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Guesthouse vacation rentals in The Hamptons

Find and book unique guesthouse rentals on Airbnb

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Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for The Hamptons guesthouse rentals

Kitchen
Wifi
Pool
Free parking on premises
Air conditioning

Family-friendly guest house rentals

A compact sleeping area features a full bed with black and white patterned pillows against a rustic wooden wall. A modern light fixture hangs above, illuminating framed art on the walls. A private bath area is visible, featuring a toilet and additional decorative items.
Private room in Fire Island Pines
4.78 out of 5 average rating, 91 reviews

Mod 8 / private bath & deck

A curvy, light-colored sofa is displayed in a well-lit room, adorned with plush pillows in neutral tones. An intricately patterned area rug with geometric designs lies beneath, adding texture to the space. A wooden console table is positioned nearby, providing a natural contrast.
Guesthouse in Hampton Bays

Cozy Home

A tranquil outdoor space features a swimming pool surrounded by a stone patio. Lounge chairs are situated by the water, while a dining area with a table is positioned nearby. Lush greenery provides privacy, and a shady umbrella is positioned adjacent to the pool.
Guesthouse in Southampton

Guest House Southampton Village

Guesthouse in Lake Ronkonkoma
New place to stay

Cozy studio in enjoyable Lake Ronkonkoma

Private room in Fire Island
5 out of 5 average rating, 3 reviews

Madison Bedroom B

A well-lit bedroom is shown featuring a spacious bed with a white comforter. A decorative chandelier provides soft lighting. A mirrored nightstand is positioned next to the bed, complemented by a lamp. A patterned rug covers the floor, enhancing the room's overall appeal.
Private room in Shirley
4.8 out of 5 average rating, 5 reviews

The cleanest place you’ll see

The exterior of a charming bungalow is seen, featuring shingled siding and a welcoming front entrance. Large windows allow natural light, while a well-maintained garden and manicured grass emphasize the outdoor space. A second-story deck is visible, equipped with seating for relaxation.
Guesthouse in Southampton

A cozy bungalow in Southampton.

A modern kitchen space is presented with sleek countertops and an island featuring a built-in cooktop. Large glass walls provide a view of the outdoor area, while a long dining table is positioned nearby, complemented by minimalist seating.
Private room in East Hampton
4.8 out of 5 average rating, 10 reviews

Steel & Modern House-

Guest house rentals with a patio

Superhost
The exterior of a quaint cottage is shown, featuring a multi-colored umbrella over a wooden picnic table. The cottage is surrounded by greenery, including plants and a garden hose, with large windows displaying a welcoming interior.
Guesthouse in Hampton Bays
4.87 out of 5 average rating, 67 reviews

Quaint One-Bedroom Cottage with Private Entry

Guesthouse in Center Moriches

Spacious cottage

Superhost
A cozy living area is highlighted by a comfortable sofa adorned with decorative pillows and a light coffee table. Natural light filters through sheer curtains, illuminating the soft area rug that adds warmth to the space. A potted plant brings a touch of greenery.
Guesthouse in Miller Place
4.74 out of 5 average rating, 66 reviews

Private guesthouse

Top guest favorite
A group of eight individuals stands in front of a brightly lit sign displaying the word 'PINES' in multicolored letters. The wooden deck is visible beneath them, with a vibrant atmosphere created by colorful lighting in the background.
Guesthouse in Fire Island Pines
5 out of 5 average rating, 28 reviews

2 BR Private Suite w/Private Living Room & Kitchen

Superhost
Guesthouse in Greenport

Cozy guesthouse in Greenport

A spacious outdoor area features a heated spillover Jacuzzi pool surrounded by comfortable lounge chairs. Bright floating pool toys can be seen in the water. A barbecue area and seating are located under a covered structure, complemented by lush green trees in the background.
Guesthouse in East Patchogue

Charming Pool House

Guest favorite
An inviting living space is displayed, featuring a white couch adorned with decorative pillows. A coffee table is centered on a patterned rug, while a dining table awaits nearby. A staircase leads to the upper level, and subtle wall color creates a calm setting.
Guesthouse in Ronkonkoma
5 out of 5 average rating, 10 reviews

The Estate Private Guest House -Lake Ronkonkoma!

Guest favorite
The interior of the studio features a cozy seating area with a loveseat and a wooden dining table set for two. Sunlight pours in through the window draped with light blue curtains, while a comfortable Queen-size bed is visible towards the back, complemented by soft bedding.
Guesthouse in Mastic Beach
4.9 out of 5 average rating, 40 reviews

Cozy Guesthouse 10 min to Ocean

Guest house rentals with a washer and dryer

Guest favorite
A spacious studio features a comfortable bed dressed in soft linens, with light coming through a large window. A vintage-style refrigerator and a modern stove are part of the kitchen area, complemented by wooden cabinetry. A houseplant adds a touch of greenery.
Guesthouse in Calverton
4.96 out of 5 average rating, 52 reviews

Private Luxe Cottage at Gates of Wine Country

Guest favorite
A spacious studio features a cozy queen bed with a light grey duvet and matching pillows, complemented by two ceiling fans. A comfortable seating arrangement includes a modern sofa and armchair. Large windows provide ample natural light, and a soft area rug enhances the warm aesthetic.
Guesthouse in Shelter Island
4.92 out of 5 average rating, 12 reviews

Stylish Studio Suite on Shelter Island

Top guest favorite
The exterior of the cottage is presented, showcasing a two-story wooden structure with dark wooden siding. Two windows are visible on the upper floor, framed by natural greenery. A small porch area, with stone accents, invites guests to step inside.
Guesthouse in East Hampton
5 out of 5 average rating, 6 reviews

Peaceful cottage

Guest favorite
A living area features a light-colored sofa accented with decorative pillows, accompanied by a blue armchair. A coffee table sits on a textured rug, with vibrant yellow accent chairs nearby. Natural light filters through a large window draped with sheer curtains.
Guesthouse in Hampton Bays
5 out of 5 average rating, 11 reviews

Retro Mid-Century Cottage 1/2 mile to CPI

A fire pit surrounded by four chairs is placed on a circular stone patio. A wooden pergola is visible in the background, featuring a dining table and grill, illuminated by overhead lights. A well-maintained lawn surrounds the area.
Guesthouse in Mount Sinai
4.58 out of 5 average rating, 57 reviews

Great Outdoors Beach, Pool & Cozy Cabin Welcome!

Top guest favorite
A serene saltwater pool is framed by lush greenery and blooming flowers, enhancing the outdoor space. A hot tub is positioned alongside, inviting relaxation. The guest house is visible in the background, surrounded by trees and well-maintained landscaping.
Guesthouse in Shelter Island
4.99 out of 5 average rating, 71 reviews

Bayfront 1BR/2BR detached guesthouse with pool

Superhost
A charming brick pathway leads to the cottage, flanked by lush greenery and vibrant hydrangeas. The covered porch features outdoor seating, providing a welcoming entryway to the private space. Tall shrubs offer natural privacy, creating a serene atmosphere.
Guesthouse in Southold
5 out of 5 average rating, 9 reviews

Charming 2 Bedroom 1 Bath Cottage w/ private yard

Guest favorite
The exterior of the cottage is characterized by a charming yellow facade, flanked by well-maintained green grass. Lush hydrangea bushes bloom near the entry, and a paved pathway enhances accessibility. Two garage doors are visible, contributing to the home's inviting curb appeal.
Guesthouse in East Quogue
4.93 out of 5 average rating, 27 reviews

Hamptons Two Bedroom Cottage

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