Guesthouse vacation rentals in Hudson Valley

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Top-rated guesthouse rentals in Hudson Valley

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Top guest favorite

A rustic office area features warm wood paneling and a functional desk made of natural wood. A large flat-screen TV is mounted above a small electric fireplace. A comfortable black office chair is positioned at the desk, complemented by a chess set and decorative plant.

Guesthouse in Woodstock

5 out of 5 average rating, 388 reviews

Steps toTown/Bus Pet Ok/No Extra Fees! &Five Star

PRIVATE Modern/Rustic Apt WALK TO TOWN 5 * Rating "premiere" NO EXTRA CHARGES! 1000 sq ft Pet Friendly n/c Park Master King Suite &I can put up 2cots /crib Full Kitchen Cathedral Living Room w/Mountainview. 1&1/2 Bath Deck for Outside Dining w/Mountainview WOOD FIREPLACE ondeck Wi-Fi Wash/Dryer Gas BBQ Steps to CTR of Town Green & NYC Bus-stop, THE COLONY, Yum Yum, Goodnight , Garden Cafe, Silvias, Bread Alone, Mud Club, Station Bar, shops . Cemetery's Bubbling Stream, PrivatePlayground

Guest favorite

A lofted bedroom features a cozy bed with a multi-striped blanket, flanked by two bedside lamps. The wooden ceiling adds warmth, while a window offers natural light and views of the surrounding greenery. Soft carpet covers the floor, enhancing the comfortable atmosphere.

Guesthouse in Mount Tremper

4.97 out of 5 average rating, 342 reviews

Artful and Serene Woodstock Getaway

Please read description thoroughly before booking. Relax with a comfortable mix of rustic and elegant in this colorful studio with loft bedroom in the Catskill Mountains of NY. Midway between lovely towns, Woodstock and Phoenicia. Full kitchen and bath, cathedral ceiling, sleeps two adults comfortably. Due to allergies, we do not allow pets. This includes service animals. We use fragrance free laundry detergent. No smoking or vaping. This listing is not suitable for children or infants.

Top guest favorite

Guesthouse in North Bennington

4.99 out of 5 average rating, 254 reviews

Birch House - lake, green trees + modern comforts

We're a little guest house near a lake in Vermont with green trees + modern comforts. Perfect for couples + individuals looking to relax + enjoy nature. Renovated, air conditioned space w/ cozy, minimalist vibes. A small modern cabin that's peaceful + private. Tucked into a quiet neighborhood. Main home is a separate building next door. Near Bennington College. 12 minutes to downtown Bennington. IG birchhousevt Please note that due to a severe allergy, it is difficult to accommodate animal

Guest favorite

The exterior of a black cabin is shown, featuring a well-maintained yard with four yellow Adirondack chairs arranged around a circular fire pit. The surrounding green grass and trees offer a natural ambiance, while a second building is visible in the background.

Guesthouse in Kingston

4.94 out of 5 average rating, 212 reviews

Campfire Cottage: Fireplace, fire pit & no chores!

Escape the city and unwind at this beautifully designed home. Just 90 minutes from Manhattan, this is the perfect place to relax and reconnect with nature, or work remotely. Enjoy downtown attractions, hiking, and the Hudson River Maritime Museum nearby. The home features a cozy living area, full kitchen, electric fireplace, and no chore list for checkout. The yard has a grill and fire pit facing the woods. Book today to retreat to your private house and enjoy the beauty of Upstate New York!

Top guest favorite

A cozy living area features a stone fireplace with a wood fire burning inside. A colorful couch adorned with various patterns is complemented by a stylish chair. Natural light enters through large windows, and a rustic table is visible in the background.

Guesthouse in Woodstock

4.96 out of 5 average rating, 350 reviews

Pick Herbs at a Quirky Stone Cottage with BBQ and Fireplace

Snuggle by a roaring fire. Eat in a corner nook or at a rustic wooden counter by a window. This quaint, whimsical home has a private deck w/bbq, a garden with a hammock and fire pit. A full size Murphy bed with a full kitchen (except for an oven). You will have access to the entire guest house. A short drive to the beautiful, eclectic, funky town of Woodstock. Art & culture, restaurants, hiking & biking all nearby. Electric heat, ceiling fan, a standing ac unit and single person shower.

Top guest favorite

An outdoor seating area is set among trees, featuring stone pathways and a gravel surface. A circular fire pit is surrounded by seating, and a small dining set with two chairs is positioned nearby. A grassy space adds greenery to the tranquil setting.

