Riverhead vacation rentals

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Top-rated vacation rentals in Riverhead

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Guest favorite

Cottage in Riverhead

4.98 out of 5 average rating, 126 reviews

Savor Blazing Ocean Sunsets at a Soothing Beachfront Haven

Newly renovated, The Beach Cottage has been designed and decorated in a modern organic style, with a palette of whites and neutrals to create a serene and peaceful escape. Relax in the airy, light and open living room, which features a wall of glass for indoor/outdoor living with expansive, uninterrupted water views. Enjoy the designer kitchen with all new appliances, as well as a brand new bathroom, updated bedrooms and outdoor shower. This chic 2-bedroom, 1-bathroom home, which can sleep up to 5, has been designed with an eye for detail, style and relaxation. The master bedroom enjoys a queen sized bed that's perfect for 2 adults. The second bedroom can accommodate up to 3 people with a double bed for two people, and a single bed for one person. Only 80-miles from Manhattan, a 90-minute drive and close to the towns of Jamesport, Southold and Greenport, The Beach Cottage is the perfect summer escape. Stay on the property for swimming, paddle boarding, beach walks and BBQs or venture out to enjoy all the North Fork has to offer. Wine tasting at the French run winery Croteaux, lunch at the world class North Fork Table and Inn, shop at the many Organic Farms or explore the charming historic seaport village of Greenport, all short drives from the cottage. Upon request, Pets are allowed, for an extra fee of $200 per stay. Guests have access the entire property, including a private path to the beach. This stylish retreat is nestled on a private Soundfront beach at the end of a 7-acre property. Wine tasting at Croteaux, lunch at world-class North Fork Table and Inn, and the historic seaport village of Greenport are all within a short drive. The closest Jitney stop is Aquebogue or Riverhead. I am an Australian born designer that lives in NYC and has been renovating homes for the past several years. Our Flatiron loft in NYC was featured in Dwell Magazine, I designed the Upper West Side apartment for the founder & CEO of Soul Cycle, and my husband and I recently renovated our family's weekend beach house on the North Fork. I have a passion for turning houses into homes by bringing the clean, breezy and natural aesthetic, inspired by my homeland in Australia.

Jan 25 – Feb 1

G$155,653 GYD per night

Guest favorite

Cottage in Riverhead

4.85 out of 5 average rating, 130 reviews

Affordable Wine Country Cozy Cottage

Cozy cottage for relaxation in the beautiful, wooded, secluded historic community in Jamesport, on the North Fork just minutes from the Hamptons, wineries, bay beaches, antique shops, farms, bicycling and shopping. A walkable vacation with 6 wineries, 6 outstanding restaurants and bay beaches. Hampton Jitney bus from Jamesport to Manhattan. The 1 BR cottage includes complete kitchen, laundry, free parking, free swimming, tennis and basketball privileges at the Town Beach and one free wine tour.

Jan 29 – Feb 5

G$51,080 GYD per night

Guest favorite

Apartment in Patchogue

4.88 out of 5 average rating, 148 reviews

1 Bedroom Apartment on Long Island

Bright & clean 1br apartment with private entrance on a quiet street. Refrigerator, microwave, keurig incl 2 miles to downtown restaurants, bars, breweries, shopping 10 miles to winery & vineyards 3 miles to beaches 3 miles to Fire Island Ferry 30miles to NYC 3 miles to Baseball Heaven 10 miles to Stonybrook University & hospital 1 mile to public horse farm & stable 3 miles to St Joseph's College .5 mile to Long Island Community Hospital 1 mile to hiking 45min to JFK 10min to McArthur airport

Sep 22 – 29

G$24,834 GYD per night

Guest favorite

Apartment in Port Jefferson Station

4.97 out of 5 average rating, 144 reviews

All Private Bright Spacious Close to All

DISINFECTED AND CLEANED BEFORE YOU ARRIVE! Spacious ground level PRIVATE apt with lots of natural light. Full kitchen/new stove/fridge/Keurig.Bedrm- queen sz bed, living rm -queen sz sofa sleeper. Also available is queen air mattress w/ topper. Washer/Dryer. Minutes away to the Port Jeff Village shops&restaurants/Ferry/LIRR, hospitals, & Stony Brook. Small beaches 10-15min drive, large beaches,Shop Outlets & Wineries 25 -60 minute. PLEASE NOTE: Extra $2 Daily Fee for charging electric car.

