Vacation rentals in Jamesport

A single-story brick house is set amidst a lush green lawn, framed by colorful flowers and bushes. A pathway leads to the front entrance, with a chimney visible on the right side. Tall trees provide shade in the background under a clear blue sky.

4.95 out of 5 average rating, 111 reviews

Walk to Vineyards, Beach, Restaurants • Sleeps 8

• Spacious 3 BR house in heart of Jamesport - includes King, Queen & 2 twin beds. Queen air mattress also available. • Great for family vacations, weekend getaways & local weddings. • Clean sheets, pillows, fresh towels & toiletries. • Backyard complete w/ outdoor bbq, fire pit, hammock & patio seating. • Cook in open kitchen fully equipped w/ dishes, utensils, spices, pots & pans; eat local ingredients from nearby farms & markets. • Indoor & outdoor dining tables seat up to 8 guests.

Superhost

A Jayco camper is situated among trees in a wooded area. An electric awning extends over a designated outdoor seating space. The ground is covered with fallen leaves, and sunlight filters through the branches above, creating a calm environment.

Camper/RV in North Fork

5 out of 5 average rating, 4 reviews

Camper on the farm woodlot

New camper located in a woodlot on a farm that has been in this family since the 1600’s . We’re 10 minutes to the Long Island sound, 10 minutes to peconic bay and 20 minutes to the Atlantic Ocean. We’re 30 minutes from the orient point ferry .Wineries, breweries, farm stands, hiking trails and restaurants are a few minutes drive away. If you’re a shopper tanger mall is 15 minutes away .We’re 1/2 hour from the hamptons. No matter your interests you can find them close by. Come and relax.

A cozy bedroom featuring a spacious bed dressed in soft linens is positioned against a light-colored wall. Natural light filters through two windows, casting gentle shadows on the warm wooden floor. A ceiling fan hangs overhead, and a mirror and chair add functional elements to the space.

4.98 out of 5 average rating, 166 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 large pool is surrounded by a well-maintained lawn, featuring shallow lounging areas and sleek white loungers. A shaded gazebo can be seen in the background, offering a space for relaxation, while trees and greenery add to the tranquil outdoor setting.

4.97 out of 5 average rating, 33 reviews

NorthFork FarmHouse, Amazing Pool, Beach,Vineyards

Relax with the whole family at this peaceful place to stay. Centrally located surround by best vineyards, farms, great neighborhood, beaches only 5 minutes away, aquarium 15', water park 15' A bustling beach town year-round From boating to wining and dining, it’s all at your fingertips in Mattituck.Locally owned restaurants, bakeries and boutiques on Love Lane; boaters have direct access to Long Island Sound via the Mattituck Inlet; and wine lovers will relish the area’s vineyards.

Guest suite in North Fork

A serene beach scene is depicted, showcasing soft white sand bordered by gentle waves. Tall grasses sway in the foreground, framing the clear blue water that extends to the horizon, providing a sense of calm and natural beauty.

4.92 out of 5 average rating, 102 reviews

Enjoy a relaxing getaway to the North Fork

One bedroom suite, with separate entrance in quiet Nassau Point; a peninsula, surrounded by beaches. Nassau Point is a great place to bike, walk and enjoy nature. Fully functioning WiFI for guests looking to extend their stay, while working from home. Fishermen's beach is a 5 minute walk Causeway beach is a 10 minute walk with parking. Point beach, 1.5 mile walk, a Southold Parking Permit required. You will find 20 wineries within 5 miles, just a short Uber ride away.

4.94 out of 5 average rating, 132 reviews

A wooden tray is centered on a neatly made bed, featuring a book and a coffee cup. The bed is dressed with a white quilt, and a softly textured pillow is placed against the headboard. A bedside lamp provides gentle illumination.

Guest suite in South End

Comfortable Suite, a walk to the beach

Keep it simple at this spacious and peaceful home. Built in 2019, this home was specially designed for sustainable, green living; ground-source heating, and super insulation allow for minimal environmental impact. Less than five minute walk to McCabe’s Beach. Very near to wineries, farms, and the quaint shops and bakeries of Southold and Greenport. Little Fish restaurant and oyster sales all down the street. Short drive from Sparkling Pointe vineyard, and Love Lane.

4.86 out of 5 average rating, 107 reviews

A spacious living area features exposed wooden beams and a cozy brick fireplace. Comfortable seating includes a brown sofa and recliner, with decorative pillows adding warmth. A glass coffee table stands on a colorful area rug, while large windows overlook the greenery outside.

Cabin in North Fork

Beach & Woods: Cozy Cabin, Hot tub, Peloton, Oh My

Welcome to nature's retreat, our secluded North Fork haven where 2+ acres of wild beauty and private beach access promise unparalleled relaxation. Delight in our hot tub's warmth under the stars, unwind on swings, or glide on bay waters with our kayak. With enchanting porch views, an invigorating outdoor shower, and nearby organic farms, our cabin is an idyllic escape. Experience the local charm with vineyard tours and return to a haven of comfort and adventure.

