Vacation rentals in Riverhead

A serene outdoor space features rustic wooden lounge chairs positioned around a fire pit. Lush greenery surrounds the area, with a glimpse of a rustic historical building in the background. The inviting entrance to a private home is visible on the right.

4.98 out of 5 average rating, 181 reviews

Quiet Canoe Lake Cottage getaway

Peaceful private home on lush green resort like compound with historical outbuildings plus an additional studio apartment available for larger groups.Ideal for couples or a small family looking to explore the North or South forks of Long Islands East End and a short drive to the Hamptons famous beaches, villages and restaurants.A true garden lovers getaway with extensive flowers, vegetable and fruits and even our own apiary providing local raw honey. Near lots of wineries, restaurants and 2 miles from Tanger outlet mall shopping & top 5 rated Splish Splash Water Park. .Adjacent to the Peconic River for canoeing, kayaking, fishing or birding. The quiet winding country roads on either side of the river are a favorite destination for walking/joggers, biking and motorcycle touring. Riverhead town is a great central location and an easy drive to bay and ocean beaches. The area is still very much a rural farming area and a foodies delight with many pick your own fields,farmers markets, farm stands, wineries, horse, buffalo, and goat farms and even a potato vodka distillery and tasting room! We have an awesome Aquarium in town and our newly reopened Suffolk Theater with nightly live music and shows. Riverhead has lots of inexpensive small cafe style eateries for those on a budget.

4.89 out of 5 average rating, 490 reviews

Cabin in Rocky Point

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!

Guest suite in North Fork

4.9 out of 5 average rating, 269 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.

5 out of 5 average rating, 9 reviews

A modern kitchen features white cabinetry contrasted by a deep navy blue island. Pendant lighting hangs above the island, and a textured backsplash provides a pop of color. Large windows offer natural light, illuminating stainless steel appliances and a spacious countertop.

Home in Rocky Point

RP modern cozy cabin

Have fun with the whole family at this NEW all electric smart home. It's just a few minutes to the Long Island Sound, 15 minutes to Baiting Hollow Farm Vineyard and a 5000+ acre preserve just to the south. In addition we have so many local amenities including the prestigious "Fish Church of Rocky Point", food spots, Starbucks & more. The sound is known for beautiful sunsets, sun tanning, paddle boarding, bike riding and fishing. The pebble beach is great to walk on with shoes or bare feet.

A serene screen porch features rustic wooden furniture, including a table and seating, with views of the expansive green yard. Light filters through large screens, creating a bright atmosphere. A walkway leads outdoors, while a dog is seen exploring the property.

4.97 out of 5 average rating, 150 reviews

Secluded Farmhouse - Studio Apartment Style Unit

Beautiful, quiet, studio apartment-style unit (private entrance w/full bath) tucked away in a modern farmhouse on a gorgeous, secluded North Fork farm. Guests have exclusive use of screen porch, fire pit, bbq and outdoor seating area. Jess is a private chef and yoga instructor, so be sure to inquire for services! Private hiking trails, fresh eggs, produce from garden, beach gear, Keurig, mini fridge, homemade granola, tea. Fresh eggs, seasonal veg from the garden, and meals (inquire!)

A spacious outdoor deck features a dining set with blue chairs and a large umbrella, offering shade. Nearby, blue beach chairs and umbrellas are arranged on the sandy beach, with a kayak resting beside them, all set against a serene waterfront view.

5 out of 5 average rating, 16 reviews

Hang by the (Chel)SEA

Enjoy a relaxing stay with family and friends at this cozy soundview beach house. Wake up to breathtaking views of the water, where you can go right into the back yard of your very own private beach! Have a morning coffee on the front balcony of the home that overlooks the beautiful marshlands and then spend the day relaxing on the beach, or kayaking in the water! End the evening with a glass of wine on the back deck, that overlooks the water with the most spectacular sunsets!

