Vacation rentals in Westhampton

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Top-rated vacation rentals in Westhampton

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Guest favourite

Guest suite in Hampton Bays

4.98 out of 5 average rating, 317 reviews

CHARMING OCEAN BUNGALOW

My ocean Bungalow is super well located in Hampton Bays. You will be 10 minutes away from the center of town where the Hampton Bays train station is. You also have Starbucks, Ride Aid, king Kullen, and great eateries at your fingertips. You will also have another two great supermarkets; Stop&Shop and Wild by Nature natural food store. You will be staying in a room with a feeling of a Junior Suite with approximately 400sq feet, a much larger area than a standard room. It has an attached small full bathroom, a living space that I call “home theater” with a 75” smart TV, a wet Bar with Coffee, Expresso and Tea, your own refrigerator. No heavy cooking is allowed indoors but I will offer a grill outside, for the most gastronomically inclined guests ... there’s no dining area but you are more welcome to use the dining table at the outdoor stone patio. One of the nicest thing about our location is that we are 5 minutes from Ponquogue Beach with excellent near by restaurants such as Oklands, Sundays on the Bay, on Beach Road and Dockers waterside on Dune Road. Meschutt beach is also a great location with live music throughout the summer, not a beach for surfers or adventure swimmers, since it’s on Peconic Bay, but on a plus side, there’s a full outdoor bar for adults, I love their Rum punch, and a full service snack bar, and a gift shop that sells beach gear... etc.

May 30 – Jun. 6

$383 CAD per night

Guest favourite

Cottage in Westhampton Beach

4.93 out of 5 average rating, 147 reviews

Cool Tiny Cottage Artist Loft!

He Loved All Things Sea & I Followed Suit. 38 Years Ago My Father Built This Very Special Artist Loft Cottage Retreat. This Tiny Home is One Of A Kind. Throughout The Years Guests & Family Have Come & Gone Creating Beautiful Memories. The Space Is Tranquil, Serene, Peaceful & Harmonious. It’s A Wonderful Romantic Space, Charming For Family Gatherings, or One For A Soul Heart In Transition. All Have Found Passion, Peace and Progress Here. The Cottage Boasts A Fully Fenced In Large Yard, Deck, Grill, Light & Airy Vaulted Ceiling In Living Room With A Chenille Slip Cover Queen Sleeper and Cool Lounger With Library Bookcase With Books And Stereo/CD/Cassette, Color TV & DVD. Staircase to Loft Full Bed & Cute Twin Bed Area. Very Clean & Decorated Adorably. Wifi. Linens & Kitchen equipped, Washer/Dryer. Dining Table for 4 W/Sliders to Deck. Outside Seating for 6 & A Gas Grill. Perfect Place for 2. Quiet At End Of St. 1.5 miles to Rogers Beach Dune Rd/Ocean. 1 Mile To Main Street Village. 15 min to North Fork Wineries & Farms. Agent owned.

Jan. 22 – 29

$395 CAD per night

Guest favourite

Apartment in Mastic

5.0 out of 5 average rating, 18 reviews

The Cozy Cellar | Private Art Deco Apartment

Centrally located 1.5 hours from NYC! We'd love to host you in our Cozy Cellar. Our Art Deco influenced basement apartment is 5 minutes from local groceries, 20 minutes to The Hamptons, 10 minutes from to Center Moriches, 8 minutes to Waterdrinker Farm and 30 minutes to Jamesport and the North Fork. Weekend getaways or Long term stays! We are just 14 minutes from Brookhaven Lab for those looking for a Corporate stay. Furry friends welcome for an additional fee (small fenced in private yard).

Mar. 18 – 25

$105 CAD per night

Guest favourite

Guesthouse in Hampton Bays

4.96 out of 5 average rating, 146 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.

May 31 – Jun. 7

$508 CAD per night

Guest favourite

Cottage in Westhampton Beach

5.0 out of 5 average rating, 15 reviews

Prime village location, walk to Main St, prvt yard

Vacationing in the Hamptons, in town for a wedding, a concert/show, wineries or work? Choose “The Cottage” located in a prime village location. WALK to coffee shops, Eckart’s Luncheonette, Main Street for cafés, boutiques, Westhampton Beach Performing Arts Center, Farmers Market, grocery store & CVS. Bike or drive to Rogers village beach (1.5 miles), passes provided or walk the bridges. Enjoy Kayaking rent at Stephens Marina, Yoga on a board in Quogue, 25-30 minutes from wineries/Southampton.

