A coastal landscape with a sandy beach, a forested area, and a golf course.

Riverhead Vacation Rentals

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Check prices for these dates

In two weeks
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

Our top choices for Riverhead vacation rentals

A dining area with a wooden table, chairs, and a decorative wall with a cityscape picture.

1. Nicely Furnished apartment; Ideal for Travelling nurses, Resident doctors, etc,

Nicely Furnished apartment; Ideal for Travelling nurses, Resident doctors, etc,
Flanders
10.0 out of 10, Exceptional, (6 reviews)
"The host was very welcoming and the house was very clean"
United States
James W.
$279 nightly
The price is $319
Oct 20 - Oct 21
Total with taxes and fees
Nicely Furnished apartment; Ideal for Travelling nurses, Resident doctors, etc,
A sign for J&S Reeves Cottages with a view of a house and trees.

2. 6th of 6 Premier Waterfront Vacation Rentals on Long Island NY in Wine Country of Famed North Fork

6th of 6 Premier Waterfront Vacation Rentals on Long Island NY in Wine Country of Famed North Fork
Riverhead
10.0 out of 10, Exceptional, (12 reviews)
"We enjoyed our stay. Very quiet and relaxing. Excellent location to many wineries. Would definitely stay again."
United States
Donna M.
$849 nightly
The price is $864
Oct 20 - Oct 21
Total with taxes and fees
6th of 6 Premier Waterfront Vacation Rentals on Long Island NY in Wine Country of Famed North Fork
A landscaped garden with a tree in a rectangular planter, surrounded by trimmed hedges and a wooden fence in the background.

3. Jacuzzi year-round - Villa Luz Private Home

Jacuzzi year-round - Villa Luz Private Home
Hampon Bays
9.6 out of 10, Exceptional, (27 reviews)
"Overall really great stay! Would definitely stay here again was so peaceful. Had a great weekend!"
United States
Annie B.
$1,575 nightly
The price is $1,668
Oct 28 - Oct 29
Total with taxes and fees
Jacuzzi year-round - Villa Luz Private Home
Room

4. Cliffside Resort Condominiums

Cliffside Resort Condominiums
3.0 star property
Greenport
9.0 out of 10, Wonderful, (297 reviews)
"Great condo. Very nice location and grounds."
United States
William
$266 nightly
The price is $304
Nov 1 - Nov 2
Total with taxes and fees
Cliffside Resort Condominiums
A modern house with a deck, outdoor seating, and a fire pit.

5. North Fork Resort

North Fork Resort
3.0 star property
Greenport
9.6 out of 10, Exceptional, (65 reviews)
"Friendly staff. Clean room had everything we needed. Enjoyed our stay!"
United States
Harold
$222 nightly
The price is $254
Oct 13 - Oct 14
Total with taxes and fees
North Fork Resort
A modern kitchen with a central island, white cabinetry, and a dining area with a table set for two.

6. Immaculate Waterfront 2 bedroom!

Immaculate Waterfront 2 bedroom!
Hampton Bays
10.0 out of 10, Exceptional, (5 reviews)
"Clean and fully updated home situated on a canal with a partial view of the bay . A perfect location ."
United States
Michael L.
$503 nightly
The price is $575
Oct 13 - Oct 14
Total with taxes and fees
Immaculate Waterfront 2 bedroom!
Roger’s Beach

7. Prime location, walk to all, cozy cottage WHB

Prime location, walk to all, cozy cottage WHB
Westhampton Beach
10.0 out of 10, Exceptional, (4 reviews)
"Erica was very communicative and helpful. Very cozy with a great location."
United States
Chris J.
$657 nightly
The price is $751
Oct 19 - Oct 20
Total with taxes and fees
Prime location, walk to all, cozy cottage WHB
A swimming pool with a white deck, surrounded by lush greenery and a swan inflatable float.

8. Elegant 5-Bedroom Hamptons Home with Private Pool

Elegant 5-Bedroom Hamptons Home with Private Pool
Hampton Bays
9.4 out of 10, Exceptional, (43 reviews)
"The house was great. Pool was beautiful and everything was a 10 minute drive! Great place to relax"
United States
Judith M.
$857 nightly
The price is $979
Oct 13 - Oct 14
Total with taxes and fees
Elegant 5-Bedroom Hamptons Home with Private Pool
A backyard with a swimming pool, outdoor furniture, and a house with solar panels.

