Guest house holiday rentals in Suffolk County

Charming 2BR Cottage, Walk to Town

Beech Tree Cottage is a charming 2-bedroom, 1-bath, two-story 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 are currently only accepting week- or month-long stays for July and August. We will open up forshort stays in summer subject to availability after May 15. (Short stays are ok in other months.) Please review our house rules before making an inquiry.

Value · Location · Air conditioning

Detached bungalow w/ private bath

Cozy, simple living, in separate guest house w/ use of amenities (shared with our family of 4) including sauna & hot tub. The bungalow/guesthouse features a Queen bed, its own private bathroom (shower), small kitchenette (countertop oven, Keurig coffee maker & small fridge) and loveseat for relaxing. There is a dedicated separate outdoor seating area for 2 guests. 2 Adult guests ONLY, no children due to size of guesthouse and proximity to the pool. Please NO pets allowed since owners have pets

Location · Value · Parking

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!

Family · Value · Hospitality

Get Back to Nature at a Modern Wood Clad Getaway

HAPPY SPRING… PEEPERS are singing. The spring birds are arriving and the crocuses are up. Hawks, cardinals, blue jays, bluebirds, gold finches and more are here. Beautiful hiking trails in the woods and along the beachfront. Great places to shop and eat or catch a show at one of New Haven’s renowned museums or broadway theatres or relax. Great restaurants along the shore. Enjoy! We want you to have a relaxing stay with us, free from worry. We are located in a private area, away from public.

Family · Value · Nearby

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.

Value · Family · Getting around

The Quail’s Nest

A beautifully landscaped tranquil oasis. Newly constructed private two bedroom, one bathroom guest extension to owner occupied house. Guests share large yard and pool with owner, and have private deck and seating area. Private entry and parking. Guest's may enjoy outdoor shower and BBQ. Please note there is no kitchen, however a small fridge, Keurig coffeemaker and microwave, plates/utensils are provided. Conveniently located to beaches, shopping and local restaurants in East Hampton.

Location · Family · TV

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!

Value · Location · Quiet

North Country Cottage

Located near Long Island's beautiful beaches, vineyards, and wedding venues, this cozy cottage in the woods provides a quiet and comfortable place to stay while visiting! A spacious patio extends the living area, adding space to enjoy the outdoors in front of the fire pit or outdoor dining table. This property is located behind the owners' home and uses a shared driveway. While the owner is close by to address any issues during your stay, your space allows for total privacy.

Value · Family · Bathroom

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.

Value · Location · Amenities

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!

Value · Location · Parking

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."

Location · Value · Parking

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.

Family · Value · Amenities