Discover Your Perfect Town of Southampton Vacation Homes

Town of Southampton Luxury Rentals

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Town of Southampton Pet Friendly Vacation Rentals

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9.5 (134 Reviews)
Bed & Breakfast
Aria & Mare Hamptons
  • Air Conditioner
  • Parking
  • Pet Friendly
View Availability
10.0 (27 Reviews)
House
The Cooper-Burke House
  • Air Conditioner
  • Parking
  • Pet Friendly
View Availability
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Why Choose Rent By Owner for your Town of Southampton Vacation Rental Homes?

What makes our Vacation Rentals special?

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Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
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Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
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Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.

Best Times to Visit Town of Southampton

When should you plan your Vacation Rentals stay?

Choosing the optimal time to visit ensures you enjoy the best experiences and availability in this destination, allowing you to make the most of your stay in the region's inviting vacation rentals.

Peak Season Highlights

summer
Summer (June to August)

During these warm months, the area experiences its highest influx of visitors seeking beachside relaxation and outdoor activities, making it an ideal time to enjoy your stay in the region's premier vacation rentals.

Average Temperature Daytime: around 75-85°F - Nighttime: mid 60s°F
autumn
Fall (September to November)

The early fall offers pleasant weather and fewer crowds, providing a perfect setting to explore the scenic landscapes while enjoying comfortable temperatures in this sought-after summer destination.

Average Temperature Daytime: mid 70s°F - Nighttime: upper 50s to low 60s°F

Off-Season Highlights

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Winter (December to February)

The quiet winter months see a slowdown in visitors, creating a peaceful atmosphere ideal for those looking to unwind in cozy vacation rentals without the typical tourist hustle.

Average Temperature Daytime: around 40-50°F - Nighttime: high 20s to mid 30s°F
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Early Spring (March to April)

As the region transitions into spring, fewer travelers arrive, offering a tranquil escape where you can enjoy mild temperatures and the area's natural beauty at a relaxed pace.

Average Temperature Daytime: mid 50s°F - Nighttime: mid 30s to low 40s°F

Weekly Weather Forecast for Town of Southampton

How to Book Your Town of Southampton Vacation Rental Home

What's our booking process?

Our platform allows you to browse a curated selection of vacation rentals. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.

Booking Steps

01

Search Properties

Use our filters to find the right property that fits your needs.
02

Select a Rental

Click on your preferred listing to view details, amenities, and pricing.
03

Book Online

Follow the link to finalize your reservation directly on the partner’s website.

Explore and book the perfect rental in Town of Southampton

More Top-Rated Vacation Rentals in Town of Southampton Area

Common Vacation Rentals Amenities

What amenities can you expect?

Our Vacation Rentals are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:

Indoor Features

  • Fully-equipped kitchens with modern appliances
  • Comfortable living areas with flat-screen TVs
  • Free Wi-Fi for staying connected
  • Air conditioning and heating for year-round comfort
  • In-unit washers and dryers for convenience
  • Luxurious bedrooms with premium bedding
  • Spa-like bathrooms with soaking tubs or walk-in showers

Outdoor Amenities

  • Enjoy outdoor grilling with a private barbecue setup for alfresco dining.
  • Relax by a sparkling swimming pool to unwind after a day exploring the region.
  • Take advantage of spacious patios or decks perfect for entertaining guests.
  • Benefit from well-maintained gardens and lush landscaping that enhance your outdoor experience.
  • Make use of a fully equipped outdoor kitchen area to prepare meals in the fresh air.
  • Unwind on comfortable loungers surrounding the pool or yard areas.
  • Access dedicated outdoor dining spaces ideal for enjoying meals under the sun or stars.

Top Attractions Around Town of Southampton

What attractions are nearby?

Within this scenic region, you can enjoy a variety of outdoor activities such as beach outings, boating, and exploring local parks, all offering the perfect way to immerse yourself in the natural beauty of the area surrounding your vacation rental.

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Family Activities

  • Coopers Beach: Enjoy a relaxing day on this renowned family-friendly beach, perfect for swimming, sandcastle building, and picnicking with your loved ones.
  • Southampton Cultural Center: Engage in educational and fun activities at this cultural hub offering art exhibits, workshops, and performances suitable for all ages.
  • Sag Harbor Life-Saving Service Station Museum: Explore maritime history through interactive exhibits that provide an entertaining and educational experience for the entire family.
  • Shinnecock Canal: Take a scenic walk or a boat tour along the canal to appreciate the tranquil waters and natural beauty that define this part of the region.
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Adult Activities

  • Visit the Southampton Arts Center: Engage with local culture through exhibitions, performances, and art classes at this vibrant community hub in the region.
  • Explore Cooper's Beach: Relax on one of the area’s most popular beaches, renowned for its pristine sands and scenic views, perfect for a leisurely day by the sea.
  • Enjoy a wine tasting tour: Discover the region’s renowned vineyards and wineries, offering tastings and tours that showcase the area's celebrated viticulture.
  • Play a round of golf: Experience world-class golf courses here, featuring stunning landscapes that cater to both beginners and seasoned enthusiasts.

