Holiday houses in The Hamptons

4.95 out of 5 average rating, 87 reviews

Cottage in Southampton

Modern Southampton Cottage | Heated Pool & Peloton

Modern Hamptons cottage with mid-century modern interior, our 3 bedroom/ 2 bathroom cottage is set on manicured grounds and perfectly equipped for your stay. Heated gunite pool (summer months only) with retractable cover, Peloton bike and Central Air throughout. Newly renovated kitchen with high end appliances, large outdoor deck perfect for entertaining with new Weber grill. Private driveway accommodates 4 cars. 4 adult bicycles. 8 min ride to Southampton village. 15 min to Coopers Beach.

4.95 out of 5 average rating, 435 reviews

Silver House: 3BR Home with Private Beach Access

Located on a half-acre property surrounded by tall oak trees, this three-bedroom, two-bathroom home is the perfect getaway. The house is part of the Clearwater Beach community with private beach access. The recently renovated kitchen and bathrooms are modern and minimal. Natural light floods the space throughout the entire house. Here is your perfect getaway from the chaos of city life The fireplace is NOT available for guest use. Early check-in and late check-out are NOT available in season

Superhost

4.87 out of 5 average rating, 208 reviews

HeatedSaltWaterPool, Walk2PrivateBeach, Yard4Dog

Meticulously cleaned home.Tranquil family neighborhood in historic artist's beach community.Heated saltwater pool.Wood burning fireplace.Private fenced-in backyard.Half mile to private bay beach. Bike great trails & savor delicious meals prepared in fully equipped kitchen.Enjoy Clearwater Beach's renowned sunset. Easy living home.We welcome all respectful guests.East Hampton's best restaurants are nearby.Smoke free.Small dogs permitted.Cell reception booster! Ask about EVcharger.RentalR-25-705

Guesthouse in Hampton Bays

4.97 out of 5 average rating, 191 reviews

WELCOME TO THE LOVE SHACK BY THE SEA

Escape the city, work in nature! Totally private cottage with garden views , central air and heated floors. 1 mile from pristine beaches and center of town, LIRR, Hampton Jitney, 3 large grocery stores, Starbucks, organic market, shopping & restaurants. King bed, cable TV, refrigerator w/ice, microwave, outdoor grill, private yard, Perfect for couples, solo, 1-2 small kids. We welcome small dogs for a $100 fee. Please message us with the size and type. Working couple/owners in main house.

4.97 out of 5 average rating, 32 reviews

Cottage in Southampton

Newly Renovated Towd Point Beach Treasure

This stylish modern chic beach home is situated by the waters edge and one of the most idyllic beaches in the Hamptons. Make this home your summer escape and enjoy the cozy interior with brand new furniture throughout, hand selected by a renowned Hamptons interior designer. Outside, relax in the gunite pool or take the scenic walk to the shore. Along Towd Point, you'll find gorgeous beach homes, friendly neighbors, summer vibes and sunsets that will create lifelong memories!

5 out of 5 average rating, 13 reviews

Home in East Marion

Kayaks ~ Bikes ~ Boards ~ 6mins> Greenport ~ 55"TV

★ "Beautiful hidden home on the water… enjoy the North Fork summer in style." Private beachfront property with 2 homes & views of Gardiner’s bay. ☞ Bikes + kayaks + paddle boards ☞ Wrap around balcony w/ seating ☞ Fully equipped + stocked kitchen ☞ Deck w/ lounging + water views ☞ Dedicated workspace + printer ☞ Master w/ king + bathroom ☞ 55” Smart TV + Xbox ☞ Indoor gas fireplace 6 mins → DT Greenport (cafes, dining, shopping) 13 mins → Orient Beach State Park ⛱

Guest suite in Sag Harbor

4.9 out of 5 average rating, 356 reviews

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 & AC. Working fireplace and spacious bathtub make for an ideal cozy and romantic getaway. Parking. Fully self contained and private.

4.97 out of 5 average rating, 29 reviews

Villa in East Hampton

SERENITY AT SHOREWOOD Luxurious Newly Renovated Mid Century Modern Home in East Hampton with Beach Car! Peaceful and stylish with three bedrooms, 3 1/2 baths, spectacular great room, huge deck, heated pool and more, less than four miles to the heart of East Hampton Village, world renowned for its restaurants, shopping and ocean beaches. A designer-curated architectural gem! Kick back and relax in this calm, stylish space.