Feb 25 – Mar 4

G$27,729 GYD per night

Guest favorite

Cabin in Rocky Point

4.9 out of 5 average rating, 387 reviews

Great little place just for a couple

The outdoor courtyard is especially nice and private-,with a fire pit, grill and comfortable chairs. It is a rustic location easy walking distance to North Shore Beach. If you want an ocean beach you can drive straight south for 20 minutes and reach Smiths Point State Park right on the ocean. The North Fork with its vineyards is a short drive and the Hamptons also only 30 minutes to West Hampton. You can fish, golf, walk among the wooded area and relax in peace. A pleasure. linen 100% cotton!

Nov 26 – Dec 3

G$28,820 GYD per night

Guest favorite

Guest suite in Wading River

4.9 out of 5 average rating, 230 reviews

Beachy En Suite /Gateway to The North Fork

Adorable,quiet,clean, w private entrance, private bedroom and bathroom,breakfast nook and patio.We are located in a beach front town dubbed“Gateway to the North Fork”. Walking/driving directions to local beaches,15minute walk to our community beach(.6mi away).Niks deli nearby.Minutes by car to wineries breweries,farm stands,EastWind 2 mi,TangerOutlets15min away,35min to Hamptons,Greenport!Hosts live in adjoining house. Rarely need access to your hallway to get to our basement.Would arrange.

Apr 29 – May 6

G$22,106 GYD per night

Guest favorite

Home in Holbrook

4.91 out of 5 average rating, 236 reviews

Cozy studio

We are 10 minutes away to MacArthur Airport in Islip, 5 minutes to shopping center where you can find supermarkets, restaurants, and stores. We are 10 minutes away from LIRR train station where you can get a ride to Manhattan. Although the studio is centrally located a car or Uber is recommended,. You'll have your own bathroom, kitchen with microwave, coffee maker, toaster, fridge, air conditioner, tv with cable and internet. Our study is a FREE SMOKING PLACE! Not smoking or vaping!

Jun 19 – 26

G$23,120 GYD per night

Guest favorite

Guesthouse in Jamesport

4.97 out of 5 average rating, 106 reviews

Walk to Beautiful Beach in Heart of Wine Country

Enjoy bright, comfortable and modern home in the heart of North Fork wine and farm country located just a quick walk from a gorgeous Peconic Bay beach with tennis/pickleball courts, volleyball and playground right on the beach. You'll have easy and quick access to the best of the east end: beautiful beaches, boating, fishing, fine and casual dining, vineyards, wineries, breweries, farms and farm stands offering fresh local produce, antique and local shops.

Sep 4 – 11

G$70,897 GYD per night

Guest favorite

Home in Cutchogue

4.96 out of 5 average rating, 190 reviews

Stunning Vinyard Views - Spring Special $475/Nt!

Enjoy spectacular wine country sunset views from the living room that extend to the gorgeous saltwater gunite pool and spa. (Please note THE POOL AND SPA (attached hot tub) are OPEN FROM MAY 1 - OCTOBER 15 only). Beautifully decorated, comfortable home with an updated chef's kitchen and fireplace. Fabulous restaurants, wineries, farms, beaches and exquisite small towns all nearby. Simply put, a magical, peaceful paradise for you and your group.