Superhost

An outdoor seating area is illuminated by string lights and lanterns, creating a cozy atmosphere. Two chairs are positioned around a circular table on a gravel surface, surrounded by lush greenery and potted plants. A chiminea stands nearby, adding character to the inviting space.

Apartment in Rocky Point

4.72 out of 5 average rating, 191 reviews

Juniper Hollow

You are just a stone’s throw from the beach in this two-guest suit. Beach key provided! This indoor space measures 400 sf but you’ll find it well laid out with twice as much private outdoor space (for you warmer weather travelers). Older reviews are from 4 years ago and pre renovation, we are refreshed. Feel free to roam the rest of the 1/3 acre property of rolling hills, old growth trees, a hammock house, tree swings on the hill, and water views from the driveway.

5 out of 5 average rating, 86 reviews

Barn in The Hamptons

The Heaven

Welcome to the Gate Way to the North and South Forks of the Hampton's in Long Island New York. Newly remodeled, when not in use as an artists studio, transforms into a relaxing oasis. Easy access to ocean and bay beaches, Vineyards, Farm stands and Villages. The Barn is good for couples for a romantic get away and business travelers looking for a retreat. Please note: Bathroom ground floor Bedrooms 1st floor Not suitable for young children No Pets allowed

4.96 out of 5 average rating, 134 reviews

A vibrant local farm stand is visible, featuring an assortment of fresh produce. Sunflowers and colorful flowers decorate the area. Red umbrellas provide shade, while baskets filled with melons and vegetables are displayed prominently. Burlap sacks hang in the background, adding to the market atmosphere.

Guesthouse in North Fork

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.

4.93 out of 5 average rating, 107 reviews

A welcoming sign stands prominently along the walkway, displaying the words 'Welcome to the RiverWalk.' Lush green trees frame the pathway, complemented by a clear blue sky, creating an inviting atmosphere for visitors exploring the area.

Apartment in North Fork

J&J's BnB Lovely, BR/Bath w/ Private Entrance!

Welcome to Jeanette and Jims Airbnb! We are avid travelers and look forward to hosting you on your trip to beautiful Long Island! Lovely, clean updated private room with private separate entrance and bathroom. Great location on a quiet wooded acre. 2 miles from Splish Splash. 3.6 miles from the Long Island Aquarium. 8.7 miles from Cupsogue Beach. 4.8 miles from Baiting Hollow Farm Vineyard. So much to do near by. Head easily to the north or south fork!

5 out of 5 average rating, 11 reviews

A light-filled living area features a beige sofa with accent pillows, complemented by two striped armchairs. Natural wood accents are present in the ceiling beams and staircase. A large window allows river views, while a surfboard adorns the wall above.

Houseboat in North Fork

Peconic River Boatel

Perfectly updated nautical houseboat situated on the scenic Peconic River. Featuring two picturesque bedrooms, a full service eat-in kitchen and a living room with panoramic river view. Enjoy your morning coffee on the outside deck while taking in the sunrise. This historic waterfront town was named to Forbes Advisor’s “Best Places to Travel in 2023” — one of just 11 U.S. destinations on this year’s list. A must see for adventurers and families alike!

4.9 out of 5 average rating, 82 reviews

A fire pit is centered on a grassy area, with vibrant flames flickering amidst burning wood. In the background, a sunset casts warm hues across the sky, while an open field stretches out softly, enhancing the serene outdoor setting.

Camper/RV in North Fork

Slide out camper on century old working farm

You will have privacy in this 29 foot long 2008 camper with one slideout. It's quite spacious and will sleep 4 adults comfortably. Kids will love the cozy bunk beds. We are located on the North Fork of Long Island close to beaches, county and state parks, wineries and breweries, farm stands. The ocean is 20 minutes away, Long Island Sound and Peconic Bay 10 minutes. Beautiful Greenport and Shelter Island are great destinations for shopping and dining.

