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Vacation rentals in Southampton

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Quick stats about vacation rentals in Southampton

  • Total vacation rentals

    Explore 610 vacation rentals in Southampton

  • Nightly prices starting at

    Southampton vacation rentals start at $98 CAD per night before taxes and fees

  • Verified guest reviews

    Over 8,940 verified reviews to help you choose

  • Family-friendly vacation rentals

    530 properties offer extra space and kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 240 rentals that welcome pets

  • Vacation rentals with a pool

    450 properties feature pools

  • Rentals with dedicated workspaces

    370 properties have a dedicated workspace

  • Wifi availability

    590 of Southampton vacation 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—averaging 4.9 out of 5!

Top-rated vacation rentals in Southampton

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

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Top guest favourite
Home in Southampton
5 out of 5 average rating, 42 reviews

Charming House In The Village

Keep it simple at this peaceful and centrally-located place in the Heart of Southampton Village Escape to this delightful house nestled in the heart of Southampton Village, offering a perfect blend of charm, comfort, and convenience. Situated just moments away from the beach, and walking distance to restaurants and entertainment. 🏠 Entire First Floor (Private) 🛏️ Bedrooms: 2
🛁 Bathrooms: 1
🌳 Outdoor Space: Private Garden 
🔥 Fire Pit and BBQ 🚘 Two Parking Spaces 👨‍🍳 Fully Stocked Kitchen

Guest favourite
Home in Hampton Bays
4.85 out of 5 average rating, 155 reviews

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!

Top guest favourite
An inviting heated pool is surrounded by lounge chairs, illuminated softly by outdoor lighting against the evening sky. The manicured grass adds a serene touch, while a patio area with tables and umbrellas offers space for relaxation and enjoyment.
Apartment in Southampton
5 out of 5 average rating, 33 reviews

Southampton Village Near Ocean & Shops - Suite "A"

Our suite "A" 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 apartment. 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.

Superhost
Home in Shinnecock Hills
4.86 out of 5 average rating, 74 reviews

Chic Southampton Home. Mins to Village and Beach!

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.

Guest favourite
A garden archway adorned with climbing greenery frames a stone pathway. The path leads through a flower-filled area, featuring a small seating arrangement made of natural stone and flowerpots. Lush foliage surrounds the space, contributing to a serene outdoor atmosphere.
Apartment in Southampton
4.88 out of 5 average rating, 41 reviews

Southampton Village Apartment

Peaceful & Super Clean Duplex Private Bathroom Bright Kitchenette/ Lounge area with Sofa Lower Level Bedroom, Comfy Double Bed with all Cotton Linens A Great Place to Cocoon (Sofa folds to Bed, see below) 20-30 min walk to LIRR, Hampton Jitney Shopping, Restaurants, Clubs & Bars 1.5 miles to Beautiful Ocean Beaches Rates are for 2 guests in 1 bed 3rd guest $150 per night 2 sleeping separately $75 per night for the first 2 nights Airbnb service fee of 15.5% is included.

Guest favourite
Home in Southampton
4.95 out of 5 average rating, 20 reviews

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.

Superhost
The living area is characterized by high vaulted ceilings and large windows allowing natural light. A sofa with light cushions is centered around a wooden coffee table on a neutral rug. A decorative fireplace is framed with a modern mantle, adding warmth to the space.
Home in Southampton
4.83 out of 5 average rating, 219 reviews

Stylish & Chic w hot tub/ Near Beaches & Village

Stylish Hamptons retreat just minutes from Southampton Village and the area's best beaches. Enjoy a private backyard with a brand-new oversized deck, new outdoor shower, hot tub, fire pit, and sun lounge - perfect after a day at the beach. Cozy up by the indoor fireplace on cooler evenings. Next to Shinnecock Hills Golf Club, 15 minutes from Poxabogue, and close to Wölffer Estate, Duck Walk, Channing Daughters, Scallop Pond Preserve, and Elizabeth A. Morton Wildlife Refuge.

Guest favourite
A serene view of calm water featuring kayakers enjoying a sunny day. The distant shoreline is dotted with houses, creating a relaxed coastal atmosphere. Clear blue skies reflect on the water, enhancing the peaceful scene.
Home in Shinnecock Hills
4.95 out of 5 average rating, 201 reviews

Southamp Waterview, DogsFREE! Kayaks, Ping-Pong

Beachy casual feel-good home easily located at the entrance to The Hamptons. Lovely views of Bay, Nightly Sunsets & birds! Launch our Kayaks at street's tiny beach flowing from Cold Spring Pond into Bay. Or cuddle by the fireplace and play our many available games. We provide soft sheets & towels for the showers and & beach...priding ourselves on your comfort! Our Private-Pool is heatable & plant-surrounded with Outdoor Shower.

