Riverhead holiday rentals

We found 2,927 holiday rentals — enter your dates for availability
Discover a selection of 57 homes and other holiday rentals in Riverhead that are perfect for your trip. Whether you’re staying in a holiday home with friends, family or even just your pets, you'll have the best amenities for spending time at your home away from home, which might include a pool and a washer and dryer. No matter what you're looking for, you'll be sure to find a property to rent to meet everyone's needs, including a place that is accessible or non-smoking.

Holiday rentals with weekly discounts – Riverhead

Showing deals for:25 Dec - 1 Jan

Main Entrance
Dining table and picnic table water view
2nd floor deck with additional dining and leisure seating.
Heated pool with gorgeous water and natural wetland view
Exceptional
(38 reviews)

Luxurious Waterfront Retreat in Southampton: Breathtaking Views, Pool, and More!

Southampton

5% off
AU$20,456
for 7 nights, 1 home
AU$2,922 per night
includes taxes & fees
Luxurious Waterfront Retreat in Southampton: Breathtaking Views, Pool, and More!
Pool
Exterior
Private kitchen
Pool
Exceptional
(6 reviews)

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

Hampton Bays

8% off
AU$14,240
for 7 nights, 1 home
AU$2,034 per night
includes taxes & fees
Newly Built Hamptons House, Pool, Beach Access + Easy Access off Montauk Highway
Patio
Private kitchen
The Harbor
Dining Room
Exceptional
(103 reviews)

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

Sag Harbor

16% off
AU$11,925
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
Private kitchen
Dining
Interior
Living area
Exceptional
(6 reviews)

Shirley Bayfront Getaway – Kayak, Swim & Relax

Shirley

8% off
AU$11,742
for 7 nights, 1 home
AU$1,677 per night
includes taxes & fees
Shirley Bayfront Getaway – Kayak, Swim & Relax
Interior
Exterior
Outdoor dining
Private kitchen
Exceptional
(8 reviews)

Beautiful Colonial Mint Condition Summer House Walking Distance to Beach

Jamesport

12% off
AU$6,049
for 7 nights, 1 home
AU$864 per night
includes taxes & fees
Beautiful Colonial Mint Condition Summer House Walking Distance to Beach
living room
aerial view
kitchen with large island and breakfast table
master bedroom with balcony
Exceptional
(7 reviews)

Everything in Hamptons special discount available for weekly and monthly renters

Water Mill

17% off
AU$81,110
for 7 nights, 1 home
AU$11,587 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$54,593
for 7 nights, 1 home
AU$7,799 per night
includes taxes & fees
Stunning fall sunsets, coveted location on Mecox Bay - recently furnished
Dining Room with seating for Ten
Pool
Outdoor dining
Master bedroom with ensuite bathroom
Exceptional
(28 reviews)

Spacious New 4 Bedroom Home With Pool on 2 Acre Property

Peconic

8% off
AU$11,932
for 7 nights, 1 home
AU$1,705 per night
includes taxes & fees
Spacious New 4 Bedroom Home With Pool on 2 Acre Property
Room
Pool
Room
Pool
Excellent
(36 reviews)

The Jahmtons Guest Room

Ridge

8% off
AU$1,461
for 7 nights, 1 room
AU$209 per night
includes taxes & fees
The Jahmtons Guest Room
Front entrance, park-like grounds
Living area
Lower deck With Pool, 9 Loungers, plus 6 pool-chairs. Upper deck dining seats 10
park-like grounds
Exceptional
(26 reviews)

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

Southampton

30% off
AU$14,236
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
Interior
Property grounds
Interior
Room
Very good
(34 reviews)

Waterfront Home With Recreational Dock! Great For Rafting, And Close To Beaches

Mastic Beach

8% off
AU$3,613
for 7 nights, 1 home
AU$516 per night
includes taxes & fees
Waterfront Home With Recreational Dock! Great For Rafting, And Close To Beaches
Spacious Main Floor Living room
Exterior
Pool
Large Dining/Kitchen Space
Exceptional
(11 reviews)

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

Southold

8% off
AU$17,527
for 7 nights, 1 home
AU$2,504 per night
includes taxes & fees
New Modern Farmhouse Estate Living in the heart of Southold with a pool!!!
More vineyard views
Outdoor dining
Welcome to Vineyard View
Exterior
Exceptional
(26 reviews)

Vineyard View, Bike to the Most Beautiful Beach

Mattituck

8% off
AU$9,805
for 7 nights, 1 home
AU$1,401 per night
includes taxes & fees
Vineyard View, Bike to the Most Beautiful Beach
Interior
Living area
Outdoor dining
Pool
Exceptional
(15 reviews)

