Guesthouse vacation rentals in Suffolk County

Find and book unique guesthouse rentals on Airbnb

Top-rated guesthouse rentals in Suffolk County

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

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Guest favorite

Guesthouse in Wilton

4.96 out of 5 average rating, 111 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 minutes to Westport center. The cottage is separate from the main house, connected by a breezeway, above the garage. It is a quaint and cozy. High end kitchen appliances include gas range, mini fridge, microwave and dishwasher drawer. The bedroom has a queen bed and the living room has a futon couch which folds down. We also have a twin air mattress. It is perfect for one or two people.

Guest favorite

Guesthouse in Hampton Bays

4.97 out of 5 average rating, 179 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.

Guest favorite

Guesthouse in Southampton

4.96 out of 5 average rating, 438 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

Guesthouse in Southampton

4.96 out of 5 average rating, 160 reviews

Wonderful Private Spacious Pool House

Light, open, spacious and private pool house less than 1/2 mile from the bay beach and 4 miles to ocean beaches. Close to Southampton, Sag Harbor, and Water Mill. Families love it as do our many girl getaways. Pool and deck and BBQ and umbrellas and pool toys and lounge chairs are for your exclusive enjoyment too. Enough beds to sleep 6, but we allow up to 3 additional guests for a total of 9 with an additional fee. Portable beds and linens will be provided. Can’t book just 1 weekend night.

Superhost

Guesthouse in Milford

4.92 out of 5 average rating, 203 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.

Guest favorite

Guesthouse in Huntington Station

4.84 out of 5 average rating, 116 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

Guesthouse in Norwalk

4.99 out of 5 average rating, 133 reviews

Private one bedroom cottage on Conn. seashore

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 friendly town; you don't even need a car while here.

Superhost

Guesthouse in East Hampton

4.81 out of 5 average rating, 308 reviews

Detached bungalow w/ private bath

Cozy, simple living, in separate guest house with use of amenities (shared with our family of 4). The bungalow/guesthouse features a Queen bed, its own private bathroom (shower), small kitchenette (countertop oven, micrwave, Keurig coffee maker & small fridge) and loveseat for relaxing. There is a dedicated separate outdoor seating area for 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.

Guest favorite

Guesthouse in Jamesport

4.95 out of 5 average rating, 127 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

Guesthouse in Brookhaven

4.97 out of 5 average rating, 224 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!

Guest favorite

Guesthouse in Guilford

4.99 out of 5 average rating, 479 reviews

Get Back to Nature at a Modern Wood Clad Getaway

FALL IS HERE. Crisp nights; gorgeous days. Hike on the trails.Stroll along the ocean. Ospreys; hawks; cardinals, blue jays, bluebirds, gold finches and more. Great places to shop and eat or just relax in our cozy guest house. Enjoy! We want you to have a relaxing stay with us, free from worry. We are located in a private area, away from public.

Guest favorite

Guesthouse in Sayville

4.96 out of 5 average rating, 198 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 are COVID conscious and employ a professional cleaning regiment.