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Bloomington Holiday Rentals

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Our top choices for Bloomington holiday rentals

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, (6 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 AU$1,193
includes taxes & fees
30 June - 1 July
Steps to the Delightful Village of Millbrook ☆ Fun Family Getaway

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 AU$701
includes taxes & fees
6 July - 7 July
Charming 2-bedroom apartment on 2nd floor in Millbrook NY, right in the village

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 AU$1,632
includes taxes & fees
29 June - 30 June
The George is an elegant restored home in the Hudson Valley

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 AU$578
includes taxes & fees
29 June - 30 June
rural, serene + sophisticated space

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 AU$346
includes taxes & fees
29 June - 30 June
Hudson Valley Farm Getaway- West/Llama Lover Lane

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 AU$1,426
includes taxes & fees
8 July - 9 July
Luxe Mountain Getaway on Private Rd Near Rhinebeck

Luxe Mountain Getaway on Private Rd Near Rhinebeck

Luxe Mountain Getaway on Private Rd Near Rhinebeck
Hyde Park
The price is AU$1,409
includes taxes & fees
1 July - 2 July
Luxe Mountain Getaway on Private Rd Near Rhinebeck

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 AU$881
includes taxes & fees
30 June - 1 July
Stunning 5-bedroom house with AC / Heat in charming Poughkeepsie NY

King Bed | Private Parking | Strong WiFi

King Bed | Private Parking | Strong WiFi
Poughkeepsie
The price is AU$497
includes taxes & fees
22 July - 23 July
King Bed | Private Parking | Strong 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 AU$484
includes taxes & fees
30 June - 1 July
King Bed / Private Parking / 300mbps+ WiFi

King Bed Private Parking Fast Internet

King Bed Private Parking Fast Internet
Poughkeepsie
King Bed Private Parking Fast Internet

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.
The price is AU$346
includes taxes & fees
29 June - 30 June
Hudson Valley Farm Getaway-East/Alpaca Lane-Apt 1

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 AU$329
includes taxes & fees
1 July - 2 July
Mid-Century DJ’s Dream

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

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 AU$488
includes taxes & fees
29 June - 30 June
Hibiscus Suite - Private Studio Apartment in Rhinebeck Village

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)
The price is AU$1,159
includes taxes & fees
29 June - 30 June
Our home is perfect for relaxing and having lots of fun, with near by activity’s

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 AU$1,330
includes taxes & fees
29 June - 30 June
Hot tub on water, 5min HITS, 20mi to Hunter skiing

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 AU$390
includes taxes & fees
28 June - 29 June
Stunning and Cozy loft apartment in kingston .

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 AU$1,176
includes taxes & fees
30 June - 1 July
Super Comfortable Water-view Home in Saugerties

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 AU$3,594
includes taxes & fees
2 July - 3 July
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

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 favourite 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 depend 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 AU$223 per night. Entering your travel dates in the search wizard might find you 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?

The Farm at Hyde Park: This holiday home rental outside of Bloomington is located in a rural location, and has a fireplace, a patio and a BBQ 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 Hudson River Maritime Museum, 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 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.