Guesthouse holiday rentals in Fire Island

4.97 out of 5 average rating, 234 reviews

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

Fantastic private cottage on Long Island's South Shore. Great access to the best beaches in the world (walk to bay, ferries to ocean). Short train ride to/from NYC, Wineries & The Hampton's. Experience the Island’s charm and culture. Enjoy Long Island summers. Maintained by professional cleaners. NOTE: Increased prices reflect a policy change from Airbnb where the host is imposed a service fee, where before it was put on the guest. At the end of the day, your total costs will not have changed.

LocationValueSleep quality

Guesthouse in Hampton Bays

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.

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.

LocationFamilyAir conditioning

4.97 out of 5 average rating, 235 reviews

4.99 out of 5 average rating, 170 reviews

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.

LocationFamilyLaundry

4.97 out of 5 average rating, 119 reviews

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.

ValueLocationTV

4.99 out of 5 average rating, 126 reviews

A well-maintained outdoor space features a large swimming pool surrounded by a wooden deck. Lounge chairs are placed around the pool, with red umbrellas providing shade. Adjacently, a patio area includes a dining table. Lush greenery frames the area, contributing to a serene ambiance.

Guesthouse in Springs

The Quail’s Nest

A beautifully landscaped tranquil oasis. Newly constructed private two bedroom, one bathroom guest extension to owner occupied house. Guests share large yard and pool with owner, and have private deck and seating area. Private entry and parking. Guest's may enjoy outdoor shower and BBQ. Please note there is no kitchen, however a small fridge, Keurig coffeemaker and microwave, plates/utensils are provided. Conveniently located to beaches, shopping and local restaurants in East Hampton.

FamilyValueCheckout

4.99 out of 5 average rating, 147 reviews

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.

LocationValueAccuracy

Guesthouse in Wading River

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.

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.

LocationFamilyBarbecue

4.99 out of 5 average rating, 128 reviews

4.98 out of 5 average rating, 114 reviews

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

Updated, private detached guest house in the center of Guilford's historic district just steps from the town center. The guest house is completely renovated. Walk to everything including shops and restaurants. Town Beach and doc are just under 1.5 miles away. The second bedroom has a twin bed. You have to walk through twin room to get to master. Apartment is one floor with no steps. Bathroom is tiled and shower is walk in with no lip or tub and is easily accessible.

LocationValueCheckout

4.99 out of 5 average rating, 527 reviews

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

Catch the early fall breeze at our private coastal cottage. Spot migrating shorebirds, terns, and early warblers. Beautiful hiking trails in the woods and along the beachfront. Great places to shop and eat or catch a show at one of New Haven’s renowned museums or broadway theatres or relax. Great restaurants along the shore. Enjoy! We want you to have a relaxing stay with us, free from worry. We are located in a private area, away from public.

FamilyValueBathroom

4.97 out of 5 average rating, 240 reviews

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!

FamilyValueGetting around

4.92 out of 5 average rating, 233 reviews

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

Just 39 miles north of Manhattan. Relax and unwind, to enjoy endless opportunity for outdoor activities, fine dining, antiquing, or just loving the peace & quiet of this private studio, in a manicured setting, with wood burning stove, porch, heated pool (June-August), and private footpaths leading to an open field.

FamilyValueGetting around

4.96 out of 5 average rating, 219 reviews

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 d/w and central air. Bdrm with queen, fine cotton sheets and towels, marble bath open living room w views.

ValueFamilyLong stay

Popular amenities for Fire Island guesthouses

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-Friendly guesthouses

Guesthouse in Fire Island

An outdoor deck area features a gas grill, a small round table with two blue chairs, and a wooden privacy screen. Surrounding greenery offers a natural backdrop, and the sunlight enhances the inviting space for relaxation or outdoor dining.

One Bedroom Cottage in Cherry Grove

ValueLocationAccuracy

4.92 out of 5 average rating, 96 reviews

Guesthouse in Fire Island

A spacious studio features a wooden accent wall, complemented by a cozy bed with patterned bedding. A small dining area includes a wooden table and chairs. Light-colored flooring enhances the bright atmosphere, with a television mounted on the wall providing entertainment options.

Newly Renovated Studio for 2 in Cherry Grove, FI

LocationCheck-inCondition

4.94 out of 5 average rating, 17 reviews

4.96 out of 5 average rating, 46 reviews

A cozy studio space features a spacious bed with crisp white linens, complemented by soft lighting. A full-length mirror reflects the room, while a small desk and chair are positioned beside a closet, which is neatly organized with towels and essentials.

