Bloomington Holiday Rentals

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Check prices for these dates

In two weeks
20 Nov - 22 Nov
In two months
1 Jan - 3 Jan
In three months
29 Jan - 31 Jan
In four months
26 Feb - 28 Feb

Our top choices for Bloomington holiday rentals

A compact living space with a kitchenette, a sofa, a coffee table, and a patterned rug.

1. Charming & Quaint 1 bed in Historic Uptown!

Charming & Quaint 1 bed in Historic Uptown!
Kingston
The price is NZ$359
includes taxes & fees
5 Nov - 6 Nov
Charming & Quaint 1 bed in Historic Uptown!
An outdoor patio with a striped rug, seating, a fire pit, and string lights.

2. 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, (39 reviews)
"Clean, host answered in timely fashion and provided accommodations if needed or requested. Great stay overall!"
United States
Erin H.
The price is NZ$434
includes taxes & fees
9 Nov - 10 Nov
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.

3. 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 NZ$442
includes taxes & fees
9 Nov - 10 Nov
Hot Tub - Fire Pit - BBQ - Hammock - Colonial
A modern kitchen with a granite countertop, stainless steel appliances, and a built-in oven.

4. 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 NZ$429
includes taxes & fees
17 Nov - 18 Nov
Campfire Cottage: Fireplace, fire pit & no chores!
A wooden vanity with a mirror, two pendant lights, and a folded towel.

5. 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 NZ$253
includes taxes & fees
1 Dec - 2 Dec
Historic Hudson Valley Farmhouse Loft in Stone Ridge Hamlet
A modern kitchen with white cabinets, a central island, and a view to the outside.

6. 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 NZ$357
includes taxes & fees
1 Dec - 2 Dec
Pleasant 1-bedroom apartment in Staatsburg perfect for your getaway,
A compact kitchen with blue cabinets, a white stove, and yellow chairs.

7. 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 NZ$433
includes taxes & fees
9 Nov - 10 Nov
Retro Retreat: 1br home w/ WFH desk, livingroom, fire pit and no chores!
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 NZ$481
includes taxes & fees
17 Nov - 18 Nov
Hibiscus Suite - Private Studio Apartment in Rhinebeck Village
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.

9. 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 NZ$451
includes taxes & fees
5 Nov - 6 Nov
Stunning and Cozy loft apartment in kingston .
A kitchen with grey cabinets, a stone floor, and a view of a garden through an open door.

10. 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 NZ$792
includes taxes & fees
5 Nov - 6 Nov
Historic Cottage * Steam Shower * Chef’s Kitchen
A deck with a red umbrella, wooden chairs, and a table with potted plants.

11. 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 NZ$410
includes taxes & fees
11 Nov - 12 Nov
Mid-Century DJ’s Dream
A wooden deck with a wood-burning stove and a door leading to an outdoor area with chairs.

12. 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 NZ$417
includes taxes & fees
1 Dec - 2 Dec
Historic Hudson Valley Farmhouse w/ Sauna in Stone Ridge Hamlet
A neatly made bed with white bedding and a few colorful pillows, a wooden headboard, and a wall-mounted light fixture.

13. 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 NZ$503
includes taxes & fees
17 Nov - 18 Nov
Retro Retreat: renovated 2BR, desk, no chore list!
A natural setting with a stream, red chairs, and a forested area.

14. Streamside Cottage Half Mile to Town of Woodstock

Streamside Cottage Half Mile to Town of Woodstock
Woodstock
10.0 out of 10, Exceptional, (308 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 NZ$537
includes taxes & fees
10 Nov - 11 Nov
Streamside Cottage Half Mile to Town of Woodstock
A modern living room with a large window, a fireplace, and a cozy seating area.

15. Mossy Moody Cabin in High Falls, NY

Mossy Moody Cabin in High Falls, NY
High Falls
9.8 out of 10, Exceptional, (24 reviews)
"It was perfect for us. Hope to be back soon."
United States
L R.
The price is NZ$728
includes taxes & fees
9 Nov - 10 Nov
Mossy Moody Cabin in High Falls, NY
A spacious room with a high ceiling, large windows, a ceiling fan, and a dining area with a table and chairs.

