Guesthouse vacation rentals in The Hamptons

Find and book unique guesthouse rentals on Airbnb

Top-rated guesthouse rentals in The Hamptons

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

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Guest favorite

Guesthouse in Sag Harbor

4.88 out of 5 average rating, 77 reviews

Guest House! Hamptons-Sag Harbor Walk to Bay Beach

We may accept your dog, please ask. We love our beautiful Guest House! Enjoy our blooming gardens. We keep the GH impeccable and welcoming. Walk to a sandy bay beach with stunning sunsets. Newly appointed with modern fixtures & finishes, high ceilings, clean & bright. New ceramic flooring, bathroom, bed, linens, furniture, appliances. Comfortably accommodates 2 adults, room for a crib/PacknPlay. Extremely quiet inside, great for sleeping after a day in The Hamptons! I’ll help with any request.

Superhost

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.

Guest favorite

Guesthouse in Hampton Bays

4.97 out of 5 average rating, 181 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

4.95 out of 5 average rating, 440 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!

Superhost

Guesthouse in Milford

4.92 out of 5 average rating, 204 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 East Hampton

5 out of 5 average rating, 90 reviews

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.

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.

Superhost

Guesthouse in Westhampton Beach

5 out of 5 average rating, 3 reviews

Summer retreat cottage in WHB

Lovely guesthouse with private patio. Steps to Main Street and houses of worship. Enjoy walking or biking to the farmer's market, restaurants, marina, and beach. Bright kitchen and comfortable living room with wifi and smart tv. BBQ and outdoor shower for your use (located on the patio of the main house). Beach pass available for stays of 30+days; access to private village beaches before 10am and after 5pm as per village policy.

Guest favorite

Guesthouse in Shelter Island

5 out of 5 average rating, 64 reviews

Bayfront 1BR/2BR detached guesthouse with pool

Perfect relaxing getaway for a couple or family. Bayfront 1BR/2BR fully detached guest house with gorgeous morning views. Property has saltwater pool + hot tub (open May -October) and bay access via private dock. Central to both north & south forks (wineries + Hamptons or Montauk just short drive away). Down the road from famous Shelter Island Sunset Beach + golf course. Come explore the beauty of the Hamptons without the stress!

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 Westhampton

4.97 out of 5 average rating, 39 reviews

The “Birdy” Guest house

Take it easy at this peaceful guesthouse near Westhampton Beach village, Country Club, wine country (North folk), Moriches Bay and Westhampton Beaches. An amazing location for birding and kayaking. Ideal place for a couple looking to escape the city, attend a wedding, or explore wine country for a weekend to get some fresh air and experience nature.