Mar 25 – Apr 1

G$173,482 GYD per night

Guest favorite

Home in Rocky Point

4.91 out of 5 average rating, 177 reviews

The Katalpa House -by the beach

-Our beach is private, key and beach tag provided- (in brown shed) This 1000+ sf home, features a newly renovated kitchen, outdoor shower, and many quirks that come with a 90 year old home. The furnishings are eclectic and vintage. Most of the flooring is also new. The beach and bluffs are only about a 2 minute walk. The 1/4 acre lot is shared with a secondary unit as you can see in the photos which is occupied by my sister.

Dec 9 – 16

G$34,320 GYD per night

Guest favorite

Cottage in Patchogue

4.95 out of 5 average rating, 202 reviews

Quaint Cottage on Long Island's South Shore.

The Cottage is a lovely space enclosed in hedges for privacy on a one acre property. I do have 3 dogs, they are kept in a separate gated area on the property. The cottage is located 3 miles from downtown Patchogue which is enjoying a renaissance. There are many restaurants and cultural activities as well as ferry access to Fire Island (Davis Park) in the warmer weather. We are also the "Gateway" to The Hamptons.

Feb 1 – 8

G$30,695 GYD per night

Guest favorite

Guest suite in Sound Beach

4.92 out of 5 average rating, 100 reviews

Charming fully equipped apt near Farms & Beaches!

Hello and welcome! We offer a wonderful AirBnB experience for everyone from the weekend traveler to the long-term guest. Close to Stony Brook, Port Jefferson, Long Island Railroad, multiple beaches (5-45 min drives), several youth sports venues, and countless farm stands. We hope that you enjoy your stay! Please read on for more information, including the house rules.

Aug 23 – 30

G$21,976 GYD per night

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Riverhead vacation rentals

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Air conditioning

Stay near Riverhead's top sights

Long Island Aquarium142 locals recommend

Tanger Outlets Riverhead242 locals recommend

Walmart5 locals recommend

Briermere Farms59 locals recommend

Costco Wholesale8 locals recommend

The Big Duck32 locals recommend

Other great vacation rentals in Riverhead

Guest favorite

Home in Brookhaven

4.95 out of 5 average rating, 125 reviews

Beautiful & Independent Guest House near the water

Feb 7 – 14

G$37,354 GYD per night

Guest favorite

Apartment in Mastic

5.0 out of 5 average rating, 14 reviews

The Cozy Cellar | Private Art Deco Apartment

Feb 23 – Mar 2

G$14,401 GYD per night

Guest favorite

Apartment in Center Moriches

4.87 out of 5 average rating, 23 reviews

Modern Private Studio close to the hamptons

Mar 16 – 23

G$26,003 GYD per night

Guest favorite

Cottage in Calverton

5.0 out of 5 average rating, 88 reviews

Riverhead Farmhouse

Aug 25 – Sep 1

G$78,862 GYD per night

Guest favorite

Guest suite in Shirley

4.8 out of 5 average rating, 30 reviews

JD Cozynest

Jan 13 – 20

G$22,544 GYD per night

Guest favorite

Home in Riverhead

4.96 out of 5 average rating, 49 reviews

Stunning Farmhouse W/Heated pool in NoFo by winery

Dec 17 – 24

G$108,586 GYD per night

Guest favorite

Camper/RV in Riverhead

4.91 out of 5 average rating, 69 reviews

Slide out camper on century old working farm

Aug 12 – 19

G$31,219 GYD per night

Guest favorite

Cottage in Riverhead

4.88 out of 5 average rating, 17 reviews

Lovely House with completely private back yard

May 2 – 9

G$93,140 GYD per night

Show all

Other great vacation rentals in Riverhead

Guest favorite

Place to stay in Coram

5.0 out of 5 average rating, 52 reviews

T&T Unique Space

May 7 – 14

G$24,699 GYD per night

Guest favorite

Home in Cutchogue

4.96 out of 5 average rating, 74 reviews

Secluded Farmhouse - Studio Apartment Style Unit

Nov 11 – 18

G$66,676 GYD per night

Guest favorite

Home in East Quogue

4.97 out of 5 average rating, 30 reviews

Hampton’s Apartment! (East Quogue)

