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Vacation rentals in Jamesport

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Top-rated vacation rentals in Jamesport

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

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A vibrant display at Jamesport Farm Brewery features colorful pumpkins and seasonal flowers arranged amidst hay bales. A welcoming sign is positioned at the center, with a ‘No Alcohol Beyond This Point’ notice nearby. Lush greenery surrounds the setup, enhancing the inviting atmosphere.

Cottage in North Fork

4.92 out of 5 average rating, 53 reviews

Beautiful cottage on East End

Beautiful cozy cottage in the heart of wine country. Perfect for a family or a couples weekend away. Close to wineries, breweries, beach, outlets, restaurants, all that the North Fork has to offer. King master with bath two queen size bedrooms all on one floor Additional bathroom. Wood burning fireplace, washer dryer Absolutely NO PETS!!! Families Or rentals for people 30 and over Please be aware we require at least a 5 night stay during the summer months. There IS NOT a pool on the property

A covered porch features a combination of white and wooden outdoor seating arrangements. A medium-sized wooden coffee table is present in the center, complemented by decorative lanterns. A soft rug lies beneath the seating, while brick walls provide a warm backdrop. Natural light brightens the space.

Home in North Fork

4.94 out of 5 average rating, 106 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.

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.

Home in North Fork

4.97 out of 5 average rating, 151 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 seating area features comfortable furniture with soft cushions, overlooking a tranquil vineyard. Large glass panels provide unobstructed views of the fields, with a table set for dining. The ambiance is enhanced by exposed wooden beams and warm lighting fixtures.

Apartment in North Fork

4.83 out of 5 average rating, 40 reviews

Berry Farm House - Apt 1

The Berry House - apt 1 is a 1,000 square foot, 1 bedroom apartment. Full renovated with a modern rustic style. It is the first floor of a 2 family home. Large private deck overlooking the fields. Open layout with large glass doors bring the view indoors. Located on a 50 acre farm. Berries, flowers, pumpkins and more growing right outside your door. (seasonally) The views are peaceful and beautiful year round. Next door to Patty's Berries & Bunches, Harbes Farm and RGNY Winery.

An entertainment space is shown, featuring a flat screen TV mounted on the wall. A gray sofa is positioned in front of a wooden coffee table. To the left, a ping pong table is visible, and a foosball table occupies the corner of the room. Exposed wooden beams are present on the ceiling.

Home in North Fork

4.96 out of 5 average rating, 56 reviews

Walk to Love Lane! Immaculate Renovated Cottage.

Take it easy at this unique and tranquil getaway. Walking distance to Strawberry Fields, festivals, Windamere restaurant on the water, and Love Lane Kitchen. 5 min drive to Macari Vineyards and Harbes farm. The den can be used as a second bedroom as it does have French doors that can be closed to make it private and two sofa twin beds. Enjoy the outdoor Solo Stove and Weber BBQ. Garage features outdoor furniture with flat screen TV, ping pong, foosball, cornhole, and refrigerator.

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.

Guest suite in North Fork

4.92 out of 5 average rating, 99 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.

Home in North Fork

4.89 out of 5 average rating, 9 reviews

Beachfront Retreat - 5BR Home with Stunning Views

Beachfront Bliss Awaits! 🏖️ Nestled on a private beach along the North Fork of Long Island, this newly updated retreat offers breathtaking Peconic Bay views and endless coastal adventures. Enjoy swimming, kayaking, clamming, fishing, or simply unwinding on the shore. With 5 spacious bedrooms, modern comforts, and just 5 minutes from top restaurants, wineries, and family fun, this is the perfect escape for relaxation and adventure. Book your stay today! 🌊✨

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

4.96 out of 5 average rating, 134 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.

Cottage in North Fork

4.9 out of 5 average rating, 60 reviews

Beach and Wine Time Country Cottage

This charming country cottage is easy walking distance to the beach, within a 3 mile radius of choice golf courses and dozens of vineyards and has a right of way with water access just across the road. Set on 3/4 of an acre with a large backyard, this home has 3 bedrooms, 2 full baths, a kitchen, dining room, fireplace, and a front and back enclosed porch. If you like, watch the sunrise over the bay and the sunset over the golf course in the backyard.

