Riverhead Vacation Rentals

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Vacation Rentals in Riverhead

Cliffside Resort Condominiums

3.0 star property
9.0 out of 10, Wonderful, (207)
"Stove it’s not efficient and refrigerator blocked with the corner of wall"
The price is ¥21,584
¥31,173 total
includes taxes & fees
Apr 30 - May 1
Cliffside Resort Condominiums

10 Bedroom Hampton House with a regulation size Pickleball

10.0 out of 10, Exceptional, (25)
"Had so much fun this weekend in Hampton Bays! House was perfect for a group of friends - many bedrooms, bathrooms, great pool with tons of outdoor games, and even the arcade room inside! So close to the beach, and a number of great restaurants. Highly recommend this house, and appreciate how helpful our host was with making sure we had everything we need and more!"
10 Bedroom Hampton House with a regulation size Pickleball

Location and views! Located directly on Shinnecock Bay!

9.2 out of 10, Wonderful, (23)
"Stay was relaxing, space was very cozy. we enjoyed our stay. "
Location and views! Located directly on Shinnecock Bay!

Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping

10.0 out of 10, Exceptional, (19)
"Perfect spot for a girls weekend! Property/house as advertised, and the house was fully stocked with all amenities. Thanks for a wonderful stay!! "
Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping

Beachy Chic South of the Hwy in Southampton Village 3blks to town/Bike to 🏖

10.0 out of 10, Exceptional, (98)
"Pam was very communicative prior to our stay and a welcoming host. The house was clean, centrally located, and spacious. "
Beachy Chic South of the Hwy in Southampton Village 3blks to town/Bike to 🏖

Year-Round Waterview 4 Beds, 2 Baths, Sleeps 13 with Linens & Towels Included

9.0 out of 10, Wonderful, (88)
"Tuvimos un finde increíble en la casa, súper cómoda y bonita "
Year-Round Waterview 4 Beds, 2 Baths, Sleeps 13 with Linens & Towels Included

WHB Village,4200sqft,Traffic Free,Private Drive,40ft Heated Pool,Beach,Family Fr

10.0 out of 10, Exceptional, (169)
"This property was amazing! My family and friends loved it and really enjoyed their time staying at this rental. We hope to rent it again in the future. "
WHB Village,4200sqft,Traffic Free,Private Drive,40ft Heated Pool,Beach,Family Fr

Stunning Hampton Holiday Family Fantasy for your Team

9.8 out of 10, Exceptional, (66)
"Great home"
Stunning Hampton Holiday Family Fantasy for your Team

Beautiful Waterfront, Sun, Sky, Hot Tub Open Year Round & Gameroom!

9.6 out of 10, Exceptional, (129)
"We came to enjoy a nice relaxing weekend with friends and were overwhelmed with how amazing the beach house was! Completely set in the perfect spot! We loved the space and all the games! Thank you for creating such a fun home! We will be back "
Beautiful Waterfront, Sun, Sky, Hot Tub Open Year Round & Gameroom!

Elegant Villa Retreat w/ Pool, 2 Hot Tubs, & Entertainment

10.0 out of 10, Exceptional, (15)
"We recently had the joy of staying here with family meeting from different parts of New York and New Jersey. House is beautiful, location is quiet and peaceful with a great view of the bay. Nearby to some great Long Island beaches. Loved the pool and amenities of the home. Faraz was an excellent host and extremely responsive to our needs "
The price is ¥130,923
¥311,435 total
includes taxes & fees
Apr 8 - Apr 9
Elegant Villa Retreat w/ Pool, 2 Hot Tubs, & Entertainment

Beach Apt. Wineries, Shopping, Dining

6.0 out of 10, (11)
"It was a decent place to stay."
The price is ¥23,225
¥45,626 total
includes taxes & fees
Apr 2 - Apr 3
Beach Apt. Wineries, Shopping, Dining

Sprawling Southampton Home: Private Pool

9.0 out of 10, Wonderful, (44)
"My family and I had a wonderful stay at this property. The house was well-situated in a quiet neighborhood - very private, surrounded by trees and a few wild turkeys. There were many amenities that made our stay enjoyable from the large patio and pool, 3 full baths in the main house, one of which had an amazing shower system with body spray, and a designated work area for those that can’t leave work behind. Communication with the property manager was easy and Debbie was very helpful and...
Sprawling Southampton Home: Private Pool

1856 Trading House w/ walk to water

9.6 out of 10, Exceptional, (41)
"It was clean and just what we needed the calling fan didn't work but the AC did so no real deal breaker"
1856 Trading House w/ walk to water

Summer 2025 Now Available! Wolffer Vineyard Close!

