Guesthouse vacation rentals in Hudson Valley

Find and book unique guesthouse rentals on Airbnb

Top-rated guesthouse rentals in Hudson Valley

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

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Guest favorite

A covered outdoor seating area features a combination of woven chairs and a sofa arranged around a stone floor. Soft lighting is provided by string lights overhead, while rustic wooden beams and walls create a warm, inviting backdrop.

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

A quaint stone cottage with blue shutters is framed by lush greenery. A small patio is visible in front, featuring an umbrella-covered table surrounded by chairs. The warm glow from the windows suggests a cozy interior, inviting a sense of comfort.

Guesthouse in Bethlehem

4.95 out of 5 average rating, 225 reviews

The Cottage at Sycamore Hill Farm

Escape to the country! The perfect mix of romance and convenience can be found at the Cottage at Sycamore Hill Farm. A newly renovated one room stone house w. a private driveway. Originally built in the late 18th Century, the cottage has wide plank floor boards and a wood burning fireplace . Modern amenities: stone-tiled bathroom w/ walk-in shower, central heat/air conditioning, electronic shades and Queen bed w/ luxury linens, futon in loft. Access to pool, hiking trails, firepit and creek.

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

A modern living space features a comfortable sofa, a circular coffee table, and a television unit. Large sliding glass doors create a seamless view of the outdoors, with natural greenery visible beyond the private deck. Soft natural light fills the room, enhancing its inviting ambiance.

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.

Guest favorite

The exterior of a charming guesthouse is highlighted, showcasing a white facade with large windows and a covered front porch. Surrounding trees provide natural greenery, while the clear blue sky offers a serene backdrop. A swing chair is visible on the porch, inviting relaxation.

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

A serene lake view is captured, with gently rippling water reflecting the bright blue sky and scattered clouds. Lush green hills frame the landscape, creating a peaceful backdrop. The shoreline is visible with rocky elements and vegetation along the water's edge.

Guesthouse in Hadley

4.9 out of 5 average rating, 130 reviews

Our Happy Place - Spectacular views and wildlife!

You'll love this property for all it has to offer! This is a beautiful and spacious loft with great views of the lake directly across the street. The guest residence is decorated in a rustic adirondack style, with spacious living room, kitchen and 2 decks overlooking the lake, and plenty of parking. Comfy queen sized beds in both bedrooms. Master bedroom has cooling mattress, so you'll sleep like a baby! The living room can accommodate a couple of additional people.

Guest favorite

A bright and airy studio space is presented, featuring a spacious bed centered under a large window. A cozy sofa in front includes colorful cushions, and two black chairs are positioned beside a small table. Natural light enhances the soothing white walls and simple decor.

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.

Superhost

A welcoming bedroom features a spacious bed dressed in soft linens, with a textured throw draping over the side. Natural light filters through sheer curtains at the window, illuminating the hardwood floors and complementing the light-colored walls.

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.

Guest favorite

The open living area features wooden floors and beams, with French doors that lead to a stone patio and views of the surrounding greenery. A wooden dining table with four chairs is positioned beside the doors, enhancing the sense of spaciousness and natural light.

Guesthouse in Bearsville, Woodstock

4.95 out of 5 average rating, 435 reviews

Stylish Woodstock Guest House..Mountain View

This 1920's converted barn has the original beams and antique fixtures w/vintage and new furnishings. The french doors on one complete wall amplify the open space with views of the Catskill Mts., pond, fields, and the vast sky. No smoking no pets. You love them, I love them, but they cannot stay here. Also, two night minimum stay. Three night minimum on holiday weekends.

Superhost

The exterior of the guest house is shown, featuring a modern design with dark wooden panels. A stone pathway leads to the entrance. A shaded sitting area with chairs and a picnic table is visible in the grassy landscape, surrounded by trees and greenery.

Guesthouse in Pownal

4.84 out of 5 average rating, 532 reviews

Bauhaus Guest House in So. VT.