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

4.93 out of 5 average rating, 107 reviews

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.

Home in North Fork

4.93 out of 5 average rating, 135 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.

Top guest favorite

The aerial view showcases a pristine beach extending into turquoise waters, merging with lush green landscape in the distance. Sandy shores curve gracefully, with small rocks visible at the water's edge. The tranquil scene highlights the natural beauty of the coastal surroundings.

Home in North Fork

5 out of 5 average rating, 13 reviews

North Fork Farm House

This home is located on the North Fork of Long Island in the heart of wine country. We have a beautiful winery within close walking distance. We are surrounded by beautiful beaches and a short ferry ride to Shelter Island. There’s great restaurants and shopping in the town of Greenport and close to Love Lane in Mattituck. There is also exciting things to do in the town of Riverhead, including shopping at Tanger and the Riverhead Raceway.

Vacation rentals for every style

Get the amount of space that is right for you

Houses

A space thats all yours, with room for everyone

Cottages

Quaint homes, peaceful surroundings

Hotels

Stylish accommodations and amenities

Popular amenities for Jamesport vacation rentals

Laptop-friendly workspace

Other great vacation rentals in Jamesport

Top guest favorite

A stylish seating area is depicted, featuring an elegant chair paired with a textured pouf. A plant in a cylindrical pot adds a touch of greenery, while a partially open glass-paneled door leads to another room. Warm, natural light enhances the inviting ambiance.

Home in North Fork

4.91 out of 5 average rating, 22 reviews

Floresta House ~ Charming, Cozy, Family Friendly!

AnneRating, 5 stars4 months ago

Great hosts!!! They were always there if we needed, even shoveled snow first thing in the morning for us! House was better than we expected, plenty of room, beds so comfy and so close to everything! Just an overall very nice experience! We will be back!

A bright and airy dining area features a round marble table surrounded by four contemporary chairs. Large windows provide ample natural light, highlighting views of the outdoor space and nearby water. Elegant wood beams accent the ceiling, adding warmth to the interior.

Home in North Fork

5 out of 5 average rating, 12 reviews

Kayaks ~ Bikes ~ Boards ~ 6mins> Greenport ~ 55"TV

TimothyRating, 5 stars1 month ago

We had a wonderful weekend stay at Eileen's beautiful waterfront home. The view from the living room and primary bedroom of the water was so peaceful. The kitchen was well appointed and the cozy living room made for a wonderful family gathering spot when we weren't dining out at the fabulous nearby restaurants, visiting wineries, or viewing local scenery. Eileen was incredibly responsive to small questions we had. We would definitely book again!!

The spacious front porch features multiple seating areas, including outdoor sofas arranged around a central coffee table. A serene view of surrounding greenery is visible, with sunlight enhancing the welcoming atmosphere of this inviting outdoor space.

Home in North Fork

5 out of 5 average rating, 37 reviews

Restored Farmhouse + Pool in Heart of Wine Country

KymberleeRating, 5 stars9 months ago

Absolutely loved our time on the farm. As someone who grew up out on the North Fork it was a return home with the most beautiful surroundings. Post Labor Day, the pool was still open (and warm)! The sun was shining during our bike rides to the incredibly close beach, and we had fresh veggies from the farm stand, right out front, every day. Such a treat, cannot wait to stay again and make some more great memories with family and friends.

A comfortable gazebo is featured, offering two wooden chairs facing a tranquil waterfront view. A vintage lantern hangs from the ceiling, creating a peaceful ambiance. Lush greenery surrounds the area, complemented by a nearby dock and boats visible in the background.

Cottage in North Fork

4.98 out of 5 average rating, 47 reviews

Stunning waterfront modern farmhouse with dock.

