South Jamesport holiday homes

We found 1,269 holiday rentals — enter your dates for availability
Discover a selection of 11 homes and other holiday rentals in South Jamesport that are perfect for your trip. Whether you're travelling with your children and pets, with friends or just your children, holiday homes have the amenities that you expect for your stay, which might include Wi-Fi and a washer and dryer. You'll be sure to find a property to rent to meet everyone's needs, including places that are non-smoking or accessible.

Holiday rentals with weekly discounts – South Jamesport

Showing deals for:18 Dec - 25 Dec

Pool
Private kitchen
Dining
Pool
Exceptional
(6 reviews)

Newly Built Hamptons House, Pool, Beach Access + Easy Access off Montauk Highway

Hampton Bays

8% off
NZ$17,397
for 7 nights, 1 home
NZ$2,485 per night
includes taxes & fees
Newly Built Hamptons House, Pool, Beach Access + Easy Access off Montauk Highway
Main Entrance
Dining table and picnic table water view
Heated pool with gorgeous water and natural wetland view
2nd floor deck with additional dining and leisure seating.
Exceptional
(38 reviews)

Luxurious Waterfront Retreat in Southampton: Breathtaking Views, Pool, and More!

Southampton

8% off
NZ$18,596
for 7 nights, 1 home
NZ$2,657 per night
includes taxes & fees
Luxurious Waterfront Retreat in Southampton: Breathtaking Views, Pool, and More!
Private kitchen
Exterior
Interior
Outdoor dining
Exceptional
(8 reviews)

Beautiful Colonial Mint Condition Summer House Walking Distance to Beach

Jamesport

12% off
NZ$8,755
for 7 nights, 1 home
NZ$1,251 per night
includes taxes & fees
Beautiful Colonial Mint Condition Summer House Walking Distance to Beach
Outdoor dining
Pool
Dining Room with seating for Ten
Exterior
Exceptional
(28 reviews)

Spacious New 4 Bedroom Home With Pool on 2 Acre Property

Peconic

8% off
NZ$15,000
for 7 nights, 1 home
NZ$2,143 per night
includes taxes & fees
Spacious New 4 Bedroom Home With Pool on 2 Acre Property
Property grounds
Living area
Living area
Exterior
Exceptional
(29 reviews)

Incredible Beachfront Home w/ Private Beach!

Mattituck

7% off
NZ$6,467
for 7 nights, 1 cottage
NZ$924 per night
includes taxes & fees
Incredible Beachfront Home w/ Private Beach!
Lower deck With Pool, 9 Loungers, plus 6 pool-chairs. Upper deck dining seats 10
Living area
Front entrance, park-like grounds
An elegant dining room (to 10 ppl, joins kitchen +8 and outdoor dining +10,)
Exceptional
(26 reviews)

Southampton Pickleball Walk to beach. Kayaks on lake Park-like grounds Pool

Southampton

30% off
NZ$17,392
for 7 nights, 1 home
NZ$2,485 per night
includes taxes & fees
Southampton Pickleball Walk to beach. Kayaks on lake Park-like grounds Pool
Living area
Outdoor dining
Welcome to Vineyard View
Exterior
Exceptional
(26 reviews)

Vineyard View, Bike to the Most Beautiful Beach

Mattituck

8% off
NZ$12,531
for 7 nights, 1 home
NZ$1,790 per night
includes taxes & fees
Vineyard View, Bike to the Most Beautiful Beach
Property grounds
Exterior
Property grounds
Interior
Exceptional
(39 reviews)

Spacious home near Aquarium & heart of wine country Shopping & close to Hamptons

Riverhead

8% off
NZ$9,018
for 7 nights, 1 home
NZ$1,288 per night
includes taxes & fees
Spacious home near Aquarium & heart of wine country Shopping & close to Hamptons
Interior
.
3 acres of beautiful land
Private kitchen
Exceptional
(81 reviews)

Southampton Estate, Newly Renovated , Excellent For Families! Sleeps 12-14

Hampton Bays

7% off
NZ$13,560
for 7 nights, 1 home
NZ$1,937 per night
includes taxes & fees
Southampton Estate, Newly Renovated , Excellent For Families! Sleeps 12-14
Interior
Living area
Dining
Terrace/patio
Excellent
(27 reviews)

Relaxing Cottage -- Walk to private Beach!