Enter through a flowering courtyard into this one room studio style guest house with full bath, closet and sliding glass doors looking out upon a lush green landscape in Southern Vermont. Parking, wi-fi and local insight included. Hosts = AMAZING :) 5 miles to Williamstown Theater Festival, Williamstown, MA 9 miles to Mass MoCA, North Adams, MA 9 miles to Bennington, VT

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What guests are saying

Cozy Catskill Cottage Perfect Getaway for Two

4.92 out of 5 average rating, 352 reviews1 month ago

I just want to say that this is a very beautiful place. Julian & Karen were extremely nice to us and to have us there. Karen made sure we were comfortable with the stay, and was very respectful and the place was very cozy and inviting. The place is beautiful and warm. Her recommendations were very helpful and we truly enjoyed ourselves! I will come back again! Thank you so much for your wonderful hospitality!

Guesthouse in Mount Tremper

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

Vermont Home Central to Ski Areas-No Cleaning Fees

4.98 out of 5 average rating, 685 reviewstoday

It was truly a pleasure staying at Jane and Fred’s. Everything is exactly as pictured. The bed is VERY cozy I had the best night sleep. Very tranquil and loved watching the horses graze in the AM. Thoughtful touches like what light switches do, chargers, and nice appliances. Instructions and communication made everything easy

Guesthouse in Wallingford

What guests are saying

Cozy Guesthouse by the Lake

4.92 out of 5 average rating, 87 reviews3 weeks ago

Heather and Mo are two of the kindest and most thoughtful Airbnb hosts I've met. They checked in to make sure I was okay when I came in later than expected (*make sure you read their check-in instructions for how to find them, as Google Maps thinks they live 9 minutes away from there*) and they were flexible with having a later check-out. As a nonbinary queer person traveling solo in rural PA, it's no small thing to stay with folks who are explicitly affirming, and who are so helpful re: orienting to the area. If you stay here, definitely find time to get out in the kayaks and get yourself a massage with Tracy from Holding Space. Such a fabulous spot and terrific people. Hoping to be back soon!

Guesthouse in Honesdale

What guests are saying

Romantic Barn Guesthouse in Village Center

4.73 out of 5 average rating, 229 reviews3 weeks ago

This is a great place. It’s really well described in the listing. It’s old and has charm. Having an open fire to keep warm on a cold night was lovely. We had -6 Celsius while we stayed but between the fire and the heating we were totally fine. We had a minor issue on check in but Jessica and Tim sorted that very quickly which was appreciated. Really well stocked kitchen. Manchester is a nice little town with all you would need and the surrounding area is fabulous.

Guesthouse in Manchester

What guests are saying

Cottage with a View

4.93 out of 5 average rating, 104 reviews1 month ago

We loved John & Anne’s place. It was cozy, warm and perfect for our getaway. We appreciated the responsiveness, ease of communication and clear, easy to follow instructions. The fireplace, hot tub and all the extra touches with the local treats made our stay extra special. We will definitely be back!

Guesthouse in Arlington

What guests are saying

Tranquil Guest House, Chatham NY

4.92 out of 5 average rating, 25 reviews2 months ago

We loved this house! The interior was spotless, well-considered, and tasteful. The beds were so comfortable and the kitchen was perfect. There is a picturesque stream at the rear of the property. Lucy was thoughtful and responsive: It snowed heavily one evening, and she immediately had the driveway plowed. We skied at Catamount, visited Mass MoCA, and had a delicious dinner at The Prairie Whale in Great Barrington. We can't wait to return!

Guesthouse in Chatham

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

Cozy Home away from Home!

4.96 out of 5 average rating, 154 reviews4 months ago

Place was clean, cozy and in a good location, close to coffee, there is a Starbucks less than 5 minutes away. Mary was responsive before and during our stay getting back to us quick. She was very thoughtful, warm and friendly. We would stay again in a heartbeat.

Guesthouse in Fairfield

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

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