Guesthouse in Mahopac

4.95 out of 5 average rating, 235 reviews

Lakeview Guesthouse with Sauna

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/ dining/ takeout options + boba tea! Drivable to farm fresh food markets, restaurants and art museums. Cedar dry Sauna on property for use. Nearby towns and hikes include Fahenstock Park, Pound Ridge, Cold Spring, Beacon, Ridgefield, or walk up the hill to trails of Volz park!

Top guest favorite

Two individuals are paddling in a bright pink canoe on a calm body of water, surrounded by lush green trees and foliage. The peaceful scene is reflective, with gentle ripples visible on the surface of the water.

Guesthouse in Delhi

4.97 out of 5 average rating, 150 reviews

Catskills Peakes Brook Cabin-Creek, Pond & Privacy

Take a breath at Peakes Brook Cabin, our cozy and private cabin on a pond, with the brook steaming beside it. Our beloved property is perfect for couples needing to escape the city, decompress and deplug. You're minutes to charming Delhi and other Catskill villages, with nature all around. We are very excited to announce that our cabin has a huge upgrade as of Spring '25. We now have a full bathroom with running water! A project over 3 years in the making. (Stayed tuned for new pics)

Guest favorite

An outdoor seating area features comfortable Adirondack chairs under a wooden roof with exposed beams. A hammock is suspended nearby, allowing for relaxation while enjoying views of the surrounding landscape. String lights are hung across the space, adding a cozy touch.

Guesthouse in Beacon

4.94 out of 5 average rating, 400 reviews

Cozy Mountainside Suite - Minutes from Beacon

The Equestrian Suite at Lambs Hill is a private estate with panoramic views overlooking the Hudson River & downtown Beacon. This beautifully-designed luxury suite sits atop a barn home to Icelandic horses & miniature donkeys, & features an outdoor hot tub, gourmet kitchen appliances, & wrap-around decks. 1 mile to Beacon's Main St, 2 miles to Metro North train station & DIA: Beacon. We can host a max of 2 guests & have some dangerous features for kids so guests should be adults only.

Top guest favorite

Guesthouse in Windham

4.99 out of 5 average rating, 161 reviews

Alpine Chalet on Spectacular Property

Inspired by their travels in the Swiss Alps, the hosts of the Mountaintop Chalet invite guests to their peaceful alpine guesthouse atop a mountain in the Northern Catskills. Nestled on a quiet, private road, the Mountaintop Chalet is just an 8 minutes drive to downtown Windham, NY, 10 minutes to Windham Mountain and 18 minutes to Hunter Mountain. This tranquil yet accessible setting makes it the perfect escape for couples, families and friends. Follow on Insta at mountaintop_chalet.

Top guest favorite

A tranquil gravel road lined with lush green trees stretches into the distance. Natural stone borders are visible along the edge of the pathway, providing a rustic charm. Soft light filters through the leaves, creating a serene and inviting ambiance.

Guesthouse in Cold Spring

4.99 out of 5 average rating, 164 reviews

Modern+bright forest escape - near village & train

Modern, efficient, and elegant private flexible garden apt. Guesthouse can be used as a studio apartment, or as a private personal retreat space for art/work/rest/meditation. Hiking trails available right out the door, and just a few minutes walk to Cold Spring's vibrant Main Street and Metro North train station to NYC and beyond. Comfortable bed, all modern amenities. Private patio. Native pollinator gardens and forest surround. Solar orientation brings in natural light.

Guest favorite

A vintage Remington Standard Typewriter No. 10 is displayed on a shelf. The typewriter features a well-preserved black body with gold lettering. The keys are arranged in a circular pattern, each displaying a distinct letter. The upper portion is equipped with a ribbon spooling mechanism.

Guesthouse in Germantown

4.96 out of 5 average rating, 198 reviews

Luxe Guest House Retreat

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

A serene river flows gently through a wooded area, surrounded by vibrant green foliage. Sunlight filters through the leaves, casting dappled light on the water's surface. Rocks and pebbles line the riverbank, creating a natural atmosphere.

Guesthouse in Tivoli

4.91 out of 5 average rating, 176 reviews

Tivoli Star Gazing Cabin

Down a long driveway, set amongst 100 year old trees and meadows, the cabin offers time in the quiet country though only minutes to the lively village of Tivoli. With a wrap around porch for morning coffee, fire fly viewing or star gazing. It has a soaking tub, with a hand held shower. The cabin is part of our family compound of a main house and a small garden hut. Each property has an independent outdoor space for relaxing and privacy.