Calverton

7% off
NZ$3,913
for 7 nights, 1 cottage
NZ$559 per night
includes taxes & fees
Relaxing Cottage -- Walk to private Beach!
Room
Dining
Living area
Private kitchen
Exceptional
(18 reviews)

Great Getaway! Exceptional Home. Walking distance to The Christmas Tree Shoppe

Cutchogue

8% off
NZ$8,630
for 7 nights, 1 cottage
NZ$1,233 per night
includes taxes & fees
Great Getaway! Exceptional Home. Walking distance to The Christmas Tree Shoppe
Spacious living room with sliders to the patio pool and backyard
Kitchen is stocked with a selection of pots dishes and utensils
Plenty of comfortable chairs for lounging
Enjoy nearby North Fork and South Fork wineries and many other local attractions
Exceptional
(108 reviews)

Hampton’s Haven: Heated Pool, Hot Tub & Gameroom! 2 miles to Rogers Beach

Westhampton Beach

8% off
NZ$9,288
for 7 nights, 1 home
NZ$1,327 per night
includes taxes & fees
Hampton’s Haven: Heated Pool, Hot Tub & Gameroom! 2 miles to Rogers Beach
Living area
Exterior
Dining area
Pool, gazebo, fire table
Exceptional
(45 reviews)

Westhampton Beach Town and Country

Westhampton Beach

8% off
NZ$14,302
for 7 nights, 1 home
NZ$2,043 per night
includes taxes & fees
Westhampton Beach Town and Country
Large wrap-around lawn
Pool
Living room
Terrace/patio
Exceptional
(27 reviews)

Modern Family Retreat with Heated Pool, Playground and Peloton

Hampton Bays

8% off
NZ$14,524
for 7 nights, 1 home
NZ$2,075 per night
includes taxes & fees
Modern Family Retreat with Heated Pool, Playground and Peloton
Room
Property grounds
Interior
Exterior
Exceptional
(17 reviews)

Charming Riverhead home with large outdoor patio & backyard firepit

Riverhead

12% off
NZ$5,199
for 7 nights, 1 home
NZ$743 per night
includes taxes & fees
Charming Riverhead home with large outdoor patio & backyard firepit
75 inch TV w/ Bose Soundbar
Dining
Living area
Resort inspired backyard with heated pool, outdoor seating, and complete privacy
Exceptional
(16 reviews)

NEW DECK! Private 1 Acre Family Friendly Home - Heated Pool, Home Office & Gym

Westhampton

7% off
NZ$11,257
for 7 nights, 1 home
NZ$1,608 per night
includes taxes & fees
NEW DECK! Private 1 Acre Family Friendly Home - Heated Pool, Home Office & Gym
Backyard Water View
Kitchen
Exterior
Living Room
Exceptional
(6 reviews)

Charming 2 bedroom house in Quaint New Suffolk -short walk to New suffolk Beach

New Suffolk

8% off
NZ$6,044
for 7 nights, 1 home
NZ$863 per night
includes taxes & fees
Charming 2 bedroom house in Quaint New Suffolk -short walk to New suffolk Beach
Bathroom 1- upstairs
Dining
Private kitchen
Fenced, backyard Hampton-style pool area with lounge chairs and patio
Exceptional
(12 reviews)

Renovated Farmhouse on Vineyard-Heated Pool + mins from Beach + Walk to Harbes!

