Bloomington Holiday Rentals

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Holiday Rentals in Bloomington

SECLUDED POOL, SPA & STREAM on 7 Acres, JUST 2 MINUTES FROM TOWN

10.0 out of 10, Exceptional, (88)
"The house and property were great. Very comfortable house that felt like home with a well equipped kitchen, two living rooms, great beds, fireplace, and spa. Pool was closed since it was winter. The property is wooded and feels like being in your own private park but is only a few minutes from downtown. Highly recommended!"
SECLUDED POOL, SPA & STREAM on 7 Acres, JUST 2 MINUTES FROM TOWN

Kingston Crawfish Cottage Near Catskills!

9.8 out of 10, Exceptional, (10)
"We enjoyed our stay at the crawfish cottage. It was clean and had everything we needed. The host, Diane, was great, friendly and very responsive. "
Kingston Crawfish Cottage Near Catskills!

Mountain View escape

10.0 out of 10, Exceptional, (46)
"We had an extremely great time at this rental house and were blown away how the layout of the house provided all our conveniences. It was clean spacious and beautifully arranged as seen in pics online . It was our mountain escape dream and we would definitely recommend and stay here again ."
Mountain View escape

'A Place in the Woods' - Cabin on Chloe's Lake on 23 acres near Woodstock, NY

8.2 out of 10, Very good, (42)
"We had a great time at the cabin! It was the perfect escape from the city. The view was gorgeous, and the cabin had everything we needed. We also tried to use the canoe but the padlock is stuck, it might be rusted/need to be replaced. Otherwise everything was perfect!"
The price is AU$236
includes taxes & fees
8 Jan - 9 Jan
'A Place in the Woods' - Cabin on Chloe's Lake on 23 acres near Woodstock, NY

The Farm at Hyde Park

9.8 out of 10, Exceptional, (64)
"Quiet spot out of the city but not too far from Hudson Valley sites. Large vaulted space, fresh eggs from the hen house next door, sky full of stars at night. Great host!"
The Farm at Hyde Park

The Studio at the Inn at High Falls

7.8 out of 10, Good, (22)
"Great communication with host. Stayed one night for event at Arrowood Farms (only 10 minutes away). Clean , nicely decorated studio with plenty of light. Lovely yard. Close to all local attractions and dining. Large shower. Great towels and toiletries.TV and A/C worked well. Appreciated the drinking water.Really cozy studio. Has frig, microwave and coffee maker.(also iron and hair dryer). A fabulous stay, although water pressure was a little low, but certainly not a deal breaker. Had people...
The price is AU$416
includes taxes & fees
20 Jan - 21 Jan
The Studio at the Inn at High Falls

Hamptons on the Hudson in South Saugerties

10.0 out of 10, Exceptional, (13)
"Our group of 7 women had a great time in the house. Beautiful property. Nice view of the Hudson. Lots of amenities. Well stocked kitchen. Cozy and comfortable. We enjoyed the Nespresso machine. Lots of room for us to spread out and to hang out together in the living room and enjoy a meal in the dining room. We would definitely stay again. "
Hamptons on the Hudson in South Saugerties

Sexiest Lil Cabin in Saugerties, NY

8.6 out of 10, Excellent, (7)
"We loved our stay here, it was the perfect short getaway. Thanks Alexandria!"
Sexiest Lil Cabin in Saugerties, NY

The Scenic Mansion With Breathtaking View

9.6 out of 10, Exceptional, (13)
"This house is so grand and perfect for a destination wedding, corprate retreat or family reunion. Host was wonderful!"
The Scenic Mansion With Breathtaking View

Dog-Friendly Hudson Valley Escape with Hot Tub & Jacuzzi

9.6 out of 10, Exceptional, (18)
"This apartment was clean and comfortable, and matched the online description. It was not particularly quiet: there is a bar next door, additional VRBO guests upstairs, and trains passing through the neighborhood throughout the night. But the owners provide white noise machines and earplugs, and the noise didn't disrupt my sleep at all. "
The price is AU$401
includes taxes & fees
21 Jan - 22 Jan
Dog-Friendly Hudson Valley Escape with Hot Tub & Jacuzzi

Mid-Century DJ’s Dream

10.0 out of 10, Exceptional, (24)
"My daughter needed a place to stay while visiting for the holiday. Kevin was easy to reach and responded quickly. The apartment is very cute and was the perfect size. Everything was clean and had some nice personal touches. Im sure a summertime stay would be lovely, when the garden is in bloom"
The price is AU$258
includes taxes & fees
30 Jan - 31 Jan
Mid-Century DJ’s Dream

The Louie II: Accord Farmhouse near Arrowood w/ Hot Tub & Large Yard

9.2 out of 10, Wonderful, (22)
"This property was clean and exactly as described. We were in the area for a family gathering and it allowed us a quiet place to regroup with our dog at night. Highly recommend and are hoping to visit again. "
The Louie II: Accord Farmhouse near Arrowood w/ Hot Tub & Large Yard

Beautiful Private Stone Home in the Hudson Valley

10.0 out of 10, Exceptional, (139)
"We had a wonderful time together. Room for everyone. We were 11. Clean and spacious. We would stay there again."
Beautiful Private Stone Home in the Hudson Valley

NEW! Herb Cottage: Historic Artist's Cottage, Wood Stove, Walk to Town!

