Holiday rentals in Southampton
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Top-rated holiday rentals in Southampton
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Southampton apt walk to village
Enjoy easy access to everything from this perfectly located Apt in Southampton Village . 10 minutes walk to downtown restaurants, bars and shopping 1.5 miles to our Glorious Village Beaches. located in a diverse, local Southampton Village neighborhood, centrally located to all Hamptons, Sag Harbor and Montauk & the North fork This place is perfect for a natural lover our garden is a pollinator sanctuary home to birds ,đ , đŚ , and other creatures . We love pets so your furry baby is welcome
Hamptons Oceanfront Oasis
Escape the hustle & bustle of city life and unwind at this stunning home in the Hamptons. The oceanfront oasis is the perfect way to wake up to ocean views, beaches and nearby restaurants. Relax on our spacious deck - perfect for morning coffees & sunset cocktails. It is just a short drive to the train station & only 15 minutes from the airport for quick getaways. For your safety, the home is equipped with Ring cameras and one-use key codes. Book now and experience the ultimate Hamptons escape!
Walk to US Golf Open! Southampton Lux Stay
Welcome to your perfect Hamptons getaway! This sun-filled, architecturally unique home is ideal for a summer retreat or a cozy weekend escape. Offering modern furnishings, and an open floor plan, this space is perfect for small groups. Whether you're enjoying the crisp evenings of early spring, sun-drenched summer days, or the vibrant fall season, this home is a serene escape year-round. Cozy up by the fire, relax on the sun-soaked balconies, or unwind in the beautifully renovated pool house.
Just renovated Southampton retreat w/ heated pool
JUST RENOVATED! INQUIRE ABOUT MONTHLY RENTALS! Come and enjoy with family and friends your own beautiful house in Southampton. 5-minute drive to Cooperâs Beach and to Southampton Village. Enjoy beautiful ocean beaches, have brunch in the Village, swim in your 32â heated salt water pool, enjoy a BBQ on your patio under the shadow of a Japanese Maple, indulge in a quiet evening with a book by the fireplace, or take advantage of the home office while your family & friends enjoy the property.
Southampton Village Near Ocean & Shops - Studio B
Our studio "B" features Location, location, location! You are so close to everything, you can leave your car behind! Just two blocks from historic Main Street. Ocean beach is less than a mile at the end of the road. Brand new lower level studio. Private entrance. Enjoy sipping wine outdoors in a private sitting area. Off street parking for one car available. Level 2 EV charger w/J1772 plug available for overnight charging. On the premises for use is a heated gunite pool & outside shower.
5 Star Rated Private Cottage Southampton/Sag Hrbr
The Honeycomb Cottage is a little retreat located on a lush acre of evergreens in Southampton rated 5 Star by every guest that has stayed. One block to Peconic Bay Beach - perfect for a day in the sun. A cozy space with TV, WiFi and Sun Deck. Luxury soaps provided, amazing shower and crisp white linens. Exclusive use of the Hot Tub for Cottage guests. Easy parking and located 15 minutes drive to Sag Harbor or Southampton Village. Koi pond with waterfall will sooth the mind and spirit.
Private & Cozy Cottage with short walk to beach!
Walking distance to Bay Beach & Rumba, & short drive to town & ocean. Quiet neighborhood, great for couples, King bed upstairs, bit of a steep staircase, so may not be suited for anyone with mobility challenges. Kayaks, paddle-boards, available to enjoy. Dog friendly with fenced in patio and doggy door. Private outdoor patio, with charcoal grill. A/C & Heat for year-round enjoyment. Easy to get in/out from the city. Close drive to visit Westhampton and Southampton Main Streets.
Hamptons WaterLiving-Dock, Kayak, Beach, EV charge
[FOLLOW US on INSTA @29watersedge] 1-mile from the beach, this child-friendly waterfront Southampton home is a perfect family getaway. Ready for watersports: kayak, paddleboard, boat, or jet ski. Walk down to the beach for a swim in the bay. At home, the backyard has it all: large dock, fire pit, swing/playset, hammock, grill, & oversized deck to take in the views. Surrounded by nature and water, you are just minutes from restaurants and shopping in Southampton Village &Sag Harbor.