Riverhead

8% off
NZ$10,740
for 7 nights, 1 home
NZ$1,534 per night
includes taxes & fees
Renovated Farmhouse on Vineyard-Heated Pool + mins from Beach + Walk to Harbes!
Interior
Pool
Dining
Exterior
Wonderful
(20 reviews)

2-Acre Modern Estate in Southampton. Beach, winery, farm, pool, and hot tub

Riverhead

7% off
NZ$7,457
for 7 nights, 1 home
NZ$1,065 per night
includes taxes & fees
2-Acre Modern Estate in Southampton. Beach, winery, farm, pool, and hot tub
Living area
Crushpad of Charming Boutique vineyard nearby- Rosehill
8 Hands Farm
Exceptional
(30 reviews)

North Fork Ranch Home in Wine Country with Pool- 2 Beaches 5 Min Walk

Laurel

26% off
NZ$4,196
for 7 nights, 1 home
NZ$599 per night
includes taxes & fees
North Fork Ranch Home in Wine Country with Pool- 2 Beaches 5 Min Walk
Game Room w Home Theater System
Pool
Living Room | Game Room | Home Theater System
Living Room
Exceptional
(14 reviews)

Luxe Westhampton Beach Home w/ Pool & Hot Tub

Westhampton Beach

5% off
NZ$14,972
for 7 nights, 1 home
NZ$2,139 per night
includes taxes & fees
Luxe Westhampton Beach Home w/ Pool & Hot Tub
Interior
Private kitchen
Outdoor dining
Living area
Exceptional
(15 reviews)

Newly renovated 4-bedroom farmhouse on beautiful vineyard - Great location.

Jamesport

16% off
NZ$10,363
for 7 nights, 1 home
NZ$1,480 per night
includes taxes & fees
Newly renovated 4-bedroom farmhouse on beautiful vineyard - Great location.
Canoe Place
Canoe Place, 3 mins walk down the road. Enjoy dinner, drinks and spa
View from deck with gas barbque, eating area, outdoor furniture.
Shinnecock Canal - 2 Blocks walking.
Exceptional
(30 reviews)

Family/pet friendly Hampton Bays home walking distance to beaches & restaurants

Hampton Bays

8% off
NZ$5,814
for 7 nights, 1 home
NZ$831 per night
includes taxes & fees
Family/pet friendly Hampton Bays home walking distance to beaches & restaurants

  • Peace of mind

    Our Book with Confidence guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Travel to scenic South Jamesport

The beaches and surrounding scenery provide a peaceful ambience to your holiday home in South Jamesport. Travellers appreciate the boating in this scenic city. If you're looking for accommodation options with space to entertain friends and family, HomeAway has plenty of options to choose from. Many rental homes offer full kitchens and laundry facilities, perfect for big groups.

Activities and attractions in South Jamesport

Are you hoping to find attractions to visit during your stay? Venture out of your cosy holiday rental and experience everything that South Jamesport has to offer. Here are some of the major attractions to see, all within 30 miles (48.2 km) of the city centre:

  • Jamesport Vineyards (1.3 mi / 2.1 km)
  • Martha Clara Vineyards (3.3 mi / 5.2 km)
  • Macari Vineyards (3.5 mi / 5.6 km)
  • Safari Adventure (5.5 mi / 8.8 km)
  • Peconic Bay Winery (7.6 mi / 12.2 km)
  • Shinnecock Hills Golf Course (7.8 mi / 12.5 km)

Exploring the natural landscape of South Jamesport

Whether you're looking for fun outdoor activities or just want to appreciate the scenery, South Jamesport is a great spot to appreciate mother nature. Here are a few of the area's most eye-catching natural features, all within 30 miles (48.2 km) of the city centre:

  • Meschutt Beach (4.9 mi / 8 km)
  • Tiana Beach (8.1 mi / 13 km)
  • Ponquogue Beach (8.2 mi / 13.2 km)
  • Shinnecock East County Park (8.5 mi / 13.6 km)
  • Cooper's Beach (10.3 mi / 16.6 km)
  • Crescent Beach (14.2 mi / 22.9 km)

Travelling to and around South Jamesport

The nearest airport is in Westhampton, NY (FOK-Francis S. Gabreski), located 7.3 mi (11.8 km) from the city centre. If you're unable to find a flight that fits your schedule, you can also fly into Shirley, NY (WSH-Brookhaven Calabro), which is 17.2 mi (27.7 km) away.