Nov. 10 – 17

$550 CAD per night

Guest favourite

Guest suite in Wading River

4.9 out of 5 average rating, 231 reviews

Beachy En Suite /Gateway to The North Fork

Adorable,quiet,clean, w private entrance, private bedroom and bathroom,breakfast nook and patio.We are located in a beach front town dubbed“Gateway to the North Fork”. Walking/driving directions to local beaches,15minute walk to our community beach(.6mi away).Niks deli nearby.Minutes by car to wineries breweries,farm stands,EastWind 2 mi,TangerOutlets15min away,35min to Hamptons,Greenport!Hosts live in adjoining house. Rarely need access to your hallway to get to our basement.Would arrange.

Jul. 27 – Aug. 3

$167 CAD per night

Guest favourite

Home in Hampton Bays

4.98 out of 5 average rating, 112 reviews

Beach House Feel - newly renovated backyard Oasis

You will love this sunny, completely renovated three bedroom ranch. It's beautifully decorated with beach and nautical themes throughout the house. You can cook or barbeque at home on your private deck or go out and enjoy the many award winning restaurants in the area. Come home from the beach or shopping and lounge by the pool. At night, gather around the fire pit while making smores or just admiring the stars. This house is perfect for families, couples, or a girls/guys getaway.

Jul. 19 – 26

$1,213 CAD per night

Guest favourite

Apartment in Hampton Bays

4.97 out of 5 average rating, 340 reviews

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.

Sep. 19 – 26

$408 CAD per night

Guest favourite

Apartment in Westhampton Beach

4.93 out of 5 average rating, 91 reviews

NEW, steps to the village 1 mile to Dune Road

Newly renovated, spacious apartment with separate entrance, on picturesque tree lined street This quaint space is steps from Main street, Farmer's Market, 1 mile to famous Hamptons Beaches. Numerous restaurants and shops are a short walk away. 42 inch HD TV with Chrome Cast for streaming TV and movies . Kitchenette stocked with all new dinner ware, glassware, coffee maker, microwave, toaster oven (no stove). We are COVID-19 compliant, wiping down all surfaces between guests.

Sep. 29 – Oct. 6

$386 CAD per night

Guest favourite

Apartment in Center Moriches

4.88 out of 5 average rating, 24 reviews

Prvt studio near LI’s annual Tulip Festival

The perfect place for a well deserved rest over the holidays. A well equipped cozy studio only 20 minutes from the Hamptons and 10 minutes away from LIRR train station to go into NYC (free parking at the train station!) This studio has a small kitchenette to warm up meals, a full size fridge, we include some snacks for those late night cravings. A queen size bed, a separate desk and chair to study or work, a couch, smart TV, and a peaceful environment to relax and unwind.

Feb. 9 – 16

$179 CAD per night

Guest favourite

Home in Westhampton Beach

4.93 out of 5 average rating, 134 reviews

Hampton's Haven

5 bedroom, 3.5 bath contemporary ranch style home, with custom shaped heated pool and meticulously maintained 7 seater hot tub. Expansive patio w/outdoor dining for 10 - close to beach, town and more! Our home has comfortable office space with gigabit wifi throughout! Fabulous game room with ping pong, 4 person air hockey, smart tv and board game lounge. Everything you'll need for a memorable gathering of friends or the perfect family vacation!

Oct. 30 – Nov. 6

$1,122 CAD per night

Guest favourite

Home in Westhampton

5.0 out of 5 average rating, 16 reviews

Family friendly home with large property

Relax with the whole family at this peaceful private home. Lots of room outdoors for children to explore and parents to relax. Your home away from home. No more worrying about what to pack! We have indoor toys, pack n play, safety features including baby gates, and outlet covers, as well as a water table and an outdoor playset complete with a mud kitchen. Just a 5 minute drive to town for all your needs and a 10 minute drive to the beach.

Aug. 5 – 12

$1,074 CAD per night