9.8 out of 10, Exceptional, (130)
"Lovely in every way except loft area around bed. Didn’t realize I couldn’t stand upright. Was difficult to get around. Carpet could be replaced on loft. No idea it had such challenging steps to the bed. Cottage had a musty smell when first entered. "
NEW! Herb Cottage: Historic Artist's Cottage, Wood Stove, Walk to Town!

Oversized Country house, Quiet Retreat & Gathering space ~NEW !!!

9.8 out of 10, Exceptional, (20)
"Large clean house. Great for families. Toys for inside and out. Huge, well stocked kitchen. Very large dining table. Responsive host. Had a great time. Thank you. "
Oversized Country house, Quiet Retreat & Gathering space ~NEW !!!

The Loft At The Inn At High Falls

8.6 out of 10, Excellent, (10)
"Frank's place had everything we needed for the perfect end to summer weekend. He was responsive and his instructions were easy. We hope to come back someday!"
The price is AU$556
includes taxes & fees
20 Jan - 21 Jan
The Loft At The Inn At High Falls

Our home is perfect for relaxing and having lots of fun, with near by activity’s

10.0 out of 10, Exceptional, (2)
"We enjoyed our stay. The host is very responsive. The location is 30 minutes from Beacon, 10 minutes from Poughkeepsie and 2 hrs from NYC. The office was a nice feature and the house has great WiFi. "
Our home is perfect for relaxing and having lots of fun, with near by activity’s

Streamside Cottage Half Mile to Town of Woodstock

10.0 out of 10, Exceptional, (226)
"Place was a perfect place to unwind. Very clean and Jane was very communicative!"
Streamside Cottage Half Mile to Town of Woodstock

Kingston 3 Bedroom 1 Bath Near the Rondout

9.4 out of 10, Exceptional, (6)
"Easy check-in, great communication from host"
Kingston 3 Bedroom 1 Bath Near the Rondout

High Point Mtn House ~ Celebrate Thanksgiving on the Mountain! Total privacy!

9.8 out of 10, Exceptional, (23)
"Let me start off by saying Bernadette is a very attentive host, communication was great despite the fact that she was dealing with a family emergency during our trip. The location is exactly what my friends and I were after - an escape with no neighbors in sight, a place where we could cook, play cards, and gaze at the stars with minimal light pollution. All the amenities promised were there, all the utilities worked as expected, and the view was phenomenal. Be aware that the home has some...
High Point Mtn House ~ Celebrate Thanksgiving on the Mountain! Total privacy!
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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Other types of properties in Bloomington you may be interested in

Hyatt Place Poughkeepsie / Hudson Valley

3.0 star property
8.6 out of 10, Excellent, (1014)
"Staff was excellent Breakfast was mediocre"
The price is AU$182
includes taxes & fees
8 Jan - 9 Jan
Hyatt Place Poughkeepsie / Hudson Valley

Wildflower Farms, Auberge Resorts Collection

5.0 star property
9.4 out of 10, Exceptional, (41)
"Beautiful place with stunning views - perfect place to unwind and relax. Food is amazing as well as friendly service. "
The price is AU$1,683
includes taxes & fees
20 Jan - 21 Jan
Wildflower Farms, Auberge Resorts Collection

DoubleTree by Hilton Poughkeepsie

4.0 star property
8.2 out of 10, Very good, (1005)
"Check in was seamless, hotel bartender was beyond nice. Thank you for a wonderful stay!"
The price is AU$196
includes taxes & fees
20 Jan - 21 Jan
DoubleTree by Hilton Poughkeepsie
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.

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?

The Studio at the Inn at High Falls: This holiday home rental outside Bloomington is located in a rural location, and offers a garden, air conditioning and WiFi to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a microwave and a coffee maker.

How many holiday rentals are there in Bloomington?

Expedia has 3 holiday rentals for your stay in Bloomington.

What can I see and do in Bloomington?

While exploring the area, visit family-friendly sights like Mid-Hudson Civic Center, or get outside and enjoy nature at Forsyth Park. Ulster Performing Arts Center and Senate House State 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.