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Guesthouse vacation rentals in Brookhaven

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Top-rated guesthouse rentals in Brookhaven

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

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Top guest favorite

A private outdoor deck features two lounge chairs facing toward a lawn, accompanied by a round dining table with four chairs and an umbrella for shade. Surrounding greenery provides a serene setting, complemented by wooden siding on the cottage's exterior.

Guesthouse in Hampton Bays

4.97 out of 5 average rating, 193 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.

A compact kitchen corner features a light blue microwave alongside a silver toaster. A decorative tray displaying a map of the Hamptons adds a local touch to the granite countertop, which reflects the kitchen’s clean, modern design.

Guesthouse in Southampton

4.95 out of 5 average rating, 442 reviews

Tiny Home in Prime Spot in Southampton Village

Located in the heart of Southampton Village, this intimate, centrally-located cottage is the perfect getaway! Nestled in an easily 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 and a 5 min. walk 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!

A private backyard area is seen, featuring a gravel patio with a gazebo, seating, and a picnic table. A grill is positioned nearby, and a fence encloses the space. Lush green grass borders the patio, complemented by a clear blue sky scattered with clouds.

Guesthouse in Milford

4.92 out of 5 average rating, 206 reviews

Chic Coastal Retreat: Modern Apt Steps from Beach

Enjoy our freshly renovated 2-bedroom apartment with a private entrance, kitchen, and in-unit washer/dryer all just a stone's throw from the beach. At Silver Sands State Park, take in views of Charles Island, accessible via a sandbar at low tide. Explore scenic bike trails or stroll the picturesque boardwalk. Perfect for families and group get togethers. Beach amenities are provided, including kayaks, and enjoy a private backyard where you can fire up the BBQ and fire pit. No pets, please.

Top guest favorite

The exterior of the cottage features a black shingle facade with two outdoor light fixtures. A glass door opens to the interior, framed by a small wooden deck. Potted plants with red flowers are positioned at the entrance, contributing to the inviting atmosphere.

Guesthouse in Southampton

4.98 out of 5 average rating, 108 reviews

5 Star Rated Private Cottage Southampton/Sag Hrbr

The Honeycomb Cottage is a little retreat located on a lush acre of evergreens in Southampton rated 5 Star by every guest that has stayed. One block to Peconic Bay Beach - perfect for a day in the sun. A cozy space with TV, WiFi and Sun Deck. Luxury soaps provided, amazing shower and crisp white linens. Exclusive use of the Hot Tub for Cottage guests. Easy parking and located 15 minutes drive to Sag Harbor or Southampton Village. Koi pond with waterfall will sooth the mind and spirit.

Top guest favorite

A charming cottage exterior is surrounded by lush greenery and autumn foliage. The two-story structure features a balcony adorned with potted plants. Large windows create a welcoming appearance, while the grassy area in front offers a peaceful outdoor setting.

Guesthouse in Wilton

4.97 out of 5 average rating, 124 reviews

The Cozy Little Cottage

Charming guest cottage on our property on 1.5 acres in pastoral neighborhood, 7 minutes to Wilton center and 8 to Westport center. The cottage is separate from the main house, connected by a breezeway, above the garage. It is quaint and cozy. High end kitchen appliances include gas range, mini fridge, microwave and mini dishwasher. The bedroom has a queen bed and the living room has a futon couch which folds down. It’s perfect for 1-2 adults, can comfortably fit 3 people if one is a child.

A vibrant local farm stand is visible, featuring an assortment of fresh produce. Sunflowers and colorful flowers decorate the area. Red umbrellas provide shade, while baskets filled with melons and vegetables are displayed prominently. Burlap sacks hang in the background, adding to the market atmosphere.

Guesthouse in North Fork

4.96 out of 5 average rating, 137 reviews

Walk to Beautiful Beach in Heart of Wine Country

Enjoy bright, comfortable and modern home in the heart of North Fork wine and farm country located just a quick walk from a gorgeous Peconic Bay beach with tennis/pickleball courts, volleyball and playground right on the beach. You'll have easy and quick access to the best of the east end: beautiful beaches, boating, fishing, fine and casual dining, vineyards, wineries, breweries, farms and farm stands offering fresh local produce, antique and local shops.

