Guest house holiday rentals in Fire Island

4.99 out of 5 average rating, 154 reviews

A modest wooden house features large glass doors that lead to a spacious deck. The surrounding green lawn is complemented by well-kept shrubs and trees. Sunlight casts a warm glow on the exterior, highlighting the structure's simple charm.

Guest house 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.

Guest house in Islip Terrace

A spacious bed is centered against a light wall, adorned with bright yellow linens and decorative pillows. Two lamps with turquoise bases provide soft lighting on either side, complemented by a framed artwork above the headboard.

4.99 out of 5 average rating, 127 reviews

The Sunshine House

Enjoy your stay and visit the Bayard Cutting Arboretum, SUSA Orlin & Cohen Sports Complex, Robert Moses Beach; centrally located between The Hamptons Vineyard Wine Tours & Manhattan. This unique home was originally built in 1921 and has since undergone renovations with additions added to the original structure, including the three bedroom / bath guest wing with a private entrance from the main house. We provide beverages and continental breakfast. Please email us for more details!

Guest house in Pound Ridge

The cottage is nestled among lush trees, highlighted by a distinctive stone chimney. Expansive glass doors reflect the surrounding greenery, inviting natural light inside. The structure is surrounded by verdant shrubs, creating a harmonious connection with nature.

4.94 out of 5 average rating, 114 reviews

A Lovely Cottage in the Woods

Welcome to our cottage located just 1 hour north of NYC! It is nestled into 2.7 acres of beautiful gardens, mossy groves, and lovely woods. Nature abounds: The property abuts the 4000 acres of the Ward Pound Ridge Reservation. A trailhead begins right across the driveway. The cottage is equipped with a stone fireplace, spacious kitchen, living room area, table for dining and working, and a sleeping loft. During the summer, a private salt water pool is available.

4.92 out of 5 average rating, 336 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.

Guest house in Westville

Square6ix Stylish Guesthouse in Westville

Inviting, eclectic, and completely private, this single family stand-alone guest house is an intimate and engaging haven. A serene private guesthouse perfect for couples, creatives, and travelers. Stylishly decorated with modern amenities, this space is a cozy retreat just a short walk to Westville Village and Edgewood Park. Ideal for weekend getaways, local visitors, or professionals seeking a quiet base with fast WiFi and free parking.

4.98 out of 5 average rating, 125 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.

Guest house in Waccabuc

French Guest House in Waccabuc

A private, European-style retreat just 60 minutes from NYC. Set on an eight-acre gated French estate with its own lake, this guest house feels like a mini Versailles with 18th-century statuary, fountains and manicured gardens. Designed by David Easton, it features heated stone floors, a heated towel rack, luxury linens, gold fixtures, fast WiFi, and a private entrance. Minutes from Waccabuc Country Club and the Katonah train station.

4.95 out of 5 average rating, 108 reviews

A bright sleeping area features a spacious bed with light bedding, positioned beneath a vaulted ceiling. Floor-to-ceiling windows provide views of the woods, while a small desk and chair are set against one wall for workspace. A television is mounted for entertainment.

Guest house in Greenwich

The Cottage in Greenwich

Brand new, light-filled private cottage guesthouse overlooking the woods in the heart of Greenwich, CT. Floor to ceiling windows, radiant heat bathroom floors, queen Casper mattress, a dedicated parking spot, Wi-Fi, TV, kitchenette with full fridge, Keurig coffee maker, microwave, toaster and induction stovetop and all utensils. Perfect for a weekend getaway or a quiet place to work.

4.93 out of 5 average rating, 303 reviews

An open studio layout features a dining island with black chairs, a cozy couch in the corner, and a spacious bed made with neutral bedding. Decorative walls showcase intricate designs, while numerous pendant lights hang from the ceiling, illuminating the area. Large windows provide natural light.

Guest house in Peekskill

Peekskill Carriage House Downtown Studio

Located close to the center of town, this is the perfect launchpad to experience local restaurants, coffee houses, the Paramount Theater, shopping, etc. and a short drive to stunning hikes, the Hudson Valley and beyond. The apartment is ideal for one or two and features a kitchenette, bathroom, dining island, comfortable queen bed, and couch. peekskillcarriagehouse.com

4.92 out of 5 average rating, 223 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.

Guest house 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.

4.96 out of 5 average rating, 222 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.

Guest house 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. We employ a professional cleaning regiment.

Guest house in South Salem

A bright sitting room features a cozy sofa adorned with colorful pillows. A wooden sideboard stands against the wall, while a small side table holds reading materials. Natural light filters in through two windows, illuminating the room's warm, wooden flooring and vibrant area rug.

4.93 out of 5 average rating, 318 reviews

1795 colonial w private 2 bd rm, 1 bth,LR,Kit apt

A unique private and quiet 2 bedroom (1 double bed, two single full beds) totally self contained apt,with sitting room, bathroom ,mud room and full eat in kitchen, in Shaker Hollow, a classic 1795 colonial.Stone patio overlooking 3 1/2 acres of garden and a meadow along with a large fire pit.

4.97 out of 5 average rating, 213 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.

Guest house in Southport

Southport, CT across from BEACH

Located at Southport beach on Westport Line, this 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.

4.81 out of 5 average rating, 116 reviews

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.

Guest house in Guilford

The Little Blue Cottage

Relax at this unique and tranquil getaway. Enjoy the charm of an antique home while being in your own private space. Minutes from all conveniences and beaches. Walking distance to town. Grill and relax on the spacious back porch. or walk to the Mill Pond to picnic.