Frequently asked questions

What is the best area to stay in South Jamesport when booking a holiday rental?
When considering a holiday rental in South Jamesport, a popular area to stay is near the charming waterfront and the scenic beaches. This picturesque neighbourhood offers a tranquil atmosphere, ideal for those looking to unwind and enjoy the beauty of nature. The area is dotted with a variety of properties, providing choices that suit different preferences and budgets.Staying in this vicinity allows easy access to the beautiful beaches, where visitors can bask in the sun or take leisurely strolls along the shore. Additionally, the nearby vineyards are a delightful attraction, offering wine tastings and tours that showcase the local produce.
Where are the best areas for renting a beach house in South Jamesport?
For renting a beach house in South Jamesport, the area along the picturesque Peconic Bay is an excellent choice. This location offers a selection of holiday rentals with stunning water views and easy access to sandy beaches. Many properties here come equipped with amenities such as spacious decks, outdoor grills, and fully stocked kitchens, making them ideal for families or groups looking to enjoy a seaside getaway.The nearby South Jamesport Beach is a popular spot for sunbathing and swimming, and rentals in this vicinity often feature private beach access or proximity to the bay, enhancing the beach experience. Additionally, visitors can explore local attractions, including charming wineries and farms, which provide a taste of the region's agricultural heritage.In the surrounding areas, you can find quaint cottages and modern homes that often include convenient amenities like air conditioning, Wi-Fi, and outdoor showers, suiting those looking to wash off the sand after a day by the water.
What is the most popular type of holiday rental accomodation in South Jamesport?
In South Jamesport, holiday houses are the most popular type of holiday rental, with around 14 available in the area. These homes typically offer spacious interiors, multiple bedrooms, and fully equipped kitchens, making them ideal for families or groups. Many also feature private outdoor spaces, such as decks or gardens, where guests can relax and enjoy the pleasant surroundings. Additionally, several cottages can be found, which provide a quaint and charming alternative for those seeking a more intimate setting.
Are there any family house rentals in South Jamesport?
In South Jamesport, there are several family-friendly house rentals available, making it an appealing destination for those travelling with children. The area is known for its charming residential neighbourhoods, where visitors can find homes featuring spacious living rooms, fully equipped kitchens for preparing family meals, and outdoor areas superb for play or relaxation. Many properties also offer amenities such as Wi-Fi and air conditioning to ensure a comfortable stay.Nearby, families can enjoy the picturesque views along the Long Island Sound and take advantage of the local parks, where children can enjoy outdoor activities. The proximity to the beaches provides additional opportunities for fun, such as swimming and building sandcastles.
Can I rent a holiday home with a pool or hot tub in South Jamesport?
In South Jamesport, there are several holiday homes available for rent that feature pools and hot tubs, making it an appealing destination for those seeking relaxation and leisure. This quaint area, located on the North Fork of Long Island, offers a picturesque setting with easy access to beautiful beaches along the Peconic Bay.Travellers can expect rentals equipped with amenities such as private swimming pools, hot tubs, and spacious outdoor areas ideal for barbecues and family gatherings. Many properties also include fully equipped kitchens, allowing guests to prepare meals and enjoy them al fresco in the pleasant surroundings.
Are there pet-friendly house rentals in South Jamesport?
In South Jamesport, there are several pet-friendly house rentals available, making it a suitable destination for travellers with furry companions. The area offers a charming mix of coastal and rural settings, with many properties featuring amenities such as spacious yards, fully equipped kitchens, and comfortable living areas, ideal for families or groups.Rentals in this region often showcase outdoor spaces, great for pets to enjoy, and some may even have features like patios or decks for relaxing in the fresh air. South Jamesport itself is known for its proximity to beautiful beaches and scenic spots, allowing for enjoyable walks with pets along the shoreline.
Are there any remote work holiday rentals in South Jamesport?
In South Jamesport, there are several remote work holiday rentals available, with around 14 options to choose from. This quaint area offers a serene environment for those looking to balance work and leisure. Many of the properties are equipped with essential amenities to support remote working, including reliable Wi-Fi, dedicated workspaces with desks and chairs, and access to printer facilities.Travellers can expect comfortable accommodations that often feature spacious living areas, well-equipped kitchens for meal preparation, and outdoor spaces for relaxation during breaks. The surrounding area is known for its peaceful charm, with proximity to beautiful beaches and local attractions, making it an ideal setting for both productivity and enjoyment. To help narrow your search, insert your dates and apply the "WiFi" filter on Bookabach.
