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 Patchogue

4.84 out of 5 average rating, 57 reviews

Charming Patchogue Cottage!!!

Enjoy this cozy Patchogue Cottage right in the heart of town!!! Just a 3 minute walk to downtown Main Street, bars, restaurants, shopping, entertainment, and more! While being a short trip away from The Great South Bay, Fire Island Ferries, and the LIRR - this space is perfect for couples, solo traveling, or professionals! Settle down in this snug space, complete with a king sized bed, full kitchen, a full bathroom, Wi-Fi, A/C, and more! Dont miss your chance to stay at The Patchogue Cottage! *

Guest favorite

Guesthouse in Hampton Bays

4.97 out of 5 average rating, 178 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, 437 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.

Superhost

Guesthouse in East Hampton

4.81 out of 5 average rating, 307 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 Southampton

4.98 out of 5 average rating, 57 reviews

Southampton Modern Barn, Private Hot Tub and Pool

This magical getaway delivers peace and relaxation. Wake up to coffee on your private deck with bucolic views. Play in your heated, saltwater pool, and relax under the stars in your hot tub (open year round). During your stay, these amenities and more will be for your personal use. Stroll to the owner’s dock on Big Fresh Pond, for paddle boarding, kayaking and sunsets. You can also drive 8 minutes to Southampton Village for shopping, restaurants, art galleries and Ocean Beaches.

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

4.69 out of 5 average rating, 36 reviews

Tennis & Sea Escape

Escape the city and enjoy a Tennis & Sea Escape at our charming cabana. The private har-tru (green clay) tennis court is perfect for tennis enthusiasts, while the spacious patio and landscaped backyard offer relaxation after a day out. Access the beach and town within minutes, and plug in your EV car before rinsing off in the outdoor shower. Enjoy a perfect blend of comfort, luxury, and convenience with coffee, TV, WiFi, and towels provided.

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.

Superhost

Guesthouse in Hampton Bays

4.86 out of 5 average rating, 58 reviews

Quaint One-Bedroom Cottage with Private Entry

Kick back and relax in this quiet, charming cottage in the heart of Hampton Bays. The house is located less than a mile from the bay, a 15 minute walk or 3 minute drive. There are two local beaches nearby: Meschutt Beach is about a 6 min drive and Ponquogue is a 9 min drive. The backyard is also a very tranquil place to unwind.