Guesthouse in Hastings-on-Hudson

4.92 out of 5 average rating, 850 reviews

★Tiny House Cottage 35 min to NYC on Hudson River★

Please read the entire listing to set expectations. Super charming, slightly quirky, private Shangri-La with backyard chickens in the artistic and quaint Rivertowns, 35 minutes from NYC along the Hudson River. The Tiny House escape is reminiscent of sleepaway camp (rustic), yet tastefully curated with eclectic art and furnishings. Sleeping loft nest with 8-step ladder or pull-out sofa bed. Fenced-in yard. FREE 24/7 street parking. Read on…

An outdoor space is furnished with multiple white chairs surrounding a central fire pit. A large umbrella stands next to the seating area. Sunlight highlights the wooden decking, with plant life subtly framing the scene, contributing to a fresh and airy environment.

Guesthouse in Mamaroneck

4.9 out of 5 average rating, 164 reviews

Your Modern Guest Wing Near NYC

Brand New Guest Wing in an exclusive private home with a separate entrance. One large bedroom, kitchenette, master bathroom, closet space & separate laundry closet. Steam shower with special steam light function and aroma therapy. High End Kitchenette. 4 minute drive to Mamaroneck train station. 35 minute train and/or drive to Grand Central (Manhattan). Close to the Village of Mamaroneck Avenue center. High speed internet. Outdoor CCTV.

Top guest favorite

Guesthouse in Brookhaven

4.97 out of 5 average rating, 225 reviews

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!

A charming guest studio features a triangular roofline and a welcoming porch. Two wooden chairs are positioned on the porch, facing double glass doors that open into the interior. The surrounding area is filled with trees, creating a natural and serene atmosphere.

Guesthouse in Bedford

4.92 out of 5 average rating, 207 reviews

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.

Guesthouse in Sayville

4.97 out of 5 average rating, 208 reviews

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.

Top guest favorite

Guesthouse in Southport

4.96 out of 5 average rating, 194 reviews

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.

Vacation rentals for every style

Get the amount of space that is right for you

Houses

A space thats all yours, with room for everyone

Bungalows

Intimate homes. inviting architecture

Cottages

Quaint homes, peaceful surroundings

Popular amenities for Brookhaven guesthouse rentals

Free parking on premises

Air conditioning

Family-friendly guest house rentals

A serene view captures the landscaped yard leading to a tidal inlet, framed by lush green grass. The calm waters reflect the blue sky and nearby trees, with residential homes visible in the background. A small dock extends into the inlet from the opposite bank.

Guesthouse in Norwalk

5 out of 5 average rating, 71 reviews

Cottage by the Sea

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.

Guesthouse in Cherry Grove, Fire Island

4.92 out of 5 average rating, 79 reviews

One Bedroom Cottage in Cherry Grove

A serene view of a spacious barn with a deck illuminated by the golden light of sunset. Surrounded by lush foliage, the barn features large windows and a welcoming porch, providing a glimpse of modern yet comfortable architecture.

Guesthouse in East Hampton

4.9 out of 5 average rating, 211 reviews

Beautiful Airy Barn in Springs

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

4.85 out of 5 average rating, 131 reviews

2 large bedrooms in cozy little neighborhood.

A calm bay scene is captured, featuring still waters reflecting clear skies. Reeds stand at the shoreline, while a small boat is visible in the distance. The sandy beach leads to the water's edge, emphasizing the serene outdoor setting.

Guesthouse in Hampton Bays

New place to stay

Waterfront cottage on beach

Lush green trees line the water's edge, reflecting shades of gold and green onto the calm surface. The tranquil scene is accentuated by the gentle ripples, creating a harmonious blend of nature and serenity.

Guesthouse in Shelter Island

4.96 out of 5 average rating, 115 reviews

Waterfront carriage house studio

A cozy lounge area is furnished with a generous sofa and two white chairs, surrounded by bookshelves filled with various books. A coffee table sits at the center, and a cast iron fireplace is present, enhancing the inviting atmosphere. Natural light fills the room through large windows.

Guesthouse in Sag Harbor

4.86 out of 5 average rating, 107 reviews

Charming 2BR Cottage, Walk to Town

The exterior of the two-story cottage is framed by lush greenery, featuring a welcoming porch with white columns. Large windows allow natural light to flood the interior. The gentle slope of the roof and classic shutters enhance the charming architecture, while a hint of red barn peeks in the background.