Jan 2 – 9

G$37,122 GYD per night

Guest favorite

Home in Ridge

4.9 out of 5 average rating, 41 reviews

Lilac Stays

Sep 21 – 28

G$32,681 GYD per night

Superhost

Cottage in Calverton

4.81 out of 5 average rating, 103 reviews

Renovated Cottage, steps to the Beach & Wine Trail

Oct 3 – 10

G$85,850 GYD per night

Guest favorite

Vacation home in Flanders

4.99 out of 5 average rating, 67 reviews

Amazing Waterfront Bungalow

Sep 2 – 9

G$131,201 GYD per night

Guest favorite

Apartment in Middle Island

5.0 out of 5 average rating, 17 reviews

Modern Farmhouse Decor With Washer/Dryer

Oct 26 – Nov 2

G$28,977 GYD per night

Guest favorite

Cottage in Flanders

4.85 out of 5 average rating, 26 reviews

Bayside bliss - Charming 2bdrm on the water w dock

Nov 24 – Dec 1

G$106,965 GYD per night

Show all

Quick stats about vacation rentals in Riverhead

Total rentals
40 properties
Rentals with a pool
10 properties have a pool
Pet-friendly rentals
10 properties allow pets
Family-friendly rentals
30 properties are a good fit for families
Total number of reviews
1.3K reviews
Nightly prices starting at
G$10,449 GYD before taxes and fees

Frequently Asked Questions

Are there pet-friendly vacation rentals in Riverhead?
Four-legged friends are welcome in Riverhead. Choose from more than 10 vacation rentals for guests traveling with pets.
Are there vacation rentals with a dedicated workspace in Riverhead?
Yes! Work meets play with ease at over 20 vacation rentals in Riverhead featuring dedicated workspaces. Stay connected and productive in your home away from home.
Are there Riverhead vacation rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 10 vacation homes with pools in Riverhead, available on Airbnb. Make a splash and soak up the sun in style!
How much does it cost to stay in house rentals in Riverhead?
Experience the best of Riverhead with our house rentals, starting at about $50 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Are there family-friendly house rentals in Riverhead?
Riverhead has more than 20 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
Do house rentals in Riverhead have air conditioning?
Absolutely! We offer over 20 house rentals with air conditioning in Riverhead. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Riverhead have wifi?
Absolutely! We offer over 20 house rentals with wifi in Riverhead. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Riverhead have a bbq area?
Absolutely! We offer over 10 house rentals with a bbq area in Riverhead. Enjoy a tailored experience with all the comforts you desire.

Riverhead vacation rentals

Top-rated vacation rentals in Riverhead

Vacation rentals for every style

Houses

Hotels

Unique stays

Popular amenities for Riverhead vacation rentals

Stay near Riverhead's top sights

Other great vacation rentals in Riverhead

Home in Brookhaven

Apartment in Mastic

Apartment in Center Moriches

Cottage in Calverton

Guest suite in Shirley

Home in Riverhead

Camper/RV in Riverhead

Cottage in Riverhead

Other great vacation rentals in Riverhead

Place to stay in Coram

Home in Cutchogue

Home in East Quogue

Home in Ridge

Cottage in Calverton

Vacation home in Flanders

Apartment in Middle Island

Cottage in Flanders

Quick stats about vacation rentals in Riverhead

Total rentals

Rentals with a pool

Pet-friendly rentals

Family-friendly rentals

Total number of reviews

Nightly prices starting at

Frequently Asked Questions

Are there pet-friendly vacation rentals in Riverhead?

Are there vacation rentals with a dedicated workspace in Riverhead?

Are there Riverhead vacation rentals on Airbnb with pools?

How much does it cost to stay in house rentals in Riverhead?

Are there family-friendly house rentals in Riverhead?

Do house rentals in Riverhead have air conditioning?

Do house rentals in Riverhead have wifi?

Do house rentals in Riverhead have a bbq area?

Destinations to explore