PERFECT GETAWAY East Hampton / Sag Harbor

East Hampton

8% off
AU$10,664
for 7 nights, 1 home
AU$1,523 per night
includes taxes & fees
PERFECT GETAWAY East Hampton / Sag Harbor
3 acres of beautiful land
.
Interior
Private kitchen
Exceptional
(82 reviews)

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

Hampton Bays

6% off
AU$11,563
for 7 nights, 1 home
AU$1,652 per night
includes taxes & fees
Southampton Estate, Newly Renovated , Excellent For Families! Sleeps 12-14
Living area
Living area
Private kitchen
Property grounds
Exceptional
(29 reviews)

Incredible Beachfront Home w/ Private Beach!

Mattituck

7% off
AU$5,199
for 7 nights, 1 cottage
AU$743 per night
includes taxes & fees
Incredible Beachfront Home w/ Private Beach!
Interior
Exterior
Private kitchen
Property grounds
Exceptional
(40 reviews)

Spacious home near Aquarium & heart of wine country Shopping & close to Hamptons

Riverhead

8% off
AU$7,297
for 7 nights, 1 home
AU$1,042 per night
includes taxes & fees
Spacious home near Aquarium & heart of wine country Shopping & close to Hamptons
Interior
Living area
Exterior detail
Exceptional
(11 reviews)

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

Sag Harbor

8% off
AU$14,546
for 7 nights, 1 cottage
AU$2,078 per night
includes taxes & fees
Secluded Sag Harbor Cottage - HUGE pool and separate bungalow/pool house
This area is perfect for reading and relaxing
Kitchen is stocked with a selection of pots dishes and utensils
Enjoy nearby North Fork and South Fork wineries and many other local attractions
Spacious living room with sliders to the patio pool and backyard
Exceptional
(108 reviews)

Hampton’s Haven: Heated Pool, Hot Tub & Gameroom! 2 miles to Rogers Beach

Westhampton Beach

8% off
AU$8,754
for 7 nights, 1 home
AU$1,251 per night
includes taxes & fees
Hampton’s Haven: Heated Pool, Hot Tub & Gameroom! 2 miles to Rogers Beach
Terrace/patio
Living area
Dining
Private kitchen
Excellent
(27 reviews)

Relaxing Cottage -- Walk to private Beach!

Calverton

7% off
AU$3,248
for 7 nights, 1 cottage
AU$464 per night
includes taxes & fees
Relaxing Cottage -- Walk to private Beach!
Hydrangeas blooming all summer.these are the August bloomers
Featured as one of most beautiful poolsides
Couches on covered porch and outdoor dining table for 8
Kitchen walks out to covered porch across length of entire back
Exceptional
(7 reviews)

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

Southampton

8% off
AU$25,862
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
living room
Dining
outdoor shower
kitchen
Exceptional
(60 reviews)

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

Southampton

8% off
AU$19,701
for 7 nights, 1 home
AU$2,814 per night
includes taxes & fees
Southampton Village Renovated Sun-filled Charming Home, Heated Salt water Pool
Living area
Exterior
Hot tub open all year
Dining area
Exceptional
(45 reviews)

Westhampton Beach Town and Country

Westhampton Beach

8% off
AU$11,203
for 7 nights, 1 home
AU$1,600 per night
includes taxes & fees
Westhampton Beach Town and Country
Large wrap-around lawn
Pool
Living room
Stairs to the upstairs living room, kitchen and dining room
Exceptional
(27 reviews)

Modern Family Retreat with Heated Pool, Playground and Peloton

Hampton Bays

8% off
AU$11,379
for 7 nights, 1 home
AU$1,626 per night
includes taxes & fees
Modern Family Retreat with Heated Pool, Playground and Peloton

  • 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

Arty Riverhead will entice you

Take a holiday to Riverhead and enjoy the area's wineries, art galleries and festivals. Renowned for its aquarium, seafood restaurants and shopping, this city welcomes all visitors. Many rental homes come with outdoor spaces, separate dining areas and full kitchens, perfect if you want to enjoy some home-cooked meals.