4.96 out of 5 average rating, 140 reviews

A modern living area is highlighted by a gray sofa centered on a low coffee table. Two armchairs are placed to one side, while a textured area rug complements the space. Wall art hangs above the sofa, and natural light enters through large windows.

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, 116 reviews

A spacious room features a queen-size bed adorned with a light gray quilt. Bedside tables with lamps flank either side, and a decorative bench sits at the foot of the bed. Natural light filters through the sheer curtains, enhancing the calming color palette.

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!

A bright living area features light-colored walls and wooden flooring. A comfortable sofa and a plush chair are arranged around a rustic coffee table. A ceiling fan hangs above, while a kitchen with a blue island is visible in the background, enhancing the space's openness.

4.93 out of 5 average rating, 138 reviews

Modern Farmhouse Steps to Beach & Love Lane

Our home is professionally designed and set on a spacious, manicured green parcel enclosed by a Cul-de-sac with complete privacy inside and out. The home is designed with all modern conveniences and is located less than a 5 minute walk to Love Lane (Mattituck's charming downtown), Veteran's Beach (one of the best beaches on the Northfork) and the Mattituck train station. It is a place to relax, unwind and enjoy all that North Fork has to offer.

5 out of 5 average rating, 92 reviews

A spacious living area features high ceilings with skylights, allowing natural light to fill the room. A comfortable sofa is paired with upholstered chairs, complemented by a decorative rug. Shelves display curated decor, with a television positioned for easy viewing.

Barn in The Hamptons

The Haven - Gateway to Hamptons & North Fork

Welcome to The Haven, your peaceful and luxurious retreat in the Hamptons. This beautifully restored and converted barn radiates creativity, tranquility, and understated elegance. Step outside into the lush gardens with your morning coffee, or spend the evening by the fire pit under a sky full of stars – pure magic. Located in Long Island, NY, it offers easy access to ocean and bay beaches, vineyards, farm stands, and charming villages.

A two-story house is set on a well-maintained lawn, featuring a paved driveway that leads to a garage. A pathway lined with shrubs directs attention to the inviting entrance with double doors, framed by decorative plants under a clear blue sky.

5 out of 5 average rating, 21 reviews

Peaceful Guesthouse

This oasis includes 2 bedrooms including a pack and play. sleeps 4 adults comfortably. 1 bath and a half. Kitchen, dinning room and living area with fireplace. An additional dining/sitting area on outside patio with an additional fireplace. The house is 1/2 mile walking distance from beach, 1 mile from eateries, 3 miles from local winery and brewery. Choice of golf courses within 5 mile radius. Certification Number: 1028

Vacation rentals for every style

Get the amount of space that is right for you

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Quaint homes, peaceful surroundings

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Popular amenities for Jamesport vacation rentals

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Air conditioning

Other great vacation rentals in Jamesport

Home in South Jamesport

4.81 out of 5 average rating, 26 reviews

Classy Getaway w/ Deck & Yard < 1 Mi to Beach

The exterior of the beach cottage is shown, featuring a white facade with large windows and a fresh, light blue front door. Lush green grass surrounds the property, complemented by carefully arranged plants and shrubs. A clear blue sky creates a serene backdrop.

5 out of 5 average rating, 5 reviews

New Jamesport Beach Cottage & Barn

A serene waterfront view is captured from the deck, showcasing a well-appointed outdoor space that includes a hot tub, dining area, and lounge chairs. The green lawns and waterway create a tranquil setting, inviting relaxation amidst nature.

Apartment in The Hamptons

4.93 out of 5 average rating, 76 reviews

Hamptons Waterfront Escape/ Hot Tub/ Resort Style

4.99 out of 5 average rating, 69 reviews

A bright kitchen and dining area features modern white cabinetry and stainless steel appliances. A round table with four white chairs is positioned in the center, with natural light flooding in through the large window. The flooring is light-colored wood, enhancing the spacious feel.

Cottage in North Fork

NOFO Waterfront Sanctuary

Farm stay in The Hamptons

A serene outdoor landscape showcases a well-manicured lawn, framed by lush greenery and colorful flowers. In the background, a fenced area contains a barn and a horse, while a vegetable garden with trellises is visible to the right.

5 out of 5 average rating, 7 reviews

The Snug on the Farm ~ Cozy cottage home

A sandy pathway leads to the beach, with wooden steps partially visible in the foreground. Gentle dunes and sparse vegetation are noted on either side. The horizon showcases a bright blue sky, complemented by soft clouds, indicating a clear day at the coast.

Home in The Hamptons

4.8 out of 5 average rating, 5 reviews

West Hampton Seahorse Cottage

4.9 out of 5 average rating, 62 reviews

A country cottage features a shaded outdoor dining area with a large umbrella. Wooden chairs surround a table on a grassy lawn, with the cottage's porch visible in the background. Verdant trees provide a natural backdrop, enhancing the calm outdoor environment.

Cottage in North Fork

Beach and Wine Time Country Cottage

A modern home is set back from the road, surrounded by greenery and trees. The driveway curves gently towards the entrance, with flower pots adding a touch of color. A balcony extends from the second floor, enhancing the exterior charm.