ChristineRating, 5 stars1 week ago

This beautiful piece of heaven was better than we could have imagined. As beautiful as the pic are, they don't do justice to the serenity of this property. Our group already decided to come back again. Michelle was lovely and thoughtful. The house was stocked with all the essentials and more. The coziness was unbeatable. We had the best weekend with the best friends.

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

4.9 out of 5 average rating, 82 reviews

Slide out camper on century old working farm

SeanRating, 5 stars8 months ago

I had a great stay. Very easy check in and check out, no problems at all. Host was friendly and responsive and had no issues with my late night arrival or early morning departure. Would absolutely stay here again.

A spacious living area features a light-colored sectional sofa, accompanied by a coffee table. Natural light pours in through large windows and a skylight. A modern kitchen is visible, equipped with stainless steel appliances, while a dining area with bar seating complements the open floor plan.

Home in North Fork

5 out of 5 average rating, 6 reviews

Mattituck Hideaway/ Luxury Wine Country Retreat

LaurenRating, 5 stars1 month ago

Fantastic experience. The place was clean, beautifully decorated and had all the amenities for a great weekend. The host was friendly and responded promptly. My family had a wonderful time, even better than the pictures!

Top guest favorite

A spacious wooden deck is showcased, featuring a grill and a large umbrella providing shade over a seating area with cushions. Potted plants are arranged around the space, enhancing the natural surroundings. Sunlight filters through the greenery, creating a serene outdoor environment.

Cottage in Hampton Bays

5 out of 5 average rating, 32 reviews

walk to bay, woods cottage

StephanieRating, 5 stars7 months ago

We had the most wonderful and peaceful fall weekend at Brooke’s cozy cottage to celebrate our anniversary, and it was truly unforgettable! The cottage itself is beautifully decorated and felt like a warm home away from home. Brooke went above and beyond to make our stay special, leaving us complimentary champagne and wine to kick off our celebration. The location was perfect for enjoying the crisp fall air and stunning foliage, providing the peaceful retreat we were hoping for. We can’t recommend this place enough and will definitely be back for another stay!

Top guest favorite

A peaceful outdoor area features a grassy lawn bordered by trees. A hammock can be seen gently swaying between two trees in the background. A fire pit sits in the foreground, with flames flickering, inviting relaxation and outdoor gatherings.

Home in North Fork

4.98 out of 5 average rating, 48 reviews

Le Petit Cottage Southold NY

CarolynRating, 5 stars1 month ago

Le Petit Cottage was an ideal stay. We enjoyed the location and David was very responsive and helpful. Would definitely stay there again.

Quick stats about vacation rentals in Jamesport

Total rentals
40 properties
Nightly prices starting at
ﺩ.ﺇ367 before taxes and fees
Total number of reviews
1K reviews
Family-friendly rentals
40 properties are a good fit for families
Pet-friendly rentals
20 properties allow pets
Rentals with a pool
10 properties have a pool

Frequently Asked Questions

How much does it cost to stay in house rentals in Jamesport?
Experience the best of Jamesport with our house rentals, starting at about $120 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Are there house rentals with a dedicated workspace in Jamesport?
Yes! Work meets play with ease at over 10 house rentals in Jamesport featuring dedicated workspaces. Stay connected and productive in your home away from home.
What are the most popular amenities for House Rentals in Jamesport?
Enhance your stay in our House Rentals with the most popular amenities: over 30 homes with wifi, over 10 homes with a bbq area, and more. Indulge in the ultimate retreat, tailored to your preferences.
Are there pet-friendly house rentals in Jamesport?
Four-legged friends are welcome in Jamesport. Choose from more than 10 house rentals for guests traveling with pets.
Do house rentals in Jamesport have wifi?
Absolutely! We offer over 30 house 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 10 house rentals with a bbq area in Jamesport. Enjoy a tailored experience with all the comforts you desire.
Are there Jamesport house rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 10 house rentals with pools in Jamesport, available on Airbnb. Make a splash and soak up the sun in style!
Are there family-friendly house rentals in Jamesport?
Jamesport has more than 20 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

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