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Bloomington Vacation Rentals

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Check prices for these dates

In two weeks
Nov 6 - Nov 8
In two months
Dec 18 - Dec 20
In three months
Jan 15 - Jan 17
In four months
Feb 12 - Feb 14

Our top choices for Bloomington vacation rentals

A wooden vanity with a mirror, two pendant lights, and a folded towel.

1. Historic Hudson Valley Farmhouse Loft in Stone Ridge Hamlet

Historic Hudson Valley Farmhouse Loft in Stone Ridge Hamlet
Stone Ridge
9.4 out of 10, Exceptional, (31 reviews)
"Absolutely beautiful place. Carefully prepared for our arrival with tea light and lampshades on throughout the accommodation. No complaints whatsoever and if anything exceeded our expectations. The location was great for our plans exploring Hudson Valley and surrounding areas. Would 100% recommend. Communication throughout was perfect 👌. Thank you for a wonderful stay ."
United Kingdom
Catherine
The price is ￥10,502
￥22,644 total
includes taxes & fees
Nov 1 - Nov 2
Historic Hudson Valley Farmhouse Loft in Stone Ridge Hamlet
A modern kitchen with a granite countertop, stainless steel appliances, and a built-in oven.

2. Campfire Cottage: Fireplace, fire pit & no chores!

Campfire Cottage: Fireplace, fire pit & no chores!
Kingston
10.0 out of 10, Exceptional, (33 reviews)
"Great multi-week stay! Would certainly stay again. "
United States
Jim R.
The price is ￥12,079
￥40,058 total
includes taxes & fees
Nov 2 - Nov 3
Campfire Cottage: Fireplace, fire pit & no chores!
A compact living space with a kitchenette, a sofa, a coffee table, and a patterned rug.

3. Charming & Quaint 1 bed in Historic Uptown!

Charming & Quaint 1 bed in Historic Uptown!
Kingston
The price is ￥16,314
￥34,354 total
includes taxes & fees
Nov 2 - Nov 3
Charming & Quaint 1 bed in Historic Uptown!
A compact kitchen with blue cabinets, a white stove, and yellow chairs.

4. Retro Retreat: 1br home w/ WFH desk, livingroom, fire pit and no chores!

Retro Retreat: 1br home w/ WFH desk, livingroom, fire pit and no chores!
Kingston
10.0 out of 10, Exceptional, (7 reviews)
"Beautiful house to stay in, convenient to numerous restaurants and hikes. Our host was very communicative and had great recommendations for the area!"
United States
Brendan B.
The price is ￥10,824
￥38,477 total
includes taxes & fees
Nov 2 - Nov 3
Retro Retreat: 1br home w/ WFH desk, livingroom, fire pit and no chores!
A modern kitchen with white cabinets, a central island, and a view to the outside.

5. Pleasant 1-bedroom apartment in Staatsburg perfect for your getaway,

Pleasant 1-bedroom apartment in Staatsburg perfect for your getaway,
Staatsburg
9.6 out of 10, Exceptional, (13 reviews)
"We thoroughly enjoyed our stay. We would definitely come back! A fantastic location. And very good communication with the host, Alexander."
United States
elizabeth
The price is ￥17,648
￥32,565 total
includes taxes & fees
Nov 2 - Nov 3
Pleasant 1-bedroom apartment in Staatsburg perfect for your getaway,
A neatly made bed with white bedding and a few colorful pillows, a wooden headboard, and a wall-mounted light fixture.

6. Retro Retreat: renovated 2BR, desk, no chore list!

Retro Retreat: renovated 2BR, desk, no chore list!
Kingston
9.6 out of 10, Exceptional, (15 reviews)
"Great, easy, full of everything you’d need. Stayed with 2 others for a work trip and it was perfect! "
United States
Kelley Marie
The price is ￥14,275
￥47,789 total
includes taxes & fees
Nov 2 - Nov 3
Retro Retreat: renovated 2BR, desk, no chore list!
A kitchen with grey cabinets, a stone floor, and a view of a garden through an open door.

7. Historic Cottage * Steam Shower * Chef’s Kitchen

Historic Cottage * Steam Shower * Chef’s Kitchen
Kingston
10.0 out of 10, Exceptional, (1 review)
"We had a great time staying here! The house is a gorgeous historic house with modern amenities. It was a short drive to Kingston which was super convenient. We loved that we could bring our dog with us as well. It is on a main road, but we didn't find that to be a disturbance at all. I would definitely come back here again!!"
United States
Laura D.
The price is ￥24,158
￥79,506 total
includes taxes & fees
Nov 9 - Nov 10
Historic Cottage * Steam Shower * Chef’s Kitchen
A neatly made bed with a white pillow, a red pillow, and a white blanket. There is a small bedside table with a lamp.

