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Guesthouse vacation rentals in Long Island

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Top-rated guesthouse rentals in Long Island

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

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Guesthouse in Hempstead

4.84 out of 5 average rating, 122 reviews

Private Guest house with pool access.

Warning‼️this listing price is for 1 adult only. A $50 daily fee will apply for additional guest. Unapproved guest will result in cancellation no refund. Clean, stylist, peaceful, private space. Seasonal Pool access from July until 1st of September . ⛔️ Do not flush toilet paper on the toilet it will overflow, garbage disposal and trash bags are available. For pets a fee will apply. No smoking 🚭, No parties, 2 guest Max. Security Cameras. No parking on premises. Street parkings are available 24/7

Guesthouse in Wilton

4.96 out of 5 average rating, 109 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.

Guesthouse in Stonington

4.97 out of 5 average rating, 256 reviews

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.

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.

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!

Guesthouse in Mahopac

4.93 out of 5 average rating, 168 reviews

Sunny Lakeview Guesthouse

Art and light filled spacious studio with panoramic views overlooking lake Mahopac perched on a steep hill. A short 5 min walk down the hill to swimming/paddleboarding/canoeing. Walkable to an on-the-lake restaurant/ other dining/ takeout options + excellent boba tea shop! Drivable to farm fresh food markets, restaurants and art museums. Endless nearby cute towns and hikes include Fahenstock Park, Pound Ridge, Cold Spring, Beacon, Ridgefield, or walk up the hill to the trails of Volz park!

Guesthouse in Hastings-on-Hudson

4.91 out of 5 average rating, 789 reviews

★Tiny House Cottage 35 min to NYC on Hudson River★

Please read the entire listing to set expectations. Super charming, slightly quirky, private Shangri-La w/backyard chickens in the artistic & quaint Rivertowns, 35 min. from NYC. The Tiny House escape is reminiscent of sleep away camp (rustic), yet tastefully curated w/eclectic art & furnishings. Sleeping loft nest w/8 step ladder or pull out sofa bed. E-fireplace inside. Firepit outside. Stars. 2 patios, yard. FREE private driveway. Close to the Hudson River. Read on...

Guesthouse in New Haven

4.94 out of 5 average rating, 279 reviews

Square 6ix

Inviting, eclectic, and completely private, this single family stand-alone guest house is an intimate and engaging haven. Stylishly decorated with mid-century modern furniture and adorned with pieces from local artists, this quiet home has a separate entrance, separate porch, high ceilings, and a fully equipped kitchen. The guest house is located a walking-block away from the charms of Westville Village and Edgewood Park.

Guesthouse in Mystic

4.98 out of 5 average rating, 596 reviews

Gorgeous Waterfront Getaway

Perfect getaway from the city for couples wanting peace and tranquility and stunning views. A beautiful waterfront one bedroom guesthouse, one and one-half miles from downtown Mystic CT. Beautifully decorated with art and antiques. Kitchenette, full bath and loft bedroom. Queen bed. Air conditioning and heated. Belgian linen bedding! Private patio. Dock. Kayak/Canoe rentals close by. Internet.

Guesthouse in Peekskill

4.93 out of 5 average rating, 245 reviews

Peekskill Carriage House Downtown Studio

Located close to the center of town, this is the perfect launchpad to experience local restaurants, coffee houses, the Paramount Theater, shopping, etc. and a short drive to stunning hikes, the Hudson Valley and beyond. The apartment is ideal for one or two and features a kitchenette, bathroom, dining island, comfortable queen bed, and couch. peekskillcarriagehouse.com

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.

Guesthouse in Bedford

4.92 out of 5 average rating, 190 reviews

Private Guest Studio

Just 39 miles north of Manhattan. Relax and unwind, to enjoy endless opportunity for outdoor activities, fine dining, antiquing, or just loving the peace & quiet of this private studio, in a manicured setting, with wood burning stove, porch, heated pool (June-August), and private footpaths leading to an open field.

Vacation rentals for every style

Get the amount of space that is right for you

Cottages

Quaint homes, peaceful surroundings

Cabins

Kick off your hiking boots at these rustic lodgings

Bungalows

Intimate homes. inviting architecture

Popular amenities for Long Island guesthouse rentals

Free parking on premises

Air conditioning

Family-friendly guest house rentals

Guesthouse in New London

4.97 out of 5 average rating, 105 reviews

Fully Renovated, Ocean Views, Fireplace & Beach

Guesthouse in Milford

4.92 out of 5 average rating, 203 reviews

Chic Coastal Retreat: Modern Apt Steps from Beach

Guesthouse in Mystic

4.79 out of 5 average rating, 100 reviews

Maxson House - a serene and stylish getaway

Guesthouse in Suffern

4.96 out of 5 average rating, 129 reviews

Hiking trails steps from your door!

Guesthouse in South Salem

4.93 out of 5 average rating, 258 reviews

1795 colonial w private 2 bd rm, 1 bth,LR,Kit apt

Guesthouse in Huntington Station

4.84 out of 5 average rating, 116 reviews

2 large bedrooms in cozy little neighborhood.

Guesthouse in Groton

4.94 out of 5 average rating, 426 reviews

Quiet studio with sleeping loft and deck

Guesthouse in Atlantic Highlands

4.88 out of 5 average rating, 318 reviews

Private cabin

Guest house rentals with a patio

Guesthouse in Weston

4.98 out of 5 average rating, 46 reviews

Weston Guest Cottage with Tennis/Pickleball Court

Guesthouse in Hampton Bays

4.86 out of 5 average rating, 58 reviews

Quaint One-Bedroom Cottage with Private Entry

Guesthouse in Greenwich

4.95 out of 5 average rating, 80 reviews

The Cottage in Greenwich

Guesthouse in Hampton Bays

5 out of 5 average rating, 4 reviews

Hill Coast Cottage: Freshly Renovated

Guesthouse in Shirley

4.96 out of 5 average rating, 72 reviews

La casita J place

Guesthouse in Clinton

4.96 out of 5 average rating, 23 reviews

Studio Cottage

Guesthouse in Bedford Hills

5 out of 5 average rating, 22 reviews

The Perch, a luxe cottage in the woods 1h from NYC

Guesthouse in Wading River

5 out of 5 average rating, 36 reviews

North Country Cottage

Guest house rentals with a washer and dryer

Guesthouse in Bedford Hills

4.88 out of 5 average rating, 128 reviews

Barrett's Sanctuary

Guesthouse in Mamaroneck

4.9 out of 5 average rating, 146 reviews

Your Modern Guest Wing Near NYC

Guesthouse in Katonah

4.91 out of 5 average rating, 109 reviews

Adorable one bedroom guesthouse

Guesthouse in Easton

4.84 out of 5 average rating, 101 reviews

Entire Guest House at Fox Pond Farm.

Guesthouse in Huntington Station

4.99 out of 5 average rating, 79 reviews

Modern fully updated 2nd Floor apartment

Guesthouse in Plainfield

4.9 out of 5 average rating, 269 reviews

Carriage House On Park (C.H.O.P.)

Guesthouse in Stonington

5 out of 5 average rating, 204 reviews

Super Adorable Cottage + Fire pit + King Bed!

Guesthouse in Bay Shore

4.87 out of 5 average rating, 15 reviews

Cozy Place

Destinations to explore