Guesthouse vacation rentals in Long Island Sound

Find and book unique guesthouse rentals on Airbnb

Top-rated guesthouse rentals in Long Island Sound

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

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Guest favorite

Guesthouse in Southbury

4.93 out of 5 average rating, 318 reviews

Charming Guest Cottage with Modern Amenities

Private Guest House set on 5+ Acres, along with Historic Colonial Home. Bright and sunny and over looks pool and gardens (seasonal). Efficiency with Kitchen featuring 2 burner stove, Microwave, Under Counter Fridge/Freezer/Ice Maker, Dishwasher, Granite Counters. . Dining Area, Great Room w/ soaring ceilings, French Doors to private patio, hardwood floors. Loft with full-sized bed, and sofa can be a to Queen Size Sleeper. Full bath with extra-large shower. Dog friendly (approval needed).

Top guest favorite

Guesthouse in Bearsville

4.98 out of 5 average rating, 526 reviews

Relax on the Ridge - 2 miles from Woodstock

Stay and relax in a private guest house on a 5+ acre picturesque property overlooking historic Woodstock, N.Y. The cottage is nestled away high on a private road in a quiet country setting, yet conveniently only 2 miles from Woodstock and 10 miles from Phoenicia! Relax on the grounds while watching our Tennessee Mountain, Cashmere & Kiko goats—drive into town to enjoy shops, restaurants, & the unique artistic culture of Woodstock—explore the many beautiful trails that the Catskill Park offers.

Guest favorite

Guesthouse in Easton

4.84 out of 5 average rating, 101 reviews

Entire Guest House at Fox Pond Farm.

Recently renovated private guest house with access to swimming pool offers sleeping for eleven in four bedrooms. Tastefully decorated with all amenities. Close to Merritt Parkway and train to Manhattan. This is a natural refuge on eleven very private acres. Large private terrace faces westerly for amazing sunsets and offers a "Plein Air" environment for alfresco meals, cocktails and relaxation. An attached vegetable and flower garden with fountain offer a quiet space to relax and reflect.

Top guest favorite

Guesthouse in Guilford

4.99 out of 5 average rating, 490 reviews

Get Back to Nature at a Modern Wood Clad Getaway

WINTER IS HERE--Glorious winter birds. Come and enjoy a cozy time in our guest house--whether it is a bright sunny day or a beautiful snowy landscape. You can still Hike on the trails. Stroll along the ocean. Ospreys; hawks; cardinals, blue jays, bluebirds, gold finches and more are here year round. 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.

Top guest favorite

Guesthouse in Portland

4.99 out of 5 average rating, 188 reviews

Guesthouse Farm Stay

Come stay with us on our working farm. Relax and take in our beautiful 12-acre property while sitting on the back deck, overlooking pastures. Or for a more interactive experience, join us on a farm tour during our morning and evening farm chores. Our farm was established in 1739 with a rich history in agriculture and livestock. Our cottage is studio-style with an open bedroom, living room, and dining area. There is a kitchette and bathroom with a shower for your convenience.

Top guest favorite

Guesthouse in Asbury Park

4.98 out of 5 average rating, 254 reviews

Peaceful Guesthouse

you will have this private, quiet guesthouse all to yourself ..14' ceilings and a 25'x10' balcony to sun on....it comes with 2 free beach passes, and a beach cart with 2 chairs and umbrella......you may have stayed in my front house with the peace sign, now, I am offering my rear guesthouse, originally built in the 1800's as a barn, this redesigned building with 14' ceilings was completely rebuilt in 2003 just 4 blocks from the beach. It is walking distance to everything.

Guest favorite

Guesthouse in New Marlborough

4.9 out of 5 average rating, 198 reviews

COZY GUESTHOUSE MINUTES AWAY FROM HIKING!

Renovated 1880's one bedroom cozy guesthouse in beautiful Southfield, MA. Full kitchen stocked with all necessities. Comfortable & stylish with a luxury king size bed. Minutes away from Ski Butternut, Berkshire attractions & trails. Walking distance to breakfast and lunch at The Southfield Store or have dinner at nearby The Old Inn On The Green and Cantina 229. 10 minutes from Great Barrington. Enjoy leaf-peeping, hiking, waterfalls, apple picking, skiing, and much more!

Guest favorite

Guesthouse in Asbury Park

4.97 out of 5 average rating, 208 reviews

Beachtown house w/ porch, workdesk, outdoor shower

Separate, renovated, sanitized cottage that sleeps 4. 1bd/1ba backhouse with a full bedroom (queen bed) and the living room includes leather sofa bed (queen). Entrance of the cottage has a porch for morning coffee or evening cocktail. Fully equipped kitchen to cook & prepare food for the beach. 42-inch TV & free Wifi. Workspace w/ desk, chair, monitor. Air conditioning/heat throughout the cottage. 2 beach passes, beach towels, beach chairs. Plenty of street parking.

Top guest favorite

Guesthouse in Berkeley Township

4.87 out of 5 average rating, 522 reviews

Walk to Bay Beach Boho Loft

🌿 Escape to our Boho-style loft—a serene retreat designed for positive vibes and great energy flow! 🛋️ Enjoy open living spaces, strong Wi-Fi for remote work 💻, and modern comforts. 🌊 Just 0.4 miles to peaceful river and bay beaches, a quaint boardwalk, hiking trails 🌳, and local dining 🍦. Perfect for families, couples, or solo travelers looking for a cozy getaway. 🎟️ Includes seasonal beach & splash pad passes for the ultimate shore town experience! 🏖️

Guest favorite

Guesthouse in Germantown

4.96 out of 5 average rating, 196 reviews

Luxe Guest House Retreat (Sauna)

Welcome to the Guest House nestled in the woods. We designed this lush and light-filled studio with peace and luxury in mind. Situated across from apple orchards, it sits ten minutes from Hudson and ten minutes from Germantown, you get the best of both worlds: country living with two amazing destinations close by. Ideal for a romantic getaway, or to be close to the sights and sounds but can retreat to natural beauty. A true sanctuary from the City.