8. Hibiscus Suite - Private Studio Apartment in Rhinebeck Village

Hibiscus Suite - Private Studio Apartment in Rhinebeck Village
Rhinebeck Village
10.0 out of 10, Exceptional, (33 reviews)
"Beautiful place has a great stay!"
United States
Heather O.
The price is ￥18,824
￥44,011 total
includes taxes & fees
Nov 3 - Nov 4
Hibiscus Suite - Private Studio Apartment in Rhinebeck Village
An outdoor patio with a striped rug, seating, a fire pit, and string lights.

9. Dog-Friendly Hudson Valley Escape with Hot Tub & Jacuzzi

Dog-Friendly Hudson Valley Escape with Hot Tub & Jacuzzi
Kingston
9.4 out of 10, Exceptional, (38 reviews)
"Clean, host answered in timely fashion and provided accommodations if needed or requested. Great stay overall!"
United States
Erin H.
The price is ￥21,516
￥46,764 total
includes taxes & fees
Nov 18 - Nov 19
Dog-Friendly Hudson Valley Escape with Hot Tub & Jacuzzi
A modern living room with a sofa, a coffee table, and a dining table. There are two doors, one black and one white, and a window with blinds.

10. Hot Tub - Fire Pit - BBQ - Hammock - Colonial

Hot Tub - Fire Pit - BBQ - Hammock - Colonial
Kingston
9.6 out of 10, Exceptional, (33 reviews)
"The rental was very clean & Beds were very comfortable. "
United States
R.A.G. Time A.
The price is ￥21,177
￥45,680 total
includes taxes & fees
Nov 18 - Nov 19
Hot Tub - Fire Pit - BBQ - Hammock - Colonial
A bedroom with a bed, a TV mounted on the wall, a window with a view of greenery, and a small seating area with a table and chairs.

11. The Studio at the Inn at High Falls

The Studio at the Inn at High Falls
High Falls
8.0 out of 10, Very good, (46 reviews)
"Great property in a serene setting. We enjoyed it very much!"
United States
John M.
The price is ￥17,648
￥42,430 total
includes taxes & fees
Oct 26 - Oct 27
The Studio at the Inn at High Falls
A covered porch with a wooden deck, white columns, wicker chairs, and a view of a house with windows.

12. Hudson Valley Apartment in a Historic Farmhouse w/ Sauna Near Stone Ridge Hamlet

Hudson Valley Apartment in a Historic Farmhouse w/ Sauna Near Stone Ridge Hamlet
Stone Ridge
8.8 out of 10, Excellent, (19 reviews)
"Clean cozy will be staying again"
United States
Michael C.
The price is ￥10,761
￥22,903 total
includes taxes & fees
Oct 26 - Oct 27
Hudson Valley Apartment in a Historic Farmhouse w/ Sauna Near Stone Ridge Hamlet
A spacious loft with a high ceiling, exposed wooden beams, a staircase, a flat-screen TV, and a round wooden coffee table with a plant.

13. Stunning and Cozy loft apartment in kingston .

Stunning and Cozy loft apartment in kingston .
Kingston
9.4 out of 10, Exceptional, (18 reviews)
"Very cute place, clean and comfortable. "
United States
Robin H.
The price is ￥23,531
￥41,640 total
includes taxes & fees
Nov 2 - Nov 3
Stunning and Cozy loft apartment in kingston .
Private kitchen

14. Woods Cabin-Kingston/Woodstock, NY.

Woods Cabin-Kingston/Woodstock, NY.
Kingston
9.2 out of 10, Wonderful, (15 reviews)
"Thank you. What an experience!"
United States
Burc
The price is ￥17,883
￥31,625 total
includes taxes & fees
Nov 10 - Nov 11
Woods Cabin-Kingston/Woodstock, NY.
A wooden deck with a wood-burning stove and a door leading to an outdoor area with chairs.

15. Historic Hudson Valley Farmhouse w/ Sauna in Stone Ridge Hamlet

Historic Hudson Valley Farmhouse w/ Sauna in Stone Ridge Hamlet
Stone Ridge
10.0 out of 10, Exceptional, (6 reviews)
"Great tastefully kept property. Our family including the 8 year felt we should have stayed here longer."
United States
Tarun
The price is ￥14,396
￥33,867 total
includes taxes & fees
Nov 1 - Nov 2
Historic Hudson Valley Farmhouse w/ Sauna in Stone Ridge Hamlet
A natural setting with a stream, red chairs, and a forested area.

