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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Guest favorite

A well-maintained garden area features colorful flower beds along a gravel pathway. Lush green grass stretches out in a spacious yard, with trees and shrubbery framing the property. A decorative lawn feature is visible, enhancing the inviting outdoor space.

Guesthouse in Middle Island

4.94 out of 5 average rating, 16 reviews

Private newly renovated apt

Newly renovated private apt. 20min to Port Jefferson, Ceder Beach, Smith point. About 30-40 min from the Hamptons bays and 45 min from south hamptons. 1 mile from Walmart. private end of the street home. Property is on 1.5 arch .1 bed room l- a queen size bed and 1 full bath. Funton for extra guest. Heated floors for the winter. 25min from Ronkonkoma train station to ride into the city in an 1 hour and 20 to Penn station. *This property is exempt from receiving service pets** not pets allowed.

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 The Hamptons

4.97 out of 5 average rating, 198 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.

Top guest favorite

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

4.99 out of 5 average rating, 145 reviews

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 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 The Hamptons

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!

Guest favorite

A charming outdoor area features a black cottage in the background, with large glass doors reflecting the surroundings. The deck is adorned with potted red geraniums and wooden seating. A hot tub is positioned adjacent to the cottage, emphasizing a tranquil retreat atmosphere.

Guesthouse in The Hamptons

4.97 out of 5 average rating, 110 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.

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

4.85 out of 5 average rating, 131 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 .

Guest favorite

A modern living area is highlighted by a gray sofa centered on a low coffee table. Two armchairs are placed to one side, while a textured area rug complements the space. Wall art hangs above the sofa, and natural light enters through large windows.

Guesthouse in North Fork

4.96 out of 5 average rating, 140 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.

Guest favorite

A spacious bedroom features a large bed with neutral bedding, complemented by a comfortable, modern seating area. Natural light fills the room through multiple windows, and built-in shelves showcase books and decorative items, adding functionality and style to the space.

Guesthouse in Mamaroneck

4.9 out of 5 average rating, 165 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.

Guest favorite

A serene canal view is presented with boats docked along the shore. The sun is setting in the background, casting warm tones over the water, while a grassy area and a flowerbed with colorful blooms are seen in the foreground.

Guesthouse in Massapequa

4.95 out of 5 average rating, 106 reviews

Private Waterfront Loft, minutes to beach

Loft above garage in our backyard. Beautiful views of the canal behind our house and a quick 10 minute drive away from Jones Beach by car. Tons of restaurants and bars in the area, 40 minutes by train to NYC. The loft has a queen size bed, central air and heat, and comes fully stocked with the basic necessities, including a mini fridge, microwave and Keurig coffee machine. Feel free to reach out with any questions :)

Top guest favorite

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

5 out of 5 average rating, 28 reviews

Guest House retreat with amazing pool !!!

Slice of Heaven #2 Bellport Village, a destination town overlooking the great south bay as seen in Coatal Living's top places to vacation. Written by Coastal Living: a gorgeously unassuming little seaport on long Island's South Shore, this village holds a royal flush of pleasures- A small town community feel, colonial style architecture, and even its own performing arts center, all 90mins from NYC.

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

4.97 out of 5 average rating, 209 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

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

4.96 out of 5 average rating, 195 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.