
Holiday rentals in Bloomington
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Top-rated holiday rentals in Bloomington
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Luxury Catskills A-Frame Cabin | Hot Tub & Sauna
Nestled in the serene woods of Saugerties, NY, this luxurious A-frame cabin offers modern comfort and natural beauty. Just 10 mins from Woodstock and 2 hrs from NYC, NJ. it sits on a private 2-acre lot. Easy Access. Featuring premium queen Casper mattresses, a Breville espresso machine, a 4K projector, a firepit, grill, a cedar wood-fired hot tub & Sauna. Dog friendly! A cozy & stylish retreat near hiking, skiing, and top dining spots in the Catskills. Visit our ig ‘highwoodsaframe’ for more!
4.99 out of 5 average rating, 159 reviews
Cozy Hillside Hideaway with Hot Tub
Enjoy the peace and quiet of the Catskills with easy access to all that mid Hudson valley has to offer. 5 minutes to Uptown Kingston and the O&W and Wallkill rail trails; 15-25 minutes to Rhinebeck, Ashokan Reservoir, Woodstock, Saugerties and New Paltz; 30-45 minutes to Lake Minnewaska, Mohonk Mtn House, Belleayre, Hunter and Wyndham. Also close to a number of wedding venues (Hasbrouck House, Senate Garage, Hutton Brickyards…). Guest apt is attached to our home but you have a private entrance.
4.99 out of 5 average rating, 128 reviews
Cabin 192
No cleaning fee and no 2-night minimum! Cabin 192 is a tiny home glamping experience located in lovely Kingston, NY. Cabin 192 takes you back to 1992 with: a vhs collection of classics, a Super Nintendo, Sega, and other fun activities. Warm and toasty in fall and winter and cool in summer you’re always comfortable at Cabin 192. Enjoy smores by the fire surrounded by trees in nature while also being able to enjoy a vibrant uptown district a 9-minute drive away! Minnewaska and Woodstock nearby!
4.92 out of 5 average rating, 320 reviews
This New House
Unique custom built new home constructed purposefully for Airbnb quests. This house offers a distinctive design with a large loft bedroom and a fully tiled bathroom. The loft overlooks the downstairs living area which has an open living room, dinning area, and kitchen. The second bedroom and bath are located on the first floor. Granite, slate, and soapstone accentuate the countertops, vanities, and floors. You will also see plenty of natural pine, hickory, and local cedar throughout the house.
4.96 out of 5 average rating, 417 reviews
Hot Tub Bliss 5mi to Kingston on 3 acres
Relax under the stars in your own 24/7 hot tub! Lounge on the 20’ long covered porch. Rest up with a great night’s sleep on our ultra comfy queen bed. There are 2 trifold queen floor mattresses as well (4”and 6”). Minutes away you can hike the Rail Trail. You have access to a grill, outdoor table, fire pit, large yard and surrounding woods. Discover Kingston, Woodstock, New Paltz, Catskill, and Mohonk (see Guidebook) | Grill | 55” TV | Fast Wi-Fi | Pets | Fire pit | Free Parking
4.91 out of 5 average rating, 175 reviews
Serendipity: Books & Botanicals!
A Cozy Retreat for Book & Coffee Lovers Step into our charming library, where every shelf holds a carefully curated selection ... Whether you’re curling up with a novel or starting your morning with the perfect brew, our coffee and tea bar has everything you need to make your stay special...Just 5 minutes from Kingston, 15 from New Paltz, and 25 from Rhinebeck, this is the perfect escape. And if you fall in love with a book, it’s yours to take home! Dogs need to be preapproved.
5.0 out of 5 average rating, 52 reviews
Fox Lodge: Hudson Valley / Catskills Getaway
This spacious mid-century lodge w/ modern amenities is the perfect setting to host your family & friends for a memorable getaway. Within just 40 mins to (favorite) Belleayre Ski Resort or 45 mins to Hunter Mountain! Fox Lodge is a split level home with 4 bedrooms and 3 full bathrooms. Step outside of the bright & vaulted great room to BBQ at the grill or relax by the fire pit surrounded by nature. Minutes from the historic Kingston Stockade District & Rondout Waterfront.
