Tuckahoe holiday rentals

We found 1,903 holiday rentals — enter your dates for availability
Discover a selection of 63 homes and other holiday rentals in Tuckahoe that are perfect for your trip. Whether you're travelling with your children and pets, with friends or just your children, holiday rentals have the best amenities for hanging out with the people that matter most, which might include air conditioning and a pool. Whatever you're looking for, you'll be able to choose a property to rent that has what everyone needs, including a place that's non-smoking or offers accessibility.

Holiday rentals with weekly discounts – Tuckahoe

Showing deals for:8 Jan - 15 Jan

master bedroom with balcony
aerial view
living room
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
AU$83,039
for 7 nights, 1 home
AU$11,863 per night
includes taxes & fees
Everything in Hamptons special discount available for weekly and monthly renters
Terrace/patio
Pool
Stairs to the upstairs living room, kitchen and dining room
Large wrap-around lawn
Exceptional
(27 reviews)

Modern Family Retreat with Heated Pool, Playground and Peloton

Hampton Bays

8% off
AU$11,649
for 7 nights, 1 home
AU$1,664 per night
includes taxes & fees
Modern Family Retreat with Heated Pool, Playground and Peloton
Hot tub open all year
Exterior
Pool, gazebo, fire table
Living area
Exceptional
(47 reviews)

Westhampton Beach Town and Country

Westhampton Beach

8% off
AU$11,470
for 7 nights, 1 home
AU$1,639 per night
includes taxes & fees
Westhampton Beach Town and Country
Interior
Exterior
Private kitchen
Outdoor dining
Exceptional
(9 reviews)

Beautiful Colonial Mint Condition Summer House Walking Distance to Beach

Jamesport

12% off
AU$6,196
for 7 nights, 1 home
AU$885 per night
includes taxes & fees
Beautiful Colonial Mint Condition Summer House Walking Distance to Beach
Pool
Pool
Terrace/patio
Outdoor dining
Exceptional
(6 reviews)

Newly Built Hamptons House, Pool, Beach Access + Easy Access off Montauk Highway

Hampton Bays

8% off
AU$14,579
for 7 nights, 1 home
AU$2,083 per night
includes taxes & fees
Newly Built Hamptons House, Pool, Beach Access + Easy Access off Montauk Highway
park-like grounds
Living area
An elegant dining room (to 10 ppl, joins kitchen +8 and outdoor dining  +10,)
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$14,853
for 7 nights, 1 home
AU$2,122 per night
includes taxes & fees
Southampton Pickleball Walk to beach. Kayaks on lake Park-like grounds Pool
Living area
Terrace/patio
Pool
Living area
Excellent
(10 reviews)

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

Water Mill

8% off
AU$55,892
for 7 nights, 1 home
AU$7,985 per night
includes taxes & fees
Stunning fall sunsets, coveted location on Mecox Bay - recently furnished
Outdoor dining
.
Private kitchen
3 acres of beautiful land
Exceptional
(84 reviews)

Southampton Estate, Newly Renovated , Excellent For Families! Sleeps 12-14

Hampton Bays

7% off
AU$10,861
for 7 nights, 1 home
AU$1,552 per night
includes taxes & fees
Southampton Estate, Newly Renovated , Excellent For Families! Sleeps 12-14
View from entry foyer into double height living room, skylights, leading to pool
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$23,703
for 7 nights, 1 home
AU$3,386 per night
includes taxes & fees
Completely Renovated Home on ~2 Private Acres, Near Beach/Town
Living area on 1st floor with wood burning fireplace
Featured as one of most beautiful poolsides
Couches on covered porch and outdoor dining table for 8
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$28,338
for 7 nights, 1 home
AU$4,048 per night
includes taxes & fees
IN THE ViILLAGE OF SOUTHAMPTON POOL,TENNIS,PICKLEBALL COURTS BEACH CHAIRS&BIKES
Pool
Exterior
Large Dining/Kitchen Space
Spacious Main Floor Living room
Exceptional
(12 reviews)

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

Southold

8% off
AU$12,173
for 7 nights, 1 home
AU$1,739 per night
includes taxes & fees
New Modern Farmhouse Estate Living in the heart of Southold with a pool!!!
Fenced, backyard Hampton-style pool area with lounge chairs and patio
Dining
Bathroom 1- upstairs
Private kitchen
Exceptional
(14 reviews)

Renovated Farmhouse on Vineyard-Heated Pool + mins from Beach + Walk to Harbes!

