Bloomington Vacation 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
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
Jul 19 - Jul 20
Tomorrow
Jul 20 - Jul 21
Next weekend
Jul 25 - Jul 27
In two weeks
Aug 1 - Aug 3

Vacation Rentals in Bloomington

The Farm at Hyde Park
Set amidst lush greenery and mature trees, this charming building features a steeply pitched roof and a brick facade.

The Farm at Hyde Park

9.8 out of 10, Exceptional, (72)
"We were visiting the Culinary Institute highly recommend it."
The Farm at Hyde Park
Esopus Creek modern Tiny house Retreat!
Enjoy a romantic dinner for two on this deck with a beautiful floral arrangement and a bottle of wine.

Esopus Creek modern Tiny house Retreat!

9.6 out of 10, Exceptional, (41)
"Had a fantastic stay for a quick overnight trip to ski."
The price is CA $204
CA $325 total
includes taxes & fees
Jul 21 - Jul 22
Esopus Creek modern Tiny house Retreat!
Hamptons on the Hudson in South Saugerties
Relax in a cozy outdoor space with a fireplace, wicker furniture, and a scenic view.

Hamptons on the Hudson in South Saugerties

10.0 out of 10, Exceptional, (23)
"Beautiful home and great location . "
Hamptons on the Hudson in South Saugerties
Streamside Cottage Half Mile to Town of Woodstock
Property grounds

Streamside Cottage Half Mile to Town of Woodstock

10.0 out of 10, Exceptional, (242)
"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
Scenic New Paltz Escape: River Views, Hot Tub & Deck | Dream House in the Gunks
Enjoy cooking in this well-equipped kitchen with a large island, oven, and stainless steel range hood.

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 CA $618
CA $892 total
includes taxes & fees
Jul 29 - Jul 30
Scenic New Paltz Escape: River Views, Hot Tub & Deck | Dream House in the Gunks
Junebug Cottage: peace, love and privacy a short walk to Woodstock village green
Set amidst a serene wooded area, this two-story house offers a retreat with a well-manicured lawn and a small deck.

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

10.0 out of 10, Exceptional, (68)
"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
Where the Broadway Stars Vacation! Private Woodstock getaway & walk to town!
Enjoy a peaceful forest view from the large window, featuring a comfortable bed below.

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

10.0 out of 10, Exceptional, (176)
"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
Situated in a lush forest, this cabin offers a serene retreat with a symmetrical facade and a well-manicured lawn.

The Studio at the Inn at High Falls

8.0 out of 10, Very good, (26)
"This was a very nice place, great value and comfortable. I would definitely return."
The price is CA $154
CA $373 total
includes taxes & fees
Jul 21 - Jul 22
The Studio at the Inn at High Falls
The Chicken Coop
Relax on the covered porch with outdoor seating and grill, surrounded by a serene backyard with a brick patio and well-maintained lawn.

The Chicken Coop

8.8 out of 10, Excellent, (5)
"Smelled like furnace oil. So we had to find a new place to stay. Don’t reserve the chicken coop. Also, no wifi on the property. "
The Chicken Coop
A Spectacular 50 Mile View of the Hudson Valley in all seasons
Perched on a rocky outcrop, this historic lighthouse offers stunning views of the surrounding waters.

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
Enjoy outdoor dining and relaxation on the spacious deck with comfortable seating and a barbecue grill.

The House In Highland- Secluded Retreat

10.0 out of 10, Exceptional, (8)
The House In Highland- Secluded Retreat
HUGE KITCHEN 4 Private Acres, 7 Min to Town, WiFi, AC, Fireplace
Hosts intimate summer concerts amidst a serene wooded setting.

HUGE KITCHEN 4 Private Acres, 7 Min to Town, WiFi, AC, Fireplace

10.0 out of 10, Exceptional, (39)
"Absolutely loved the property and its proximity to the Bearsville Theatre where we had a 2-day concert. We only wish we could have stayed longer than a quick weekend trip!"
HUGE KITCHEN 4 Private Acres, 7 Min to Town, WiFi, AC, Fireplace
Lighthouse Walk - Full Floor Suite in the heart of Downtown
Relax in this stylish living room with a flat-screen TV, comfortable sofa, and a cozy reading nook.

Lighthouse Walk - Full Floor Suite in the heart of Downtown

8.8 out of 10, Excellent, (16)
"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
Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream
Two houses nestled among lush greenery, surrounded by a park with a play structure.

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 CA $247
CA $418 total
includes taxes & fees
Jul 27 - Jul 28
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
Relax on the cabin's open porch, surrounded by tall trees in a secluded forest setting.

'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 CA $172
CA $223 total
includes taxes & fees
Jul 27 - Jul 28
'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.
Relax in this inviting living area with a plush sofa, wooden floor, and ceiling fan.

‘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.
A-Frame of Mind
Set amidst a serene natural setting, this house features a balcony and a well-manicured lawn.

A-Frame of Mind

10.0 out of 10, Exceptional, (60)
"Great place, great host. {ictures dont do it justice"
A-Frame of Mind
Sioux Tipi on Chloe's Lake
Escape to a secluded cabin nestled in a forest, surrounded by tall trees and a natural backdrop.

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 CA $151
CA $200 total
includes taxes & fees
Jul 27 - Jul 28
Sioux Tipi on Chloe's Lake
New Breathtaking Catskill Retreat with Views and Hot Tub, The Nest Retreat in Woodstock Catskill
Relax in a spacious bedroom with a large bed, bedside table, and lamp, offering a view of the balcony and adjacent room.

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
Many perfect sunsets at the magical house on the lake
Enjoy a serene view of the water from this tranquil outdoor space.

Many perfect sunsets at the magical house on the lake

9.8 out of 10, Exceptional, (128)
"As always - such a lovely get away to the lake cottage in Rifton! "
The price is CA $453
CA $842 total
includes taxes & fees
Aug 13 - Aug 14
Many perfect sunsets at the magical house on the lake
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
Sign in
Sign up, it's free

Top Bloomington Hotel Reviews

Hampton Inn & Suites Poughkeepsie

Hampton Inn & Suites Poughkeepsie

10/10 Excellent
"Was clean and front desk was very pleasant "
Matthew 1-night trip
Posted 3 days ago
Hampton Inn & Suites Poughkeepsie

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.

How many vacation rentals are there in Bloomington?

Expedia has 3 vacation 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 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.