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Bloomington Vacation Rentals

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Check prices for these dates

In two weeks
10 Jul - 12 Jul
In two months
21 Aug - 23 Aug
In three months
18 Sep - 20 Sep
In four months
16 Oct - 18 Oct

Our top choices for Bloomington vacation rentals

Interior

Steps to the Delightful Village of Millbrook ☆ Fun Family Getaway

Steps to the Delightful Village of Millbrook ☆ Fun Family Getaway
Millbrook
10.0 out of 10, Exceptional, (4 reviews)
"This is a charming, historic, well-maintained home on a beautifully landscaped lot. The updates in the home balance a respect for tradition while also providing modernization. The village of Millbrook is a quintessential twee New England village. The house felt very comfortable and homey and the caretaker was attentive and accommodating. We enjoyed our stay!"
United States
Beth E.
The price is SAR 1,501
SAR 3,155 total
includes taxes & fees
29 Jun - 30 Jun
Steps to the Delightful Village of Millbrook ☆ Fun Family Getaway
Exterior

Charming 2-bedroom apartment on 2nd floor in Millbrook NY, right in the village

Charming 2-bedroom apartment on 2nd floor in Millbrook NY, right in the village
Millbrook
9.6 out of 10, Exceptional, (4 reviews)
"We had a wonderful time at this property. It was quaint and clean and right in the middle of town near everything. Thank you, Tanya."
United States
Laurie F.
The price is SAR 1,201
SAR 1,839 total
includes taxes & fees
23 Jun - 24 Jun
Charming 2-bedroom apartment on 2nd floor in Millbrook NY, right in the village
Dining

The George is an elegant restored home in the Hudson Valley

The George is an elegant restored home in the Hudson Valley
Stanfordville
9.6 out of 10, Exceptional, (7 reviews)
"This our 3rd stay at the property and once again we thoroughly enjoyed the house and the grounds. We had an opportunity to enjoy horseback riding on site and would definitely recommend that to any visitors. The hosts were very kind and hospitable. "
United States
Eric L.
The price is SAR 2,703
SAR 4,144 total
includes taxes & fees
29 Jun - 30 Jun
The George is an elegant restored home in the Hudson Valley
Interior

rural, serene + sophisticated space

rural, serene + sophisticated space
Red Hook
10.0 out of 10, Exceptional, (8 reviews)
"Beautiful property with unique accommodations in the Hudson Valley"
United States
BRIAN PATRICK M.
The price is SAR 1,197
SAR 1,513 total
includes taxes & fees
29 Jun - 30 Jun
rural, serene + sophisticated space
Property grounds

Hudson Valley Farm Getaway- West/Llama Lover Lane

Hudson Valley Farm Getaway- West/Llama Lover Lane
Hyde Park
9.8 out of 10, Exceptional, (8 reviews)
"Perfect little apartment on an amazing farm property...thanks for having us and look forward to returning! "
United States
ADRIENNE
The price is SAR 647
SAR 842 total
includes taxes & fees
23 Jun - 24 Jun
Hudson Valley Farm Getaway- West/Llama Lover Lane
House (3 Bedrooms) | Interior

Luxe Mountain Getaway on Private Rd Near Rhinebeck

Luxe Mountain Getaway on Private Rd Near Rhinebeck
3.0 star property
Hyde Park
The price is SAR 2,526
SAR 4,273 total
includes taxes & fees
1 Jul - 2 Jul
Luxe Mountain Getaway on Private Rd Near Rhinebeck
Dining

Luxe Mountain Getaway on Private Rd Near Rhinebeck

Luxe Mountain Getaway on Private Rd Near Rhinebeck
Hyde Park
The price is SAR 2,252
SAR 4,251 total
includes taxes & fees
1 Jul - 2 Jul
Luxe Mountain Getaway on Private Rd Near Rhinebeck
Interior

Stunning 5-bedroom house with AC / Heat in charming Poughkeepsie NY

Stunning 5-bedroom house with AC / Heat in charming Poughkeepsie NY
Poughkeepsie
9.6 out of 10, Exceptional, (4 reviews)
"Beautiful property with ample space for parking. Host was super nice and met all of our needs!"
United States
Nicole Y.
The price is SAR 1,056
SAR 2,226 total
includes taxes & fees
23 Jun - 24 Jun
Stunning 5-bedroom house with AC / Heat in charming Poughkeepsie NY
Smart TV

King Bed | Private Parking | Strong WiFi

King Bed | Private Parking | Strong WiFi
Poughkeepsie
The price is SAR 293
SAR 1,227 total
includes taxes & fees
24 Jun - 25 Jun
King Bed | Private Parking | Strong WiFi
2 bedrooms, desk, WiFi

King Bed / Private Parking / 300mbps+ WiFi

King Bed / Private Parking / 300mbps+ WiFi
Poughkeepsie
5.0 out of 10, (2 reviews)
"Christina was extremely quick with her responses. My wife and I stayed at this place for the weekend and enjoyed the neighborhood. There's plenty to do, and the apartment is quaint and cozy. The only thing I'd change is adding a curtain to the bathroom window so people can't see you from the outside in."
United States
Jacob E.
The price is SAR 330
SAR 1,240 total
includes taxes & fees
30 Jun - 1 Jul
King Bed / Private Parking / 300mbps+ WiFi
1 bedroom, WiFi

