Guesthouse vacation rentals in Brookhaven

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Top-rated guesthouse rentals in Brookhaven

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Superhost

A private deck is shown, featuring a small wooden table set for two with a vase of purple flowers. Two reclining chairs are positioned nearby, offering a peaceful view of lush greenery and ferns beyond the trellis screen.

Guesthouse in Sag Harbor

4.86 out of 5 average rating, 106 reviews

Charming 2BR Cottage, Walk to Town

Beech Tree Cottage is a charming 2-bedroom, 1-bath cottage conveniently located in the peaceful historic district of Sag Harbor, NY. It is a 5-minute walk along the waterfront to Main Street and the center of the village. PLEASE NOTE: We have a 1 MONTH MINIMUM stay for bookings in July and August, and 1 WEEK for June until May 15. Thereafter, we accept requests for short stays subject to availability. Please review our booking and cancellation policy and house rules before making a request.

Top guest favorite

An outdoor deck features lounge chairs under a shaded umbrella and a small dining set surrounded by blooming flowers. A rose bush is prominently placed in a planter, complementing the natural greenery in the background and creating a serene outdoor space.

Guesthouse in Hampton Bays

4.97 out of 5 average rating, 185 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 spacious living area with high wooden cathedral ceilings is illuminated by natural light streaming through skylights. A comfortable white sofa with plaid cushions faces a compact kitchen. A dining table for two is positioned beside floor-to-ceiling windows, enhancing the bright and airy atmosphere.

Guesthouse in Rowayton

4.99 out of 5 average rating, 137 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 staircase with wooden steps is highlighted by a blue patterned runner. A small table with a plant is visible at the top of the stairs. The wall fixtures and doors are subtly illuminated.

Guesthouse in Huntington Station

4.85 out of 5 average rating, 127 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

The exterior of the guest cottage is surrounded by a lush landscape with ivy covering the walls. Colorful autumn leaves blanket the ground, and a serene atmosphere is created by the trees and shrubs. A gravel driveway leads to the garage.

Guesthouse in Wilton

4.97 out of 5 average rating, 118 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.

Superhost

The exterior of a two-story guesthouse is showcased, featuring a blue facade and a well-maintained front lawn. Stone steps lead to the entrance, flanked by vibrant greenery and shrubs. A driveway and additional parking space are visible, providing easy access to the home.

Guesthouse in Southeastern Queens

4.82 out of 5 average rating, 121 reviews

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

Experience the best of both worlds –city convenience and suburban serenity. This is a 2 bedroom 2nd floor guesthouse with 1 King bed and 2 Queen beds. It has a small kitchen, dining + living, and 1 bathroom. 12 mins (without traffic) from JFK, very close to USB Arena, 40 mins to Manhattan, 1.2 miles from LIRR Metro, 25 mins to Long Beach, 30 mins to Jones Beach.Important-this is not a party house. No unregistered guests or visitors allowed without prior consent. max capacity- 6

Guest favorite

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

4.91 out of 5 average rating, 159 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.

Superhost

A well-lit staircase leads to the upper levels of the house. The steps are adorned with a contemporary gray-brown flooring, complemented by crisp white trim along the walls. Natural light enters from a nearby window, enhancing the inviting atmosphere.

Guesthouse in Yonkers

4.75 out of 5 average rating, 122 reviews

St James Guest House

My place is 5 minutes from Empire Casino. Fabulous spot with fine dining and horse racing as well. We are also close to lots of diversified restaurants, family-friendly activities, nightlife, public transport, shopping, Manhattan. You’ll love my place because of the location and the neighborhood. My place is good for couples, business travelers, families (with kids), and big groups.

Guest favorite

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

4.92 out of 5 average rating, 201 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.

Guest favorite

An inviting loft area features a comfortable chair next to a wall-mounted mirror. A separate door leads to a modern bathroom with light blue walls and a white tiled floor. Natural light fills the space, showcasing warm wood flooring.

Guesthouse in Sayville

4.97 out of 5 average rating, 202 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.

Superhost

Lush greenery frames the view of a serene river bordered by trees. The calm water reflects the surroundings, creating a peaceful atmosphere. Small birds can be seen in the distance, adding a sense of tranquility to the natural landscape.

Guesthouse in Shelter Island

4.96 out of 5 average rating, 115 reviews

Waterfront carriage house studio

Access to endless pool/spa, private beach around corner, breathtaking views, access for kayak, sup etc on property, playful friendly dog, easy access to all including sunset beach, beautiful breeze, private location, 46 foot classic powerboat available for charter at discounted rate w/ rental

Top guest favorite

Guesthouse in Southport

4.96 out of 5 average rating, 189 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.