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Guesthouse vacation rentals in Long Island

Find and book unique guesthouse rentals on Airbnb

Top-rated guesthouse rentals in Long Island

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

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Guest favorite
Guesthouse in Valley Stream

GuesTiny Suite - 30 min NYC / 15 min JFK

Its coziness will make you feel at home the second you step in. This cute ground floor 280 sq ft Tiny Guest Suite is Fully furnished and nicely decorated - it comes with anything you can possibly imagine. It consist of 1 bedroom 1 bathroom & a kitchen/dining/living room area Rooms' sizes: Bedroom: 10ft x 7 1/2ft LR kitchen DR area: 19ft x 10ft Bath: 40" x 80" Given how close it is from everything - It is perfect for guests who plan on commuting to the city by train or move around by Uber.

ValueLocationDecor

4.93 out of 5 average rating, 102 reviews
Top guest favorite
A bright living and dining area features a navy blue sofa adorned with decorative pillows. A wooden dining table set for four occupies one side, while a light rug anchors the space. Sunlight filters through sheer curtains, enhancing the room's inviting ambiance.
Guesthouse in Huntington Station

Modern fully updated 2nd Floor apartment

Arrive to an apartment decorated to make you feel comfortable and at home. There is one bedroom with one queen bed, a dresser, a night table and a closet. One full bath with basic amenities for you. The kitchen has a microwave, blender, coffee machine, toaster, fridge, washer/dryer, full range electrical stove, dinnerware, silverware, glassware, pots, liquid dish soap and sponge. Living/dining room area: dining set for 4; queen sofa bed, Cable TV and closet. Wifi is available! no pets policy!

LocationValueHeating

4.97 out of 5 average rating, 119 reviews
Top guest favorite
Guesthouse in Rowayton

1BR full cottage, 1 min walk to private beach

Enjoy time at this lovely studio located in the heart of Rowayton, a charming New England seaside village bounded on one side by Long Island sound and the other by a tidal inlet. Based in the southwest corner of CT, we are just a 1 minute walk to 2 separate and secluded beaches as well as 2 private, well manicured parks. Great amenities in town including tennis, sailing, outdoor yoga, sunbathing, plus nice restaurants. Pedestrian and dog friendly town; you don't even need a car while here.

FamilyValueTV

4.99 out of 5 average rating, 174 reviews
Top guest favorite
A cozy living room features a large flat-screen TV mounted on the wall, accompanied by a sleek entertainment unit. A comfortable couch is draped with a soft blanket, and an armchair is positioned nearby. Natural light enters through two windows, brightening the neutral decor.
Guesthouse in Mamaroneck

Spacious guest suite near water

Welcome to your perfect home away from home! Enjoy a spacious and newly renovated basement suite with windows and separate entrance in a private house, perfect for up to four guests. Ideal for couples, small families, or business travelers. This cozy retreat, combines privacy and comfort in a quiet neighborhood. Whether you’re here for a short trip or an extended stay, this apartment offers everything you need for a comfortable and relaxing experience. Book now and start planning your visit.

FamilyValueSleep quality

4.97 out of 5 average rating, 125 reviews
Top guest favorite
A private outdoor space is showcased with a wooden deck, featuring two lounge chairs and a dining table shaded by an umbrella. Potted flowers add color, while a path leads through the well-maintained garden, enhancing the serene atmosphere of the yard.
Guesthouse in Hampton Bays

WELCOME TO THE LOVE SHACK BY THE SEA

Cozy winter getaway with heated floors throughout! Escape the city, work in nature-private cottage with garden views. 1 mile from pristine beaches, 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.

FamilyLocationDecor

4.97 out of 5 average rating, 239 reviews
Guest favorite
The exterior of the guest house is framed by manicured gardens, featuring two decorative statues positioned beside a pea gravel walkway. A small patio area includes a round table with two chairs, creating a serene spot for outdoor relaxation.
Guesthouse in Waccabuc

French Estate Guest House on Private Lake

A private, European-inspired guest house set on an eight-acre gated French estate, just 60 minutes from NYC. Surrounded by manicured gardens, 18th-century statuary, and a private lake, the setting feels transportive—a French countryside retreat. Designed by architect David Easton, the space blends classic elegance with modern comfort: heated stone floors, a heated towel rack, fine linens, curated finishes, and a private entrance. Perfect for a refined weekend escape or a quiet reset.

