
Holiday rentals in Bloomington
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Top-rated holiday rentals in Bloomington
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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.

Boulder Tree House
Boulder Tree House 🌲🌲🌲 SMOKE FREE • ALLERGY FREE Rates Include a 15.5% AirBB Service Fee Early Check In & Late Check Out Boulder Tree House is an Inhabitable Work of Art, created by owner architects. The design is based on organic and innovative blending of natural elements and environmentally conscious technology, creating a happy and healthy living space. Boulder Tree House is ideal for a couple looking for an exciting, romantic, unique experience but can accommodate a 3rd person.

Rosendale vacation
VACATION RENTAL: Kick back & relax in this stylish ALL NEW Johnny Poux Design original house. From the fixtures to the custom built cabinetry, everything is intentionally designed for relaxation, simplicity, and beauty. Spacious open floor plan, new appliances, 2 zen bedrooms w/ queen beds, 2 full baths, generous deck. Occupancy limited to 4 guests, non-smoking & pets not allowed. On road along Rondout Creek, kayaking, trails, mountains, skiing, 2 historic towns w/ cafes, shops, movie house!

Rubystar Haven~ rejuvenate in your tranquil escape
The experience of a boutique B&B within the warmth & privacy of a home. Built new 2024, this apt best suits a Couples Retreat while perfectly meeting the needs of small groups, sleeping up to 4! Every amenity, appliance, & furnishing you’d expect or could imagine! Included with the spacious Bed, Bath, Kitchen, & Living Space. 9min between New Paltz & Kingston 2min to Rosendale INSIDE: High-Speed Wi-Fi, fireplace, 72" TV, adjustable KING bed, work desk & space, massive sectional couch, & more

Couples Hot Tub Bliss, 5mi to Kingston
Relax under the stars in your own 24/7 hot tub! Lounge on your own private deck overlooking the large peaceful yard. Rest up on our ultra comfy queen bed. 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, and surrounding woods. Discover Kingston, Woodstock, New Paltz, Catskill, and Mohonk (see Guidebook) | Grill | 55” TV | Fast Wi-Fi | Pets | Fire pit | Outdoor Dining | Free Parking

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.

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.

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.

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!

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.

'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.

Swan Cottage with Expansive Hudson River Views
The Swan Cottage was built in 1923 and was fully renovated in 2020. The idyllic location, on a bluff overlooking the Hudson River, is the perfect perch to relax and get away from it all. The front porch is a nice spot to have a cup of coffee and watch the sailboats on the river, while the huge wraparound porch affords terrific views of the river as well as the forest that gives this home a feeling of being high in the tree tops.
Popular amenities for Bloomington holiday rentals
Other great holiday rentals in Bloomington

Waterfront Lakehouse near Kingston Hot Tub & Sauna

Wooded Family Getaway

Hudson Waterfront Mid-Century Modern Home

Cozy Hudson Valley Retreat

VIEWS on Hudson River / Luxury Modern Home

Maple Ridge Modern Rustic Retreat

Stylish Rosendale Escape by Shops & Trails

Trestle House - Bliss on the Rail Trail!
Destinations to explore
- New York Holiday rentals
- Montreal Holiday rentals
- Philadelphia Holiday rentals
- Washington Holiday rentals
- Boston Holiday rentals
- Ocean City Holiday rentals
- 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
- Bash Bish Falls State Park
- Peekamoose Blue Hole
- Hunter Mountain Resort
- Kent Falls State Park
- Brotherhood, America's Oldest Winery
- Harriman State Park
- Mohawk Mountain Ski Area
- Mount Peter Ski Area
- Storm King Art Center
- Millbrook Vineyards & Winery





