Vacation rentals in Jamesport

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Top-rated vacation rentals in Jamesport

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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 20 – 27

R14,070 ZAR per night

Guest favorite

Cottage in Riverhead

4.85 out of 5 average rating, 131 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.

Dec 10 – 17

R4,620 ZAR per night

Guest favorite

Home in Jamesport

5.0 out of 5 average rating, 59 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.

Nov 6 – 13

R13,224 ZAR per night

Guest favorite

Cabin in Rocky Point

4.9 out of 5 average rating, 394 reviews

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!

Jan 7 – 14

R2,793 ZAR per night

Guest favorite

Guest suite in Wading River

4.9 out of 5 average rating, 231 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.

Sep 4 – 11

R2,182 ZAR per night

Guest favorite

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.

Sep 1 – 8

R3,925 ZAR per night

Superhost

Home in Greenport

4.94 out of 5 average rating, 136 reviews

Harbor Heights

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 13 – 20

R1,483 ZAR per night

Guest favorite

Guest suite in Southold

4.94 out of 5 average rating, 99 reviews

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.

Mar 23 – 30

R2,931 ZAR per night

Guest favorite

Guesthouse in Jamesport

4.97 out of 5 average rating, 107 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.

Jan 14 – 21

R7,380 ZAR per night

Guest favorite

Home in Mattituck

4.92 out of 5 average rating, 92 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.

Apr 25 – May 2

R8,899 ZAR per night

Guest favorite

Home in Cutchogue

4.96 out of 5 average rating, 190 reviews

Private Oasis W/Stunning Vinyard And Pool Views

Enjoy spectacular wine country sunset views from the living room that extend to the gorgeous saltwater gunite pool and spa. (Please note THE POOL AND SPA (attached hot tub) are OPEN FROM MAY 1 - OCTOBER 15 only). Beautifully decorated, comfortable home with an updated chef's kitchen and fireplace. Fabulous restaurants, wineries, farms, beaches and exquisite small towns all nearby. Simply put, a magical, peaceful paradise for you and your group.

Mar 7 – 14

R15,700 ZAR per night

Guest favorite

Home in Cutchogue

4.96 out of 5 average rating, 76 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.

Dec 22 – 29

R6,020 ZAR per night

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Jamesport vacation 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 vacation rentals in Jamesport

Guest favorite

Cottage in Mattituck

4.94 out of 5 average rating, 33 reviews

Cozy Cottage By The Bay, Farms & Vineyards!

Oct 6 – 13

R5,962 ZAR per night

Guest favorite

Home in Cutchogue

4.97 out of 5 average rating, 31 reviews

Cozy Cottage with Views

Aug 20 – 27

R5,964 ZAR per night

Guest favorite

Apartment in Center Moriches

4.88 out of 5 average rating, 24 reviews

Prvt studio near LI’s annual Tulip Festival

Mar 3 – 10

R2,388 ZAR per night

Guest favorite

Home in Aquebogue

4.92 out of 5 average rating, 13 reviews

Vineyard Views from the Backyard

Jun 16 – 23

R11,302 ZAR per night

Guest favorite

Home in Mattituck

4.94 out of 5 average rating, 35 reviews

Walk to Love Lane! Immaculate Renovated Cottage.

Dec 8 – 15

R7,377 ZAR per night

Guest favorite

Home in Mattituck

5.0 out of 5 average rating, 31 reviews

Immaculate NOFO Beach House Steps from Beach

Oct 8 – 15

R16,247 ZAR per night

Guest favorite

Home in Aquebogue

5.0 out of 5 average rating, 23 reviews

Entire Home @ Heart of Long Island Wine Country

Feb 5 – 12

R12,907 ZAR per night

Guest favorite

Home in Mattituck

4.9 out of 5 average rating, 10 reviews

NorthFork FarmHouse, Amazing Pool, Beach,Vineyards

Mar 25 – Apr 1

R20,880 ZAR per night

Show all

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
1.4K reviews
Nightly prices starting at
R1,666 ZAR before taxes and fees

Frequently Asked Questions

Do house rentals in Jamesport have air conditioning?
Absolutely! We offer over 40 house 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 30 vacation rentals in Jamesport featuring dedicated workspaces. Stay connected and productive in your home away from home.

Vacation rentals in Jamesport

Top-rated vacation rentals in Jamesport

Vacation rentals for every style

Cottages

Houses

Hotels

Popular amenities for Jamesport vacation rentals

Stay near Jamesport's top sights

Other great vacation rentals in Jamesport

Cottage in Mattituck

Home in Cutchogue

Apartment in Center Moriches

Home in Aquebogue

Home in Mattituck

Home in Mattituck

Home in Aquebogue

Home in Mattituck

Quick stats about vacation rentals in Jamesport

Total rentals

Rentals with a pool

Pet-friendly rentals

Family-friendly rentals

Total number of reviews

Nightly prices starting at

Frequently Asked Questions

Do house rentals in Jamesport have air conditioning?

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

Are there pet-friendly vacation rentals in Jamesport?

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

Are there family-friendly vacation rentals in Jamesport?

Do cottage rentals in Jamesport have wifi?

Do house rentals in Jamesport have a bbq area?

Are there vacation rentals with a dedicated workspace in Jamesport?

Destinations to explore