Vacation rentals in Jamesport

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Top-rated vacation rentals in Jamesport

Guests agree: these stays are highly rated for location, cleanliness, and more.

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.

Mar 26 – Apr 2

G$155,994 GYD per night
Guest favorite

Cottage in Riverhead

4.85 out of 5 average rating, 127 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.

Mar 8 – 15

G$51,192 GYD per night
Guest favorite

Home in Jamesport

5.0 out of 5 average rating, 56 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.

Feb 18 – 25

G$140,458 GYD per night

Popular amenities for Jamesport vacation rentals

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 vacation rentals in Jamesport

Guest favorite

Vacation home in Flanders

4.99 out of 5 average rating, 67 reviews

Amazing Waterfront Bungalow

Apr 3 – 10

G$94,858 GYD per night
Guest favorite

Home in Mattituck

5.0 out of 5 average rating, 28 reviews

Immaculate NOFO Beach House Steps from Beach

Dec 9 – 16

G$183,726 GYD per night
Guest favorite

Home in Riverhead

4.96 out of 5 average rating, 48 reviews

Stunning Farmhouse W/Heated pool in NoFo by winery

Jan 13 – 20

G$176,876 GYD per night
Guest favorite

Home in Mattituck

4.93 out of 5 average rating, 44 reviews

North Fork Wine Country Cottage Heart of Mattituck

Oct 25 – Nov 1

G$60,729 GYD per night
Guest favorite

Apartment in Center Moriches

5.0 out of 5 average rating, 18 reviews

Modern Private Studio Perfect for Relaxing Getaway

Feb 3 – 10

G$26,920 GYD per night
Guest favorite

Home in Cutchogue

4.96 out of 5 average rating, 24 reviews

North Fork Estate in Midst of Vinyard

Dec 7 – 14

G$119,791 GYD per night
Guest favorite

Home in Cutchogue

5.0 out of 5 average rating, 17 reviews

North Fork Escape Heated Pool Beach & Wineries

Oct 30 – Nov 6

G$136,160 GYD per night
Guest favorite

Home in Mattituck

4.94 out of 5 average rating, 16 reviews

Elena’s Beach house

Jul 1 – 8

G$146,722 GYD per night
Guest favorite

Cottage in Riverhead

4.93 out of 5 average rating, 43 reviews

Beautiful cottage on East End

Nov 4 – 11

G$108,296 GYD per night
Guest favorite

Home in Riverhead

5.0 out of 5 average rating, 7 reviews

Private Beach access along the Wine Trail

Nov 17 – 24

G$71,832 GYD per night
Guest favorite

Home in Mattituck

4.91 out of 5 average rating, 58 reviews

Walk to Breakwater Beach in Heart of Wine Country

May 10 – 17

G$142,002 GYD per night
Guest favorite

Home in Aquebogue

5.0 out of 5 average rating, 22 reviews

Entire Home @ Heart of Long Island Wine Country

Dec 30 – Jan 6

G$168,156 GYD per night

Quick stats about vacation 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

1.2K reviews

Nightly prices starting at

G$18,850 GYD before taxes and fees

Frequently Asked Questions

  • Do cottage rentals in Jamesport have air conditioning?

    Absolutely! We offer over 10 cottage rentals with air conditioning in Jamesport. Enjoy a tailored experience with all the comforts you desire.

  • How much does it cost to stay in house rentals in Jamesport?

    Experience the best of Jamesport with our house rentals, starting at about $90 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Are there pet-friendly vacation rentals in Jamesport?

    Four-legged friends are welcome in Jamesport. Choose from more than 20 vacation rentals for guests traveling with pets.

  • What are the most popular amenities for House Rentals in Jamesport?

    Enhance your stay in our House Rentals with the most popular amenities: over 40 homes with air conditioning, over 40 homes with wifi, over 30 homes with a bbq area, and more. Indulge in the ultimate retreat, tailored to your preferences.

  • Are there family-friendly vacation rentals in Jamesport?

    Jamesport has more than 50 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

  • Do cottage rentals in Jamesport have wifi?

    Absolutely! We offer over 10 cottage rentals with wifi in Jamesport. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Jamesport have a bbq area?

    Absolutely! We offer over 30 house rentals with a bbq area in Jamesport. Enjoy a tailored experience with all the comforts you desire.

  • Are there vacation rentals with a dedicated workspace in Jamesport?

    Yes! Work meets play with ease at over 20 vacation rentals in Jamesport featuring dedicated workspaces. Stay connected and productive in your home away from home.

Destinations to explore

  1. Airbnb
  2. United States
  3. New York
  4. Suffolk County
  5. Jamesport