LocationValuePets

4.99 out of 5 average rating, 151 reviews
Guest favorite
A spacious living area features a blue sectional sofa adorned with orange cushions. Two floral-patterned ottomans provide additional seating, complemented by a wooden coffee table. Wall art hangs above the sofa, and soft lighting from recessed fixtures illuminates the tiled floor.
Guesthouse in Yonkers

Cozy 2 Bedroom in Yonkers NY

Mi casa es tu casa! Kick back and relax in this calm, stylish private guest suite apartment. 20 minutes from NYC. 10 minutes walk to Metro North. Close to shops and restaurants 10 min walk to Saint Vincent college. Free parking access. 30 to Johnn f Kennedy and 20 to LaGuardia. Includes spacious backyard, perfect to enjoy with friends and family. Early luggage drop off available per request. NO SMOKING INSIDE THE APARTMENT. ONLY CIGARETTE SMOKING IS ALLOW IN THE PATIO AREA

LocationFamilyHot tub

4.86 out of 5 average rating, 391 reviews
Top guest favorite
A cozy living area features a sectional sofa and two armchairs arranged around a glass-top coffee table. A rug provides a soft touch to the wood flooring. The kitchenette, equipped with modern appliances, is visible in the background, alongside large windows that invite natural light.
Guesthouse in Wading River

North Country Cottage

Located near Long Island's beautiful beaches, vineyards, and wedding venues, this cozy cottage in the woods provides a quiet and comfortable place to stay while visiting! A spacious patio extends the living area, adding space to enjoy the outdoors in front of the fire pit or outdoor dining table. This property is located behind the owners' home and uses a shared driveway. While the owner is close by to address any issues during your stay, your space allows for total privacy.

FamilyValueComfort

4.99 out of 5 average rating, 135 reviews
Top guest favorite
The cottage is tucked amidst vibrant autumn foliage, framed by trees. A large front deck, furnished with two chairs, provides a serene entry, while the three expansive windows invite natural light. The wooden exterior blends harmoniously with the surrounding woodland.
Guesthouse in Bedford Hills

The Perch, a Woodland Cottage Retreat

The Perch, a design-forward woodland cottage surrounded by nature just one hour from NYC perfect for couples escaping the city for a quiet Hudson Valley weekend. Spend slow mornings overlooking the woods, afternoons by the saltwater pool, and evenings exploring Bedford’s historic village restaurants and trails. "The Perch is a peaceful, thoughtfully appointed woodland haven." - Elyssa *Pool closes for the season on Sept 15 and reopens May 2027* inquire for details

LocationFamilyCondition

5.0 out of 5 average rating, 100 reviews
Top guest favorite
A vibrant garden area is depicted, featuring a variety of blooming flowers in decorative pots. Greenery surrounds the space, with bushes adorned with purple blossoms. A wooden deck offers a view over the lush, well-maintained landscape.
Guesthouse in Brookhaven

The Unhampton

This Brookhaven Hamlet detached space (totally separate) is for people who love nature and preserved quiet spaces. Fire Island is a ferry ride away, Manhattan is one hour by train and the Hamptons are a 25 minute ride.15 minutes from the restaurants and coffee shops in Patchogue and just a couple of minutes from Bellport Village. Centrally located and truly peaceful!

FamilyValueBreakfast

4.97 out of 5 average rating, 243 reviews
Top guest favorite
A modern white structure with large windows is surrounded by lush greenery, including a prominent tree and shrubs. A small seating area with a table and chairs is visible in the gravel courtyard, providing a tranquil outdoor setting embraced by nature.
Guesthouse in Southport

Southport, CT across from BEACH

Located at Southport beach on Westport Line, this recently renovated 1 bedroom apartment totally private located above the garage and includes a full kitchen with new appliance and W/D and central air. Bdrm with queen, fine cotton sheets and towels, marble bath open living room w views.

FamilyValueBathroom

4.96 out of 5 average rating, 222 reviews
Superhost
Guesthouse in Stamford

Small Studio. Private Entrance and bathroom

Welcome, this is a small and cozy studio for one person located in a quiet and safe area near Harbor Point with a private entrance, private bathroom, and a small kitchenette. 1 miles from downtown and a 3 minutes drive to the train station and I95. Spot for parking.

