Wainscott holiday rentals

We found 2,125 holiday rentals — enter your dates for availability
Discover a selection of 38 homes and other holiday rentals in Wainscott that are perfect for your trip. Whether you're travelling with family, friends or just your furry companion, holiday homes have the best amenities for hanging out with the people that matter most, which might include Wi-Fi and a hot tub. No matter what you're looking for, you'll be able to choose a property to rent to meet everyone's needs, including a place that's non-smoking or offers accessibility.

Holiday rentals with weekly discounts – Wainscott

Showing deals for:18 Dec - 25 Dec

The Harbor
Private kitchen
Patio
Dining Room
Exceptional
(102 reviews)

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

Sag Harbor

16% off
AU$11,866
for 7 nights, 1 home
AU$1,695 per night
includes taxes & fees
Beautiful 3600sq ft Sag Harbor Village Home, Saltwater Pool, Walk to Beach &Town
master bedroom with balcony
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

16% off
AU$84,388
for 7 nights, 1 home
AU$12,055 per night
includes taxes & fees
Everything in Hamptons special discount available for weekly and monthly renters
Living area
Terrace/patio
Pool
Exterior
Excellent
(10 reviews)

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

Water Mill

8% off
AU$54,228
for 7 nights, 1 home
AU$7,747 per night
includes taxes & fees
Stunning fall sunsets, coveted location on Mecox Bay - recently furnished
Den
Pool
Front Porch
New Kitchen
Exceptional
(48 reviews)

Quiet Family Friendly Hideaway With Pool And Poolhouse

East Hampton

8% off
AU$18,594
for 7 nights, 1 home
AU$2,656 per night
includes taxes & fees
Quiet Family Friendly Hideaway With Pool And Poolhouse
An elegant dining room (to 10 ppl, joins kitchen +8 and outdoor dining +10,)
Living area
park-like grounds
Lower deck With Pool, 9 Loungers, plus 6 pool-chairs. Upper deck dining seats 10
Exceptional
(26 reviews)

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

Southampton

30% off
AU$14,141
for 7 nights, 1 home
AU$2,020 per night
includes taxes & fees
Southampton Pickleball Walk to beach. Kayaks on lake Park-like grounds Pool
Living area
Living area
Interior
Outdoor dining
Exceptional
(14 reviews)

PERFECT GETAWAY East Hampton / Sag Harbor

East Hampton

8% off
AU$10,593
for 7 nights, 1 home
AU$1,513 per night
includes taxes & fees
PERFECT GETAWAY East Hampton / Sag Harbor
Covered porch on backside of main house
Pool area viewed from side with teak loungers and umbrellas
Main house living room
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
AU$47,392
for 7 nights, 1 home
AU$6,770 per night
includes taxes & fees
Amagansett Beach Estate with Award Winning Outdoor Amenities
living room
Dining
kitchen
outdoor shower
Exceptional
(60 reviews)

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

Southampton

8% off
AU$19,569
for 7 nights, 1 home
AU$2,796 per night
includes taxes & fees
Southampton Village Renovated Sun-filled Charming Home, Heated Salt water Pool
Exterior detail
Living area
Interior
Exceptional
(10 reviews)

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

Sag Harbor

8% off
AU$14,349
for 7 nights, 1 cottage
AU$2,050 per night
includes taxes & fees
Secluded Sag Harbor Cottage - HUGE pool and separate bungalow/pool house
Living area on 1st floor with wood burning fireplace
Featured as one of most beautiful poolsides
Kitchen walks out to covered porch across length of entire back
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
AU$25,395
for 7 nights, 1 home
AU$3,628 per night
includes taxes & fees
IN THE ViILLAGE OF SOUTHAMPTON POOL,TENNIS,PICKLEBALL COURTS BEACH CHAIRS&BIKES
Zepherine Drouhin, c. 1868 French thornless rose cultivar famed for its scent
Facade
From the bedroom
Front yard closeup
Exceptional
(22 reviews)

Private Hamptons cottage in ideal Amagansett location

Amagansett

8% off
AU$7,595
for 7 nights, 1 cottage
AU$1,085 per night
includes taxes & fees
Private Hamptons cottage in ideal Amagansett location
Exterior
Dining
Living area
Room
Exceptional
(10 reviews)

Southampton Village Charmer - South of Highway

Southampton

8% off
AU$30,239
for 7 nights, 1 home
AU$4,320 per night
includes taxes & fees
Southampton Village Charmer - South of Highway
Dining
Pool
Living area
Terrace/patio
Exceptional
(17 reviews)

