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 6 – 13

G$155,236 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.

Nov 6 – 13

G$50,943 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.

Sep 14 – 21

G$28,053 GYD per night

Guest favorite

Apartment in Patchogue

4.88 out of 5 average rating, 150 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 19 – 26

G$24,768 GYD per night

Guest favorite

Apartment in Milford

4.97 out of 5 average rating, 509 reviews

Water front studio apartment with fireplace.

This is a beautifully appointed studio apartment located off the patio level of a water front home. Guests enjoy a large private patio over looking gorgeous sweeping views of Long Island Sound. A private entrance and off street parking. The amazing views and amenities make this space the perfect romantic getaway! Close to I95 and Metro North railroad. Ten minutes to great dining in downtown Milford. A true waterfront oasis! Come and experience this beautiful retreat! You won't be disappointed!

Sep 26 – Oct 3

G$41,877 GYD per night

Guest favorite

Apartment in Deer Park

4.97 out of 5 average rating, 112 reviews

Best Studio-Private Entrance+Parking-Close To All

Make yourself at home! This Deer Park Den is your perfect suburban hideaway in the heart of Long Island, close to everything and right in the middle of all the fun. Walking distance to lots of great restaurants that give you plenty of great options for ordering in or dining out. Other local destinations include: - Tanger outlets (1 Mile) - Heartland Golf Park (1.5 Miles) - Edgewood Oak Brush Plains Preserve (0.5 Mile) - Robert Moses state park (12 Miles) - Sunken Meadow state park (12 miles)

Feb 6 – 13

G$23,935 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.

Oct 6 – 13

G$24,266 GYD per night

Guest favorite

Home in Brookhaven

4.95 out of 5 average rating, 127 reviews

Beautiful & Independent Guest House near the water

Welcome to our beautiful yet very private guest house in Brookhaven. You are walking distance from the Deer Run Farm (fresh eggs every morning), Post-Morrow Nature Trails and a short drive to Bellport Village Historic District. We are also very close to Wine Country, The Hamptons & Fire Island. We offer all the accommodations you might need for longer stays Washer & Dryer; Dishwasher; High Speed internet and TVs with all the premium channels. EV Charger available (Tesla - Fees applies).

Feb 1 – 8

G$37,390 GYD per night

Guest favorite

Home in Holbrook

4.91 out of 5 average rating, 237 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!

Jul 12 – 19

G$23,383 GYD per night

Guest favorite

Home in Greenport

4.92 out of 5 average rating, 423 reviews

Blue Bay Dream

Newly renovated 2-Family Home! Located right in Greenport Village providing walking distance to all the restaurants, bars, shopping, coffee shops, and Shelter Island Ferry, Long Island Railroad (LIRR), and Hampton Jitney. My place is close to restaurants and dining, the beach, family-friendly activities, nightlife, and public transport. You’ll love my place because of Location!. My place is good for couples, solo adventurers, business travelers, families (with kids).

Jan 20 – 27

G$25,381 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.

Oct 15 – 22

G$75,291 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.

Mar 28 – Apr 4

G$30,612 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 Cutchogue

4.96 out of 5 average rating, 190 reviews

Stunning Vinyard Views - Spring Special $475/Nt!

Jan 4 – 11

G$173,017 GYD per night

Guest favorite

Home in Wading River

4.96 out of 5 average rating, 457 reviews

Your Zen Retreat

Jul 5 – 12

G$102,753 GYD per night

Guest favorite

Guest suite in Hampton Bays

4.98 out of 5 average rating, 315 reviews

CHARMING OCEAN BUNGALOW

Oct 27 – Nov 3

G$59,695 GYD per night

Guest favorite

Home in Rocky Point

4.91 out of 5 average rating, 178 reviews

The Katalpa House -by the beach

Mar 14 – 21

G$35,757 GYD per night

Guest favorite

Apartment in Mastic

5.0 out of 5 average rating, 15 reviews

The Cozy Cellar | Private Art Deco Apartment

Feb 19 – 26

G$14,363 GYD per night

Guest favorite

Apartment in Center Moriches

4.88 out of 5 average rating, 24 reviews

Modern Private Studio close to the hamptons

Mar 27 – Apr 3

G$26,300 GYD per night

Guest favorite

Guest suite in Shirley

4.8 out of 5 average rating, 30 reviews

JD Cozynest

Jan 5 – 12

G$22,484 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

May 4 – 11

G$31,135 GYD per night

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Other great vacation rentals in Riverhead

Guest favorite

Home in Riverhead

4.96 out of 5 average rating, 49 reviews

Stunning Farmhouse W/Heated pool in NoFo by winery

Feb 10 – 17

G$273,469 GYD per night

Guest favorite

Home in Mattituck

4.92 out of 5 average rating, 92 reviews

Modern Farmhouse Steps to Beach & Love Lane

Sep 26 – Oct 3

G$85,896 GYD per night

Guest favorite

Apartment in Middle Island

5.0 out of 5 average rating, 17 reviews

Modern Farmhouse Decor With Washer/Dryer

Nov 1 – 8

G$28,899 GYD per night

Guest favorite

Place to stay in Coram

5.0 out of 5 average rating, 52 reviews

T&T Unique Space

May 8 – 15

G$24,633 GYD per night

Guest favorite

Home in Cutchogue

4.96 out of 5 average rating, 74 reviews

Secluded Farmhouse - Studio Apartment Style Unit

Apr 9 – 16

G$66,528 GYD per night

Guest favorite

Guesthouse in Shirley

4.97 out of 5 average rating, 34 reviews

La casita J place

Dec 29 – Jan 5

G$33,792 GYD per night

Guest favorite

Apartment in Shirley

5.0 out of 5 average rating, 23 reviews

Boho Beach Vibez Retreat! Private entrance

Jan 11 – 18

G$28,192 GYD per night

Guest favorite

Apartment in Medford

4.89 out of 5 average rating, 88 reviews

Cozy Apartment with King Bed - Separate Entrance

Aug 13 – 20

G$26,802 GYD per night

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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$10,421 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 Cutchogue

Home in Wading River

Guest suite in Hampton Bays

Home in Rocky Point

Apartment in Mastic

Apartment in Center Moriches

Guest suite in Shirley

Camper/RV in Riverhead

Other great vacation rentals in Riverhead

Home in Riverhead

Home in Mattituck

Apartment in Middle Island

Place to stay in Coram

Home in Cutchogue

Guesthouse in Shirley

Apartment in Shirley

Apartment in Medford

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