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Bloomington Vacation Rentals

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Check prices for these dates

In two weeks
Sep 25 - Sep 27
In two months
Nov 6 - Nov 8
In three months
Dec 4 - Dec 6
In four months
Jan 1 - Jan 3

Our top choices for Bloomington vacation rentals

Property grounds

1. Many perfect sunsets at the magical house on the lake

Many perfect sunsets at the magical house on the lake
Ulster Park
9.8 out of 10, Exceptional, (154 reviews)
"Highly recommend!"
United States
Seth M.
The price is ￥51,566
￥98,356 total
includes taxes & fees
Oct 1 - Oct 2
Many perfect sunsets at the magical house on the lake
Room

2. 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.
The price is ￥41,596
￥80,541 total
includes taxes & fees
Sep 8 - Sep 9
Kapitan’s cottage a Rustic Private Catskill Getaway Near Kingston
Terrace/patio

3. 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 ￥16,876
￥41,128 total
includes taxes & fees
Sep 9 - Sep 10
Dog-Friendly Hudson Valley Escape with Hot Tub & Jacuzzi
Property grounds

4. Maple Ridge Modern Rustic Retreat where Modern comfort meets Rustic Charm

Maple Ridge Modern Rustic Retreat where Modern comfort meets Rustic Charm
Ulster Park
9.8 out of 10, Exceptional, (20 reviews)
"Easy access and checkout, extremely clean, accurate pictures, comfy beds, well stocked kitchen. Great for groups. Would gladly stay again!"
United States
Emily F.
The price is ￥45,414
￥128,046 total
includes taxes & fees
Sep 10 - Sep 11
Maple Ridge Modern Rustic Retreat where Modern comfort meets Rustic Charm
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 ￥16,173
￥39,290 total
includes taxes & fees
Sep 10 - Sep 11
Hot Tub - Fire Pit - BBQ - Hammock - Colonial
Living area

6. 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 ￥27,705
￥67,606 total
includes taxes & fees
Sep 8 - Sep 9
Mossy Moody Cabin in High Falls, NY
Interior

7. 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 ￥26,127
￥79,455 total
includes taxes & fees
Sep 29 - Sep 30
Luxe Historical Style - 2 FP’s & Soaking Tub
Outdoor spa tub

8. Welcome to The Boathouse! Waterfront/Boats/Hot tub

Welcome to The Boathouse! Waterfront/Boats/Hot tub
New Paltz
9.6 out of 10, Exceptional, (11 reviews)
"We enjoyed our stay very much! Everything was as described, inside was very clean, host was excellent with communication. Scenic, serene spot!"
United States
Jessica B.
The price is ￥38,284
￥63,704 total
includes taxes & fees
Sep 15 - Sep 16
Welcome to The Boathouse! Waterfront/Boats/Hot tub
Living area

9. 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 ￥39,065
￥86,981 total
includes taxes & fees
Sep 22 - Sep 23
Hot Tub - Hammock- Games - Grill - Large Colonial
Property grounds

10. 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 ￥14,963
￥34,183 total
includes taxes & fees
Sep 9 - Sep 10
Historic Hudson Valley Farmhouse w/ Sauna in Stone Ridge Hamlet
Interior

11. 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 ￥9,218
￥21,313 total
includes taxes & fees
Sep 8 - Sep 9
Historic Hudson Valley Farmhouse Loft in Stone Ridge Hamlet
Private kitchen

12. NEW: Family Pool Retreat in Stone Ridge

NEW: Family Pool Retreat in Stone Ridge
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 ￥38,502
￥147,100 total
includes taxes & fees
Sep 15 - Sep 16
NEW: Family Pool Retreat in Stone Ridge
Interior

13. 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, (99 reviews)
"Convenient and comfortable stay"
United States
Cathy G.
The price is ￥26,720
￥41,652 total
includes taxes & fees
Sep 13 - Sep 14
Esopus Creek modern Tiny house Retreat in Woodstock &Kingston Catskill area!
Property grounds

14. Streamside Cottage Half Mile to Town of Woodstock

Streamside Cottage Half Mile to Town of Woodstock
Woodstock
10.0 out of 10, Exceptional, (297 reviews)
"Wonderful property with an easy check in and checkout process. The property and surrounding areas are beautiful. We would stay here again. "
United States
Anonymous traveler
The price is ￥22,361
￥48,319 total
includes taxes & fees
Sep 27 - Sep 28
Streamside Cottage Half Mile to Town of Woodstock
Interior

15. 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 ￥23,439
￥41,653 total
includes taxes & fees
Sep 9 - Sep 10
Stunning and Cozy loft apartment in kingston .
Private kitchen

16. 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 ￥10,782
￥38,328 total
includes taxes & fees
Sep 8 - Sep 9
Retro Retreat: 1br home w/ WFH desk, livingroom, fire pit and no chores!
Interior

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

Campfire Cottage: Fireplace, fire pit & no chores!
Kingston
10.0 out of 10, Exceptional, (33 reviews)
"The place was amazing! Very easy check in/out process and the host is very responsive. "
United States
Samuel M.
The price is ￥12,657
￥40,953 total
includes taxes & fees
Sep 23 - Sep 24
Campfire Cottage: Fireplace, fire pit & no chores!
Interior

18. Charming & Quaint 1 bed in Historic Uptown!

Charming & Quaint 1 bed in Historic Uptown!
Kingston
The price is ￥20,158
￥38,653 total
includes taxes & fees
Sep 23 - Sep 24
Charming & Quaint 1 bed in Historic Uptown!
Private kitchen

19. 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 ￥17,439
￥32,456 total
includes taxes & fees
Sep 16 - Sep 17
Pleasant 1-bedroom apartment in Staatsburg perfect for your getaway,
Property grounds

20. Mid-Century DJ’s Dream

Mid-Century DJ’s Dream
Staatsburg
10.0 out of 10, Exceptional, (58 reviews)
"Quiet clean accommodations in a central location for exploring the Hudson Valley."
United States
Alexandra R.
The price is ￥25,377
￥40,906 total
includes taxes & fees
Sep 13 - Sep 14
Mid-Century DJ’s Dream
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

Americas Best Value Inn New Paltz

Americas Best Value Inn New Paltz

8/10 Good
"Room was clean and friendly staff, plenty of parking. Good location, close to Main Street where a lot of shops and restaurants to venture. Happy that it’s also only 18 min drive to the Arts and Crafts Fair, which was the main reason for our trip! All in all very satisfied except the bed was a bit too firm for me."
Valerie 2-night trip
Posted 13 hours ago
Americas Best Value Inn New Paltz

Find out more about Bloomington

Search for holiday rentals in Bloomington on Expedia! You can easily find your home rentals, villas, holiday apartments in Bloomington using one of the methods below:

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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?

The Chicken Coop: Visitors like this Bloomington vacation home rental. It is located in a rural location and has a patio, a garden, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop.

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.