9. Near the Hamptons - Private Pool, Jacuzzi Retreat

Near the Hamptons - Private Pool, Jacuzzi Retreat
Calverton
6.0 out of 10, (1 review)
"Upon arrival, there was a notice of non payment of almost 4000 from the electric company on the door so I was concerned I would lose electric. The grounds seemedover grown and unkept. There was no TV, no hot water in the kitchen with a brokenhot water knob which would have needed a wrench. Although it had in room air conditioners vented outside, they were taped in place with open air coming inside. One of the open areas actually had live tree vines coming inside which I pulled out. There was...
United States
Theresa M.
$1,300 nightly
The price is $1,485
Oct 13 - Oct 14
Total with taxes and fees
Near the Hamptons - Private Pool, Jacuzzi Retreat
A beach with footprints leading to the water, a sunset in the background, and a clear sky.

10. Walk to Beach | Seabreeze Cottage #4

Walk to Beach | Seabreeze Cottage #4
Hampton Bays
8.6 out of 10, Excellent, (8 reviews)
"Great stay. Would stay again. "
United States
Weston B.
$399 nightly
The price is $424
Oct 13 - Oct 14
Total with taxes and fees
Walk to Beach | Seabreeze Cottage #4
A spacious living area with a fireplace, a wooden staircase, and large windows.

11. Cozy beach hose minutes from Hamptons

Cozy beach hose minutes from Hamptons
Calverton
8.2 out of 10, Very good, (11 reviews)
"Very responsive host and a beautiful house."
United States
Robin M.
$634 nightly
The price is $724
Oct 21 - Oct 22
Total with taxes and fees
Cozy beach hose minutes from Hamptons
A modern building with large windows overlooking a beach.

12. Beachfront Jacuzzi All Year - Black Swan Home

Beachfront Jacuzzi All Year - Black Swan Home
Hampton Bays
9.4 out of 10, Exceptional, (21 reviews)
"Views are incredible. Lucky enough to have had great weather before Memorial Day weekend! Our family loved it! Hot tub was wonderful."
United States
Donald J.
$1,124 nightly
The price is $1,193
Oct 13 - Oct 14
Total with taxes and fees
Beachfront Jacuzzi All Year - Black Swan Home
A rocky beach with clear water and a forested hillside in the background.

13. North Fork Fall Escape—Vineyards, Apple Picking & Greenport

North Fork Fall Escape—Vineyards, Apple Picking & Greenport
Mattituck
9.6 out of 10, Exceptional, (7 reviews)
"Stayed with several friends for a wedding in Jamesport"
United States
Glenn F.
$1,097 nightly
The price is $1,253
Oct 24 - Oct 25
Total with taxes and fees
North Fork Fall Escape—Vineyards, Apple Picking & Greenport
A suburban house with a driveway and parked cars.

14. Cozy Studio Apartment with Private Yard

Cozy Studio Apartment with Private Yard
Ridge
9.6 out of 10, Exceptional, (22 reviews)
"Clean and comfortable. Very quiet and pleasant place to stay."
United States
Gene
$267 nightly
The price is $305
Oct 19 - Oct 20
Total with taxes and fees
Cozy Studio Apartment with Private Yard
A modern kitchen with white cabinets, a dining area with a round table, and a living area with a sofa and decorative pillows.

15. Cozy Hamptons Escape 3BR Minutes From Beach!

Cozy Hamptons Escape 3BR Minutes From Beach!
Hampton Bays
9.2 out of 10, Wonderful, (7 reviews)
"Great place. It's exactly like the listing! Would stay again!"
United States
Taylor H.
$1,371 nightly
The price is $1,566
Oct 13 - Oct 14
Total with taxes and fees
Cozy Hamptons Escape 3BR Minutes From Beach!
Terrace/patio

16. 5th of 6 Premier Waterfront Vacation Rentals on Long Island NY in Wine Country of Famed North Fork

5th of 6 Premier Waterfront Vacation Rentals on Long Island NY in Wine Country of Famed North Fork
Aquebogue
10.0 out of 10, Exceptional, (3 reviews)
"Fantastic experience. Cabin was clean and quiet. Beautiful mornings on the water."
United States
Leah O.
$893 nightly
The price is $908
Oct 13 - Oct 14
Total with taxes and fees
5th of 6 Premier Waterfront Vacation Rentals on Long Island NY in Wine Country of Famed North Fork
A modern living room with a grey sofa, round coffee table, and a white fireplace.