FamilyLocationAir conditioning

4.8 out of 5 average rating, 188 reviews

Popular amenities for Long Island guesthouse rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Family-friendly guest house rentals

Guest favorite
A vibrant blue entrance door is framed by neatly trimmed evergreen shrubs, with a welcome mat placed on stone steps leading to the inviting threshold of the home. A mailbox is positioned beside the door, adding to the entrance's charm.
Guesthouse in Guilford

The Little Blue Cottage

LocationFamilyIndoor spaces

4.84 out of 5 average rating, 161 reviews
Top guest favorite
A modern living space features a comfortable sofa, a circular coffee table, and a television unit. Large sliding glass doors create a seamless view of the outdoors, with natural greenery visible beyond the private deck. Soft natural light fills the room, enhancing its inviting ambiance.
Guesthouse in Guilford

Get Back to Nature at a Modern Wood Clad Getaway

FamilyLocationBiking

4.99 out of 5 average rating, 530 reviews
Top guest favorite
A charming guest studio is set among trees, featuring large glass doors that open to a stone patio. Four white adirondack chairs surround a fire pit, providing a relaxed outdoor gathering space. The studio's design reflects a serene and inviting atmosphere in nature.
Guesthouse in Bedford

Private Guest Studio

ValueLocationComfort

4.92 out of 5 average rating, 236 reviews
Guest favorite
A cozy bedroom features a spacious bed covered with layered bedding, including patterned throws in navy and orange. A small nightstand is situated beside the bed, and a stylish bench is placed at the foot. Textured blue walls enhance the room's warm and inviting ambiance.
Guesthouse in Huntington Station

2 large bedrooms in cozy little neighborhood.

ValueLocationAccess

4.83 out of 5 average rating, 152 reviews
Top guest favorite
A light-filled living space features two skylights allowing natural light to illuminate the wooden floors. A spacious sofa is accompanied by a small coffee table and a seating area is positioned beside a contemporary television. Potted plants add a touch of greenery to the room.
Guesthouse in Milford

The studio downtown

FamilyLocationCleanliness

4.99 out of 5 average rating, 112 reviews
Top guest favorite
A comfortable living area is featured, showcasing a brown sofa with colorful pillows and a small table. Large windows are adorned with checkered curtains, allowing natural light to fill the room. A light fixture hangs above a blue cabinet, adding a touch of charm.
Guesthouse in Sayville

Great South Bay Cottage

LocationValueParking

4.97 out of 5 average rating, 238 reviews
Guest favorite
The interior features large windows allowing natural light to illuminate the space. A spiral staircase leads to the loft. A cozy seating area includes a white sofa and a decorative fireplace. Lake views are visible through the glass doors, enhancing the serene atmosphere.
Guesthouse in Brewster

The Cottage by the Lake: Hudson Valley Indulgence

ValueLocationLong stay

4.99 out of 5 average rating, 330 reviews
Guest favorite
A charming cottage exterior features white clapboard siding and dark blue shutters. A sloped asphalt roof and a front door with decorative glass provide focal points. Landscaped greenery and a gravel pathway enhance the welcoming entrance, surrounded by trees that offer natural shade.
Guesthouse in Clinton

The Gardener's Cottage Dog friendly/weekly/monthly

LocationValuePets

4.95 out of 5 average rating, 255 reviews

Guest house rentals with a patio

Top guest favorite
A charming cottage with a light-colored exterior sits in a manicured yard. The structure features multiple windows that allow natural light to fill the space. A small staircase leads to the entrance, surrounded by greenery and decorative landscaping, providing a welcoming facade.
Guesthouse in Madison

The Rising Tide Cottage

LocationFamilyHiking

4.97 out of 5 average rating, 100 reviews
Top guest favorite
A spacious studio cottage features a comfortable queen bed and a sitting area with two upholstered chairs. Natural light filters through the multiple windows, highlighting the neutral decor and soft area rug on the floor.
Guesthouse in Clinton

Studio Cottage

FamilyLocationAir conditioning

4.97 out of 5 average rating, 100 reviews
Top guest favorite
The exterior of a private guest house is depicted, showcasing a blue facade complemented by multiple windows. A spacious stone patio features outdoor seating surrounded by lush greenery and garden flowers. The roof is sloped, and trees provide a natural canopy overhead.
Guesthouse in Guilford

Page Guest House

LocationFamilyCondition

4.98 out of 5 average rating, 118 reviews
Superhost
The exterior of the cottage is shown with a welcoming porch featuring a red umbrella over a dining table. Potted plants are arranged along the walkway, while a grill and a trash bin are visible nearby. Lush greenery surrounds the property, enhancing the serene environment.
Guesthouse in Cortlandt

Charming 2 bedroom Cottage w/ patio & yard.