Riverhead

8% off
AU$8,837
for 7 nights, 1 home
AU$1,262 per night
includes taxes & fees
Renovated Farmhouse on Vineyard-Heated Pool + mins from Beach + Walk to Harbes!
Exterior
Private kitchen
Dining Room
Patio
Exceptional
(104 reviews)

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

Sag Harbor

16% off
AU$12,074
for 7 nights, 1 home
AU$1,725 per night
includes taxes & fees
Beautiful 3600sq ft Sag Harbor Village Home, Saltwater Pool, Walk to Beach &Town
Outdoor dining
Private kitchen
Living area
Room
Exceptional
(17 reviews)

Newly renovated 4-bedroom farmhouse on beautiful vineyard - Great location.

Jamesport

16% off
AU$7,949
for 7 nights, 1 home
AU$1,136 per night
includes taxes & fees
Newly renovated 4-bedroom farmhouse on beautiful vineyard - Great location.
Interior
Dining
Main living room and dining room
Night time at the pool
Exceptional
(29 reviews)

9BR Sag Harbor PRIVATE w/ Pool-Tennis- B-ball- HotTub

Sag Harbor

8% off
AU$17,362
for 7 nights, 1 home
AU$2,480 per night
includes taxes & fees
9BR Sag Harbor PRIVATE w/ Pool-Tennis- B-ball- HotTub
primary bedroom #1main floor
seating area rear deck
view of pool
dining area, expandable table
Exceptional
(15 reviews)

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

Water Mill

8% off
AU$23,920
for 7 nights, 1 home
AU$3,417 per night
includes taxes & fees
Sunsets Sweeping Farmland Views, Great Retreat Minutes from Flying Point Beach
Dining Room with seating for Ten
Pool
Outdoor dining
Master bedroom with ensuite bathroom
Exceptional
(29 reviews)

Spacious New 4 Bedroom Home With Pool on 2 Acre Property

Peconic

8% off
AU$12,216
for 7 nights, 1 home
AU$1,745 per night
includes taxes & fees
Spacious New 4 Bedroom Home With Pool on 2 Acre Property
Pool
Terrace/patio
Private kitchen
Living area
Exceptional
(21 reviews)

Hampton bays summer home get away!

Hampton Bays

8% off
AU$8,352
for 7 nights, 1 home
AU$1,193 per night
includes taxes & fees
Hampton bays summer home get away!
Living room open to the sunroom
American Beech (Greenport)
Sunroom can easily convert into a queen sleeping area with armoire for storage
Pool overlooking horse farm
Exceptional
(20 reviews)

Modern farmhouse w/ heated pool, beach, horses and winery in heart of North Fork

Mattituck

7% off
AU$3,452
for 7 nights, 1 home
AU$493 per night
includes taxes & fees
Modern farmhouse w/ heated pool, beach, horses and winery in heart of North Fork
Private kitchen
Dining
Living area
Room
Exceptional
(18 reviews)

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

Cutchogue

8% off
AU$7,095
for 7 nights, 1 cottage
AU$1,014 per night
includes taxes & fees
Great Getaway! Exceptional Home. Walking distance to The Christmas Tree Shoppe
Second eating area
Wrap around deck
Living room
Exterior
Exceptional
(34 reviews)

Our Peaceful, Beach Escape From the City

Sag Harbor

8% off
AU$13,260
for 7 nights, 1 home
AU$1,894 per night
includes taxes & fees
Our Peaceful, Beach Escape From the City
Outdoor dining
Private kitchen
Dining
Living area
Exceptional
(13 reviews)

Enjoy a lovely summer retreat in Sag Harbor Village, 1 mile to Main Street

Sag Harbor

8% off
AU$20,411
for 7 nights, 1 home
AU$2,916 per night
includes taxes & fees
Enjoy a lovely summer retreat in Sag Harbor Village, 1 mile to Main Street
Outdoor dining
Private kitchen
Dining
Living area
Exceptional
(10 reviews)

Best View + Private Beach + Putting Green

Hampton Bays

8% off
AU$7,221
for 7 nights, 1 home
AU$1,032 per night
includes taxes & fees
Best View + Private Beach + Putting Green
Room
Kitchen
Backyard Water View
Exterior
Exceptional
(6 reviews)

Charming 2 bedroom house in Quaint New Suffolk -short walk to New suffolk Beach

New Suffolk

8% off
AU$4,940
for 7 nights, 1 home
AU$706 per night
includes taxes & fees
Charming 2 bedroom house in Quaint New Suffolk -short walk to New suffolk Beach
  • 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

The picturesque setting of Tuckahoe is ready to explore

Enjoy the monuments and other features of Tuckahoe. This welcoming city is known for its golfing, beaches and coffee shops. If you need more space to accommodate a family holiday or a trip with friends, rental homes often come with separate dining areas and spacious living rooms.