16. 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 NZ$1,502
includes taxes & fees
16 Nov - 17 Nov
NEW: Family Retreat * Fireplace * Spa Bathroom
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.

17. The Studio at the Inn at High Falls

The Studio at the Inn at High Falls
High Falls
8.2 out of 10, Very good, (47 reviews)
"Great property in a serene setting. We enjoyed it very much!"
United States
John M.
The price is NZ$458
includes taxes & fees
5 Nov - 6 Nov
The Studio at the Inn at High Falls
Private kitchen

18. Woods Cabin-Kingston/Woodstock, NY.

Woods Cabin-Kingston/Woodstock, NY.
Kingston
9.2 out of 10, Wonderful, (17 reviews)
"We loved the little cabin in the woods!"
United States
Patti G.
The price is NZ$362
includes taxes & fees
10 Nov - 11 Nov
Woods Cabin-Kingston/Woodstock, NY.
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.

19. Hot Tub - Hammock- Games - Grill - Large Colonial

Hot Tub - Hammock- Games - Grill - Large Colonial
Kingston
10.0 out of 10, Exceptional, (12 reviews)
"We had a great stay! Great location and was clean and comfortable for all of our friends."
United States
Amanda R.
The price is NZ$933
includes taxes & fees
9 Nov - 10 Nov
Hot Tub - Hammock- Games - Grill - Large Colonial
A view from a room with a sliding glass door leading to an outdoor deck with a wooden fence, a chair, and a bench.

20. Esopus Creek modern Tiny house Retreat in Woodstock &Kingston Catskill area!

Esopus Creek modern Tiny house Retreat in Woodstock &Kingston Catskill area!
Kingston
9.6 out of 10, Exceptional, (110 reviews)
"Wonderful stay. Lovely tiny house in a beautiful wooded setting. Woke to the sounds of birds singing. Would stay again"
United States
Nan
The price is NZ$476
includes taxes & fees
9 Nov - 10 Nov
Esopus Creek modern Tiny house Retreat in Woodstock &Kingston Catskill area!
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

A buffet with various food items, including omelets and baked goods, served in metal containers.
Holiday Inn Express & Suites Kingston-Ulster by IHG

Holiday Inn Express & Suites Kingston-Ulster by IHG

Holiday Inn Express & Suites Kingston-Ulster by IHG
Lake Katrine

8/10 Good

I liked the large light brightly decorated rooms and comfy bed. I felt that the hot offerings for breakfast were not tasty at all.
Australia
Andrew
Reviewed September 19, 2019
Holiday Inn Express & Suites Kingston-Ulster by IHG

Find out more about Bloomington

Everything you need to know about Bloomington holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Bloomington holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Bloomington holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Bloomington holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Bloomington. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Bloomington holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Bloomington holiday rentals we have selected for you start as low as NZ$253 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Bloomington rentals

At Expedia, we put the best Bloomington holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Bloomington rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Bloomington holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Bloomington. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently Asked Questions

Can I find holiday rentals in Bloomington?

Yes, there are holiday rentals close to the most popular sights in Bloomington, or you can select a more secluded option if you're looking for a relaxing stay.

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

Esopus Creek modern Tiny house Retreat in Woodstock &Kingston Catskill area!: This holiday home rental outside of Bloomington is located on a river, and has a fireplace, a patio and a BBQ 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 that 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 wider area.

What are holiday rentals like in Bloomington?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Bloomington. Holiday rentals feature amenities such as WiFi and washers and dryers so you'll have a home away from home. If you're concerned about cleanliness, holiday rentals can offer a sense of safety away from shared hotel lifts and busy front desks while still allowing you a great travel experience. You'll also get more space in a holiday rental than in a hotel, which makes a holiday rental a great option for a family trip.