Riverhead Holiday Rentals

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Holiday Rentals in Riverhead

East End Escape
The price is NZ$958
includes taxes & fees
25 Oct - 26 Oct
East End Escape
Cliffside Resort Condominiums
3.0 star property
9.0 out of 10, Wonderful, (244)
"Nice location and good for staying with families. The rooms could have been a little cleaner and updated. Hotel communication was excellent for checking in. "
United States
dean
The price is NZ$521
includes taxes & fees
2 Nov - 3 Nov
Cliffside Resort Condominiums
Cozy Bungalow Available Nearby Bridgehampton and Sag Harbor
2.5 star property
9.6 out of 10, Exceptional, (15)
"We had a one-night stay at this location. It was perfect for us from many perspectives and we enjoyed staying there. Very nice place!Thanks! "
United States
James S.
The price is NZ$652
includes taxes & fees
28 Oct - 29 Oct
Cozy Bungalow Available Nearby Bridgehampton and Sag Harbor
The SandPiper
9.8 out of 10, Exceptional, (27)
"My wife and I stayed at the Sandpiper for a long weekend. The property was very clean with a warm welcoming feeling. It is within walking distance to the beach and downtown shopping. Great location. I would recommend it to everyone."
United States
steve
The SandPiper
Fairy Tale Guest Cottage in Magic Garden by Pool
10.0 out of 10, Exceptional, (76)
"It was a beautiful cottage on a gorgeous property with gracious hosts. I recommend it!!!!"
United States
Lisa
Fairy Tale Guest Cottage in Magic Garden by Pool
WHB Village,4200sqft,Traffic Free,Private Dr,40ft Heated Pool OPEN,Beach,Fam Fr
10.0 out of 10, Exceptional, (192)
"House was more then I can imagine , host was great , house literally have anything you forgot at home . "
United States
Isiah L.
WHB Village,4200sqft,Traffic Free,Private Dr,40ft Heated Pool OPEN,Beach,Fam Fr
East End Retreat - Water Front - Available for the US Open Shinnecock Hills 2026
10.0 out of 10, Exceptional, (104)
"Great indoor and outdoor spaces to hang out. Took SUP on the water - so nice and calm. "
United States
Rachel
The price is NZ$1,067
includes taxes & fees
10 Nov - 11 Nov
East End Retreat - Water Front - Available for the US Open Shinnecock Hills 2026
Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping
9.8 out of 10, Exceptional, (32)
"Wonderful outdoor space and great pool. Host was responsive and property was close to all things needed and wanted! Great rental for families."
United States
Patricia Fox M.
Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping
Walk to Beach 2BR Near Dining & Shopping
6.8 out of 10, (22)
"Stay away"
United States
Alex H.
The price is NZ$406
includes taxes & fees
28 Oct - 29 Oct
Walk to Beach 2BR Near Dining & Shopping
11-Bedroom Mansion with an Seasonal Outdoor Pool 10.5 bathrooms
9.6 out of 10, Exceptional, (34)
"We had a amazing stay and plan to come back next July again"
United States
Gina G.
11-Bedroom Mansion with an Seasonal Outdoor Pool 10.5 bathrooms
Work and Play Special! Extended Stay Discount
10.0 out of 10, Exceptional, (52)
"Really great property, had a relaxing lovely time!"
United States
Nava S.
The price is NZ$2,319
includes taxes & fees
5 Nov - 6 Nov
Work and Play Special! Extended Stay Discount
Beautiful Waterfront, Sun, Sky, Hot Tub Open Year Round & Gameroom!
9.6 out of 10, Exceptional, (141)
"Perfect property to hangout and stay entertained for hours"
United States
Ryder I.
Beautiful Waterfront, Sun, Sky, Hot Tub Open Year Round & Gameroom!
Modern Vacation home. Close to The Hamptons
10.0 out of 10, Exceptional, (3)
"good time"
United States
Roy T.
The price is NZ$1,155
includes taxes & fees
3 Nov - 4 Nov
Modern Vacation home. Close to The Hamptons
Grab a Fun Fall Weekend by Wolffer Vineyard! Columbus Day Holiday Now Available
10.0 out of 10, Exceptional, (89)
"Great house with awesome backyard, host responsive and very easy to work with! Would stay again!"
United States
Kilee B.
Grab a Fun Fall Weekend by Wolffer Vineyard! Columbus Day Holiday Now Available
Spacious multiples bedroom house in enchanting Calverton with WiFi, AC
2.0 star property
8.4 out of 10, Very good, (7)
"prefect experience! The house is clean and well decorated with a large organized yard. Many parking spaces. "
United States
Riyao
The price is NZ$1,591
includes taxes & fees
25 Oct - 26 Oct
Spacious multiples bedroom house in enchanting Calverton with WiFi, AC
Southampton Estate, Newly Renovated , Excellent For Families! Sleeps 12-14
9.4 out of 10, Exceptional, (74)
"As always everything was excellent, This is our third stay at this property and we are booked for 2026"
United States
Michael R.
Southampton Estate, Newly Renovated , Excellent For Families! Sleeps 12-14
Stunning Hampton Holiday Family Fantasy for your Team
9.8 out of 10, Exceptional, (74)
"Everything was great!!!"
Mexico
Mauricio E.
Stunning Hampton Holiday Family Fantasy for your Team
Modern Sag Harbor Escape, Moments from the Water and Long Beach to View...
8.0 out of 10, Very good, (3)
"Great location and comfortable stay, amazing sheets.Ended up buying for my home. "
United States
David Y.
Modern Sag Harbor Escape, Moments from the Water and Long Beach to View...
Private One Bedroom Apartment with full kitchen, living room and full bath.
9.4 out of 10, Exceptional, (8)
"Tammy was a lovely host. She provided very detailed instructions on how to get to the Vrbo, parking location, and access in advance. Vrbo was just as pictured too! "
United States
Kristyn R.
Private One Bedroom Apartment with full kitchen, living room and full bath.
Summer getaway
9.0 out of 10, Wonderful, (14)
"Perfect location for a family holiday "
Germany
Olaf U.
Summer getaway
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Riverhead Hotel Reviews

