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Guesthouse vacation rentals in The Hamptons

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Top-rated guesthouse rentals in The Hamptons

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

Guest favorite
Guesthouse in Stonington
True Artist Loft, 5 minutes to downtown Mystic
The Dacha, as it has lovingly been called for almost 80 years was built in 1945 originally as a studio for the artist that resided on the property. The unique structure is truly one of a kind, fully insulated for winter and tucked away from the road, sitting on a quiet piece of land, just 5 minutes to downtown Mystic. Enjoy modern comforts and a designers decor, while settling in front of the fire, or taking a short drive to all that Mystic has to offer- hiking, water, shops and restaurants.
$205 per night
Guest favorite
Guesthouse in Hampton Bays
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.
$300 per night
Guest favorite
Guesthouse in Southampton
Tiny Home in Prime Spot in Southampton Village
Located in the heart of Southampton Village, this intimate, centrally-located cottage is the ideal 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!
$199 per night

Popular amenities for The Hamptons guesthouse rentals

Family-friendly guest house rentals

Guest favorite
Guesthouse in Groton
Quiet studio with sleeping loft and deck
$98 per night
Guest favorite
Guesthouse in Fairfield
Southport, CT across from BEACH
$232 per night
Guest favorite
Guesthouse in Jamesport
Walk to Beautiful Beach in Heart of Wine Country
$195 per night
Guest favorite
Guesthouse in Charlestown
Cozy All Season Cabin Near Beach at Rockbriar Farm
$88 per night
Guest favorite
Guesthouse in Shelter Island
Waterfront carriage house studio
$375 per night
Guest favorite
Guesthouse in Sag Harbor
Charming 2BR Cottage, Walk to Town
$339 per night
Guest favorite
Guesthouse in Mystic
Maxson House - a serene and stylish getaway
$150 per night
Guest favorite
Guesthouse in New London
Fully Renovated, Ocean Views, Fireplace & Beach
$300 per night
Guest favorite
Guesthouse in Cherry Grove, Fire Island
One Bedroom Cottage in Cherry Grove
$250 per night
Guest favorite
Guesthouse in East Hampton
Beautiful Airy Barn in Springs
$200 per night
Guest favorite
Guesthouse in Milford
Silversands Air-Bnb You’re right Here!
$170 per night
Guest favorite
Guesthouse in Norwalk
Cottage by the Sea
$189 per night

Guest house rentals with a patio

Guest favorite
Guesthouse in Bridgehampton
Central Hamptons Guesthouse
$156 per night
Guest favorite
Guesthouse in Hampton Bays
Quaint One Bedroom Cottage with Private Entrance
$125 per night
Superhost
Guesthouse in Westhampton Beach
Tennis & Sea Escape
$99 per night
Guest favorite
Guesthouse in Shirley
La casita J place
$158 per night
Guest favorite
Guesthouse in Shelter Island
Bayfront 1BR/2BR detached guesthouse with pool
$350 per night
Guest favorite
Guesthouse in Miller Place
Private guesthouse
$99 per night
Guest favorite
Guesthouse in Guilford
Guilford Lakes Cottage, with hot tub and fire pit.
$275 per night
Superhost
Guesthouse in Hampton Bays
Retro Mid-Century Cottage 1/2 mile to CPI
$395 per night
Guest favorite
Guesthouse in Madison
The Rising Tide Cottage
$225 per night
Guest favorite
Guesthouse in Hampton Bays
The Driftwood Cottage
$350 per night
Guest favorite
Guesthouse in Madison
Beachy & Bright Carriage House/5 min walk to Beach
$145 per night
Guest favorite
Guesthouse in Guilford
Page Guest House
$200 per night

Guest house rentals with a washer and dryer

Guest favorite
Guesthouse in Brookhaven
The Unhampton
$159 per night
Guest favorite
Guesthouse in Bay Shore
Cottage on the bay in Bay Shore
$199 per night
Superhost
Guesthouse in Southampton
Modern Guesthouse
$200 per night
Superhost
Guesthouse in Southampton
Southampton Village Getaway
$300 per night
Guest favorite
Guesthouse in Southold
Southold- Adorable 1 Bedroom Cottage
$200 per night
Guest favorite
Guesthouse in Madison
The Barn by the Sound
$200 per night
Guest favorite
Guesthouse in Westerly
Escape To The Coast
$215 per night
Guest favorite
Guesthouse in Mystic
HERON HOUSE MYSTIC, CT.
$250 per night
Guest favorite
Guesthouse in East Haven
Adorable private 1-bedroom guesthouse with parking
$167 per night
Guest favorite
Guesthouse in Redding
The Cottage in Redding
$176 per night
Guest favorite
Guesthouse in Stonington
Merry Hall Farmhouse
$263 per night
Superhost
Guesthouse in Fairfield
Fairfield Town/Beach "Story-Book" Cottage w/Pool
$264 per night

Destinations to explore