16. Streamside Cottage Half Mile to Town of Woodstock

Streamside Cottage Half Mile to Town of Woodstock
Woodstock
10.0 out of 10, Exceptional, (307 reviews)
"It was the perfect place for a weekend away from home! The location was only a few minutes from town and was the perfect size for a couple. Would definitely reccomend!"
United States
Kristen S.
The price is ￥22,448
￥49,386 total
includes taxes & fees
Nov 10 - Nov 11
Streamside Cottage Half Mile to Town of Woodstock
A forest campsite with a tent, a fire pit, and a bench.

17. Glamping Tent & Campsite by Minnewaska State Park

Glamping Tent & Campsite by Minnewaska State Park
Kerhonkson
9.0 out of 10, Wonderful, (4 reviews)
"This place was amazing and our hosts were as equally as awesome as their campsite. My family highly recommends this place! It's got everything you need and is close to so many beautiful hiking and swimming areas!"
United States
Andie C.
The price is ￥13,412
￥23,806 total
includes taxes & fees
Oct 26 - Oct 27
Glamping Tent & Campsite by Minnewaska State Park
A deck with a red umbrella, wooden chairs, and a table with potted plants.

18. Mid-Century DJ’s Dream

Mid-Century DJ’s Dream
Staatsburg
10.0 out of 10, Exceptional, (61 reviews)
"Quiet clean accommodations in a central location for exploring the Hudson Valley."
United States
Alexandra R.
The price is ￥23,970
￥39,892 total
includes taxes & fees
Oct 26 - Oct 27
Mid-Century DJ’s Dream
A staircase with wooden steps and a black handrail, leading to a white door.

19. NEW: Family Retreat * Fireplace * Spa Bathroom

NEW: Family Retreat * Fireplace * Spa Bathroom
Cottekill
10.0 out of 10, Exceptional, (1 review)
"Property was great for our girls weekend! Eight of us fit very comfortably. Host was very responsive to all of our needs! We had a great time!"
United States
Shannon M.
The price is ￥25,884
￥131,677 total
includes taxes & fees
Oct 26 - Oct 27
NEW: Family Retreat * Fireplace * Spa Bathroom
A rural landscape with a barn, a silo, and a bridge with rocks and purple flowers in the foreground.

20. A Cozy Private Suite Near New Paltz: Farms, Nature, Hiking & Bike the rail trail

A Cozy Private Suite Near New Paltz: Farms, Nature, Hiking & Bike the rail trail
Wallkill
9.2 out of 10, Wonderful, (18 reviews)
"The room was super cute and clean. It had everything that I needed."
United States
Carrie
The price is ￥11,295
￥22,314 total
includes taxes & fees
Oct 28 - Oct 29
A Cozy Private Suite Near New Paltz: Farms, Nature, Hiking & Bike the rail trail
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Bloomington Hotel Reviews

Residence Inn by Marriott Kingston

Residence Inn by Marriott Kingston

8/10 Good
"clean room, good breakfast, helpful staff"
patricia 1-night trip
Posted 10 hours ago
Residence Inn by Marriott Kingston

Find out more about Bloomington

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Look no further and take a look at our great range of rental properties in Bloomington!

Frequently asked questions

Can I find vacation rentals in Bloomington?

Yes, we have vacation rentals close to well known points of interest in Bloomington, or you can choose a more remote option if you're looking for relaxation.

What are some of the best vacation rentals that Bloomington has to offer?

Esopus Creek modern Tiny house Retreat in Woodstock &Kingston Catskill area!: You might want to consider this vacation home rental near Bloomington, which is located on a river and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a fridge, a stovetop, and a microwave, so you can cook with friends or family.

What can I see and do in Bloomington?

While exploring the area, visit family-friendly sights like Hudson River Maritime Museum, or get outside and enjoy nature at Esopus Creek. Ulster Performing Arts Center and Vanderbilt Mansion National Historic Site are a couple of places you'll find in the larger area.

What are vacation rentals like in Bloomington?

Vacation rentals are private accommodations you can reserve for a short or long stay in Bloomington. Vacation rentals feature amenities such as patios, hot tubs, and fire pits so you'll have all the conveniences of home. If you're concerned about a sanitized environment, a vacation rental can offer a sense of security away from shared hotel elevators and busy front desks while still allowing you the experience of travel. You'll also get more space in a vacation rental than in a hotel, which makes a vacation rental an attractive option for family gatherings.