiday home booking on Stayz?
To find Wainscott Woods holiday rentals with free cancellation, just use Stayz's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Wainscott Woods?
A long-stay holiday home in Wainscott Woods is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Stayz?
Stayz's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favourites, and build the perfect itinerary together.
How early should I book a Wainscott Woods holiday home?
Book your Wainscott Woods holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Wainscott Woods?
Prices for holiday homes in Wainscott Woods vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in Wainscott Woods to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
Why should I join Stayz as a host?
Joining Stayz as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Stayz makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

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