Sightseeing in and around Riverhead

Are you hoping to find attractions to see during your stay? Although it can be tempting to stay in your comfortable holiday rental, you'll want to experience everything that makes Riverhead a fun place to get away to. These are some of the major attractions to see, all within 30 miles (48.2 km) of the city centre:

  • Safari Adventure (0.9 mi / 1.5 km)
  • Splish Splash Water Park (3.6 mi / 5.8 km)
  • Jamesport Vineyards (4 mi / 6.5 km)
  • Martha Clara Vineyards (5.9 mi / 9.5 km)
  • Macari Vineyards (6.9 mi / 11.1 km)
  • Swan Lake Golf Club (7.2 mi / 11.6 km)

Exploring the natural features in Riverhead

Whether you're an adventurous traveller or just want to appreciate the scenery, Riverhead is a great place to get outside. These are some of the area's most eye-catching features, all within 30 miles (48.2 km) of the city centre:

  • Meschutt Beach (8.6 mi / 13.8 km)
  • Tiana Beach (10 mi / 16.1 km)
  • Ponquogue Beach (10.4 mi / 16.7 km)
  • Shinnecock East County Park (11.2 mi / 18 km)
  • Smith Point County Park (13 mi / 20.9 km)
  • Cooper's Beach (13.9 mi / 22.3 km)

Transport options to and around Riverhead

Fly into Westhampton, NY (FOK-Francis S. Gabreski), the closest airport, located 5.3 mi (8.5 km) from the city centre. If you're unable to find a flight that fits your schedule, you could book a flight to Shirley, NY (WSH-Brookhaven Calabro), which is 12.7 mi (20.4 km) away.

If you'd rather travel by train, you can make your way to Riverhead Station.

