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Bloomington Holiday Rentals

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Check prices for these dates

In two weeks
11 Sept - 13 Sept
In two months
23 Oct - 25 Oct
In three months
20 Nov - 22 Nov
In four months
18 Dec - 20 Dec

Our top choices for Bloomington holiday rentals

Interior

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, (30 reviews)
"Great location close to town. Cute and clean. Great little spot."
United States
Stephen
The price is HK$684
HK$1,299 total
includes taxes & fees
2 Sept - 3 Sept
Historic Hudson Valley Farmhouse Loft in Stone Ridge Hamlet
Private kitchen

2. 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, (6 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 HK$541
HK$1,949 total
includes taxes & fees
31 Aug - 1 Sept
Retro Retreat: 1br home w/ WFH desk, livingroom, fire pit and no chores!
Interior

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

Campfire Cottage: Fireplace, fire pit & no chores!
Kingston
10.0 out of 10, Exceptional, (32 reviews)
"The place was amazing! Very easy check in/out process and the host is very responsive. "
United States
Samuel M.
The price is HK$713
HK$2,089 total
includes taxes & fees
13 Sept - 14 Sept
Campfire Cottage: Fireplace, fire pit & no chores!
Terrace/patio

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

Dog-Friendly Hudson Valley Escape with Hot Tub & Jacuzzi
Kingston
9.2 out of 10, Wonderful, (35 reviews)
"Clean, host answered in timely fashion and provided accommodations if needed or requested. Great stay overall!"
United States
Erin H.
The price is HK$988
HK$2,256 total
includes taxes & fees
27 Aug - 28 Aug
Dog-Friendly Hudson Valley Escape with Hot Tub & Jacuzzi
Living area

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

Hot Tub - Fire Pit - BBQ - Hammock - Colonial
Kingston
9.6 out of 10, Exceptional, (31 reviews)
"Wonderful apartment with everything our family of five needed. We enjoyed the hot tub on two snowy evenings. Thank you for a great stay!"
United States
Clara L.
The price is HK$1,019
HK$2,256 total
includes taxes & fees
10 Sept - 11 Sept
Hot Tub - Fire Pit - BBQ - Hammock - Colonial
Private kitchen

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

Pleasant 1-bedroom apartment in Staatsburg perfect for your getaway,
Staatsburg
9.8 out of 10, Exceptional, (7 reviews)
"Nice stay for our quick overnight Comfortable space "
United States
jay c.
The price is HK$811
HK$1,547 total
includes taxes & fees
1 Sept - 2 Sept
Pleasant 1-bedroom apartment in Staatsburg perfect for your getaway,
Room

7. Totally secluded Yurt surrounded by waterfalls, brooks, cliffs and forest

Totally secluded Yurt surrounded by waterfalls, brooks, cliffs and forest
Ulster Park
10.0 out of 10, Exceptional, (111 reviews)
"Always love the yurt "
United States
Curt B.
The price is HK$1,842
HK$3,889 total
includes taxes & fees
27 Aug - 28 Aug
Totally secluded Yurt surrounded by waterfalls, brooks, cliffs and forest
Living area

8. 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, (3 reviews)
"Great tastefully kept property. Our family including the 8 year felt we should have stayed here longer."
United States
Tarun
The price is HK$935
HK$1,951 total
includes taxes & fees
2 Sept - 3 Sept
Historic Hudson Valley Farmhouse w/ Sauna in Stone Ridge Hamlet
Room

9. Charming & Quaint 1 bed in Historic Uptown!

Charming & Quaint 1 bed in Historic Uptown!
Kingston
The price is HK$1,129
HK$2,100 total
includes taxes & fees
22 Sept - 23 Sept
Charming & Quaint 1 bed in Historic Uptown!
Interior

10. Luxe Historical Style - 2 FP’s & Soaking Tub

Luxe Historical Style - 2 FP’s & Soaking Tub
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 HK$1,311
HK$4,012 total
includes taxes & fees
27 Aug - 28 Aug
Luxe Historical Style - 2 FP’s & Soaking Tub
Room

11. 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 HK$886
HK$2,642 total
includes taxes & fees
15 Sept - 16 Sept
Retro Retreat: renovated 2BR, desk, no chore list!
Terrace/patio