17. 5 Bedrooms! 4 Min to the Beach! HEATED POOL!

5 Bedrooms! 4 Min to the Beach! HEATED POOL!
Westhampton Beach
10.0 out of 10, Exceptional, (6 reviews)
"awesome house and awesome host"
United States
Matthew M.
$2,423 nightly
The price is $2,768
Oct 13 - Oct 14
Total with taxes and fees
5 Bedrooms! 4 Min to the Beach! HEATED POOL!
A sign for J&S Reeves Cottages with a view of a house and trees.

18. 4th of 6 Premier Waterfront Vacation Rentals on Long Island NY in Wine Country of Famed North Fork

4th of 6 Premier Waterfront Vacation Rentals on Long Island NY in Wine Country of Famed North Fork
Aquebogue
9.8 out of 10, Exceptional, (19 reviews)
"Great cottage on amazing grounds! We loved the screened in porch. Sandy and john are great hosts. We also loved using the kayaks and checking out the bay."
United States
Richard C.
$915 nightly
The price is $931
Oct 13 - Oct 14
Total with taxes and fees
4th of 6 Premier Waterfront Vacation Rentals on Long Island NY in Wine Country of Famed North Fork
A living room with a sofa, a coffee table, a TV mounted on the wall, and a window with a view of houses outside.

19. Homelike, peaceful and centrally- home located in the hamlet of Rocky Point NY

Homelike, peaceful and centrally- home located in the hamlet of Rocky Point NY
Rocky Point
10.0 out of 10, Exceptional, (28 reviews)
"It was perfect for what we needed and the hostess made it very simple and easy to check in and check out and answer any questions thank you"
United States
ken g.
$481 nightly
The price is $549
Oct 13 - Oct 14
Total with taxes and fees
Homelike, peaceful and centrally- home located in the hamlet of Rocky Point NY
A covered outdoor seating area with wicker furniture and a view of boats on a lake.

20. 3rd of 6 Premier Waterfront Vacation Rentals on Long Island NY in Wine Country of Famed North Fork

3rd of 6 Premier Waterfront Vacation Rentals on Long Island NY in Wine Country of Famed North Fork
Aquebogue
8.6 out of 10, Excellent, (7 reviews)
"We loved everything about our stay at the cottage. Such beautiful property and surroundings. If you’re looking to spend some quality time with family in a quiet setting with beautiful surroundings , look no further. Thanks Sandy. We will be Back."
United States
Wendy B.
$996 nightly
The price is $1,014
Oct 13 - Oct 14
Total with taxes and fees
3rd of 6 Premier Waterfront Vacation Rentals on Long Island NY in Wine Country of Famed North Fork
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

Holiday Inn Express & Suites Riverhead - Long Island by IHG

Holiday Inn Express & Suites Riverhead - Long Island by IHG

8/10 Good
"Everything was fine, but the room we stayed was getting noise from the street and also toilet flush noise from upper n next rooms"
Mehmet 1-night trip
Posted 10 hours ago
Holiday Inn Express & Suites Riverhead - Long Island by IHG

Find out more about Riverhead

Everything you need to know about Riverhead vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Riverhead vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Riverhead vacation 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 low season months. For more hustle and bustle, you may prefer to visit Riverhead in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $247 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Riverhead rentals

At Expedia, we put the best Riverhead vacation 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 vacation.

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.

Explore a world of travel with Expedia

Frequently asked questions

Can I find vacation rentals in Riverhead?

Yes, you can find vacation rentals in Riverhead close to Suffolk Theater, 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?

WHB Village,4200sqft,Traffic Free,Private Dr,40ft Heated Pool,Beach,Fam/Pet Frly: This vacation home rental outside of Riverhead offers an outdoor pool, a patio, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 6 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a garden and a selection of games.

How many vacation rentals are there in Riverhead?

Expedia has 57 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 The Suffolk. 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.