King Bed Private Parking Fast Internet

King Bed Private Parking Fast Internet
Poughkeepsie
King Bed Private Parking Fast Internet
Property grounds

Hudson Valley Farm Getaway-East/Alpaca Lane-Apt 1

Hudson Valley Farm Getaway-East/Alpaca Lane-Apt 1
Hyde Park
8.0 out of 10, Very Good, (3 reviews)
"Great spot if you’re looking for a quiet rural area ! Seeing the llamas made the stay more fun. We weren’t there when the store was open so it was a bit disappointing we couldn’t see more of what the farm offers. We’d definitely go again."
United States
Meg H.
Hudson Valley Farm Getaway-East/Alpaca Lane-Apt 1
Property grounds

Mid-Century DJ’s Dream

Mid-Century DJ’s Dream
Staatsburg
10.0 out of 10, Exceptional, (53 reviews)
"Great host and excellent accommodations! "
United States
Elaine L.
The price is SAR 480
SAR 815 total
includes taxes & fees
23 Jun - 24 Jun
Mid-Century DJ’s Dream
Fridge, oven, stovetop, coffee/tea maker

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, (5 reviews)
The price is SAR 845
SAR 1,321 total
includes taxes & fees
5 Jul - 6 Jul
Pleasant 1-bedroom apartment in Staatsburg perfect for your getaway,
1 bedroom, desk, free WiFi, bed sheets

Hibiscus Suite - Private Studio Apartment in Rhinebeck Village

Hibiscus Suite - Private Studio Apartment in Rhinebeck Village
Rhinebeck Village
10.0 out of 10, Exceptional, (31 reviews)
"Beautiful place has a great stay!"
United States
Heather O.
The price is SAR 492
SAR 1,091 total
includes taxes & fees
1 Jul - 2 Jul
Hibiscus Suite - Private Studio Apartment in Rhinebeck Village
Interior

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

Our home is perfect for relaxing and having lots of fun, with near by activity’s
Highland
9.6 out of 10, Exceptional, (12 reviews)
"We had was great time and the host Mary was amazing and excellent at communicating. Everything was perfect in the home. Thank you"
United States
Pinal
The price is SAR 1,037
SAR 2,885 total
includes taxes & fees
23 Jun - 24 Jun
Our home is perfect for relaxing and having lots of fun, with near by activity’s
Terrace/patio

Hot tub on water, 5min HITS, 20mi to Hunter skiing

Hot tub on water, 5min HITS, 20mi to Hunter skiing
Malden
10.0 out of 10, Exceptional, (7 reviews)
"It was terrific!"
United States
Alexandra M.
The price is SAR 1,484
SAR 3,699 total
includes taxes & fees
7 Jul - 8 Jul
Hot tub on water, 5min HITS, 20mi to Hunter skiing
Interior

Stunning and Cozy loft apartment in kingston .

Stunning and Cozy loft apartment in kingston .
Kingston
9.4 out of 10, Exceptional, (16 reviews)
"The apartment was very clean and updated! Small back deck was nice to drink my morning coffee! Only issue was kids yelling and screaming in the neighborhood till almost 11pm."
United States
Donna
The price is SAR 563
SAR 988 total
includes taxes & fees
23 Jun - 24 Jun
Stunning and Cozy loft apartment in kingston .
Dining

Super Comfortable Water-view Home in Saugerties

Super Comfortable Water-view Home in Saugerties
Saugerties
9.8 out of 10, Exceptional, (7 reviews)
"Very comfortable home, everything that’s needed is there "
United States
gianni g.
The price is SAR 685
SAR 2,415 total
includes taxes & fees
23 Jun - 24 Jun
Super Comfortable Water-view Home in Saugerties
Outdoor dining

Church Des Artistes a Hudson Valley retreat

Church Des Artistes a Hudson Valley retreat
Rondout
9.8 out of 10, Exceptional, (10 reviews)
"Beautiful, unique stay! Julie was really kind walking us through the ins and outs of the property during check-in. So much care and attention put into every room. And the book collection is amazing."
United States
Molly M.
The price is SAR 5,630
SAR 9,505 total
includes taxes & fees
29 Jun - 30 Jun
Church Des Artistes a Hudson Valley retreat
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

Beekman Arms and Delamater Inn

Beekman Arms and Delamater Inn

10/10 Excellent
"This hotel is a very old historic hotel. It has several different locations around the property to stay in. The restaurant was very good. The town is a fun place to visit. I would recommend this hotel."
annemarie 1-night trip
Posted 4 hours ago
Beekman Arms and Delamater Inn

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 Farm at Hyde Park: Visitors like this Bloomington vacation home rental. It is located in a rural location and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. Kick off your shoes and enjoy yourself with a garden and a selection of games.

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 Catskill Mountains. Forsyth Park and Ulster Performing Arts Center 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.