Bloomington Holiday Rentals

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Check prices for these dates

In two weeks
3 Oct - 5 Oct
In two months
14 Nov - 16 Nov
In three months
12 Dec - 14 Dec
In four months
9 Jan - 11 Jan

Holiday Rentals in Bloomington

Our top choices for Bloomington holiday rentals

Esopus Creek modern Tiny house Retreat!
Outdoor dining

Esopus Creek modern Tiny house Retreat!

9.8 out of 10, Exceptional, (55)
"We enjoyed our stay. It was very comfortable and very clean and communication with the host was always available, when needed. We look forward to staying here again!!"
The price is AU$360
includes taxes & fees
18 Sept - 19 Sept
Esopus Creek modern Tiny house Retreat!
Hamptons on the Hudson in South Saugerties
Terrace/patio

Hamptons on the Hudson in South Saugerties

10.0 out of 10, Exceptional, (30)
"Lovely property, well-maintained, clean and comfortable, and the host was especially responsive to all communications. Highly recommend."
Hamptons on the Hudson in South Saugerties
'A Place in the Woods' - Cabin on Chloe's Lake on 23 acres near Woodstock, NY
Exterior

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

8.2 out of 10, Very good, (46)
"A quirky tiny cabin off the beaten path but in need of some upkeep, e.g. toilet not fully attached to the floor in the Tipi room, water has sulphur smell. We were only there for an overnight stay, and I sent a note once we were home, so hopefully the owners get a chance to fix things up! Pricey for its current condition."
The price is AU$246
includes taxes & fees
21 Sept - 22 Sept
'A Place in the Woods' - Cabin on Chloe's Lake on 23 acres near Woodstock, NY
The Farm at Hyde Park
Exterior

The Farm at Hyde Park

9.8 out of 10, Exceptional, (78)
"Great place to stay. Glen was a great host and give us different items from the area to try from local farms"
The Farm at Hyde Park
Charming Cottage in the Heart of the Shawangunks
Fridge, microwave, oven, stovetop

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!"
Charming Cottage in the Heart of the Shawangunks
1 Br Private Victorian Apt in Convenient City Location on Half Acre Sleeps 4
Apartment, 1 Bedroom, Balcony, Garden View | Living area

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

2.0 star property
9.0 out of 10, Wonderful, (8)
"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$305
includes taxes & fees
18 Sept - 19 Sept
1 Br Private Victorian Apt in Convenient City Location on Half Acre Sleeps 4
New Breathtaking Catskill Retreat with Views and Hot Tub, The Nest Retreat in Woodstock Catskill
2 bedrooms, iron/ironing board, WiFi, bed sheets

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

10.0 out of 10, Exceptional, (21)
"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
Minutes to Saugerties & HITS Horse show. Above garage w/ own private entrance.
Private kitchen

Minutes to Saugerties & HITS Horse show. Above garage w/ own private entrance.

2.0 star property
The price is AU$346
includes taxes & fees
21 Sept - 22 Sept
Minutes to Saugerties & HITS Horse show. Above garage w/ own private entrance.
A Spectacular 50 Mile View of the Hudson Valley in all seasons
Exterior

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
The Chicken Coop
Exterior

The Chicken Coop

9.4 out of 10, Exceptional, (9)
"Very cool place everything u need is just a short drive away "
The Chicken Coop
PERFECT ESCAPE For Total Privacy, Rustic Modern Cabin, 15 Pvt. Ac, WiFi, Heat/AC
Smart TV

PERFECT ESCAPE For Total Privacy, Rustic Modern Cabin, 15 Pvt. Ac, WiFi, Heat/AC

9.8 out of 10, Exceptional, (9)
"The cabin is beautiful,clean and private all the amenities are there and if you feel like venturing out the town of Woodstock is close by "
The price is AU$726
includes taxes & fees
18 Sept - 19 Sept
PERFECT ESCAPE For Total Privacy, Rustic Modern Cabin, 15 Pvt. Ac, WiFi, Heat/AC
Junebug Cottage: peace, love and privacy a short walk to Woodstock village green
Exterior

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

10.0 out of 10, Exceptional, (74)
"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
Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream
Children’s area

Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream

9.2 out of 10, Wonderful, (44)
"This is a great place to stay. Really loved the fire pit by the creek for evening cocktails and conversation."
The price is AU$469
includes taxes & fees
21 Sept - 22 Sept
Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream
Sioux Tipi on Chloe's Lake
Exterior

Sioux Tipi on Chloe's Lake

9.8 out of 10, Exceptional, (6)
"This was such a cool experience Id love to go back! "
The price is AU$221
includes taxes & fees
21 Sept - 22 Sept
Sioux Tipi on Chloe's Lake
Scenic New Paltz Escape: River Views, Hot Tub & Deck | Dream House in the Gunks
Fridge, microwave, oven, stovetop

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

2.0 star property
9.8 out of 10, Exceptional, (17)
"The property was perfectly secluded while being close to town. We observed lots of wildlife including deer, a woodchuck family, and a turtle laying eggs! The house was roomy and comfortable with just enough upscale elegance that made us feel pampered."
The price is AU$760
includes taxes & fees
30 Sept - 1 Oct
Scenic New Paltz Escape: River Views, Hot Tub & Deck | Dream House in the Gunks
Our home is perfect for relaxing and having lots of fun, with near by activity’s
Terrace/patio

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
The Studio at the Inn at High Falls
Exterior

The Studio at the Inn at High Falls

8.2 out of 10, Very good, (28)
"I had a great stay here, it’s just as listed; simple but has everything that I needed, check in was easy, communication was good, and bed was comfortable!"
The price is AU$407
includes taxes & fees
23 Sept - 24 Sept
The Studio at the Inn at High Falls
Totally secluded Yurt surrounded by waterfalls, brooks, cliffs and forest
1 bedroom, travel cot, free WiFi, bed sheets

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

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

10.0 out of 10, Exceptional, (66)
"This is a beautiful property. The apartment was very clean and comfortable with everything we could need. The view was spectacular and the host made it so easy to check in and out. This property is top of the list for our next visit."
The price is AU$356
includes taxes & fees
23 Sept - 24 Sept
Create Memories at our Modern Waterfront 1 BR Apartment: Hike, Sip Wine, Relax!
Streamside Cottage Half Mile to Town of Woodstock
Property grounds

Streamside Cottage Half Mile to Town of Woodstock

10.0 out of 10, Exceptional, (251)
"A beautiful quiet setting! "
Streamside Cottage Half Mile to Town of Woodstock
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

Americas Best Value Inn New Paltz

Americas Best Value Inn New Paltz

10/10 Excellent
"Rooms were clean and comfortable."
Paula 1-night trip
Posted 1 day ago
Americas Best Value Inn New Paltz

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$221 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?

Esopus Creek modern Tiny house Retreat!: This holiday home rental outside of Bloomington is located on a river, and has a fireplace, a BBQ and air conditioning to put you at ease 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.

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.