Bloomington Holiday Rentals

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Holiday Rentals in Bloomington

Our top choices for Bloomington holiday rentals

Hamptons on the Hudson in South Saugerties

10.0 out of 10, Exceptional, (26)
"Beautiful home and great location . "
Hamptons on the Hudson in South Saugerties

Create Memories at our Modern Waterfront 1 BR Apartment: Hike, Sip Wine, Relax!

10.0 out of 10, Exceptional, (66)
"The yard and river are so beautiful. It’s a wonderful place to stay!"
The price is AU$319
includes taxes & fees
7 Sept - 8 Sept
Create Memories at our Modern Waterfront 1 BR Apartment: Hike, Sip Wine, Relax!

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

8.2 out of 10, Very good, (46)
"Perfect place to reconnect with natural world and yourself"
The price is AU$251
includes taxes & fees
7 Sept - 8 Sept
'A Place in the Woods' - Cabin on Chloe's Lake on 23 acres near Woodstock, NY

A Spectacular 50 Mile View of the Hudson Valley in all seasons

9.8 out of 10, Exceptional, (92)
"Had an absolutely fantastic time. Beautiful property and the owners are incredibly kind and welcoming "
A Spectacular 50 Mile View of the Hudson Valley in all seasons

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

9.8 out of 10, Exceptional, (6)
"Really liked that each room had it's own temperature control"
Our home is perfect for relaxing and having lots of fun, with near by activity’s

1 Br Private Victorian Apt in Convenient City Location on Half Acre Sleeps 4

2.0 star property
9.6 out of 10, Exceptional, (7)
"Gary is a great host and provides a wonderful experience. He is the best and it was a very nice stay. Best host I have had before."
The price is AU$312
includes taxes & fees
14 Sept - 15 Sept
1 Br Private Victorian Apt in Convenient City Location on Half Acre Sleeps 4

Esopus Creek modern Tiny house Retreat!

9.8 out of 10, Exceptional, (50)
"We stayed one night, and it was great! We met one of the owners too. He was very nice and helpful. The property was neat and clean. It has one bedroom, one loft bedroom area, and one pull out couch. We really enjoyed our stay!"
The price is AU$369
includes taxes & fees
10 Sept - 11 Sept
Esopus Creek modern Tiny house Retreat!

Streamside Cottage Half Mile to Town of Woodstock

10.0 out of 10, Exceptional, (250)
"A beautiful quiet setting! "
Streamside Cottage Half Mile to Town of Woodstock

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

10.0 out of 10, Exceptional, (92)
"We loved this stay! The yurt was absolutely charming! Such an amazing location within easy distance of hiking and the Empire State Trail bicycle path, plus great dining in New Paltz and Kingston."
Totally secluded Yurt surrounded by waterfalls, brooks, cliffs and forest

Charming Cottage in the Heart of the Shawangunks

10.0 out of 10, Exceptional, (15)
"The gatehouse was a perfect spot for a girls trip getaway. Secluded enough, but close to some local activities and restaurants! Cozy vibe and place had everything we needed!"
The price is AU$872
includes taxes & fees
16 Sept - 17 Sept
Charming Cottage in the Heart of the Shawangunks

The Farm at Hyde Park

9.8 out of 10, Exceptional, (76)
"We enjoyed our stay...lots to do in the area. Glen was very friendly and accommodating. "
The Farm at Hyde Park

NEW Spectacular Views & Private space on a Scenic Mountain 40ft Salt Water Pool

10.0 out of 10, Exceptional, (131)
"Stunning views, lovely house and pool, large kitchen, well equipped. Very responsive owner. Strongly recommend for family. "
NEW Spectacular Views & Private space on a Scenic Mountain 40ft Salt Water Pool

Peaceful River Retreat with Fireplace & Panoramic Views

10.0 out of 10, Exceptional, (14)
"Very nice location, beautiful views of the Hudson river . Modern house, clean and good amenities. Owner was responsive to any question we had. We really enjoyed our stay, would highly recommend. "
Peaceful River Retreat with Fireplace & Panoramic Views

Welcome to New Paltz. Charming 3-bedroom house with AC, WIFI,

The price is AU$919
includes taxes & fees
8 Sept - 9 Sept
Welcome to New Paltz. Charming 3-bedroom house with AC, WIFI,

Junebug Cottage: peace, love and privacy a short walk to Woodstock village green

10.0 out of 10, Exceptional, (73)
"We were in Woodstock for a wedding. Junebug Cottage was perfect for our stay! "
Junebug Cottage: peace, love and privacy a short walk to Woodstock village green

Private 3-bedroom home bordering the Mohonk Preserve, Dog friendly

10.0 out of 10, Exceptional, (11)
"My friends and I had a really nice time at Sheila's property for a spring weekend! When you're sitting in the living room, it really feels like you're in a tree house. It was comfortable for 6 of us (2 in each room) to hang out inside when it was rainy outside. Check in and check out was easy. Location was perfect for our needs (hiking in Minnewaska and Mohonk and roller skating at Skate Time in Accord). I recommend bringing coffee filters if you're planning on making coffee! Also, just a quick...
Private 3-bedroom home bordering the Mohonk Preserve, Dog friendly

Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream

9.2 out of 10, Wonderful, (43)
"This is a great place to stay. Really loved the fire pit by the creek for evening cocktails and conversation."
The price is AU$479
includes taxes & fees
7 Sept - 8 Sept
Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream

Cozy Bedroom With Fireplace

10.0 out of 10, Exceptional, (1)
"Very nice and cozy room. Golden was great."
The price is AU$314
includes taxes & fees
11 Sept - 12 Sept
Cozy Bedroom With Fireplace

<br>Escape to our incredibly private home on 30 acres!

10.0 out of 10, Exceptional, (141)
"If you’re looking for a quiet, hidden retreat with endless things to do, this is your spot! Such a gem tucked away into the woods. "
<br>Escape to our incredibly private home on 30 acres!

Scenic New Paltz Escape: River Views, Hot Tub & Deck | Dream House in the Gunks

2.0 star property
9.6 out of 10, Exceptional, (15)
"A group of girlfriends stayed for a 2 night visit. Everything was just as listed, the home was in the perfect location, well stocked, and beautiful inside. We would definitely return again. "
The price is AU$765
includes taxes & fees
29 Sept - 30 Sept
Scenic New Paltz Escape: River Views, Hot Tub & Deck | Dream House in the Gunks
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

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$251 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?

Hamptons on the Hudson in South Saugerties: This holiday home rental outside of Bloomington is located on a river, and has an outdoor pool, a fireplace and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a balcony, a garden and a selection of games so that you can immerse yourself in your holiday.

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. Ulster Performing Arts Center and Esopus Creek 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.