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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Guest favorite

Guesthouse in Oyster Bay

4.96 out of 5 average rating, 182 reviews

GORGEOUS & SERENE in Oyster Bay - LI/NY

Our small, modern bungalow is completely private. Perfect for working as it is for a romance, or just coming to LI-NY for the weekend. The luxurious queen bed is great, alone, or shared, and the custom sofa converts into another bed or two in a pinch (ask us about this before booking, it's got its limits); keep in mind that this is an open loft-like space. We're located on Long Island's North Shore, close to beaches yet only 45-minutes from Manhattan, and less than an-hour to The Hampton's.

Guest favorite

Guesthouse in Stonington

4.97 out of 5 average rating, 225 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.

Guest favorite

Guesthouse in Hampton Bays

4.96 out of 5 average rating, 149 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, 413 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 Norwalk

4.97 out of 5 average rating, 216 reviews

Adorable one-bedroom guesthouse with parking

Private, peaceful, cozy renovated cottage next to my house in a quiet residential neighborhood. Originally used as a painting and design studio, ideal for short stays and as a workspace. Luxury queen bed in upstairs loft; downstairs with refrigerator/freezer, Keurig with coffee and tea; microwave; Wifi, heat, air conditioning. There is NO RUNNING WATER in the cottage, but a lovely PRIVATE FULL BATH is just steps away in the main house AVAILABLE 24/7 exclusively for you during your stay.

Guest favorite

Guesthouse in Charlestown

4.89 out of 5 average rating, 271 reviews

Cozy All Season Cabin Near Beach at Rockbriar Farm

Small vintage vacation cabin located in Charlestown, RI a 1 mile walk/bike to the town beach. Located on 7 acres called Rockbriar Farm, the cabin is in a wooded setting away from our home affording privacy for guests. One large room includes the futon bed/couch and the one sink; the shower and toilet are in separate room. Cabin also has a cedar enclosed hot water outdoor shower. Clean, cozy but not luxurious! No stove, but coffee maker, microwave, outside grill, and mini fridge.

Guest favorite

Guesthouse in New Haven

4.94 out of 5 average rating, 246 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.

Guest favorite

Guesthouse in Mahopac

4.93 out of 5 average rating, 119 reviews

Sunny Lakeview Guesthouse

Art and light filled spacious studio with panoramic views overlooking lake Mahopac. Walkable to swimming/paddleboarding; skating/ice fishing. Many fine restaurants or casual takeout options, and boasting an excellent coffee shop. Train ride from Grand Central to Croton Falls, then a 12 minute drive or shuttle ride. Close to Fahenstock Park, Cold Springs, Beacon, Ridgefield,or walk up the hill to the trails of Volz park

Guest favorite

Guesthouse in Mystic

4.99 out of 5 average rating, 551 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.

Guest favorite

Guesthouse in Peekskill

4.94 out of 5 average rating, 213 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

Guest favorite

Guesthouse in Guilford

4.99 out of 5 average rating, 458 reviews

Get Back to Nature at a Modern Wood Clad Getaway

SPRING BIRDS HAVE ARRIVED. Spring is here!!. Beautiful days and nights. Hike on the trails. Bike along the ocean. 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 Brewster

5.0 out of 5 average rating, 291 reviews

The Cottage by the Lake: Hudson Valley Indulgence

The Cottage by the Lake is a cozy, secret get-away on the scenic banks of the Croton Watershed. About an hour from NYC, it’s on the property of an 1850 farmhouse & has a fully equipped kitchen & bath, cathedral ceiling, working fireplace & cozy sleeping loft. The patio has a fire pit and gas bbq. It’s the ideal place for those seeking to work from home.