4.86 out of 5 average rating, 111 reviews

Apartment in Montauk

Recharge at our Renovated ocean front unit

Looking for a relaxing weekend to recharge on the beach? Then this newly renovated, bohemian-chic, apartment is perfect for you. Imagine waking up every morning to beautiful unobstructed ocean views and ending your night with a drink in hand watching the sunset. If you’re lucky, you might see some whales or dolphins breaching in the water right off our private beach. We would love to host you for your Montauk beach getaway.

Superhost

Home in Rocky Point

4.93 out of 5 average rating, 107 reviews

Luxury modern farmhouse with heated pool & hot tub

*pool is now open! This beautiful modern farmhouse is located on a one-acre lot and features a custom designed open-concept living space with vaulted ceilings that opens directly into a pool area. Hidden behind a bookshelf, you'll find a gorgeous game room with a piano and a pool table that can be easily converted into a ping pong table or working space. Please note that we do not allow weddings and events at this time.

Apartment in Hampton Bays

4.97 out of 5 average rating, 109 reviews

Walk to Bay and Ocean-Newly Renovated

Newly renovated! Walking distance to beautiful bays , ocean beaches, restaurants and bars. Perfect Hamptons vacation getaway. Wine Country and Montauk are great day trips from this centrally located spot. Easily access Hampton Bays with public transportation via LIRR or Hampton Jitney, than a 3-5 minute Uber to apartment. Monthly stays will have cleaning service provided every two weeks.

4.88 out of 5 average rating, 243 reviews

Cottage in Montauk

Waterfront Cottage, Fort Pond MTK

Perfect cottage perched above Fort Pond with epic views and relaxed bohemian vibes. The cottage is private with a private deck on shared grounds with a fire pit, hammocks, paddle boards, kayak, and lake access. The grounds are expertly landscaped and take full advantage of fort pond views. We do live on the property full time and enjoy making our space a safe and clean environment.

Holiday rentals for every style

Get the amount of space that is right for you

Bungalows

Intimate homes, inviting architecture

Villas

Luxurious estates for the ultimate escape

Houses

A space that's all yours, with room for everyone

Popular amenities for The Hamptons holiday rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in The Hamptons

5 out of 5 average rating, 16 reviews

Renovated 4Bedroom Farmhouse Pool Steps from Beach

SarahRating, 5 stars8 months ago

We had such a lovely time at Morgan’s home! She was extremely responsive and even allowed us to check in early as well as leaving baby items for us to use. Our dog loved the fenced in yard and despite the rain ruining our pool plans, we had a cozy wonderful stay. We had an absolutely lovely stay and can’t wait to return next summer!

5 out of 5 average rating, 24 reviews

Walk to village and hidden from the hustle EH home

Sneha SusanRating, 5 stars14 months ago

Victors place was warm and cozy - the perfect retreat from the hustle and bustle of everyday life. It was private and made us feel right at home. Victors house is well stocked with all the required supplies. They have the Monopoly - Hampton edition which made it fun while driving around the Hamptons.

5 out of 5 average rating, 10 reviews

Home in Water Mill

Waterfront home next to the beach in Southampton !

ManuelaRating, 5 stars3 weeks ago

Our family of five just spent Memorial Day weekend at this house. The views and location are amazing. Rohit is very responsive and friendly. The house is very practical, super clean, very nice kitchen, everything is new. Hope to go back soon!

4.82 out of 5 average rating, 28 reviews

Historic East Hampton Home - Private Beach Access

KyleRating, 5 stars1 month ago

Elizabeth was a wonderful host - we traveled with a toddler and an infant and Elizabeth could not have been more accommodating. She was so responsive and friendly before and during the entire trip. The house and property are absolutely beautiful— you can’t beat being able to walk right down to the beach. Highly recommend!

5 out of 5 average rating, 8 reviews

Apartment in Southampton

Southampton apt walk to village

RoshniRating, 5 stars2 weeks ago

Had a lovely stay! Beautiful apartment with private entrance. The living spaces, bathroom, kitchen and bedroom were modern, very clean and had all the necessary amenities for a comfortable stay. The place is within walking distance of the train station and village. Would absolutely stay here again.

5 out of 5 average rating, 17 reviews

Home in Sag Harbor

Sag Harbor Village Waterfront

PeterRating, 5 stars1 month ago

This is a very clean and comfortable house with good quality linen and towels. There is minimal clutter and the place is well furnished with everything you need in the kitchen. The house gives off very good vibes. The view from the French windows across the deck to the little bay is exquisite. All in all, highly recommended.

4.93 out of 5 average rating, 30 reviews

Home in Southampton

Charming Village home in the heart of Southampton

BridgetRating, 5 stars5 months ago

An ideal location in Southampton, Lori’s house is clean, cozy and peaceful; we thoroughly enjoyed spending our New Years there!