Guesthouse vacation rentals in Suffolk County

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.

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.

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!

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 .

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.

Entire Guest House at Fox Pond Farm.

Recently renovated private guest house with access to swimming pool offers sleeping for eleven in four bedrooms. Tastefully decorated with all amenities. Close to Merritt Parkway and train to Manhattan. This is a natural refuge on eleven very private acres. Large private terrace faces westerly for amazing sunsets and offers a "Plein Air" environment for alfresco meals, cocktails and relaxation. An attached vegetable and flower garden with fountain offer a quiet space to relax and reflect.

The Gardener's Cottage Dog friendly/weekly/monthly

The Gardener's Cottage, less then a mile from the Long Island Sound, is a great alternative to the common hotel. Situated a stones throw from Hammonasset State Park and Beach, Clinton Outlets, and the Shore Line East train station. Near by you will find places to kayak, Chamard Wineries, Marinas and many quaint New England towns. The Cottage is fitted with it's own router coupled with an eating nook that can double as a work space. Pets are allowed. Self check-in

Chic Coastal Escape - 5 Mins to the Beach

Charming, spacious, and just 5 minutes to the beach, this one-of-a-kind carriage house is the perfect escape. Set on nearly an acre, it’s ideal for a romantic weekend, girls’ trip, or family getaway. Enjoy a private deck, huge backyard, and easy access to town, wineries, antique shops, seafood spots, and scenic trails. Relax, explore, and make unforgettable memories by the sea.

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.