Holiday rentals with breakfast in Montauk

4.93 out of 5 average rating, 27 reviews

A serene poolside area features six lounge chairs arranged along the edge of a saltwater pool. Stylish umbrellas offer shade, complemented by decorative stone pavers leading to grassy borders. Lush greenery surrounds the space, enhancing a relaxing atmosphere for guests.

Home in Bellport

Gorgeous Renovated Bellport Village home w/ Gym

Lovely beach getaway with all the comfort of home. Fully updated 3-bedroom, 2-bath home set on .35 acre just a short walk to local shops, restaurants and ferry to HoHum, Bellport Village's private beach on Fire Island. Spacious backyard with stunning saltwater pool, large deck + BBQ. Wide, light-filled open plan kitchen, dining + living space that accommodates up to 8 adult guests. New AC system, fast WiFi, smart TV w/ Netflix, Hulu, HBO, Washer/Dryer, Dishwasher, Alarm, large driveway. Peloton.

A large, heated pool is surrounded by a white deck and a protective fence, offering a safe space for relaxation. The serene setting includes trees in the background, and a modern house is visible with oversized windows reflecting natural light.

5 out of 5 average rating, 18 reviews

NEW: Charming East Hampton home w/ POOL!

Welcome to our charming 3 bedroom, 2.5 bath, 1,700+ SF home. Enjoy the heated pool all summer or relax by the fireplace in the fall and winter months. Sunlight shines through two skylights and oversized windows for the beautiful natural light that East Hampton Springs are famous for. We are just a few minutes drive to all EH bay and ocean beaches as well as EH Town and Amagansett Village. Countless restaurants, shops, farmer's markets, vineyards, art galleries, etc. are all very close by!

A bright and open living area features a large sectional sofa with colorful accent pillows and light-colored armchairs. A dining area with modern chairs is visible in the background, while floor-to-ceiling windows provide a view of the outdoor pool and greenery.

5 out of 5 average rating, 13 reviews

Chic, Modern, Family-Friendly Home in East Hampton

This clean, beautiful, well appointed home is the perfect place for your summer (or winter) getaway! With updated appliances and designer furniture, this chic getaway is both fun and sophisticated. Whether you're a family or a small group of friends, you will make wonderful memories swimming in the heated gunite pool, playing badminton in the yard, grilling on the deck or sipping wine on the balcony. Close to the village, and both bay and ocean beaches! Rental Registry Certificate: RR-25-371

4.98 out of 5 average rating, 41 reviews

A decorative mailbox featuring a starry night design stands at the entrance, with the number 33 visibly displayed. Bright orange flowers and lush green foliage surround the mailbox, while the cottage is partially visible in the background, framed by a white fence.

Cottage in North Fork

A Cheerful 2 - Bedroom Cottage

The cottage is the perfect resting spot for travelers. While staying here you can enjoy nature, farms, vinyards, beaches, golfing, and local attractions. We are conveniently located between the North and South Forks of Long Island. We are in walking distance to the Hampton's Jitney. A 2 min drive to the LIE. And just a 40 min drive to the Orient Pt Ferry. We are 30 mins to The Hamptons, and 5 mins to the LIRR. Most importantly we can assure your stay with us will be, peaceful and comfortable.

The landscaped backyard features a heated mineral spring pool with clear blue water. Surrounding the pool are loungers and a shaded cabana with a striped canopy. Lush greenery and colorful foliage add to the serene environment.

4.95 out of 5 average rating, 20 reviews

POOL + Beach Oasis! Winter deals 2+ nights!

Chef kitchen: 2 ovens/lux app's/coffee bar w/ Nespresso/Keurig 2 living rooms Dining room seats 10 1st floor Primary Suite: king bed, gas fireplace, furnished deck overlooking pool, 4 piece bath: huge shower & jacuzzi tub 2 of 4 Guest rooms on 1st fl Gym/yoga rm: bench + weights (no treadmill) TV's in bedrooms inc. Firesticks Fenced backyard oasis w/ heated mineral spring pool, loungers, shaded cabana, outdoor dining, & Weber BBQ, outdoor shower Kitchenette in den/office Central AC/heat/fans

An airy kitchen features white cabinetry and a large island with seating. Modern appliances are included, and a glass atrium provides sunlight. Potted greenery adds a touch of nature, and a view of the outdoor pool is available through expansive glass windows.