4.9 out of 5 average rating, 195 reviews
Shack in the Heart of Rosendale
This unique, centrally located 500 sq ft ground-floor, 1.5 story apartment is in an ideal location to explore Rosendale and the surrounding areas. Located in a 1890s Brownstone, the Shack is a comfortable refurbished studio with hand hewn beams, brick walls and a wood burning stove. Sleep in a queen Murphy bed (pulls down) and prepare food in the kitchenette. Keep in mind nobody above you and the town shuts down at 10 PM so you have a decent amount of peace and quiet.
4.92 out of 5 average rating, 203 reviews
Hudson Valley Hygge House~ comfort in the country!
Experience the cozy charm of hygge at the farmhouse by a tranquil pond in Rosendale. Nestled in the Hudson Valley, just minutes from Kingston, Stone Ridge, and High Falls—and only 90 miles from NYC—this retreat offers pure serenity. Located on a quiet country road, enjoy the sounds of birdsong, evening frog lullabies, and a gas fireplace for a cozy winter escape. Set on over 3 acres, nature abounds here. Come and enjoy all the Hudson Valley has to offer!
4.95 out of 5 average rating, 374 reviews
Airy Two-Bedroom in a 1735 Stone Landmark
This two-story apartment is part of the Colonel Abraham Hasbrouck House, a registered landmark built in 1735 in Kingston's walkable Stockade District. Tall colonial Dutch windows light the hand-restored wide-board floors in the living room, and the renovated kitchen and dining nook look out on the backyard through a split Dutch door. Upstairs are two queen bedrooms and a modern bath with a heated towel rack. Dual-zone climate control and keyless entry.
4.98 out of 5 average rating, 786 reviews
'The Blue Jay Cottage' - Privacy With A View!
Come, get away from the craziness of life, calm your body, clear your mind and channel your energy by staying at a very special little gem. Once you arrive you won't want to leave. A newly renovated cozy cottage, where you won't believe your view when you wake up in the morning with your first cup of tea or coffee overlooking the best spot in this area from the deck. A perfect getaway on almost 5 acres of creek frontage to find your inner peace.
4.97 out of 5 average rating, 594 reviews
Romantic House on a Magical Lake
This amazing jewel offers a creative refuge from the city 180 degrees view on the Sturgeon lake, one can finally connect to oneself, converse, recharge, rejuvenate, get in touch with your passion, or contemplate the next big idea. A magical Place. Enjoy the sun set from the large cedar deck, hang out on the cedar dock, take a nap in the daybed at the water, have tea in the beautiful gazebo overlooking the water, take the boat for a row....
4.91 out of 5 average rating, 210 reviewsPopular amenities for Bloomington holiday rentals
Other great holiday rentals in Bloomington

Rosendale vacation
4.93 out of 5 average rating, 60 reviews
Rubystar Haven~ rejuvenate in your tranquil escape
4.88 out of 5 average rating, 25 reviews
Hudson Valley Green House
4.91 out of 5 average rating, 75 reviews
Waterfront Lakehouse near Kingston Hot Tub & Sauna
5.0 out of 5 average rating, 70 reviews
Cozy Hudson Valley Retreat
4.99 out of 5 average rating, 83 reviews
Wooded Family Getaway
5.0 out of 5 average rating, 26 reviews
Shatemuc, a magical getaway on the Hudson River
4.97 out of 5 average rating, 69 reviews
Hudson Waterfront Mid-Century Modern Home
4.97 out of 5 average rating, 86 reviewsDestinations to explore
- New York Holiday rentals
- Montreal Holiday rentals
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- Niagara Falls Holiday rentals
- Jersey City Holiday rentals
- Portland Holiday rentals
- Newark Holiday rentals
- Baltimore Holiday rentals
- Mont-Tremblant Holiday rentals
- Hunter Mountain
- Belleayre Mountain Ski Center
- Bear Mountain State Park
- Minnewaska State Park Preserve
- Thunder Ridge Ski Area
- Bethel Woods Center for the Arts
- Resorts World Catskills
- Windham Mountain
- Catamount Mountain Ski Resort
- Butternut Ski Area and Tubing Center
- Storm King Art Center
- Taconic State Park
- Plattekill Mountain
- Mohonk Preserve
- Peekamoose Blue Hole
- Hunter Mountain Resort
- Kent Falls State Park
- Bash Bish Falls State Park
- Brotherhood, America's Oldest Winery
- Harriman State Park
- Mount Peter Ski Area
- Mohawk Mountain Ski Area
- Millbrook Vineyards & Winery
- Storm King Art Center