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
8.6 out of 10, Excellent, (18 reviews)
"Clean cozy will be staying again"
United States
Michael C.
The price is HK$670
HK$1,276 total
includes taxes & fees
15 Sept - 16 Sept
Hudson Valley Apartment in a Historic Farmhouse w/ Sauna Near Stone Ridge Hamlet
Room

13. 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, (41 reviews)
"I had a great stay here, it’s just as listed; simple but has everything that I needed, check in was easy, communication was good, and bed was comfortable!"
United States
Jamie M.
The price is HK$882
HK$2,138 total
includes taxes & fees
30 Aug - 31 Aug
The Studio at the Inn at High Falls
Interior

14. Stunning and Cozy loft apartment in kingston .

Stunning and Cozy loft apartment in kingston .
Kingston
9.4 out of 10, Exceptional, (17 reviews)
"Very cute place, clean and comfortable. "
United States
Robin H.
The price is HK$1,176
HK$2,107 total
includes taxes & fees
30 Aug - 31 Aug
Stunning and Cozy loft apartment in kingston .
Private kitchen

15. Woods Cabin-Kingston/Woodstock, NY.

Woods Cabin-Kingston/Woodstock, NY.
Kingston
9.4 out of 10, Exceptional, (9 reviews)
"The cabin is awesome. Surrounded by forrest you feel like youre the only person in the world. What's even cooler is its off grid but you dont miss a thing. Lights. Music. Bathroom. There were even a couple board games. Outside fire ready to go. Exactly what I was looking for."
United States
Carrie
The price is HK$894
HK$1,598 total
includes taxes & fees
30 Aug - 31 Aug
Woods Cabin-Kingston/Woodstock, NY.
Room

16. Hibiscus Suite - Private Studio Apartment in Rhinebeck Village

Hibiscus Suite - Private Studio Apartment in Rhinebeck Village
Rhinebeck Village
10.0 out of 10, Exceptional, (32 reviews)
"Beautiful place has a great stay!"
United States
Heather O.
The price is HK$974
HK$2,272 total
includes taxes & fees
1 Sept - 2 Sept
Hibiscus Suite - Private Studio Apartment in Rhinebeck Village
Living area

17. Mossy Moody Cabin in High Falls, NY

Mossy Moody Cabin in High Falls, NY
High Falls
9.8 out of 10, Exceptional, (22 reviews)
"Had a great fall weekend staying at the cabin. Cute place and the location was perfect for our activities in the nearby towns like Kingston and Accord."
United States
Steve H.
The price is HK$1,658
HK$3,779 total
includes taxes & fees
1 Sept - 2 Sept
Mossy Moody Cabin in High Falls, NY
Property grounds

18. Mid-Century DJ’s Dream

Mid-Century DJ’s Dream
Staatsburg
10.0 out of 10, Exceptional, (57 reviews)
"Quiet clean accommodations in a central location for exploring the Hudson Valley."
United States
Alexandra R.
The price is HK$1,047
HK$1,761 total
includes taxes & fees
31 Aug - 1 Sept
Mid-Century DJ’s Dream
Room

19. Kapitan’s cottage a Rustic Private Catskill Getaway Near Kingston

Kapitan’s cottage a Rustic Private Catskill Getaway Near Kingston
Kingston
9.6 out of 10, Exceptional, (10 reviews)
"Perfect place for a short vacation in the Catskills!"
United States
Jennifer C.
Kapitan’s cottage a Rustic Private Catskill Getaway Near Kingston
Living area

20. Private, Cozy, Clean apartment in lovely Hyde Park

Private, Cozy, Clean apartment in lovely Hyde Park
Hyde Park
10.0 out of 10, Exceptional, (2 reviews)
"The host was great, the place was really nice and cozy. I would definitely stay here again!!! "
United States
Janet M.
The price is HK$1,072
HK$1,639 total
includes taxes & fees
31 Aug - 1 Sept
Private, Cozy, Clean apartment in lovely Hyde Park
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

Howard Johnson by Wyndham Saugerties

Howard Johnson by Wyndham Saugerties

8/10 Good
"good facility"
Andrea 1-night trip
Posted 1 hour ago
Howard Johnson by Wyndham Saugerties

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 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.