PRIVATE POOL ~ PERFECT HAMPTONS GETAWAY ~ WBH

East Hampton

8% off
AU$22,962
for 7 nights, 1 home
AU$3,280 per night
includes taxes & fees
PRIVATE POOL ~ PERFECT HAMPTONS GETAWAY ~ WBH
Kitchen with Wolf stove, Sub Zero fridge, pass-through serving area to dining.
Living room, looking out toward Accabonac Harbor, water views.
Bar area pass-through to kitchen, with bar seating.
Lovely seating in pool area for morning coffee.
Exceptional
(7 reviews)

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

East Hampton

8% off
AU$22,314
for 7 nights, 1 home
AU$3,188 per night
includes taxes & fees
WATER VIEWS RETREAT, SPRINGS, EAST HAMPTON, POOL, FIRE PIT, 10 MINUTES TO BEACH!
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$10,181
for 7 nights, 1 home
AU$1,454 per night
includes taxes & fees
Beautiful 4 bedroom house with tranquil gardens close to bay beaches.
Private kitchen
Private kitchen
Dining
Room
Exceptional
(14 reviews)

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

Southold

8% off
AU$6,373
for 7 nights, 1 home
AU$910 per night
includes taxes & fees
Steps from Cedar Beach ! Tranquil Retreat in the Heart of Wine Country
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
View from entry foyer into double height living room, skylights, leading to pool
Frankel Residence
Exceptional
(6 reviews)

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

Wainscott

8% off
AU$22,997
for 7 nights, 1 home
AU$3,285 per night
includes taxes & fees
Completely Renovated Home on ~2 Private Acres, Near Beach/Town
Interior
Living area
Living area
Dining
Exceptional
(9 reviews)

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

East Hampton

7% off
AU$7,679
for 7 nights, 1 home
AU$1,097 per night
includes taxes & fees
Modern Home in East Hampton great for a summer or winter retreat.
Private kitchen
Dining
Outdoor dining
Living area
Exceptional
(9 reviews)

Chic Modern Private Designer 1.5 Acre Private Oasis

East Hampton

26% off
AU$41,406
for 7 nights, 1 home
AU$5,915 per night
includes taxes & fees
Chic Modern Private Designer 1.5 Acre Private Oasis
Exterior
Large pool heated pool
Main living area
Dining area
Exceptional
(21 reviews)

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

East Hampton

7% off
AU$7,180
for 7 nights, 1 home
AU$1,026 per night
includes taxes & fees
Charming, spacious 3 bedroom, 3 bath East Hampton Springs house
Living area
Terrace/patio
Living area
Interior
Exceptional
(12 reviews)

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

East Hampton

12% off
AU$12,325
for 7 nights, 1 home
AU$1,761 per night
includes taxes & fees
Large East Hampton house with heated pool and home gym - fully fenced
Room
Private kitchen
Living area
Living area
Exceptional
(10 reviews)

Springs Chic, Steps from private Gardiners Bay beach!

East Hampton

8% off
AU$8,050
for 7 nights, 1 home
AU$1,150 per night
includes taxes & fees
Springs Chic, Steps from private Gardiners Bay beach!
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.
Sunlit living room w/ coffered ceilings, tv, fireplace, & French doors to pool
Living room on main floor with mid-century modern sofa
Exceptional
(18 reviews)

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

East Hampton

16% off
AU$11,544
for 7 nights, 1 home
AU$1,649 per night
includes taxes & fees
Prime East Hampton Village Location. Heated Pool. Walk To All!
Primary bedroom w/California king, vaulted ceilings, tv, & private bathroom
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$8,946
for 7 nights, 1 home
AU$1,278 per night
includes taxes & fees
Stylish East Hampton Village Retreat- Heated Pool and Sauna, Steps to Village

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  • More quality time

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    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Travel to relaxing Wainscott

The beaches and surrounding scenery provide a peaceful ambience to your holiday home in Wainscott. This relaxing city attracts visitors thanks to its bars and coffee shops. A holiday rental can help make your stay complete—many rentals come with a full kitchen and laundry facilities.