ValueLocationDecor

4.86 out of 5 average rating, 103 reviews
Guest favorite
The interior features a cozy sleeping area with a bed adorned in patterned linens. A convertible sofa is positioned across the room with warm lighting. A glass dining table is surrounded by four chairs, each set with blue plates and glassware, creating a welcoming dining space.
Guesthouse in Highlands

The Bungalow at Sandy Hook House

ValueLocationIndoor spaces

4.89 out of 5 average rating, 160 reviews
Guest favorite
A single-story house with light yellow siding is shown, featuring a covered porch and white railings. A small area of vibrant greenery and shrubs surrounds the entrance, complementing the peaceful outdoor space.
Guesthouse in Roosevelt

Home away from home

ValueFamilyIndoor spaces

4.89 out of 5 average rating, 54 reviews
Guest favorite
Guesthouse in Center Moriches

PrivatePool/Cozy Guesthouse Near Hamptons&Wineries

ValueLocationDecor

4.94 out of 5 average rating, 16 reviews
Top guest favorite
A spacious bedroom features an elegantly designed headboard with a floral pattern. The walls are adorned with a soft blue and white mural, complemented by natural light filtering through a window. A tall mirror reflects the room, enhancing the sense of openness.
Guesthouse in Port Jefferson

The Buccaneer Suite ~ Your Private Seaside Escape

FamilyLocationKitchen

5.0 out of 5 average rating, 24 reviews

Guest house rentals with a washer and dryer

Top guest favorite
A charming garage is depicted, featuring double doors with window panels and a decorative weather vane atop the peaked roof. Lush greenery surrounds the structure, enhancing the natural setting. The exterior is finished in calming blue tones, complemented by light-colored trim.
Guesthouse in Mystic

HERON HOUSE MYSTIC, CT.

LocationValueOutdoor spaces

4.96 out of 5 average rating, 192 reviews
Top guest favorite
A spiral staircase with a sleek black railing leads to the loft bedroom. A mirror with a burgundy frame is mounted against the wall, reflecting the light. The open living area features a light-colored couch and a wooden dining table, visible through large windows offering views of the outdoors.
Guesthouse in Mystic

Gorgeous Waterfront Getaway

FamilyLocationParks

4.98 out of 5 average rating, 719 reviews
Guest favorite
A cozy living area features mid-century modern furniture, including an orange armchair and a sleek glass coffee table. A gallery wall displays various artworks, complemented by natural light from two windows. A small dining area with a round table and four chairs contributes to the inviting layout.
Guesthouse in New Haven

Westville Hideaway | Stylish Guesthouse + Parking

ValueFamilyNearby

4.91 out of 5 average rating, 362 reviews
Top guest favorite
A cozy living space features a brown leather sofa and a white coffee table on a geometric patterned rug. A large window allows natural light to fill the room, showcasing a wall-mounted fish decor and colorful accents. A decorative plant sits on the table.
Guesthouse in Southampton

Tiny Home in Prime Spot in Southampton Village

ValueFamilyNearby

4.96 out of 5 average rating, 475 reviews
Top guest favorite
A cozy sleeping area features a neatly made bed with light bedding and a textured throw. Above the bed, three decorative prints hang on the wall. A mirrored closet reflects the space, creating an open feel, while soft lighting enhances the peaceful ambiance.
Guesthouse in Montclair

The cozy studio apartment of Montclair

FamilyValueBathroom

4.87 out of 5 average rating, 133 reviews
Top guest favorite
A serene outdoor space features four grey Adirondack chairs arranged around a small table, set on a lush green lawn. Surrounding foliage adds a touch of nature, while a clear sky provides a bright backdrop.
Guesthouse in New London

Charming Carriage House-Ocean View-Beach-Fireplace

LocationFamilyParking

4.98 out of 5 average rating, 137 reviews
Top guest favorite
Guesthouse in Westerly

Holiday Escape ~ Quiet Woods Fall Colors ~ 499Mbps

LocationFamilyPets

4.99 out of 5 average rating, 126 reviews
Top guest favorite
A calm waterfront scene captures a vibrant sunset, with clouds reflecting in the still water. Silhouetted boats can be seen along the shore, and a dock extends into the water, enhancing the tranquil ambiance of the landscape.
Guesthouse in Hampton Bays

1 Bedroom Hamptons Waterfront Cottage Heated Pool

LocationValueAmenities

5.0 out of 5 average rating, 37 reviews

Destinations to explore