Brand New Sun Filled Home
OUR HOUSE A beautiful newly renovated Southampton two story home with spectacular light, offering the best of indoor-outdoor living. A large deck off of the kitchen with small porches off of two primary suites and a small sitting area off the first floor junior suite. On almost one acre of land, there is plenty of peaceful space. Very central - two miles from the beach and town. Two car garage with built in electric vehicle charger. Gas fireplace. All appliances are brand new.
Enchanting Cottage in the Heart of Southampton Vil
Enchanting Cottage in the Heart of Southampton Village Escape to this delightful cottage nestled in the heart of Southampton Village, offering a perfect blend of charm, comfort, and convenience. Situated just moments away from the beach, restaurants, and entertainment, this retreat boasts private gardens and access to a refreshing pool. đď¸ Bedrooms: 1 â¨đ Bathrooms: 1â¨đł Outdoor Space: Private gardensâ¨đ Pool Access: Available (open MDW -LDW) đ Two Parking Spaces
Tiny Home in Prime Spot in Southampton Village
Located in the heart of Southampton Village, this intimate cottage is the perfect getaway! Nestled in an accessible, safe, and well-lit neighborhood, it is ideal for those with or without a vehicle. Only a 5 min. walk from the train station or to town, which includes premier shopping and restaurants. Enjoy nearby wineries, museums, golf, and pristine, top-ranked beaches. Be close to everything Southampton has to offer while enjoying absolute peace and quiet.
Sunny Southampton Studio
Newly renovated sun drenched, spacious studio in Southampton. Five minute drive to Main Street, while still in close proximity to some of the most beautiful beaches. Queen size bed and queen size pull out couch. Full kitchen with new appliances and full bathroom. BEACH PASS for Coopers beach is available upon advanced requestâplease let me know the day before you arrive
Popular amenities for Southampton holiday rentals
Stay near Southampton's top sights
Other great holiday rentals in Southampton
Hamptons Tiny House!
Luxury Southampton Home/outdoor Sauna/hottub
Swimming pool w/Hot tub Fire Pit Coffee Bar
Modern Southampton Cottage | Heated Pool & Peloton
Southampton Village Apartment
By US OPEN! Waterview, DogsFree! Kayaks, PingPong
5 Min Walk to 2026 US Open|Southampton|4 Bedrooms
Southampton Cottage
When is the best time to visit Southampton?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $851 SGD | $793 SGD | $757 SGD | $726 SGD | $902 SGD | $1,031 SGD | $1,187 SGD | $1,288 SGD | $865 SGD | $709 SGD | $772 SGD | $771 SGD |
| Avg. temp | 0°C | 1°C | 4°C | 10°C | 15°C | 21°C | 24°C | 23°C | 19°C | 13°C | 8°C | 3°C |
Frequently Asked Questions
What are the best places to stay in Southampton?
Vacation rentals near the beach, village area, and residential neighborhoods are frequently suggested. Many homes have easy access to local shops, green spaces, and coastal walks.
What are the best things to do in Southampton with kids?
Kids often enjoy exhibits at the Childrenâs Museum of the East End, beach outings, and biking village paths. Seasonal events, local playgrounds, and parks add to the family fun.
What are some of the best things to do in Southampton?
Enjoy the sandy stretches at Coopers Beach, browse local art at Southampton Arts Center, and learn history at the Southampton Historical Museum. In summer, farm stands and outdoor markets are frequently suggested stops.
How is the weather in Southampton?
Southampton has chilly winters around 25â44°F (-4â7°C) with frequent rain, and warm summers near 66â83°F (19â28°C) with coastal breezes. Spring and fall have mild temperatures; bring layers for changing conditions.
When is the best time to visit Southampton?
Late spring through early fall is often recommended for warmer beach weather, outdoor events, and lively markets. Off-season months have a quieter atmosphere and mild coastal walks.
What are the best places to visit in Southampton?
Coopers Beach is often recommended for its sandy shoreline, and the Southampton Historical Museum shares local heritage. The Parrish Art Museum draws visitors with regional and contemporary art exhibits.