Guesthouse in Rowayton

5 out of 5 average rating, 23 reviews

Guest Cottage in Rowayton

Guest house rentals with a patio

Top guest favorite

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

4.95 out of 5 average rating, 95 reviews

The Cottage in Greenwich

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, 18 reviews

2 BR Private Suite w/Private Living Room & Kitchen

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.

Guesthouse in Southeastern Queens

4.78 out of 5 average rating, 136 reviews

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

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.

Guesthouse in Hampton Bays

5 out of 5 average rating, 4 reviews

Hill Coast Cottage: Freshly Renovated

A comfortable sleeping area features a spacious bed with a blue quilt and decorative pillows. Two side tables with lamps are placed beside the bed. A small arrangement of flowers adds a touch of color. Blinds cover the window, allowing for adjustable natural light.

Guesthouse in Shirley

4.95 out of 5 average rating, 84 reviews

La casita J place

Top guest favorite

A modern kitchen features a central island with a sleek cooking range and ventilation hood. Bright windows provide views of Norwalk Harbor and the surrounding landscape. Light cabinetry complements the stainless steel appliances, creating a clean and airy space for meal preparation.

Guesthouse in Norwalk

5 out of 5 average rating, 21 reviews

Waterfront Getaway - Norwalk, CT

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

4.98 out of 5 average rating, 61 reviews

North Country Cottage

A cozy living area is visible from the mezzanine, featuring a beige sofa with two dark cushions. Artwork hangs on the wall above the sofa, complemented by modern floor lamps. Natural light filters through the window shutters, illuminating the wooden flooring.

Guesthouse in Weston

5 out of 5 average rating, 71 reviews

Adorable 1-Bedroom Cottage w/ Mezzanine Weston, CT

Guest house rentals with a washer and dryer

A hot tub filled with clear water is positioned in a serene outdoor setting, surrounded by lush trees and manicured greenery. Pathways and landscaping elements create a tranquil retreat, promoting relaxation and outdoor enjoyment.

Guesthouse in North Fork

4.98 out of 5 average rating, 47 reviews

Private Luxe Cottage at Gates of Wine Country

Top guest favorite

A well-maintained garden features lush green grass and a variety of trees and flowering plants, creating a vibrant natural setting. The surrounding property presents a charming two-story building, partially obscured by foliage, against a clear blue sky, enhancing the tranquil ambiance.

Guesthouse in Larchmont

4.98 out of 5 average rating, 45 reviews

Beautiful guesthouse - Larchmont

A spacious kitchen features light-colored cabinetry and wooden countertops. Two bar stools are positioned at a kitchen island. A white refrigerator and a small black appliance can be seen, with a large window offering natural light and views of the outdoors.

Guesthouse in Pound Ridge

4.81 out of 5 average rating, 21 reviews

Pound Ridge Cottage

Guesthouse in Stamford

4.93 out of 5 average rating, 44 reviews

Carriage house flat near 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.

Guesthouse in Fairfield

4.95 out of 5 average rating, 21 reviews

The Creekside Cottage

Top guest favorite

A brick pathway leads through a green lawn, flanked by round white lights along its edges. On the right, stairs ascend to a pale yellow building, while a solid white fence encloses the backyard area beyond.

Guesthouse in Huntington Station

4.97 out of 5 average rating, 94 reviews

Modern fully updated 2nd Floor apartment

A bright living area is framed by large windows showcasing a wooded view. A dark green sofa with white pillows is positioned alongside two light-colored armchairs. A wooden coffee table rests on a patterned area rug, with a dining table visible in the background.

Guesthouse in Pound Ridge

5 out of 5 average rating, 16 reviews

Renovated guesthouse on private 7 acre property

A kitchen countertop is displayed featuring a coffee maker along with a clear container holding coffee pods and assorted condiments. The surface has a sleek, speckled appearance, adding a touch of modernity to the space.

Guesthouse in Bay Shore

4.85 out of 5 average rating, 34 reviews

Cozy Place

Quick stats about guesthouse rentals in Brookhaven

Total rentals
40 properties
Total number of reviews
1.4K reviews
Pet-friendly rentals
10 properties allow pets
Rentals with a pool
10 properties have a pool
Rentals with dedicated workspaces
20 properties have a dedicated workspace
Wifi availability
40 properties include access to wifi

Destinations to explore