Find out more about Riverhead

Everything you need to know about Riverhead holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Riverhead holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Riverhead holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Riverhead holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Riverhead. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Riverhead holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Riverhead holiday rentals we have selected for you start as low as NZ$406 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Riverhead rentals

At Expedia, we put the best Riverhead holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Riverhead rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Riverhead holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Riverhead. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Can I find holiday rentals in Riverhead?

Yes, there are holiday rentals in Riverhead close to Safari Adventure, or you can select a more secluded option if you're looking for a relaxing stay. Visitors like the top-notch restaurants and aquarium in Riverhead. Give yourself some extra time to check out the shops and wineries during your trip.

What are some of the best holiday rentals that Riverhead has to offer?

Cozy Bungalow Available Nearby Bridgehampton and Sag Harbor : This holiday home rental outside of Riverhead offers an outdoor pool, a fireplace and a BBQ to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. It offers a patio, a garden and 1 hot tub so that you can immerse yourself in your holiday.

How many holiday rentals are there in Riverhead?

Expedia has 60 holiday rentals for your stay in Riverhead.

What’s there to see and do in Riverhead?

Safari Adventure and All Star Bowling are a couple of the family-friendly sights, whereas cultural attractions include Suffolk Theater and Hallockville Museum Farm. While here, Tanger Outlet Center and Jamesport Vineyards are other places worth a visit.

What’s a holiday rental in Riverhead like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Riverhead. Holiday rentals offer extras such as laundry facilities and kitchens to help you enjoy your stay. If you're concerned about a sanitised environment, holiday rentals can offer a sense of safety away from shared hotel lifts and busy concierge desks while still allowing you a great travel experience. You'll also find more space in a holiday rental than in a traditional hotel, which makes a holiday rental a great option for family trips.