
Vacation rentals in Southampton
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Top-rated vacation rentals in Southampton
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Relax into Coastal Life at a Sun-Drenched Sag Harbor Home
Take a bike ride to Havens Beach and feel the sand in your toes. Walk to explore the shops, restaurants and bars on the quaint Main Street of Sag Harbor. Repair to your sun drenched home away from home to enjoy a relaxed meal alfresco on the deck. Unwind under the umbrellas on the expansive deck surveying the private fenced in backyard. Take in all the amenities of a newly renovated home situated in the Hampton - recent updates include a furnished basement, ping pong table, smart TVs and sound system. Extra touches include beach towels, beach chairs, bikes, cooler, games and more. This beautifully renovated 3 BR, 2 Bath home is situated on a quiet street, with a fenced half acre yard. It is located less than a mile to the shops, bars and restaurants of Main Street and the Hampton Jitney stop with service to NYC. The open floor plan boasts an abundance of natural light with 4 skylights and large windows to bring the outdoors in. Brand new appliances, custom kitchen cabinets, large center island with bar stools are perfect for hosting friends & family. Central AC/forced air heating controlled by the Nest ensure your complete comfort. The master BR features a king bed and ensuite Bath with custom tile shower. The guest BRs have a queen bed and full bed respectively and share the hall bathroom with tub/shower. The large deck runs the length of the home and is perfect for al fresco dining & entertaining. Totally furnished with everything you need to enjoy yourself from the second you enter the home! We have four brand new adult bikes, helmets and locks for your enjoyment. Explore the village, bike to the beach or get some exercise while you're here. If you prefer to stay in, you'll find a games console / DVD player in the front room with a good selection of games and movies. Additionally, we provide 4 beach chairs, beach towels and a small cooler for your use. Enjoy! Guests have access to the entire house, backyard, deck, garage and driveway parking. We can be reached via cell or email and are very responsive. We will also have a friend who is local to the area who will be able to assist with any issues. Sag Harbor is the coolest, most authentic town in the Hamptons. Home to household names, the town retains its small-town charm and rustic maritime vibe. Browse the artsy, eclectic stores and strike up conversations in the coffee shops and local bars. Sag Harbor is a quaint, walkable town on the wharf with great restaurants and bars. The house is located less than a mile's walk into the main street. Beaches are accessible via bike or car. The Jitney stop from Manhattan is located on Main Street less than a mile from the house. There are taxis in the area available via phone for pick up. We provide four adult bikes, helmets and locks for your use.

Southampton Charmer, 5 bedrooms w pool - Location
This 5-bedroom home boasts en-suite baths and elegant furnishings. The gourmet kitchen features marble countertops and stainless steel appliances, leading to a dining area. The lower level includes a spacious seating area and a game room with toys. The second floor houses a master suite with stunning views and three additional en-suite bedrooms. Located minutes from the village center, with restaurants, shops, and beaches nearby. A heated pool invites you to relax and enjoy the comfort of home.

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!

Savor Ocean Sunsets at a Soothing Beachfront Haven
Newly renovated and featured as a top Airbnb by New York Magazine, 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. Stay on the property for swimming, beach walks, sunsets and BBQs - or venture out to enjoy all the North Fork has to offer.

Artists Sag Harbor Village Retreat
This light and spacious Sag Harbor Village studio apartment is a 10 minute walk from historic Main St. 5 minutes to Village beach. French doors open onto outdoor sitting area. Ideal for a fall or winter visit to explore the area during the quieter season. Main Street is lively and all restaurants are open. Central heat with it’s own thermostat controls & AC. Working fireplace and spacious bathtub make for an ideal cozy and romantic getaway. Parking. Fully self contained and private.

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.

Charming Southampton Light filled Cottage
Escape and relax in this beautiful tranquil Southampton retreat! Newly remodeled cottage just blocks from the water. The home is nestled on 1/2acre quiet park-like setting located at the end of a long gravel driveway. Enjoy the private outdoor space with a fire pit, outdoor dining table, new dual BBQ and lounge chairs. Inside, the large dining room table easily sits 8. This stylish Coastal farmhouse has all new beds and furniture. Complete with Wifi, Cable, AC and Nespresso maker!

