Holiday houses in Bloomington

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Top-rated holiday rentals in Bloomington

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Top Guest favourite
Apartment in Kingston
4.97 out of 5 average rating, 751 reviews

Vintage-Inspired Revitalized Historical Bau Guesthaus, A

Re-capture the allure of the past while indulging in modern luxury in this home originally built in the 1890s. The residence showcases original detailed ceilings, a mid-century design aesthetic, repointed original brick, and bright splashes of color. Entire 900sqf 1st floor unit. Includes 1 bedroom(Queen), private kitchen/dinning room, living room and a bathroom. The townhouse is restored with beautiful, vintage details but also with all the comforts of modern living like high speed Wifi, digital thermostats and entry to the home via smart lock. *additional one time fee of $25 to set up air mattress for 2 guests. All guests are welcome to use all facilities on our property; including our backyard. The property is centrally located in the heart of historical uptown Kingston. Explore the weekend farmers market just steps from the front porch, as well as local cafes, restaurants, museums, and music venues. The Bau Guesthouse is easily accessible. It is 7min walk from the Kingston Trailways bus stop and 5min drive from I-87 throughway exit 19. Parking on our street is metered Monday - Friday 9am to 5pm. Also free street parking is available just around corner from us.

Guest favourite
Cabin in Kingston
4.93 out of 5 average rating, 250 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!

Top Guest favourite
Cottage in Kingston
4.93 out of 5 average rating, 392 reviews

Kapitan’s Cottage Private Upstate Catskill Retreat

A vintage rustic country retreat with two floors with modern amenities. 2BR, full & half bathroom. Family & Pet friendly. Large yard surrounded by a mature tree line for secluded privacy. Private stone deck w/ fire pit, BBQ & comfortable deck furniture. Summer Pool access and Generator on site. Close to Kingston, High Falls, Stone Ridge and Woodstock yet just far enough out to feel you're away from city hustle and bustle. Close to miles of hiking, outdoor activities, parks & Ski slopes.

Top Guest favourite
Home in Kingston
4.96 out of 5 average rating, 365 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.

Superhost
Guest suite in Kingston
4.93 out of 5 average rating, 136 reviews

Upstate Daydreamers Guest Suite

A spacious 3-room private suite for 1-2 guests. The vibe is cozy, quiet, safe, peaceful, comfy — unwind and make yourself at home! Explore our 14 acres of lush forest and creeks, take a bubble bath in the clawfoot tub, soak in the jacuzzi, play mini pool, and collect fresh organic eggs from the chickens. Free on-site parking, excellent cell reception & wifi. Please note, we're no longer serving breakfast - visit our restaurant Ace of Cups (inside Tubby’s) & receive free dumplings instead!

Top Guest favourite
Home in Kingston
4.97 out of 5 average rating, 115 reviews

Hillside Views in Hudson Valley

Escape to this modern, cozy retreat where nature surrounds you. Fall asleep to owls, crickets, and frogs. Just 2 mins from Rosendale and a short drive to Kingston, New Paltz, and Stone Ridge, with restaurants and trails nearby. Enjoy a gas fireplace, a reading nook with treetop views, and a large deck that feels like you’re in the trees. The private outdoor space includes a fire pit, all on a serene 3-acre lot offering total peace and quiet. Your perfect Hudson Valley escape awaits!

Superhost
Home in Bloomington
4.94 out of 5 average rating, 249 reviews

Couples Getaway, Hot Tub, 3 acres, 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 with a great night’s sleep on our ultra comfy queen bed. 5 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 | Large Yard | Fire pit | Outdoor Dining | Free Parking

Top Guest favourite
Guesthouse in Tillson
4.98 out of 5 average rating, 281 reviews

The Garden Studio: Private, Tranquil, & Central

Near New Paltz, Kingston, many other Hudson Valley destinations. Relax after a day of hiking, biking, climbing, & exploring the beautiful Hudson Valley in your private, clean & cozy cottage! This former artist studio's creative décor reflects local artists the area is known for. Your private patio features a fire table for comfort & ambiance. Complimentary snacks & S'mores provided. We're centrally located in the Hudson Valley - only a 90 min +/- drive from the NYC area.

Top Guest favourite
Guest suite in Ulster Park
4.94 out of 5 average rating, 122 reviews

Sunny and Spacious Studio - a serene getaway

Modern Light Filled Garage Conversion with a small kitchen, full bath with an open deck off the back. A beautiful quiet spot with birds, tall trees and a small creek on 3 acres. The bedroom has a comfortable Queen bed with a small ladder to a little sleeping loft for the kids. There is also a pull out couch in the open kitchen living room area with a deck off the back. This is a small apartment attached to our house that has been designed with care and privacy in mind.

Guest favourite
Apartment in Rosendale
4.93 out of 5 average rating, 143 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.

Top Guest favourite
Apartment in Tillson
4.98 out of 5 average rating, 164 reviews

Woodland Neighborhood Retreat

Relax in a cozy studio in the peaceful woods. Tasteful high-quality touches will have you feeling comfortable right away! This is an ideal space for up to 2 adults and up to 2 children. We live upstairs & offer self-check-in. A rare find in the Hudson Valley, our neighborhood is mostly flat, with walkable, quiet roads, and excellent bird-watching. It's an easy bike ride to connect to the vast state-wide rail trail system & all that the Mohonk Preserve has to offer.

Guest favourite
Cottage in Bloomington
4.97 out of 5 average rating, 552 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.

Popular amenities for Bloomington holiday rentals

  1. Airbnb
  2. United States
  3. New York
  4. Ulster County
  5. Bloomington