10.0 out of 10, Exceptional, (83)
"Our stay was amazing! The house was fabulous, beautifully appointed, very clean, private and secluded. Lots to do in the area. Jay was very responsive and helpful when we had questions. Would definitely stay again. "
Summer 2025 Now Available! Wolffer Vineyard Close!

1856 Trading House close to water

9.4 out of 10, Exceptional, (12)
"Has character, cute. I did hit my head on the Murphy bed, we needed trash bags and forks. Really enjoyed the outdoors fire pit, needed lots of bug spray. Comfortable AC, wish the Bathroom was bigger, kitchen was great."
1856 Trading House close to water

Gorgeous private Hamptons house with pool and volleyball court

8.4 out of 10, Very Good, (17)
"Enjoyed this house in a great location. It was perfect for attending a family wedding!"
Gorgeous private Hamptons house with pool and volleyball court

11-Bedroom Mansion with an Seasonal Outdoor Pool 10.5 bathrooms

9.6 out of 10, Exceptional, (33)
"We had a great time at the house – it was spacious, clean, and well-maintained. However, after our stay, we realized we had left a winter coat and a blazer. We immediately contacted the property manager, who confirmed they had found our belongings and promised to send them to us. Despite multiple emails and their initial confirmation, they stopped responding and never sent our items. This was very disappointing, especially given the cost of our stay. We’ve rented other properties before, and...
11-Bedroom Mansion with an Seasonal Outdoor Pool 10.5 bathrooms

East End cottage on water!Pet Friendly! Wood FP Minutes from Hamptons & wineries

10.0 out of 10, Exceptional, (84)
"Place was beautiful. It was very clean. Easy to get to. Would stay again"
The price is ¥44,218
¥91,277 total
includes taxes & fees
Apr 6 - Apr 7
East End cottage on water!Pet Friendly! Wood FP Minutes from Hamptons & wineries

Private Waterfront on Peconic Bay in Hampton Bays - Southampton - Fall Special!

9.8 out of 10, Exceptional, (17)
"The house was clean and the location was magnificent. Jake was great, offered us early check in and late check out. The neighborhood was lovely, walked my pup and admired all of the beautiful homes. Definitely will stay there again. "
Private Waterfront on Peconic Bay in Hampton Bays - Southampton - Fall Special!

Work and Play Special! Extended Stay Discount at a hideaway with Stellar Wifi!

10.0 out of 10, Exceptional, (41)
"This is the most magical property with a gorgeous pool, beautiful large trees, a pond and a badmitten court. My two children loved it. The property was a 3-4 minute drive from everything and yet felt totally isolated and removed from everything. I will say that the house was more cozy than we expected as the bedrooms upstairs were a steep walk and there was only one bathroom for the entire house. But we made do and had a lovely time."
The price is ¥119,912
¥214,920 total
includes taxes & fees
Apr 30 - May 1
Work and Play Special! Extended Stay Discount at a hideaway with Stellar Wifi!
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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Other types of properties in Riverhead you may be interested in

Hyatt Place Long Island East End

3.0 star property
9.2 out of 10, Wonderful, (1095)
"amazing would definitely stay again thank you! "
The price is ¥19,030
¥21,741 total
includes taxes & fees
Apr 9 - Apr 10
Hyatt Place Long Island East End

Residence Inn by Marriott New York Long Island East End

3.0 star property
9.0 out of 10, Wonderful, (920)
"Everything was perfectly, except the pool. It was to cold. But the jacuzi was fine."
The price is ¥17,704
¥20,227 total
includes taxes & fees
Apr 3 - Apr 4
Residence Inn by Marriott New York Long Island East End

Hilton Garden Inn Riverhead

3.0 star property
8.6 out of 10, Excellent, (1070)
"Good!"
The price is ¥17,705
¥20,228 total
includes taxes & fees
Apr 8 - Apr 9
Hilton Garden Inn Riverhead
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.

Frequently asked questions

Can I find vacation rentals in Riverhead?

Yes, you can find vacation rentals in Riverhead close to Safari Adventure, or you can choose a 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's the top vacation rental in Riverhead?

10 Bedroom Hampton House with a regulation size Pickleball: This vacation home rental outside of Riverhead is located near the beach and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 10 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games.

How many vacation rentals are there in Riverhead?

Expedia has 64 vacation 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 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 vacation rental in Riverhead like?

Vacation rentals are privately owned properties you can book for a few weeks or just a few days in Riverhead. Vacation rentals feature extras like kitchens and laundry facilities so you'll feel just like you're at home. If you're concerned about a clean environment, vacation rentals can provide a sense of safety away from shared hotel elevators and lobbies bustling with people while still allowing you to travel. You'll also find more space in a vacation rental than in a standard hotel, which makes a vacation rental a popular option for families.