Guest favourite
A cozy living area features a comfortable sofa adorned with neutral-toned cushions. A large television is mounted on the wall. Natural light filters through multiple windows, brightening the space. A small side table and an armchair complement the seating arrangement, creating an inviting atmosphere.
Apartment in Southampton
5 out of 5 average rating, 37 reviews

Southampton apt walk to village

Enjoy easy access to everything from this perfectly located apartment in Southampton Village. You are just a 10-minute walk to downtown and 1.5 miles to our glorious village beaches. We are centrally located to all of the Hamptons, Sag Harbor, Montauk, and the North Fork. Ideal for nature lovers, our garden is a pollinator sanctuary home to birds, 🐝, 🦋, and other wildlife. We love pets, so your furry baby is welcome!

Guest favourite
Home in Southampton
4.91 out of 5 average rating, 11 reviews

Southampton Village Escape

Welcome to 86 Hildreth St, a 3BR, 3.5BA gem steps from Main St. Built in 1930 and thoughtfully updated with central AC and bright, sun-filled interiors, it blends charm and comfort. The yard features a gunite pool and bluestone patio. Bike to Coopers Beach, grab lunch at Citarella, hit SLT, and make it to Sant Ambroeus for dinner. It’s walkable village life with a great Hamptons vibe.

Guest favourite
A wide sandy beach stretches towards the horizon, where soft waves gently lap at the shore. Tall lifeguard stands are positioned along the beach, with a few distant figures walking. The sky features a gradient of muted colors as the sun sets, creating a serene atmosphere.
Apartment in Shinnecock Hills
4.95 out of 5 average rating, 241 reviews

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 request—please let me know the day before you arrive

Top guest favourite
Apartment in Southampton
4.89 out of 5 average rating, 123 reviews

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

KitchenWifiPoolFree parking on premisesAir conditioning

Stay near Southampton's top sights

Cooper's Beach, Southampton

233 locals recommend

Parrish Art Museum

326 locals recommend

Duck Walk Vineyard

103 locals recommend

Southampton Arts Center

50 locals recommend

Agawam Park

49 locals recommend

Hank's Pumpkintown

43 locals recommend

Other great vacation rentals in Southampton

Guest favourite
An outdoor seating area features a round black table accompanied by a chair with a cushion. The tiny house is visible in the background, showcasing its modern black exterior and large windows, surrounded by trees and a gravel landscape.
Tiny homes in Southampton
4.98 out of 5 average rating, 65 reviews

Hamptons Tiny House!

Guest favourite
A light-filled living area features a comfortable sectional sofa with decorative pillows. A coffee table rests on a textured area rug, accompanied by framed art on the white walls. Natural light enters through a window overlooking greenery, accentuating a serene environment.
Apartment in Southampton
4.91 out of 5 average rating, 68 reviews

Spacious One Bedroom Apt, Close to Beaches

Guest favourite
Home in Southampton
4.92 out of 5 average rating, 62 reviews

Luxury Village Beach House 4Br/4Bath

Guest favourite
A cozy living area features a yellow sofa and a comfortable seating arrangement with diverse cushions. Natural light filters through the window, illuminating the wooden floors and layered textures. Decorative art pieces adorn the walls, contributing to the personal and eclectic aesthetic.
Apartment in Southampton
4.91 out of 5 average rating, 23 reviews

Vintage Village Apartment

Guest favourite
A sparkling pool reflects the clear blue sky, surrounded by a sleek stone patio. Lounge chairs are positioned nearby, inviting relaxation. Lush greenery and vibrant gardens frame the space, enhancing the private outdoor setting.
Home in Shinnecock Hills
4.98 out of 5 average rating, 55 reviews

Luxury Hamptons Poolside Paradise w/ Outdoor Sauna

Top guest favourite
A spacious lawn is bordered by tall trees, providing a natural frame for the cottage. The vibrant green grass leads to a serene waterfront, where the lake reflects the sunlight. The peaceful setting invites relaxation and outdoor activities.
Cottage in Water Mill
4.97 out of 5 average rating, 79 reviews

Head of Pond House - Waterfront Cottage

Guest favourite
A bright and airy outdoor space features a long pool bordered by lounge chairs and greenery. The white house stands in the background, with large windows reflecting the blue sky. An umbrella provides shade beside the pool, promoting relaxation.
Home in Shinnecock Hills
4.98 out of 5 average rating, 60 reviews

Luxe Southampton Home w/Pool 5 Min To Town & Beach

Top guest favourite
Home in Shinnecock Hills
5 out of 5 average rating, 31 reviews

Dream Colonial with Heated Pool Southampton, NY

When is the best time to visit Southampton?

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Avg. price$920 CAD$858 CAD$819 CAD$899 CAD$1,272 CAD$1,569 CAD$1,284 CAD$1,393 CAD$936 CAD$767 CAD$835 CAD$834 CAD
Avg. temp0 °C1 °C4 °C10 °C15 °C21 °C24 °C23 °C19 °C13 °C8 °C3 °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.

Destinations to explore