Bloomington Holiday Rentals

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Holiday Rentals in Bloomington

The Farm at Hyde Park

9.8 out of 10, Exceptional, (71)
"We were visiting the Culinary Institute highly recommend it."
The Farm at Hyde Park

Esopus Creek modern Tiny house Retreat!

9.8 out of 10, Exceptional, (37)
"Had a fantastic stay for a quick overnight trip to ski."
The price is AU$373
includes taxes & fees
16 July - 17 July
Esopus Creek modern Tiny house Retreat!

Hamptons on the Hudson in South Saugerties

10.0 out of 10, Exceptional, (23)
"Beautiful property- not too far from Hunter Mt or Woodstock. House has a lot to offer for adults and/or families with kids. Would highly recommend!"
Hamptons on the Hudson in South Saugerties

Streamside Cottage Half Mile to Town of Woodstock

10.0 out of 10, Exceptional, (241)
"Incredible location and comfortable space. Would make this my exclusive place to stay everytime I visit woodstock."
Streamside Cottage Half Mile to Town of Woodstock

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

10.0 out of 10, Exceptional, (65)
"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

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

2.0 star property
9.8 out of 10, Exceptional, (11)
"My husband and I had an amazing time. Absolutely beautiful home, great location, and overall amazing experience. "
The price is AU$909
includes taxes & fees
16 July - 17 July
Scenic New Paltz Escape: River Views, Hot Tub & Deck | Dream House in the Gunks

Where the Broadway Stars Vacation! Private Woodstock getaway & walk to town!

10.0 out of 10, Exceptional, (175)
"We loved our stay at this home! It is full of so much light and good vibes. We planned the weekend around a concert at Levon Helms studio, which was right down the street. The owners/management were wonderful & easy to get in touch with (not that we needed anything). The deck & music room were enjoyed the most :)"
Where the Broadway Stars Vacation! Private Woodstock getaway & walk to town!

The Studio at the Inn at High Falls

8.0 out of 10, Very good, (25)
"This was a very nice place, great value and comfortable. I would definitely return."
The price is AU$418
includes taxes & fees
15 July - 16 July
The Studio at the Inn at High Falls

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

9.8 out of 10, Exceptional, (88)
"This was exactly what we needed for a quick getaway after Christmas. Myra & Jerry were fantastic hosts, and the accommodations were cozy. We'd definitely come back. Thanks Myra & Jerry!"
A Spectacular 50 Mile View of the Hudson Valley in all seasons

The House In Highland- Secluded Retreat

10.0 out of 10, Exceptional, (6)
The House In Highland- Secluded Retreat

Lighthouse Walk - Full Floor Suite in the heart of Downtown

8.8 out of 10, Excellent, (15)
"Inside of appartment was nice, clean and maintained. Outside of rear entrance was overgrown and unkept. Entry door not marked clearly. Great location for dinning and walking around village. Over all, served what we needed but needs to clean up outside."
Lighthouse Walk - Full Floor Suite in the heart of Downtown

The Chicken Coop

8.0 out of 10, Very good, (3)
"Very cool place everything u need is just a short drive away "
The Chicken Coop

Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream

9.0 out of 10, Wonderful, (42)
"This is a great place to stay. Really loved the fire pit by the creek for evening cocktails and conversation."
The price is AU$470
includes taxes & fees
27 July - 28 July
Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream

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

8.2 out of 10, Very good, (42)
"Perfect place to reconnect with natural world and yourself"
The price is AU$251
includes taxes & fees
23 July - 24 July
'A Place in the Woods' - Cabin on Chloe's Lake on 23 acres near Woodstock, NY

‘A Quiet Place’ 3-bedrm house. Mid-Hudson Valley.

10.0 out of 10, Exceptional, (13)
"Our stay was great."
‘A Quiet Place’ 3-bedrm house. Mid-Hudson Valley.

Sioux Tipi on Chloe's Lake

9.6 out of 10, Exceptional, (5)
"This was such a cool experience Id love to go back! "
The price is AU$226
includes taxes & fees
14 July - 15 July
Sioux Tipi on Chloe's Lake

New Breathtaking Catskill Retreat with Views and Hot Tub, The Nest Retreat in Woodstock Catskill

10.0 out of 10, Exceptional, (16)
"Really enjoyed this place . Very clean , beautiful views, close to Woodstock town !"
New Breathtaking Catskill Retreat with Views and Hot Tub, The Nest Retreat in Woodstock Catskill

A-Frame of Mind

10.0 out of 10, Exceptional, (58)
"Great place, great host. {ictures dont do it justice"
A-Frame of Mind

Spacious A-Frame w/ Game Room, Fire Pit & Modern Comforts in Hudson Valley

10.0 out of 10, Exceptional, (7)
"We booked this home as additional housing for a corporate retreat. It was very close to the meeting location, as well as Main Street in the nearby town. Home was very clean and beautifully decorated. We traveled there during single digit temps and it was warm and cozy inside. Host is very responsive to questions and inquiries as well. Highly recommend if you are traveling to this area. "
The price is AU$1,029
includes taxes & fees
15 July - 16 July
Spacious A-Frame w/ Game Room, Fire Pit & Modern Comforts in Hudson Valley

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

10.0 out of 10, Exceptional, (4)
"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
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.
Save an average of 15% on thousands of hotels when you're signed in

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?

Esopus Creek modern Tiny house Retreat!: This holiday home rental outside of Bloomington is located on a river, and offers a BBQ, air conditioning and a Smart TV to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms, as well as a kitchen with a fridge, a stovetop and a microwave, so that you can cook with friends or family.

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 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.