5 out of 5 average rating, 10 reviews

Beautiful 4/bedroom Sag Harbor Home /Heated pool

Spacious 4 bedroom, 3 1/2 bathrooms,Heated pool with outdoor shower.Located on one acre, in beautiful upscale neighborhood,at end of quiet cul-de-sac street. Large 65"TV in huge cathedral ceiling main living room . 65'screen TV in large separate den,with treadmill. King size bed on 1st floor bedroom with 2 beds next door New large Spa bathroom on 1st floor. King size master bedroom 2nd floor,55"TV,with en-suite 2 beds in add bedroom, with en-suite bath July and August are Monthly Rentals

A cozy bedroom featuring a spacious bed dressed in soft linens is positioned against a light-colored wall. Natural light filters through two windows, casting gentle shadows on the warm wooden floor. A ceiling fan hangs overhead, and a mirror and chair add functional elements to the space.

4.97 out of 5 average rating, 184 reviews

Secluded Farmhouse - Studio Apartment Style Unit

Beautiful, quiet, studio apartment-style unit (private entrance w/full bath) tucked away in a modern farmhouse on a gorgeous, secluded North Fork farm. Guests have exclusive use of screen porch, fire pit, bbq and outdoor seating area. Jess is a private chef and yoga instructor, so be sure to inquire for services! Private hiking trails, fresh eggs, produce from garden, beach gear, Keurig, mini fridge, homemade granola, tea. Fresh eggs, seasonal veg from the garden, and meals (inquire!)

5 out of 5 average rating, 13 reviews

A serene coastal sunset is captured over the water, with vibrant sunflowers framing the foreground. The sun dips into the horizon, casting warm hues across the sky and reflecting on the tranquil ocean waves, while lush greenery lines the scenic coastline.

Home in Shoreham

Beach home waterfront LI amazing view 3/3 bed bath

Beach front home with spa/ PRIVATE BEACH , Water park, wineries, aquarium & ocean within20 min. Granite covered barbecue, wet bar and 55” TV . Fire pit, comfortable seating while watching sunrise or sunset from your overlook onto LI SOUND. 3 bedroom , 3 full bathroom with 2 queen beds and 1 king. Enjoy spectacular views from the windows with cozy relaxed living and dining areas. Day trip to Hamptons, Montauk all attractions and highways. Hiking trails , parks and recreation.

A bright living area features a light-colored sectional sofa adorned with decorative cushions. A wooden coffee table is positioned in front, with two dark wooden chairs beside it. Natural light filters through the large windows, highlighting the textured walls and elegant decor.

5 out of 5 average rating, 18 reviews

Bright and airy East Hampton cottage

Charming East Hampton cottage with heated saltwater pool and pool/guest house. This recently renovated 2000 square foot home is the quintessential Hamptons cottage The location is within walking distance to the town of East Hampton and the train station and there are several ocean beaches within 2 miles. This is the perfect house for a family beach vacation, or a get together with friends. No large groups or parties please. We love our house and our quiet neighborhood!

Guest suite in The Hamptons

A spacious king bed is positioned against a dark wall, adorned with a variety of decorative pillows and a textured throw blanket. Soft lamps flank the bed, illuminating the space alongside natural light flowing through a window adorned with multiple panes.

4.97 out of 5 average rating, 173 reviews

Peaceful private village adjacent 2 bths fireplace

Beautiful, bright, spacious King suite w fireplace, two en-suite bathrooms & private separate poolside entrance. We are just minutes to beaches, boating, golf, hiking, biking, yoga and wineries. Play games, grill or cozy up fireside w a good book or movie. The space is creatively designed with a nod to natural elements and luxe comfort. Sleep your very best on our super deluxe king sized bed w/your choice of pillows. Complimentary coffee/tea/treats

Superhost

Apartment in The Hamptons

4.84 out of 5 average rating, 31 reviews

Holidays in The Hampton! 2BR Getaway w/Xmas tree

Holiday Retreat ready for you to enjoy. Welcome to our charming 2BR, 1BA Hampton's Retreat apt. in Hampton Bays, NY! Your stay offers a bright, airy space with a large screen TV, board games, and a private work area. The split-unit AC/heating ensures comfort w/ a fenced back yard with BBQ for your family’s pleasure. We're just 1 mile from the bay, 2 miles from the ocean, and only 1.5 miles to the town’s shops, dining, and local happenings.

A clear blue saltwater pool is surrounded by a landscaped yard featuring green grass and shrubs. Several lounge chairs are positioned nearby under light blue umbrellas, providing shade. A two-story house is visible in the background, framed by tall trees.

4.9 out of 5 average rating, 229 reviews

Greenport Beach house Mini Resort Spa & Catering

Nestled steps from the beach, and all that Greenport and the North Fork has to offer, this exquisitely charming 3 bedroom 2 bathroom waterfront home is absolutely delightful.. You’ll love my place because of the views, the location, the people, the ambiance, the outdoors space, and the Saltwater pool.. My place is good for couples, solo adventurers, business travelers, families (with kids), groups, and furry friends (pets).

