Holiday rentals in Jamesport

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Top-rated holiday rentals in Jamesport

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Guest favourite

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.

11–18 Jan

€ 721 per night

Guest favourite

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.

6–13 Mar

€ 243 per night

Guest favourite

Home in Jamesport

5.0 out of 5 average rating, 57 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.

29 Mar – 5 Apr

€ 652 per night

Guest favourite

Home in Cutchogue

4.96 out of 5 average rating, 74 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. Home was designed by well known home and garden designer, Conni Cross. 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.

18–25 Mar

€ 304 per night

Guest favourite

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.

31 Jul – 7 Aug

€ 114 per night

Guest favourite

Cottage in Mattituck

4.97 out of 5 average rating, 31 reviews

Cozy Cottage By The Bay, Farms & Vineyards!

Welcome to our cozy cottage in the heart of the North Fork! Our centrally located dog friendly cottage is perfect for your North Fork get away. Walkable to the Peconic bay, Love Lane, Hampton Jitney, grocery store, Starbucks, local brewery, movie theatre, and town ice cream shop all while being right in the heart of wine country! Whether you are here to get out of the busy city, wine tour with friends or explore local farms with your family, our charming cottage is a great place for you!

28 Oct – 4 Nov

€ 294 per night

Guest favourite

Guest suite in Cutchogue

4.9 out of 5 average rating, 83 reviews

Enjoy a relaxing getaway to the North Fork

Newly renovated, 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.

1–8 Sep

€ 196 per night

Guest favourite

Home in Cutchogue

4.97 out of 5 average rating, 30 reviews

Cozy Cottage with Views

Take it easy at this unique and tranquil getaway centrally located in Cutchogue on the North Fork of Long Island. This newly renovated cottage has plenty of natural light, a full kitchen with all new appliances, one bedroom with a queen size bed, a bathroom with a walk in shower, a spacious living room with vaulted ceilings and a private outdoor space with a gas grill. A short drive in either direction allows you the opportunity to experience all that the North Fork has to offer.

13–20 Jan

€ 324 per night

Guest favourite

Home in Riverhead

4.96 out of 5 average rating, 49 reviews

Stunning Farmhouse W/Heated pool in NoFo by winery

Welcome to our stunning farmhouse! A stylish and relaxing place to stay while you discover all the North Fork and the Hamptons have to offer. Our 1-acre outdoor recreation area has the perfect setting for sunbathing by the pool, or enjoying a serene evening under the starry sky with a refreshing ocean breeze. Additionally, with beautiful beaches, renowned wineries, charming farmstands, picturesque hiking trails, as well as local restaurants and coffee shops just a few minutes away.

16–23 Dec

€ 530 per night

Guest favourite

Home in Aquebogue

4.92 out of 5 average rating, 13 reviews

Vineyard Views from the Backyard

Introducing our Vineyard Views getaway! Get ready to immerse yourself in the beauty of the surrounding vineyards, as stunning vistas await you from every corner of this charming and spacious 4-bedroom, 2-bathroom house. As you step onto the expansive 20x40' deck, prepare to be captivated by the panoramic views of the adjacent vineyard. Whether you're enjoying a morning coffee or unwinding in the evening, the deck provides the ideal spot to soak in the beauty of your surroundings.

10–17 Aug

€ 589 per night

Guest favourite

Flat in Center Moriches

4.87 out of 5 average rating, 23 reviews

Modern Private Studio close to the hamptons

The perfect place for a well deserved rest over the holidays. A well equipped cozy studio only 20 minutes from the Hamptons and 10 minutes away from LIRR train station to go into NYC (free parking at the train station!) This studio has a small kitchenette to warm up meals, a full size fridge, we include some snacks for those late night cravings. A queen size bed, a separate desk and chair to study or work, a couch, smart TV, and a peaceful environment to relax and unwind.

3–10 Jan

€ 123 per night

Guest favourite

Guest house 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.

5–12 Mar

€ 427 per night

Holiday rentals for every style

Get the amount of space that is right for you

Popular amenities for Jamesport holiday rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Stay near Jamesport's top sights

South Jamesport Beach9 locals recommend

Main Road Biscuit32 locals recommend

Cliff's Elbow Room15 locals recommend

Grana38 locals recommend

The Vineyards at Aquebogue3 locals recommend

Jedediah Hawkins Inn26 locals recommend

Other great holiday rentals in Jamesport

Guest favourite

Home in Mattituck

5.0 out of 5 average rating, 30 reviews

Immaculate NOFO Beach House Steps from Beach

13–20 Nov

€ 729 per night

Guest favourite

Home in Mattituck

4.9 out of 5 average rating, 10 reviews

NorthFork FarmHouse, Amazing Pool, Beach, Wineries

7–14 Dec

€ 1,101 per night

Guest favourite

Holiday home in Flanders

4.99 out of 5 average rating, 67 reviews

Amazing Waterfront Bungalow

10–17 Jul

€ 646 per night

Guest favourite

Bungalow in Mattituck

4.91 out of 5 average rating, 55 reviews

Incredible Beach Front Bungalow w/ Private Beach!

16–23 Oct

€ 503 per night

Guest favourite

Cottage in Cutchogue

5.0 out of 5 average rating, 18 reviews

Renovated 2-Bedroom Cottage on the North Fork

13–20 Dec

€ 376 per night

Guest favourite

Flat in Mastic

5.0 out of 5 average rating, 13 reviews

The Cozy Cellar | Private Art Deco Apartment

9–16 Mar

€ 72 per night

Guest favourite

Home in Mattituck

4.92 out of 5 average rating, 59 reviews

Walk to Breakwater Beach in Heart of Wine Country

2–9 Feb

€ 508 per night

Guest favourite

Cottage in Riverhead

4.93 out of 5 average rating, 43 reviews

Beautiful cottage on East End

1–8 Feb

€ 511 per night

Show all

Quick stats about holiday rentals in Jamesport

Total rentals	70 properties
Rentals with a pool	10 properties have a pool
Pet-friendly rentals	20 properties allow pets
Family-friendly rentals	50 properties are a good fit for families
Total number of reviews	1.4K reviews
Nightly prices starting at	€ 85 before taxes and fees

Holiday rentals in Jamesport

Top-rated holiday rentals in Jamesport

Cottage in Riverhead

Cottage in Riverhead

Home in Jamesport

Home in Cutchogue

Guest suite in Wading River

Cottage in Mattituck

Guest suite in Cutchogue

Home in Cutchogue

Home in Riverhead

Home in Aquebogue

Flat in Center Moriches

Guest house in Jamesport

Holiday rentals for every style

Houses

Cottages

Hotels

Popular amenities for Jamesport holiday rentals

Stay near Jamesport's top sights

Other great holiday rentals in Jamesport

Home in Mattituck

Home in Mattituck

Holiday home in Flanders

Bungalow in Mattituck

Cottage in Cutchogue

Flat in Mastic

Home in Mattituck

Cottage in Riverhead

Quick stats about holiday rentals in Jamesport

Total rentals

Rentals with a pool

Pet-friendly rentals

Family-friendly rentals

Total number of reviews

Nightly prices starting at

Destinations to explore