Popular amenities for guest house rentals in Fire Island

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly guest house rentals

5 out of 5 average rating, 25 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.

Guest house in Waterford

A Little House by the sea

A cozy living area is present with a light-colored sectional sofa facing a television. A soft throw blanket rests on the sofa. Large windows allow natural light, while a floor lamp and a small side table complement the space. A white armchair adds additional seating.

4.91 out of 5 average rating, 34 reviews

The Hide-A-Way

4.96 out of 5 average rating, 28 reviews

A well-lit sleeping area features a full-size bed with patterned bedding in calming colors. Two decorative lamps with green shades stand on either side of the bed. A vintage mirror adorns the wall above a stylish desk, while light flows through a large window dressed with sheer white curtains.

Guest house in Harlem

Verde Private Room

4.98 out of 5 average rating, 62 reviews

A detached studio with a charming exterior is surrounded by lush greenery and landscaped gardens. The structure features large windows framed in dark trim, allowing natural light to fill the interior. A stone pathway leads up to the entrance, enhancing the inviting appearance of the property.

Guest house in Larchmont

Beautiful guesthouse - Larchmont

4.93 out of 5 average rating, 485 reviews

A kitchen area is visible with modern appliances, including a stove and refrigerator, complemented by a breakfast bar with two stools. A ship's ladder leads to the sleeping loft above. Natural light fills the space through a window, enhancing the clean, contemporary design.

Guest house in Groton

Quiet studio with sleeping loft and deck

4.89 out of 5 average rating, 45 reviews

A charming cottage is nestled among lush greenery, featuring a light-colored exterior with multiple windows. The inviting entrance is framed by neatly trimmed shrubs, while a stone pathway leads to the front door. A spacious yard with trees adds to the serene setting.

Guest house in Greenwich

Beautiful Cottage in Greenwich CT

Guest house 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.

4.99 out of 5 average rating, 99 reviews

North Country Cottage

Guest house in Essex Village

A charming antique home is depicted with a well-maintained white exterior and contrasting black roof. Lush green lawns surround the property, with colorful flowering shrubs adding vibrancy. The structure features multiple windows and a decorative cupola, amid tall trees that provide a serene backdrop.

4.98 out of 5 average rating, 56 reviews

Adorable 2 bedroom guesthouse in Essex village

Guest house rentals with a patio

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.

4.87 out of 5 average rating, 67 reviews

Quaint One-Bedroom Cottage with Private Entry

A charming exterior view of the studio guesthouse showcases light gray shingle siding and an inviting white door framed by large, multi-paned windows. Colorful hydrangeas decorate the entrance, with lush greenery and trees providing a serene background.

5 out of 5 average rating, 26 reviews

Romantic studio cottage; Walk to town

Guest house in Fire Island Pines

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.

5 out of 5 average rating, 28 reviews

2 BR Private Suite w/Private Living Room & Kitchen

Guest house in Valley Stream

A spacious outdoor balcony is visible, featuring a railing with potted plants. The surrounding landscape includes trees and green foliage under a bright blue sky with scattered clouds. The area provides an open view, enhancing the feeling of tranquility.

4.8 out of 5 average rating, 188 reviews

Cozy 2 BR guest suite very close to JFK, UBS Arena

Superhost

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.

Guest house in Roosevelt

4.83 out of 5 average rating, 29 reviews

Home away from home

4.77 out of 5 average rating, 105 reviews

Guest house in Yonkers

Apartment in New York near to Manhattan.

Guest house in East Norwalk

5 out of 5 average rating, 31 reviews

Waterfront Getaway - Norwalk, CT

5 out of 5 average rating, 9 reviews

A modern kitchen is showcased with white cabinetry and stainless steel appliances, including a refrigerator, oven, and microwave. A sleek countertop offers workspace, complemented by a geometric tile backsplash. Light wood flooring adds warmth to the overall design.

Guest house in Nesconset

Quiet Family Guest Suite

Guest house rentals with a washing machine and dryer

Guest house in New London

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.

4.98 out of 5 average rating, 124 reviews

Fully Renovated, Ocean Views, Fireplace & Beach

Guest house in Mount Kisco

The living area showcases a light-colored sofa adorned with patterned throw pillows, set next to a dark wooden coffee table. A dining area is visible, featuring a kitchen island with seating, and modern appliances can be seen in the well-lit space.

5 out of 5 average rating, 37 reviews

White Cedar Cottage

Superhost

A bright living space features a light-colored sofa arranged with decorative pillows. A wooden coffee table sits atop a textured rug, providing a central gathering point. Natural light filters through multiple windows adorned with white blinds, and framed artwork complements the room's modern aesthetic.

Guest house in Westport

5 out of 5 average rating, 3 reviews

Serene Stay Guest House

Guest house in Fairfield Beach

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.

4.97 out of 5 average rating, 36 reviews

The Creekside Cottage

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.

5 out of 5 average rating, 13 reviews

Peaceful cottage

Guest house 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.

4.97 out of 5 average rating, 109 reviews

Modern fully updated 2nd Floor apartment

4.96 out of 5 average rating, 117 reviews

A spacious living area features a large, comfortable sofa facing a stone fireplace with a modern television mounted above it. A skylight allows natural light to brighten the room, and an open kitchen is visible in the background with sleek cabinetry and barstool seating.

Guest house in Guilford

Guilford Lakes Cottage, with hot tub and fire pit.