Vacation rentals for every style

Get the amount of space that is right for you

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Popular amenities for Riverhead vacation rentals

Self check-in

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Other great vacation rentals in Riverhead

Superhost

A cozy outdoor seating area features bright yellow chairs arranged around a modern fire pit. Lush greenery including bamboo adds a natural touch, while large windows of a building reflect the surrounding space.

Apartment in Stamford

4.83 out of 5 average rating, 6 reviews

Sunny 1BR Apartment

JoanRating, 5 stars5 months ago

Clean , modern apt. Very easy to navigate with the technology. Staff very friendly and helpful. A bit noisy on street outside with traffic. Will definitely rent again with URBY, but request a courtyard side unit

A screened-in patio offers a comfortable seating area with dark blue sofas and a light wooden table. A ceiling fan provides airflow, while large windows showcase views of the spacious yard and surrounding trees. Natural light enhances the inviting atmosphere.

4.98 out of 5 average rating, 181 reviews

Greenport Village walking distance to all

WilliamRating, 5 stars3 weeks ago

Kristin was a great host. Everything was as described. Great location to shopping, restaurants and ferry in Greenport. We would definitely stay here again.

Cottage in Shelter Island

Two wooden chairs are positioned on a grassy area overlooking the calm water. A fire pit sits in between the chairs, and a swing hangs from a nearby tree. In the background, a dock extends into the water, framed by trees.

4.97 out of 5 average rating, 108 reviews

Shelter Island Waterfront Getaway

CindyRating, 5 stars5 months ago

Great stay, Maureen is very communicative and super helpful. Beautiful views

Superhost

A serene water landscape is presented, featuring calm blue waters bordered by natural greenery. Gentle slopes and sandy areas are visible in the distance, while a clear blue sky provides a tranquil backdrop, reflecting the peaceful setting of the surrounding environment.

Home in Waterford

4.94 out of 5 average rating, 18 reviews

Summer Beach Cottage Harknes, Ocean Beach N

JenniferRating, 5 stars9 months ago

It was a perfect spot for our little family vacation. We were so close to a few really nice beaches and the area is a short drive to mystic aquarium and village. Patsy and family are very nice and gave some great suggestions for activities in the area.

4.89 out of 5 average rating, 103 reviews

A hot tub is situated on a wooden deck, surrounded by tall green hedges that offer privacy. The clear blue sky overhead adds to the tranquil atmosphere, while string lights can be seen overhead, creating a relaxed outdoor vibe.

Home in The Hamptons

Hamptons Escape minutes from Beaches and Nightlife

DanielRating, 5 stars2 weeks ago

Aida was a great host and very approachable. The house was beautiful in a very pleasant neighborhood

4.98 out of 5 average rating, 45 reviews

A shaded porch is visible, featuring a round table with a floral tablecloth and several chairs. The tranquil ocean is seen in the background, while distant land can be discerned on the horizon. Soft light illuminates the space, enhancing the inviting setting.

Home in Milford

Beachfront paradise- come, stay, relax!

ManishRating, 5 stars1 month ago

I had a great stay - the views were amazing all day long. Francesco was very responsive and friendly.

5 out of 5 average rating, 52 reviews

A serene sunset over the ocean is captured, with the sun dipping below the horizon. The sky is painted in warm hues of orange and blue, while the calm water reflects the colorful sky, enhancing the peaceful coastal scenery.

Home in Old Saybrook

Great Hammock Getaway | Beaches, Views & Hot Tub

JoanaRating, 5 stars2 weeks ago

We spent a few days at this amazing place and absolutely loved it! The house is cozy, very clean, well-organized, and beautifully decorated – great taste in every detail. We especially enjoyed the hot tub and the fireplace – perfect spots to relax. The location is also excellent. The host provides bikes, and we used them to explore the nearby beaches and ride around the town. It was exactly the peaceful and relaxing break we needed from our busy routine. We would definitely come back! ♥️