What are popular rental amenities in South Jamesport?
In South Jamesport, popular rental amenities include well-equipped kitchens, allowing travellers to prepare their own meals during their stay. Many properties also feature decks or patios, providing a pleasant outdoor space to relax and enjoy the scenic surroundings. Onsite parking is commonly available, making it convenient for those arriving by car. Additionally, rentals often come equipped with coffee and tea makers, superb for enjoying a warm beverage in the mornings. Some properties also boast gardens, offering a tranquil setting for guests to unwind after a day of exploration.
When is the best time to visit South Jamesport for a holiday rental?
The best time to visit South Jamesport for a holiday rental is during the peak season from March to May, with May being particularly popular among travellers. This period is ideal for those seeking a delightful escape, as the weather warms up and outdoor activities abound. Visitors can enjoy leisurely strolls along the picturesque beaches, partake in local festivals, and savour the fresh seafood that the region is known for.As temperatures typically range from 10 to 20 degrees Celsius in May, the climate is pleasantly mild, making it superb for beach outings and sightseeing. The blooming landscapes and vibrant local life during this time create a friendly space for families and couples alike, ensuring that there are plenty of activities to engage in.For those looking for a more affordable option, consider visiting in December. While the tourist activity may be lower, this month offers a unique charm with holiday decorations and a quieter ambiance, making it an excellent time for those who appreciate a more serene experience.
What are the top attractions in South Jamesport?
In South Jamesport, visitors can enjoy a serene coastal experience with several attractions along the scenic North Fork of Long Island. The picturesque beaches, such as the local Jamesport Beach, offer a tranquil setting for sunbathing and swimming. Nearby, the gorgeous vineyards and wineries in this wine country region provide opportunities for wine tasting and tours, making it a great destination for oenophiles.The charm of South Jamesport is further enhanced by its proximity to the Peconic River, where guests can enjoy various water activities, including kayaking and paddleboarding. Additionally, the area boasts charming local shops and restaurants that showcase fresh seafood and farm-to-table cuisine, allowing visitors to savour the local flavours. The nearby Long Island Sound also offers beautiful views and is a great spot for picnics or leisurely strolls along the shore.
Are all fees included in the South Jamesport holiday homes prices shown on Bookabach?
Bookabach provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
Are there any South Jamesport holiday homes with parking?
Bookabach offers a wide selection of holiday homes in South Jamesport with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Are there any discounts for South Jamesport holiday homes?
You can find great discounts on holiday homes in South Jamesport on Bookabach, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for last-minute bookings, and early-bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Can I change or cancel my South Jamesport holiday home booking on Bookabach?
To find South Jamesport holiday rentals with free cancellation, just use Bookabach's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Whether you're adjusting your plans or looking for flexible payment options, Bookabach makes it easy to book with confidence.
Can I find long-stay holiday homes in South Jamesport?
A long-stay holiday home in South Jamesport is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Bookabach?
Bookabach's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favourites, and build the perfect itinerary together.
How early should I book a South Jamesport holiday home?
Book your South Jamesport holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Bookabach booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in South Jamesport?
Prices for holiday homes in South Jamesport vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Bookabach offers something for every taste and budget, from affordable homes in South Jamesport to more spacious homes.
What can I expect from Bookabach customer service and Bookabach Care™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, Bookabach Care™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Bookabach customer service is available 24/7 to support you every step of the way. Bookabach also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is Bookabach Care™ and how does it work?
Bookabach's mission is to help guests relax, reconnect, and enjoy precious time together. With Bookabach Care™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
Why should I join Bookabach as a host?
Joining Bookabach as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Bookabach makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Bookabach handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.