Sightseeing in and around Wainscott

Do you want to discover top things to see and do in the area? Venture out of your cosy holiday rental and check out everything that makes Wainscott a fun spot to go on holiday. These are some of the most popular attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • Wolffer Estates Vineyard (1.9 mi / 3 km)
  • LongHouse Reserve (3.9 mi / 6.3 km)
  • Duck Walk Vineyards (6.9 mi / 11.1 km)
  • Noyac Golf Club (7.2 mi / 11.5 km)
  • Shinnecock Hills Golf Course (10.7 mi / 17.2 km)
  • Raphael Winery (13.2 mi / 21.3 km)

Exploring the natural landscape of Wainscott

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

  • Georgica Beach (1.4 mi / 2.3 km)
  • East Hampton Main Beach (2.6 mi / 4.1 km)
  • The Hamptons Beaches (3.2 mi / 5.1 km)
  • LongHouse Reserve (3.9 mi / 6.3 km)
  • Indian Wells Beach (5.7 mi / 9.2 km)
  • Atlantic Avenue Beach (6.6 mi / 10.7 km)

Seasonal weather in Wainscott

If you're planning a holiday around the weather, August, July, September and June are the hottest months to visit, when temperatures average 21°C.

Transport options to and around Wainscott

The nearest airport is in East Hampton, NY (HTO), located 1.7 mi (2.7 km) from the city centre. If you're unable to find a flight that fits your schedule, you could also fly into Montauk, NY (MTP), which is 19 mi (30.7 km) away.