Guest favorite

Guesthouse in Mount Tremper

4.92 out of 5 average rating, 352 reviews

Cozy Catskill Cottage Perfect Getaway for Two

NEWLY RENOVATED, COZY, CLEAN, PRIVATE AND SECURE Cottage in scenic and peaceful locale. Convenient and easy to find near the town of Phonecia, NY. 100 PACES to the ESOPUS RIVER and its trout fishing, trail heads and scenic hikes less than a mile away. Close to numerous sophisticated dining and shopping options. Less than 30 minutes to BelleAyre and Hunter Summer Happenings. Perfect for couples who need a weekend country getaway.

Superhost

Guesthouse in Saugerties

4.85 out of 5 average rating, 137 reviews

Private Guesthouse in Saugerties

Welcome to the cutest detached Guest House in the village of Saugerties, comfortable walk to restaurants, parks, and HITS. Set on a quiet street with ample street parking . This charming 1 bedroom will surely fit all your needs. Nicely refinished hardwood floors in Living and Bedroom area, also offers Washer/Dryer and storage. Nice sized rooms the bedroom offering a queen bed with big walk- in closet.

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What guests are saying

Game House in Historic Accord

5 out of 5 average rating, 20 reviews4 months ago

This was the perfect place for us to stay for Thanksgiving in Accord with family. Although attached to Jolle's house, it was entirely private with its own entrance and parking area. The cottage is pristine, very nicely put together and so very comfortable. Underfloor heating made it even cosier on a very wintery snowy Thanksgiving Day! Jolle's very welcoming gift of local chocolates, a bottle of wine and coffee in the freezer made us feel welcome. All the local recommendations were helpful and we all decided that this was the place to come back to next time we return to Accord! Highly recommended.

Guesthouse in Accord

What guests are saying

The Guesthouse Gem

4.85 out of 5 average rating, 39 reviews2 months ago

Nice place, very new, and great location - walkable to the train station and a bunch of the restaurants and shops in Asbury Park. Interior was nicely done, and the bed is good if you like really soft mattress toppers. We did have one homeless person approach our car in the driveway as we were preparing to go out one time; he didn't cause any trouble, but he also didn't leave until we pulled away. Nothing we haven't seen in NY or elsewhere; it wouldn't stop me from staying here again, and (as a male) I felt safe walking to and from the train or the restaurants, even at night.

Guesthouse in Asbury Park

What guests are saying

Spacious Guest Studio in Park Like Setting

4.94 out of 5 average rating, 255 reviews2 weeks ago

I absolutely loved my stay at the corn crib. It was a beautiful, cozy, and inviting studio with lots of natural light. Veronika was communicative, check in and check out were easy and very reasonable. Pros: Easy to find, safe area, easy check in, clean space, warm, comfortable, great host. Also location was great. Its approximately 5-8 minutes from everything we needed near Princeton, so very convenient but you still get to feel like you're in a quiet remote area. Cons: Veronika mentions in her guidebook that the water heater is small and provides tips on how to use it but even following all the tips, you only get a solid 7 minutes of hot water in the shower before it turned cold so you need to take really quick showers :( Other than that, everything was perfect

Guesthouse in Princeton

What guests are saying

Modern and warm guesthouse

4.97 out of 5 average rating, 31 reviews3 months ago

Denise’s place was an amazing gateway from the craziness of the city. If somebody wants to escape and feel the quiet of the nature please book this right away. My boyfriend and me enjoyed this place a lot for the only two days we stay. Thanks Denise’s ❤️✨

Guesthouse in High Falls

What guests are saying

Mt. Guardian Guest House Exquisite Mountain Views

4.98 out of 5 average rating, 612 reviews4 weeks ago

A haven of trees, even in the season when the trees are bare, provided breathtaking views from every angle, creating exactly the restorative environment we needed for a weekend away. The kitchen was well-stocked with everything needed to cook at home, but of course Woodstock just around the corner is in incredible town with so much to offer and explore! Everything was perfect. We hope to return.

Guesthouse in Bearsville

What guests are saying

Page Guest House

4.99 out of 5 average rating, 89 reviews4 months ago

We were in town for a family Christmas party and were very happy staying at The Page Guest House. It was the perfect choice, especially since my 91-year-old mother was with me. The walk-in shower and the small step to get in made it easy. As former residents of Guilford, I highly recommend this centrally located, cozy guest house to anyone visiting the area.

Guesthouse in Guilford

What guests are saying

Perfect guest house very private

5 out of 5 average rating, 18 reviews4 months ago

Don‘s place was spotless and private. Don himself was very easy to communicate with and responded almost immediately. We were happy to stay at his place and visit nearby relatives. We would recommend Don‘s place to anyone wanting a lovely, private and spotless place to stay.

Guesthouse in Wallingford

What guests are saying

Adorable 1BR Guesthouse & Patio NYC EWR Prudential

4.95 out of 5 average rating, 19 reviews1 week ago

One of the best Airbnbs I’ve ever stayed at. Super clean, matches the listing description, and its also very quiet. The place is well taken care of, you can tell Carla really puts effort into keeping it clean. Also the place has everything you would need for a long-term stay and the location is pretty good too. She is really flexible, and always replies fast. Definitely recommended it.

Guesthouse in Newark

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