Bloomington Holiday Rentals

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Holiday Rentals in Bloomington

Cottage in Saugerties

10.0 out of 10, Exceptional, (12)
"Cozy and beautiful house. "
United States
Seung L.
The price is AU$273
includes taxes & fees
7 Dec - 8 Dec
Country Cottage with beautiful views and easy access to Catskills activities.

Apartment in Wallkill

9.6 out of 10, Exceptional, (24)
"Over all the property was clean and staff was very cooperative. Only problems were the beds were very hard which made it hard for us to get a good nights sleep. The larger room had bugs but the owner took care of it right away. We enjoyed our stay."
United States
Harriet
The price is AU$290
includes taxes & fees
6 Jan - 7 Jan 2026
Dream getaway apartment in the foot of Gunks Ridge

Holiday Home in Kingston

9.6 out of 10, Exceptional, (14)
"Great little space. Perfect for two adults. Chill living room and well appointed kitchen. It’s a perfect alternative to a hotel, and reasonably priced for what you get. "
United States
Chris S.
The price is AU$437
includes taxes & fees
10 Dec - 11 Dec
Retro Retreat: renovated 2BR, desk, no chore list!

Holiday Home in Kingston

10.0 out of 10, Exceptional, (29)
"Great multi-week stay! Would certainly stay again. "
United States
Jim R.
The price is AU$385
includes taxes & fees
14 Dec - 15 Dec
Campfire Cottage: Fireplace, fire pit & no chores!

Holiday Home in Kerhonkson

10.0 out of 10, Exceptional, (14)
"Can’t emphasize how nice the surrounding area and property itself are. Very relaxing while still being close to several small towns with great restaurants. Communication was excellent, overall a great experience! "
United States
jose f.
Art Studio Retreat with Sauna Fireplace Forest Views | Dream House in the Gunks

Cottage in Kerhonkson

9.4 out of 10, Exceptional, (12)
"Charming and relaxing cottage. Perfect location for hiking or enjoying Lake Minnewaska or Mohonk Preserve. "
United States
Patrick S.
The price is AU$374
includes taxes & fees
15 Dec - 16 Dec
Cozy Cottage Near Hiking, Infrared Sauna & Fireplace | Dream House in the Gunks

Apartment in Plattekill

2.0 star property
10.0 out of 10, Exceptional, (2)
"Beautiful location and great stay! Would come here again in a heartbeat. "
United States
Gavin
The price is AU$399
includes taxes & fees
7 Dec - 8 Dec
Modern Hudson Valley Retreat Near Mohonk

Cabin in Saugerties

8.2 out of 10, Very good, (46)
"We had an amazing peaceful time at this property. Check in was seamless and we got lots of great recommendations from our hosts that we really enjoyed! It was very private and cozy and really helped us relax and renew! We will definitely be returning. "
United States
Josh M.
The price is AU$248
includes taxes & fees
7 Dec - 8 Dec
'A Place in the Woods' - Cabin on Chloe's Lake on 23 acres near Woodstock, NY

Apartment in RHINEBECK

10.0 out of 10, Exceptional, (25)
"This a an adorable, well designed, spotless space which was perfect for our over night stay in Rhinebeck. Property a quick walk away from the fairgrounds and downtown was also walkable…the host was absolutely amazing with great communication and detailed instructions! "
United States
Kathy
The price is AU$365
includes taxes & fees
8 Dec - 9 Dec
Private Studio Close to Downtown Rhinebeck

Holiday Home in Kingston

10.0 out of 10, Exceptional, (4)
"Beautiful house to stay in, convenient to numerous restaurants and hikes. Our host was very communicative and had great recommendations for the area!"
United States
Brendan B.
The price is AU$336
includes taxes & fees
9 Dec - 10 Dec
Retro Retreat: 1br home w/ WFH desk, livingroom, fire pit and no chores!

Chalet in Gardiner

2.0 star property
10.0 out of 10, Exceptional, (7)
"Great weekend getaway to reconnect with old friends!"
United States
Lisa D.
The price is AU$402
includes taxes & fees
5 Jan - 6 Jan 2026
Modern Zen Chalet at the Foot of Gunks w Mt. View and barrel outside sauna

Apartment in Kingston

9.6 out of 10, Exceptional, (25)
"A lovely place and Seth is always so helpful."
United States
Lynn L.
The price is AU$346
includes taxes & fees
8 Dec - 9 Dec
Dog-Friendly Hudson Valley Escape with Hot Tub & Jacuzzi

Apartment in Staatsburg

10.0 out of 10, Exceptional, (44)
"Location is well furnished and near many attractionHost versatile and well versed"
United States
Alberto M.
The price is AU$299
includes taxes & fees
11 Dec - 12 Dec
Mid-Century DJ’s Dream

Apartment in Stone Ridge

9.4 out of 10, Exceptional, (14)
"Clean cozy will be staying again"
United States
Michael C.
The price is AU$263
includes taxes & fees
7 Dec - 8 Dec
Cozy Apartment with Sauna in Historic Stone Ridge

Apartment in Wallkill

10.0 out of 10, Exceptional, (70)
"Everything was great nexactly as advertised. Terrific stargazing at night by the fire pit. Will definitely come back."
United States
David C.
The price is AU$356
includes taxes & fees
7 Dec - 8 Dec
Create Memories at our Modern Waterfront 1 BR Apartment: Hike, Sip Wine, Relax!

Holiday Home in Saugerties

10.0 out of 10, Exceptional, (13)
"Lovely home! Easy check in and in a quiet area. "
United States
Rachel B.
The price is AU$418
includes taxes & fees
17 Dec - 18 Dec
Peaceful Cabin w/ Fire Pit & Creek Access

Holiday Home in High Falls

8.0 out of 10, Very good, (33)
"Perfect location. Easy access to great surrounding area. Nice space. We had only one night. Wish it was longer!"
United States
loretta p.
The price is AU$408
includes taxes & fees
7 Dec - 8 Dec
The Studio at the Inn at High Falls

Apartment in Kingston

9.4 out of 10, Exceptional, (22)
"This was a great stay away, just for a couple of quiet days. Inside the house was excellent. "
United States
Dennis M.
The price is AU$347
includes taxes & fees
7 Dec - 8 Dec
Hot Tub - Fire Pit - BBQ - Hammock - Colonial

Cabin in Hyde Park

10.0 out of 10, Exceptional, (1)
"Great communication with the host. They thought of every detail down to a bone for our dog. Property is gorgeous with plenty of room to relax, enjoy a fire, and have hours of fun in the game room. We felt super relaxed when we walked in - like being home. "
United States
Darlene D.
The price is AU$591
includes taxes & fees
8 Dec - 9 Dec
Charming 2-bedroom cabin on 25 acres with loft space and full basement

Holiday Home in New Paltz

10.0 out of 10, Exceptional, (3)
"Lovely home in a beautiful area of New York state. Would stay here again! "
United States
Jason W.
The price is AU$805
includes taxes & fees
7 Dec - 8 Dec
Quaint & Cozy Cottage | Wood Stove, Pet Friendly
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$248 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 Hyde Park Station, or get outside and enjoy nature at Esopus Creek. Ulster Performing Arts Center and Hudson Valley Mall 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.