Frequently asked questions

What is the best area to stay in Riverhead when booking a holiday rental?
When considering a holiday rental in Riverhead, New York, the downtown area is an excellent choice. This vibrant neighbourhood boasts a variety of properties, from charming cottages to modern apartments, offering something for every taste and budget. Staying in the heart of Riverhead allows you to easily access local attractions, such as the stunning Long Island Aquarium, which is superb for families and marine enthusiasts alike. Another highlight is the picturesque Riverhead Farmers Market, where you can immerse yourself in the local culture and sample fresh produce and artisanal goods.Additionally, the nearby North Fork region, known for its beautiful vineyards and scenic views, is just a short drive away. This area is ideal for wine lovers, as it features numerous wineries that offer tastings and tours.
Where are the best areas for renting a beach house in Riverhead?
For renting a beach house in Riverhead, the scenic area along the Peconic River is an excellent choice. This location offers a variety of holiday rentals with wonderful waterfront views and easy access to the river's sandy beaches. Many properties here come with amenities such as private docks, outdoor decks for barbecuing, and fully equipped kitchens, making them superb for families or groups looking to enjoy a relaxing getaway by the water.Additionally, the nearby Indian Island County Park provides a lovely beach area where visitors can enjoy picnicking and swimming. Rentals in this vicinity often include features like spacious backyards and outdoor seating, ideal for soaking up the sun and enjoying the natural surroundings. The charming downtown Riverhead area, with its diverse dining options and local shops, adds to the convenience for holidaymakers.Exploring the nearby Long Island Wine Country is another highlight, where many properties are situated close to vineyards and tasting rooms.
Are there any houseboat rentals in Riverhead?
In Riverhead, there are several houseboat rentals available, providing a unique way to experience this charming area. Many of these houseboats are situated near the picturesque Peconic River, allowing guests to enjoy scenic views and easy access to local attractions. Amenities typically include comfortable sleeping arrangements, fully equipped kitchens, and outdoor decks for relaxing or dining al fresco. Additionally, some houseboats may feature modern conveniences such as air conditioning and Wi-Fi, enhancing the overall experience.
What is the most popular type of holiday rental accomodation in Riverhead?
In Riverhead, holiday houses are the most popular type of holiday rental, with around 136 available throughout the area. These properties are often situated in family-friendly neighbourhoods and provide ample space, featuring multiple bedrooms, fully equipped kitchens, and outdoor areas for relaxation. Many of these houses also include amenities like BBQ facilities and large gardens, making them ideal for gatherings. Additionally, there are about 20 cottages and 20 apartments, which offer a cozier alternative for smaller groups or couples. Villas and houseboats are also available, adding unique options for those looking for a different experience.
Are there any family house rentals in Riverhead?
In Riverhead, New York, there are numerous family-friendly house rentals available, with around 33 options scattered throughout the area. This town is a delightful choice for families, thanks to its proximity to various attractions such as the Long Island Aquarium and the beautiful beaches of the North Fork. Many of these homes come equipped with spacious living areas, full kitchens for preparing meals, and outdoor spaces great for children to enjoy.Visitors can also expect amenities like Wi-Fi, air conditioning, and sometimes even game rooms or private pools, enhancing the comfort and enjoyment of their stay.
Can I rent a holiday home with a pool or hot tub in Riverhead?
In Riverhead, there are several holiday homes available for rent that feature pools or hot tubs, making it an excellent choice for those seeking relaxation and leisure. This charming town on Long Island is known for its vineyards, beautiful parks, and proximity to the scenic North Fork beaches.Travellers can expect a variety of amenities in these rentals, which often include private pools, inviting hot tubs, and spacious outdoor areas great for family gatherings or barbecues. Many properties also come equipped with fully stocked kitchens, allowing for convenient meal preparation.
Are there pet-friendly house rentals in Riverhead?
In Riverhead, there are numerous pet-friendly house rentals available, with around 25 options to choose from. These holiday homes typically feature amenities that cater to both pets and their owners, such as spacious backyards, durable flooring, and easy access to outdoor areas. Many properties come equipped with modern kitchens, comfortable living spaces, and sometimes even additional features like pet beds or feeding stations to ensure a comfortable stay for your furry friends.The area around Riverhead is also appealing for pet owners, as it's close to several parks and natural spaces where you can enjoy walks and outdoor activities with your pets. Nearby, the scenic Riverhead Town Park offers ample green space, walking trails, and picnic areas, making it an excellent spot for spending quality time outdoors.
Are there any remote work holiday rentals in Riverhead?
In Riverhead, New York, there is a substantial selection of remote work holiday rentals, with around 180 options available. The area is well-suited for those looking to balance work and leisure, offering properties equipped with essential amenities such as high-speed Wi-Fi, dedicated workspaces with desks and chairs, and comfortable living areas conducive to productivity.Many rentals feature modern kitchens, allowing for convenient meal preparation, and some may include outdoor spaces where guests can unwind after a day of work. Riverhead's proximity to local attractions such as the Long Island Aquarium and the scenic vineyards of the North Fork provides a delightful backdrop for downtime. To help narrow your search, insert your dates and apply the "WiFi" filter on Stayz.
What are popular rental amenities in Riverhead?
In Riverhead, popular holiday rental amenities include fully equipped kitchens, which allow guests to prepare their own meals at their convenience. Many properties also feature outdoor decks or patios, providing a lovely space to relax and enjoy the pleasant surroundings. Onsite parking is commonly available, making it easier for travellers with vehicles to access the area. Additionally, rentals often come with a coffee and tea maker, as well as a blender, suiting those who appreciate home comforts and wish to enjoy a morning beverage or prepare smoothies.
When is the best time to visit Riverhead for a holiday rental?
The most popular time to visit Riverhead is during the peak summer season, from June to August, when the vibrant energy of the area attracts a number of holidaymakers. This period is ideal for those looking to enjoy outdoor activities, from exploring local wineries to relaxing on the beautiful beaches nearby. With temperatures often reaching the high 20s to low 30s Celsius, visitors can expect warm, sunny days superb for sightseeing and outdoor enjoyment.July stands out as the busiest month, offering a lively option filled with events and activities. During this time, you can immerse yourself in the local culture, partake in summer festivals, and indulge in fresh, seasonal produce at farmers' markets.For travellers seeking a more budget-friendly option, consider planning your visit in December. While the weather is cooler, with temperatures dropping to around 0 to 5 degrees Celsius, this month provides a unique charm with holiday festivities, fewer crowds, and the opportunity to explore the area's winter attractions.Ultimately, the best time to book a holiday rental in Riverhead depends on whether you are drawn to the bustling summer months filled with activities or prefer the quieter, more intimate experience that the off-peak season offers.
What are the top attractions in Riverhead?
In Riverhead, visitors can explore a variety of attractions that showcase the charm of this Long Island town. The Long Island Aquarium is a major draw, featuring a diverse range of marine life and interactive exhibits, making it a favourite for families. Nearby, the Riverhead Raceway offers exciting motorsport events throughout the year, attracting both locals and tourists.For those interested in wine, the surrounding North Fork region is renowned for its vineyards and wineries, where visitors can enjoy tastings and tours, making it an ideal spot for wine enthusiasts. The picturesque Splish Splash Water Park provides a fun-filled day for families during the warmer months, with numerous water rides and attractions.Additionally, the town's proximity to the scenic Peconic River allows for recreational activities such as kayaking and fishing.
Are all fees included in the Riverhead 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 Riverhead holiday homes with parking?
Stayz offers a wide selection of holiday homes in Riverhead 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 Riverhead holiday homes?
You can find great discounts on holiday homes in Riverhead 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 Riverhead holiday home booking on Stayz?
To find Riverhead 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 Riverhead?
A long-stay holiday home in Riverhead 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 Riverhead holiday home?
Book your Riverhead 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 Riverhead?
Prices for holiday homes in Riverhead 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 Riverhead 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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