Guesthouse in Islip

Over the Moon

LocationFamilyAccess

Guesthouse in East Hampton

The exterior of the cottage is surrounded by lush, vibrant greenery, with climbing plants and flowering shrubbery. Natural light illuminates the soft colors of the cottage, which features multiple windows and a door framed by greenery, presenting an inviting and tranquil setting.

Enchanting studio cottage, walk everywhere

LocationKitchenDecor

4.95 out of 5 average rating, 19 reviews

4.96 out of 5 average rating, 23 reviews

Enchanting Guest Cottage

LocationFamilyNearby

Guesthouse in East Quogue

A bright pool cottage is set amid a lush, green backyard. The cottage features a white exterior and is surrounded by landscaped gardens. A saltwater pool reflects the surrounding trees, while a spacious lawn offers ample room for relaxation and outdoor activities.

Charming & Bright Pool Cottage

LocationCleanlinessAmenities

5.0 out of 5 average rating, 33 reviews

Superhost

The exterior of a spacious beachfront home is displayed with a wide front porch featuring white railings. Lush greenery surrounds the entrance, with potted flowers adding color to the scene. The two-story structure is designed for outdoor relaxation, inviting guests to enjoy the coastal environment.

Guesthouse in Old Lyme

BEACHFRONT HOME GREAT LOCATION!STEPS TO THE BEACH!

LocationFamilyAccuracy

4.68 out of 5 average rating, 22 reviews

5.0 out of 5 average rating, 12 reviews

Fairfield Suite

ValueLocationNearby

Guesthouses with a patio

4.97 out of 5 average rating, 126 reviews

Natural light fills the bright living area, featuring a comfortable seating arrangement with decorative cushions, a wooden coffee table, and an elegant antique cabinet. High ceilings with exposed beams enhance the spaciousness, complemented by large windows offering views of the greenery outside.

Guesthouse in Madison

Beachy & Bright Coastal Escape - 5 Mins to Beach

LocationFamilyLayout

Guesthouse in Fire Island

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.

2 BR Private Suite w/Private Living Room & Kitchen

ValueLocationKitchen

5.0 out of 5 average rating, 39 reviews

4.96 out of 5 average rating, 46 reviews

A well-maintained outdoor space features a spacious pool surrounded by lounge chairs and umbrellas. Lush greenery and ornamental plants frame the area, while a wooden deck provides ample seating options, creating a tranquil retreat. The sun-drenched scene enhances a sense of relaxation.

Guesthouse in Bellport

Guest House retreat with amazing pool !!!

FamilyLocationAccuracy

4.94 out of 5 average rating, 16 reviews

Guesthouse in Bellport

Bellport Captain's Carriage House (2 Floors)

LocationValueQuiet

4.98 out of 5 average rating, 48 reviews

Guesthouse in Norwalk

Waterfront Getaway - Norwalk, CT

FamilyLocationParks

Guesthouse in Port Jefferson

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.

The Buccaneer Suite ~ Your Private Seaside Escape

LocationFamilySleep quality

5.0 out of 5 average rating, 22 reviews

5.0 out of 5 average rating, 27 reviews

Natural wood walls and ceiling create a warm environment in this studio. A queen bed is positioned below a loft area with two twin beds accessible by a wooden ladder. Light enters through windows, illuminating a side table and a cozy reading nook.

Guesthouse in Waterford

A Little House by the sea

ValueFamilyCheck-in

5.0 out of 5 average rating, 16 reviews

Guesthouse in Trumbull

Private Garden Cottage w/ Patio

LocationValueAccuracy

Guest house rentals with a washing machine and dryer

Guesthouse in Huntington Station

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.

Modern fully updated 2nd Floor apartment

FamilyLocationIndoor spaces

4.96 out of 5 average rating, 114 reviews

4.92 out of 5 average rating, 354 reviews

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

ValueFamilyLong stay

Guesthouse in Southampton

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.

Tiny Home in Prime Spot in Southampton Village

ValueLocationSolo travel

4.96 out of 5 average rating, 470 reviews

4.94 out of 5 average rating, 253 reviews

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

LocationFamilyComfort

4.98 out of 5 average rating, 135 reviews

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

FamilyValueWi-Fi

A scenic view of a calm waterway is framed by a wooden deck. Two white chairs with blue stripes are positioned for relaxation. A small table holds decorative items, while a dock extends into the water, surrounded by greenery and gentle waves.

4.96 out of 5 average rating, 52 reviews

The Creekside Cottage

LocationFamilyAmenities

Superhost

A simple studio space featuring a queen-size bed dressed in white bedding and adorned with two decorative pillows. Nearby, a nightstand holds a lamp. Soft towels and personal items are displayed on open shelving. A small dining table for two occupies one corner.

Guesthouse in Brentwood

Cozy Place

LocationValueCleanliness

4.9 out of 5 average rating, 59 reviews

Superhost