PRIVATE BASEMENT APARTMENT WITH POOL IN SAG HARBOR
Beautiful basement apartment partially in-ground, with many windows and private entrance is located in Sag Harbor , 3 minutes from village and Heavens Bech by car or 15 minutes walking distance . The apartment has king size bed and comfortable sofa in the living room . In the kitchen you can find coffe maker , toaster , microwave, dishwasher, small fridge , hot plate for light cooking . Tv , WiFi , Airconditoining , access to pool from May till end of the September .
Tiny Home in Prime Spot in Southampton Village
Price drop! 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, and pristine, top-ranked beaches. Be close to everything Southampton has to offer while enjoying absolute peace and quiet.

Private Cozy Cottage with Pool / Private Beach
**POOL CLOSES SEPTEMBER 30TH** **POOL opens last week of May** This is a guest house for 1 or 2 adults. Its separate from the main house. Kids are allowed but must bring own sleeping arrangements. You do NOT have to do any chores before checking out. **PETS NOT ALLOWED** I hate to do this but someone ruined it for everyone. Max Occupancy: 4 Guests can only bring 1 vehicle since there is not enough room in the driveway

MONTAUK OCEAN FRONT!
Charming oceanfront Montauk locale with perfect proximity to all town activities! Fall asleep to the lull of ocean waves. Ocean view and steps to the sand and town! New kitchen, Queen bedroom,Queen sofabed in living area, new rain shower bathroom, plus a large front deck for al fresco dining! Perfect for families, and a girls weekend!

Oasis Hampton getaway
Located in the heart of southampton. 3miles away from main shopping areas.Room is newly remodeled and furnished . All upscale Ammenities. Electric toilet ,free WiFi, free Netflix , use of pool and bbq grill, fire pit, living room with 52”flat screen tv, kitchenette and dining area and driveway parking .
Popular amenities for Southampton vacation rentals
Stay near Southampton's top sights
House rentals in Southampton

Spectacular Southampton Retreat!

Contemporary house in the woods.

Brand new house with an all year round hot tub.

Relax Villa ,Hot tub /New pool,7min from the beach

Dune Road Steps to the Beach - 4 Bedroom Home

Beach House Feel - Newly renovated Backyard Oasis

Renovated Southampton Home+Pool

Dream Colonial with Heated Pool Southampton, NY
Other great vacation rentals in Southampton

Hamptons Tiny House!

Storybook Cottage Seconds to East Hampton Village

Peaceful Retreat in Immaculate Architect’s House

Charming Cottage in Historic Sag Harbor

The Quail’s Nest

Modern Southampton Cottage | Heated Pool & Peloton

Southampton apt walk to village

Sag Harbor Cottage, Walk to the Beach!
When is the best time to visit Southampton?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ﺩ.ﺇ1,836 | ﺩ.ﺇ1,836 | ﺩ.ﺇ1,895 | ﺩ.ﺇ2,068 | ﺩ.ﺇ2,571 | ﺩ.ﺇ2,938 | ﺩ.ﺇ3,382 | ﺩ.ﺇ3,669 | ﺩ.ﺇ2,464 | ﺩ.ﺇ2,020 | ﺩ.ﺇ2,200 | ﺩ.ﺇ2,196 |
| 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 Children’s 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 25–44°F (-4–7°C) with frequent rain, and warm summers near 66–83°F (19–28°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 Children’s 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 vacation rentals in Southampton

Total vacation rentals
Explore 490 vacation rentals in Southampton

Nightly prices starting at
Southampton vacation rentals start at ﺩ.ﺇ331 per night before taxes and fees

Verified guest reviews
Over 8,950 verified reviews to help you choose

Family-friendly vacation rentals
420 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 220 rentals that welcome pets

Vacation rentals with a pool
380 properties feature pools

Rentals with dedicated workspaces
300 properties have a dedicated workspace

Wi-Fi availability
480 of Southampton vacation rentals include wi-fi 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—averaging 4.9 out of 5!
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- Yale University
- Foxwoods Resort Casino
- Cooper's Beach, Southampton
- Fairfield Beach
- Southampton Beach
- Robert Moses State Park Beach
- Ocean Beach Park
- Mohegan Sun
- Sunken Meadow State Park
- Hammonasset Beach State Park
- Powder Ridge Mountain Park & Resort
- Long Island Aquarium
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- Yale University Art Gallery
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