Frequently asked questions

What is the best area to stay in Wainscott when booking a holiday rental?
When considering a holiday rental in Wainscott, New York, the area offers a delightful mix of charm and convenience. One of the best neighbourhoods to stay in is the vicinity of Wainscott's scenic beaches, which provide easy access to the beautiful coastline. This area boasts a serene atmosphere, ideal for those looking to relax by the sea or enjoy outdoor activities.In addition to the stunning beaches, visitors can explore nearby attractions such as the iconic Wainscott Pond, a lovely spot for picnics and birdwatching, and the local vineyards, which offer tasting tours and a taste of the region's agricultural richness. The neighbourhood is home to a variety of holiday rentals, ranging from quaint cottages to more luxurious homes, suiting different preferences and budgets.
Where are the best areas for renting a beach house in Wainscott?
For renting a beach house in Wainscott, the area around the sandy shores of the Atlantic Ocean is particularly appealing. The neighbourhood is known for its stunning beachfront properties that often feature amenities such as private pools, expansive decks, and direct access to the beach. Many of these homes come equipped with modern kitchens, spacious living areas, and outdoor dining spaces, making them great for families and groups looking to enjoy a seaside getaway.Nearby, the scenic landscapes of East Hampton offer additional options, where charming cottages and larger homes can be found, often located among lush gardens. These properties frequently include features like barbecues, fire pits, and outdoor showers, enhancing the beach experience. The proximity to local attractions, such as the East Hampton Village with its boutiques and restaurants, adds to the convenience for visitors.Moreover, Wainscott is close to various natural preserves and parks, providing ample opportunities for outdoor activities like hiking and biking. Rentals in the area often reflect a blend of luxury and comfort, ensuring that guests can fully immerse themselves in the serene beach atmosphere while enjoying modern amenities.
What is the most popular type of holiday rental accomodation in Wainscott?
In Wainscott, holiday houses are the predominant choice for holiday rentals, with around 116 available throughout the area. These properties typically feature spacious interiors with multiple bedrooms, fully equipped kitchens, and inviting living areas, making them ideal for families or groups. Many holiday houses come with outdoor spaces, such as gardens or patios, superb for enjoying the pleasant surroundings. Located in a tranquil setting, these rentals provide a comfortable home base for exploring nearby attractions like the charming local shops and beautiful beaches of the Hamptons.
Are there any family house rentals in Wainscott?
In Wainscott, New York, there are some family-friendly house rentals available—approximately 21 options for those seeking a getaway. This charming area, known for its scenic beauty and proximity to beaches, offers spacious homes that cater well to families. Many properties come equipped with full kitchens, allowing for easy meal preparation, and feature ample living spaces where everyone can relax together. Outdoor amenities such as gardens or patios provide a lovely setting for children to play or for family gatherings during the warmer months.Visitors will appreciate Wainscott's close proximity to the stunning beaches, where families can enjoy sunbathing, swimming, and various water activities. Additionally, the local shops and restaurants are just a short drive away, offering an array of dining options and unique finds.
Can I rent a holiday home with a pool or hot tub in Wainscott?
In Wainscott, there are plenty of holiday homes available for rent that feature pools and hot tubs, with around 26 options to choose from. This charming area, located in the Hamptons, offers a tranquil atmosphere while being close to the beautiful beaches of the Atlantic. Many properties come equipped with private pools, inviting hot tubs, and spacious outdoor areas great for relaxation and entertaining.Travellers can expect amenities such as fully equipped kitchens, generous living spaces, and outdoor dining areas. Some rentals may also include luxurious features like fire pits and landscaped gardens, making them ideal for families or groups seeking a memorable getaway.
Are there pet-friendly house rentals in Wainscott?
In Wainscott, travellers will find a range of pet-friendly house rentals available, with about 14 options to choose from. This charming area, located near the scenic Hamptons, offers holiday homes that often feature spacious backyards, modern kitchens, and comfortable living spaces, ideal for families or groups travelling with pets. Many properties are equipped with amenities such as outdoor grills, patios for al fresco dining, and laundry facilities for added convenience.Wainscott is also conveniently situated close to several beaches and parks, making it a great spot for pet owners. Nearby, the beautiful Wainscott Beach allows for leisurely walks along the shore, while the surrounding areas offer trails and open spaces superb for exercising pets. Additionally, the local community is known for its welcoming atmosphere, with several pet-friendly cafes and shops enhancing the overall experience for visitors.
Are there any remote work holiday rentals in Wainscott?
In Wainscott, there are numerous holiday rentals suitable for remote work, with around 108 options available. This charming area, located in the Hamptons, offers a serene environment that is ideal for productivity while enjoying a holiday. Many of the properties come equipped with amenities tailored for remote workers, including high-speed Wi-Fi, dedicated workspaces with desks and chairs, and comfortable living areas to ensure a pleasant working experience.Wainscott is conveniently situated near beautiful beaches, art galleries, and local dining options, providing opportunities for relaxation and exploration after work hours. The surrounding natural beauty, with easy access to parks and walking paths, adds to the appeal, making it a great location for those seeking a balance between work and leisure. To help narrow your search, insert your dates and apply the "WiFi" filter on Stayz.
What are popular rental amenities in Wainscott?
In Wainscott, popular rental amenities include kitchens, which allow guests to prepare their own meals, and private pools for relaxation and entertainment during warmer months. Many properties also feature decks or patios, providing outdoor spaces for dining or enjoying the fresh air. Cozy fireplaces are common, offering a warm atmosphere for cooler evenings, and some rentals even include amenities like blenders for those who enjoy making smoothies or cocktails.
When is the best time to visit Wainscott for a holiday rental?
April marks the beginning of the peak season in Wainscott, making it an ideal time for holiday rentals. With the arrival of spring, this charming village in New York comes alive, attracting visitors keen on enjoying the beautiful beaches and scenic landscapes. As the weather warms up, temperatures typically range from 8 to 17 degrees Celsius, creating a pleasant environment for outdoor activities such as cycling, walking, and exploring local parks.From April to June, Wainscott experiences vibrant tourist activity, with many guests drawn to its picturesque coastline and quaint shops. This is the superb time for those who appreciate a lively option while still enjoying the natural beauty of the area. Early spring also offers opportunities for sightseeing, such as visiting nearby vineyards or indulging in fresh seafood at local restaurants.For those looking for a more budget-friendly option, consider visiting in December. While this month may be quieter, it provides a great experience of Wainscott, with fewer crowds and a chance to appreciate the serene winter landscape. You can enjoy peaceful walks along the shore and take in the beauty of the area at your own pace.Ultimately, the best time to book a holiday rental in Wainscott depends on whether you prefer the vibrant energy of spring and early summer or the tranquil charm of the off-peak season.
What are the top attractions in Wainscott?
In Wainscott, visitors can enjoy a quintessential Hamptons experience with its proximity to beautiful beaches and charming local spots. The area is known for its serene atmosphere and is just a short distance from the popular beaches of East Hampton and Montauk, where sunbathing, surfing, and beachside dining are readily available.Wainscott is also close to the stunning natural scenery of the Long Island Nature Conservancy, offering opportunities for hiking and birdwatching. Visitors can explore local farm stands and markets, which provide fresh produce and artisanal goods, enhancing the local experience.
Are all fees included in the Wainscott 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 holiday homes with parking?
Stayz offers a wide selection of holiday homes in Wainscott 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 holiday homes?
You can find great discounts on holiday homes in Wainscott 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 holiday home booking on Stayz?
To find Wainscott 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?
A long-stay holiday home in Wainscott 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 holiday home?
Book your Wainscott 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?
Prices for holiday homes in Wainscott 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 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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