Sightseeing in and around Tuckahoe

Are you hoping to find things to do while you're in town? Venture out of your holiday home and check out everything that makes Tuckahoe a one-of-a-kind holiday spot. These are some of the top attractions to see, all within 30 miles (48.2 km) of the city centre:

  • Shinnecock Hills Golf Course (1.5 mi / 2.5 km)
  • Duck Walk Vineyards (2.3 mi / 3.8 km)
  • Wolffer Estates Vineyard (7.7 mi / 12.3 km)
  • Peconic Bay Winery (9 mi / 14.5 km)
  • Bedell Cellars (9.5 mi / 15.2 km)
  • Pindar Vineyards (9.6 mi / 15.5 km)

Exploring the natural landscape of Tuckahoe

Whether you're looking for exciting outdoor activities or just want to appreciate the scenery, Tuckahoe is a great place to get out in nature. Here are a few of the area's most enchanting natural features, all within 30 miles (48.2 km) of the city centre:

  • Cooper's Beach (2.5 mi / 4 km)
  • Meschutt Beach (4.7 mi / 7.6 km)
  • The Hamptons Beaches (6 mi / 9.6 km)
  • Ponquogue Beach (6.2 mi / 10 km)
  • Georgica Beach (10.5 mi / 16.9 km)
  • East Hampton Main Beach (11.7 mi / 18.8 km)

Seasonal weather in Tuckahoe

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

Transport options to and around Tuckahoe

Fly into East Hampton, NY (HTO), the closest airport, located 9.5 mi (15.4 km) from the city centre. If you can't find a flight that's convenient for your trip, you can also fly into Westhampton, NY (FOK-Francis S. Gabreski), which is 12.6 mi (20.3 km) away.

Frequently asked questions

What is the best area to stay in Tuckahoe when booking a holiday rental?
When considering a holiday rental in Tuckahoe, New York, the best area to stay is the vicinity around the Tuckahoe village centre. This charming neighbourhood offers a delightful blend of convenience and community spirit, making it an ideal base for your visit. You'll find a variety of properties available, suiting different preferences and budgets.One of the major attractions nearby is the picturesque Tuckahoe Town Park, which is superb for leisurely strolls or enjoying a picnic. Additionally, the historic Tuckahoe Historic District features beautiful architecture and is a lovely area to explore. For those interested in dining and shopping, the local area boasts a selection of quaint cafes and boutiques that add to the neighbourhood's charm.Staying in the village centre not only places you in close proximity to these attractions but also provides easy access to public transport, allowing you to venture further afield to explore the wider Westchester County region.
What are the top attractions in Tuckahoe?
In Tuckahoe, visitors can enjoy a charming blend of local attractions and nearby points of interest. The village itself is known for its quaint downtown area, featuring a variety of shops, cafes, and restaurants that reflect the community's character.One of the highlights is the Tuckahoe Historical Society, which offers insights into the local history and culture. For those who appreciate the outdoors, the nearby Bronx River Parkway Reservation provides scenic walking and biking paths along the river, great for leisurely strolls or active outings.Additionally, the area is conveniently located near the larger attractions of White Plains and Yonkers, where you can find shopping centres, parks, and cultural venues.
Are all fees included in the Tuckahoe 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 Tuckahoe holiday homes with parking?
Stayz offers a wide selection of holiday homes in Tuckahoe 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 Tuckahoe holiday homes?
You can find great discounts on holiday homes in Tuckahoe 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 Tuckahoe holiday home booking on Stayz?
To find Tuckahoe 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 Tuckahoe?
A long-stay holiday home in Tuckahoe 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 Tuckahoe holiday home?
Book your Tuckahoe 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 Tuckahoe?
Prices for holiday homes in Tuckahoe 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 Tuckahoe 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.