Guesthouse holiday rentals in Brookhaven

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.

4.97 out of 5 average rating, 109 reviews

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!

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.

4.97 out of 5 average rating, 212 reviews

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.

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.

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.

Guesthouse in Huntington Station

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.

4.86 out of 5 average rating, 139 reviews

2 large bedrooms in cozy little neighborhood.

Very spacious -2 bdrms , sleeps 6 + crib on 2nd floor. Bath, Living rm and Snack area on the main floor. The guest suite is private, spacious and will accommodate those looking to spend time in the area . The suite is attached to the main house by locked French doors . There are no shared spaces .Close to public transportation (LIRR- HUNTINGTON STATION) ,Paramount Theater & Huntington Village . In town for weddings & events in Woodbury/ Syosset ? It's a great place to tip off from .

Guesthouse 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!

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.

4.96 out of 5 average rating, 458 reviews

Tiny Home in Prime Spot in Southampton Village

Price drop! Located in the heart of Southampton Village, this intimate cottage is the perfect getaway! Nestled in an accessible, safe, and well-lit neighborhood, it is ideal for those with or without a vehicle. Only a 5 min. walk from the train station or to town, which includes premier shopping and restaurants. Enjoy nearby wineries, museums, and pristine, top-ranked beaches. Be close to everything Southampton has to offer while enjoying absolute peace and quiet.

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.

Guesthouse 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.

4.97 out of 5 average rating, 236 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!

The exterior of the studio cottage is showcased, featuring a blue facade with white lattice detailing. A vibrant garden with various flowers and greenery surrounds the property. The structure is accented by a classic chimney and large windows allowing daylight to enter.

4.83 out of 5 average rating, 143 reviews

Sag Harbor Cottage in historic district

Charming studio cottage in the historic district of Sag Harbor. Comfortable queen bed. Walk to shops or restaurants downtown. Nearby beaches for swimming, kayaking or sailing. Great location to explore all of the Hamptons or get to know Sag Harbor with its unique charm and friendly atmosphere. We are the "un-Hamptons."

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.

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.

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.

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. We employ a professional cleaning regiment.

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.

Guesthouse 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.

Popular amenities for Brookhaven guesthouses

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Family-Friendly guesthouses

A studio space features a stylish red and gray color scheme. A spacious bed with patterned bedding is accompanied by bedside lamps. A compact kitchen area includes a red refrigerator, microwave, and sink. A round dining table with red seats is nearby, enhancing the modern decor.

Guesthouse in Bay Shore

4.89 out of 5 average rating, 122 reviews

Detach cozy Retro style cottage/studio

4.91 out of 5 average rating, 215 reviews

A spacious living area features a large sectional sofa adorned with decorative pillows, complementing a dining area with a round table and four chairs. Bright overhead lights illuminate the space, which includes a modern kitchen visible in the background.

Guesthouse in Milford

Chic Coastal Retreat: Modern Apt Steps from Beach

Guesthouse 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

4.95 out of 5 average rating, 22 reviews

The exterior of the cottage is framed by lush greenery and flowering bushes. Two chairs sit on a gravel patio area, inviting relaxation in a natural setting. A wooden step leads to the entrance of the cottage, which is partially obscured by the surrounding foliage.

Guesthouse in Rowayton

Adorable 1-Bedroom Guest Cottage in Rowayton

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

4.85 out of 5 average rating, 13 reviews

A charming exterior of a wooden house is framed by lush greenery, including climbing plants. A welcoming deck with steps leads to the entrance. A variety of potted plants are arranged along the path, adding natural beauty to the setting. Large windows allow light to fill the interior.

Guesthouse in North Fork

Beautiful 2 bdrm cottage on NoFo

Guesthouse in Shelter Island

A spacious outdoor area is highlighted by a refreshing pool surrounded by lounge chairs. The pool house, featuring a white exterior, sits in the background amidst lush greenery. Flower pots and garden plants frame the scene, enhancing the tranquil environment.

4.96 out of 5 average rating, 27 reviews

Sleek and Chic cottage/Pool House

4.86 out of 5 average rating, 29 reviews

A classic three-story guest house is set against a twilight sky, featuring white architectural details. The front porch offers ample space, framed by greenery. A ladder and additional lighting elements are visible, indicating ongoing improvements, while a warm glow from outdoor lights enhances the evening scene.

Guesthouse in Greenwich

Lost in Decision Forest Guesthouse

Guesthouses with a patio

Guesthouse in West Hempstead

4.75 out of 5 average rating, 12 reviews

The Ultimate Family & Friends Home

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

Guesthouse 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

An open kitchen and living area is showcased, featuring modern appliances and ample counter space. Large windows allow natural light to fill the room, while a light wood ceiling adds warmth. A dining area with two stools is present near the kitchen.

4.94 out of 5 average rating, 17 reviews

Hill Coast Cottage: Freshly Renovated

4.83 out of 5 average rating, 29 reviews

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

Guesthouse 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.

Guesthouse in Nesconset

Quiet Family Guest Suite

Guest house rentals with a washing machine and dryer

4.96 out of 5 average rating, 53 reviews

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 North Fork

Private Luxe Cottage at Gates of Wine Country

A serene outdoor space showcases a heated saltwater pool framed by neatly trimmed hedges. Comfortable lounge chairs are arranged beside the water, while a large umbrella provides shade. A two-story house is visible in the background, surrounded by greenery.

4.92 out of 5 average rating, 13 reviews

3 Bedroom Guest House in Southampton

Guesthouse in Pound Ridge

A cozy sleeping space showcases a spacious bed dressed in white linens, complemented by neatly arranged towels. Floral wallpaper adorns the walls, while natural light enters through the double windows, enhancing the room's serenity. A comfortable chair is positioned in a corner, adding to the inviting atmosphere.

4.84 out of 5 average rating, 25 reviews

Pound Ridge Cottage

4.94 out of 5 average rating, 49 reviews

The living area features a light-colored sectional sofa facing a mounted flat-screen television. A wooden console table with decorative accents is positioned in front. The space is illuminated with track lighting and has an open entryway leading to a bedroom area.

Guesthouse in Stamford

Carriage house flat near beach

5 out of 5 average rating, 3 reviews

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.

Guesthouse in Westport

Serene Stay Guest House

Guesthouse 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

4.89 out of 5 average rating, 19 reviews

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

The Private Guest House -Lake Ronkonkoma!