Other Places to Stay in Town of Southampton, NY

South Fork
South Fork Vacation Rentals
Southampton
Southampton Vacation Rentals
Hampton Bays
Hampton Bays Vacation Rentals
Sag Harbor
Sag Harbor Vacation Rentals
Noyack
Noyack Vacation Rentals
Tuckahoe
Tuckahoe Vacation Rentals
North Sea
North Sea Vacation Rentals
Westhampton Beach
Westhampton Beach Vacation Rentals
Shinnecock Hills
Shinnecock Hills Vacation Rentals
Water Mill
Water Mill Vacation Rentals
Village of Southampton
Village of Southampton Vacation Rentals
East Quogue
East Quogue Vacation Rentals
More Places to Stay Near Town of Southampton

Town of Southampton Travel Tips

How Can You Make the Most of Your Stay?

  • Plan Your Activities in Advance: Take advantage of the area's popular spots by booking activities and dining reservations early to ensure you make the most of your time here.
  • Explore Local Beaches and Nature Spots: Use your stay to discover the region's scenic beaches and nature trails, ideal for relaxation and outdoor adventures.
  • Discover Unique Local Culture: Immerse yourself in the local art galleries, shops, and events to experience the authentic vibe of this destination.
  • Choose Convenient Accommodation Near Key Attractions: Opt for vacation rentals close to main attractions or transportation hubs to maximize convenience during your visit.

Transportation Options

  • Car Rentals: Renting a car offers flexibility to explore the area at your own pace, making it an ideal transportation option during your stay in this destination.
  • Public Transit Services: Buses and local shuttles provide affordable and convenient transportation for getting around the region without the need for a private vehicle.
  • Taxi and Ride-Sharing: Taxis and ride-sharing services like Uber and Lyft are readily available, offering quick and reliable transportation within the area.
  • Biking and Walking: The area features scenic bike paths and walkable streets, allowing you to enjoy the natural beauty while exploring locally on foot or by bicycle.

Local Customs Options

  • Traditional East End Hospitality: Embrace the region’s welcoming spirit by respecting local customs of politeness and friendliness, which are highly valued in the area’s social interactions.
  • Respect for Nature and Environment: Practice eco-conscious behaviors, such as minimizing waste and preserving the pristine beaches and natural landscapes that define this destination’s charm.
  • Local Dining Etiquette: When dining at locally cherished establishments, it’s customary to appreciate farm-to-table cuisine and engage politely with staff who take pride in their regional produce.
  • Celebration of Arts and Culture: Show appreciation during community events or art exhibitions, reflecting the area's rich cultural heritage and support for local artisans and performers.

Frequently Asked Questions About Town of Southampton?

1. What are the top vacation rentals in Town of Southampton?

There are a lot of options in Town of Southampton. If you plan on staying in the Town of Southampton area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Town of Southampton:

2. How many vacation rentals have private pools in Town of Southampton?

There are 1475 vacation rentals with private pools near Town of Southampton. Top-rated RBO homes that have access to a swimming pool include:

3. Which vacation homes in Town of Southampton are best for families?

If you are looking for a family-friendly vacation home in Town of Southampton, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Town of Southampton:

4. How many Rentbyowner vacation rentals are available in Town of Southampton?

Currently, the total number of properties listed by Rent By Owner in 2025 is over 2921 in the Town of Southampton area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Town of Southampton. 

5. What is the cancellation policy for vacation rentals in this area?

Cancellation policies vary by property, so be sure to review the specific listing details. You can find this information on the property page or contact the owner directly for clarification.

6. Are there any house rules I should be aware of when booking a vacation rental here?

Yes, each property may have its own house rules, including pet policies, smoking restrictions, and check-in/check-out times. These details are typically listed in the property description or provided by the host upon booking.

7. How do I ensure my reservation is confirmed for a vacation rental in this region?

Reservations are generally confirmed once you complete the booking process and receive a confirmation email. For added assurance, verify the listing’s status and communicate with the host if needed.

8. Do vacation rentals in this destination provide amenities like Wi-Fi and air conditioning?

Most properties in the area offer essential amenities such as Wi-Fi and climate control. However, it's best to check the amenities list on the individual property page to confirm before booking.

9. What should I do if I need assistance during my stay in a vacation rental here?

If you encounter issues during your stay, contact the property host directly through the messaging platform. Additionally, support services are available to help resolve any booking or accommodation concerns.

Town of Southampton Top Rated Vacation Rentals

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