What are some hiking trails in Southampton?
Explore shaded woodland trails at the Downs, stroll through nature on the Great Peconic Bay trails, or hike coastal paths around Mashashimuet Park. These areas have a mix of forest, beach, and freshwater views.
What are some family activities we can do in Southampton?
Families often explore the Childrenâs Museum of the East End, play in park areas, and visit local farms for fresh produce and seasonal events. Beach days, mini-golf, and bike rides are frequently recommended.
What are some of the best day trip ideas from Southampton?
Explore vineyard tours around Long Island, stroll antique shops in Sag Harbor, or enjoy nature preserves in nearby towns. Art museums and waterfront villages around the Hamptons region are frequently suggested.
Are there any pet friendly accommodations available in Southampton?
Southampton has many vacation rentals that welcome pets, especially near the beach and in residential neighborhoods. Look for listings with outdoor spaces or walking paths nearby.
What are some local tips for visiting Southampton?
Consider visiting farm stands early for fresh selections, use bikes to explore scenic local neighborhoods, and check village calendars for markets or arts events. Beaches can be busiest in summer, so arrive early for quieter moments.
What is Southampton known for?
Southampton is known for its scenic beaches, vibrant arts scene, and historic districts. Visitors often explore elegant estates, local galleries, and areas shaped by maritime history.
What are the best hidden gems to explore in Southampton?
Discover small art galleries tucked along village streets, quiet nature trails at Mashashimuet Park, and garden walks at the historic Rogers Mansion. Local bookshops and farm stands around Southampton invite relaxed browsing.
What are the best foods to try in Southampton?
Seasonal seafood, farm-fresh produce, and classic local pies are frequently suggested. Many visitors also enjoy lobster rolls, clam chowder, and baked goods from neighborhood bakeries.
What should I bring for a trip to Southampton?
Pack layers for changing coastal weather, comfortable shoes for exploring beaches and villages, and sun protection for outdoor activities. Consider bringing a rain jacket and reusable water bottle.
What is the nightlife in Southampton like?
Southampton has a mix of relaxed lounges, music bars, and restaurants that fill up in summer. Village hotspots host live entertainment, while waterfront spots have outdoor patios and local wines.
What are the most popular events or festivals in Southampton?
Southampton has arts fairs and seasonal film festivals, with farmers markets blooming in late spring and music events often filling summer weekends. Holiday parades and cultural celebrations are highlights around the village.
Are there family friendly vacation rentals in Southampton?
Southampton has many family-friendly vacation rentals, especially around quiet neighborhoods and near beaches. Look for homes with spacious yards, multiple bedrooms, or easy access to parks.
Quick stats about holiday rentals in Southampton
Total holiday rentals
Explore 550 holiday rentals in Southampton
Nightly prices starting at
Southampton holiday rentals start at $116Â SGD per night before taxes and fees
Verified guest reviews
Over 8,800 verified reviews to help you choose
Family-friendly holiday rentals
480 properties offer extra space & child-friendly amenities
Pet-friendly holiday rentals
Find 220 rentals that welcome pets
Holiday rentals with a pool
420 properties feature pools
Rentals with dedicated workspaces
340 properties have a dedicated workspace
Wifi availability
540 of Southampton holiday rentals include wifi access
Popular amenities for guests
Guests love Self check-in, Gym and BBQ grill across Southampton rentals
4.9 Average rating
Southampton stays are highly rated by guests â averaging 4.9 out of 5!
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- Beach
- Yale University
- Cooper's Beach, Southampton
- Fairfield Beach
- Mohegan Sun
- Southampton Beach
- Ocean Beach Park
- Robert Moses State Park Beach
- Foxwoods Resort Casino
- Mystic Seaport Museum
- Sunken Meadow State Park
- Hammonasset Beach State Park
- Sleeping Giant State Park
- Powder Ridge Mountain Park & Resort
- Yale University Art Gallery
- Long Island Aquarium
- Blue Shutters Beach
- WĂślffer Estate Vineyard
- Orient Beach State Park
- Ocean Beach
- Meschutt Beach
- Mystic Aquarium
- Dunewood
- Brownstone Adventure Sports Park