Popular amenities for Montauk Holiday Accommodation with Breakfast

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Holiday House Rentals with breakfast

A rectangular swimming pool is surrounded by a wooden deck, featuring several lounge chairs positioned nearby. Lush green grass extends beyond the pool area, complemented by decorative planters. Natural greenery provides a serene, private setting for relaxation.

5 out of 5 average rating, 28 reviews

Sag Harbor King Bedroom + Pool Private Bath

A spacious beach house is set against a backdrop of lush greenery, surrounded by mature trees. The structure features large windows that invite natural light. A driveway leads up to the home, partially visible in the foreground.

Home in Shelter Island Heights

4.63 out of 5 average rating, 8 reviews

RENOVATED AND SPACIOUS SUMMER HOME WITH WATER VIEW

A bright living area features a large cream-colored sofa facing a wooden coffee table. Natural light filters through window blinds, illuminating the space. An elegant spiral staircase ascends to the loft, while the adjacent kitchen is visible through an open layout.

4.86 out of 5 average rating, 22 reviews

Sag Harbor Beach Cottage

5 out of 5 average rating, 12 reviews

Kayaks Serenity Sag Harbor Village

A charming cottage is surrounded by lush greenery, featuring large windows that allow natural light to fill the interior. The welcoming front porch is adorned with steps leading up to the main entrance, which is framed by decorative foliage.

4.88 out of 5 average rating, 50 reviews

Greenport Sleeps 10. Walkable to Beach & Town

The entrance features planters with vibrant red geraniums, contrasting against a light-colored exterior. The wooden deck is shaded by surrounding trees, creating an inviting entryway. A small decorative object rests on a stool, adding character to the natural setting.

4.87 out of 5 average rating, 39 reviews

Noreen's Get Away No 1

A cozy seating area is showcased, featuring a light-colored armchair complemented by a patterned throw. A modern console table is situated against a wall, supporting a large flat-screen TV. Floor-to-ceiling curtains frame the glass door, providing natural light and access to a balcony.

4.97 out of 5 average rating, 346 reviews

Private one bedroom studio apartment

A spacious living area features large windows that open up to a green landscape. Comfortable seating options are arranged around a central area rug, with a modern coffee table nearby. A sleek television is mounted above a minimalist fireplace, and natural light floods the room.

4.95 out of 5 average rating, 21 reviews

Modernist House with a Heated Pool near Sag Harbor Village

Apartment rentals with breakfast

Apartment in Shirley

A beautiful luxury 2 bedrooms apartment near beach

A light-filled bedroom features a spacious bed adorned with a red and white striped pillow. A sleek dresser sits against the wall, complemented by framed artwork. Natural light enters through partially closed blinds, highlighting the soft carpeted floor and neutral-colored walls.

Private room in Shelter Island

Queen room with ensuite bathroom

A sandy beach stretches along a calm shoreline, meeting clear blue waters. The sky is adorned with wispy clouds, creating a serene atmosphere. In the distance, trees line the shore, contributing to the tranquil setting.

Apartment in North Fork

4.7 out of 5 average rating, 57 reviews

By The Bay B&B, Cutchogue, NY

Apartment in Shirley

4.55 out of 5 average rating, 11 reviews

A 1 BR home away from home to relax and unwind.

Bed and breakfast rentals with breakfast

Private room in Shelter Island Heights

5 out of 5 average rating, 4 reviews

SEVEN on Shelter - Queen Guest Room

Superhost

A spacious studio features a king bed with plush white bedding and a dark blue throw. A mirrored dresser is positioned near the entrance, while a decorative mural with floral motifs adorns the wall above the bed. A small coffee table holds a meal setup, enhancing the living area.

4.76 out of 5 average rating, 42 reviews

1KING, Beaches, Kayaks, Wineries

Private room in South End

5 out of 5 average rating, 14 reviews

Vine + Sand Southold, NY's Newest B&B-Room 2

4.98 out of 5 average rating, 64 reviews

Southampton Center ~ Light & Airy Private Room

5 out of 5 average rating, 9 reviews

Head of Pond House - The Mill Pond Suite

Superhost

5 out of 5 average rating, 5 reviews

1KING,Min to Beaches,KayaksPaddleboards,Wineries

An en-suite room features a spacious bed with crisp linens. Natural light filters through the large windows with blinds, illuminating a cozy armchair and small side table. Two pieces of wall art add subtle color, while a neutral rug anchors the space.

5 out of 5 average rating, 9 reviews

Head of Pond House- Edge of Woods Room

A cozy bedroom features a spacious bed adorned with neutral bedding and a decorative throw. A classic wooden dresser and a chair are visible, complemented by bedside lamps. Natural light enters through a window, creating a calm and inviting environment.