Bloomington Holiday Rentals

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Check prices for these dates

In two weeks
9 Jan - 11 Jan
In two months
20 Feb - 22 Feb
In three months
20 Mar - 22 Mar
In four months
17 Apr - 19 Apr

Our top choices for Bloomington holiday rentals

Terrace/patio
Dream getaway apartment in the foot of Gunks Ridge

Dream getaway apartment in the foot of Gunks Ridge

Dream getaway apartment in the foot of Gunks Ridge
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 HK$483
HK$1,318 total
includes taxes & fees
4 Jan - 5 Jan 2026
Dream getaway apartment in the foot of Gunks Ridge
Fridge, microwave, oven, stovetop
Cozy Cottage Near Hiking, Infrared Sauna & Fireplace | Dream House in the Gunks

Cozy Cottage Near Hiking, Infrared Sauna & Fireplace | Dream House in the Gunks

Cozy Cottage Near Hiking, Infrared Sauna & Fireplace | Dream House in the Gunks
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 HK$805
HK$1,675 total
includes taxes & fees
4 Jan - 5 Jan 2026
Cozy Cottage Near Hiking, Infrared Sauna & Fireplace | Dream House in the Gunks
Interior
Art Studio Retreat with Sauna Fireplace Forest Views | Dream House in the Gunks

Art Studio Retreat with Sauna Fireplace Forest Views | Dream House in the Gunks

Art Studio Retreat with Sauna Fireplace Forest Views | Dream House in the Gunks
Kerhonkson
10.0 out of 10, Exceptional, (14)
"Beautiful place tucked back in the woods. Very relaxing and incredibly clean. The free coffee was a nice touch too. Will 100% be returning to The Gunks because of this house. "
United States
Kyle T.
The price is HK$739
HK$1,427 total
includes taxes & fees
8 Jan - 9 Jan 2026
Art Studio Retreat with Sauna Fireplace Forest Views | Dream House in the Gunks
Terrace/patio
Modern Zen Chalet at the Foot of Gunks w Mt. View and barrel outside sauna

Modern Zen Chalet at the Foot of Gunks w Mt. View and barrel outside sauna

Modern Zen Chalet at the Foot of Gunks w Mt. View and barrel outside sauna
2.0 star property
Gardiner
10.0 out of 10, Exceptional, (7)
"Great weekend getaway to reconnect with old friends!"
United States
Lisa D.
The price is HK$925
HK$1,839 total
includes taxes & fees
8 Jan - 9 Jan 2026
Modern Zen Chalet at the Foot of Gunks w Mt. View and barrel outside sauna
Terrace/patio
Country Cottage with beautiful views and easy access to Catskills activities.

Country Cottage with beautiful views and easy access to Catskills activities.

Country Cottage with beautiful views and easy access to Catskills activities.
Saugerties
10.0 out of 10, Exceptional, (13)
"Cozy and beautiful house. "
United States
Seung L.
The price is HK$770
HK$1,385 total
includes taxes & fees
4 Jan - 5 Jan 2026
Country Cottage with beautiful views and easy access to Catskills activities.
Outdoor dining
Mid-Century DJ’s Dream

Mid-Century DJ’s Dream

Mid-Century DJ’s Dream
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 HK$869
HK$1,528 total
includes taxes & fees
4 Jan - 5 Jan 2026
Mid-Century DJ’s Dream
Fridge, microwave, oven, stovetop
Retro Retreat: renovated 2BR, desk, no chore list!

Retro Retreat: renovated 2BR, desk, no chore list!

Retro Retreat: renovated 2BR, desk, no chore list!
Kingston
9.6 out of 10, Exceptional, (15)
"Great, easy, full of everything you’d need. Stayed with 2 others for a work trip and it was perfect! "
United States
Kelley Marie
The price is HK$692
HK$2,282 total
includes taxes & fees
21 Jan - 22 Jan 2026
Retro Retreat: renovated 2BR, desk, no chore list!
Fridge, microwave, oven, stovetop
Campfire Cottage: Fireplace, fire pit & no chores!

Campfire Cottage: Fireplace, fire pit & no chores!

Campfire Cottage: Fireplace, fire pit & no chores!
Kingston
10.0 out of 10, Exceptional, (29)
"Great multi-week stay! Would certainly stay again. "
United States
Jim R.
The price is HK$576
HK$1,986 total
includes taxes & fees
6 Jan - 7 Jan 2026
Campfire Cottage: Fireplace, fire pit & no chores!
Fridge, microwave, oven, stovetop
Retro Retreat: 1br home w/ WFH desk, livingroom, fire pit and no chores!

Retro Retreat: 1br home w/ WFH desk, livingroom, fire pit and no chores!

Retro Retreat: 1br home w/ WFH desk, livingroom, fire pit and no chores!
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 HK$505
HK$1,829 total
includes taxes & fees
21 Jan - 22 Jan 2026
Retro Retreat: 1br home w/ WFH desk, livingroom, fire pit and no chores!
Dining
Peaceful Cabin w/ Fire Pit & Creek Access

Peaceful Cabin w/ Fire Pit & Creek Access

Peaceful Cabin w/ Fire Pit & Creek Access
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 HK$651
HK$2,036 total
includes taxes & fees
5 Jan - 6 Jan 2026
Peaceful Cabin w/ Fire Pit & Creek Access
Property grounds
Create Memories at our Modern Waterfront 1 BR Apartment: Hike, Sip Wine, Relax!

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

Create Memories at our Modern Waterfront 1 BR Apartment: Hike, Sip Wine, Relax!
Wallkill
10.0 out of 10, Exceptional, (72)
"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 HK$896
HK$1,805 total
includes taxes & fees
29 Dec - 30 Dec
Create Memories at our Modern Waterfront 1 BR Apartment: Hike, Sip Wine, Relax!
Exterior
The Studio at the Inn at High Falls

The Studio at the Inn at High Falls

The Studio at the Inn at High Falls
High Falls
8.0 out of 10, Very good, (34)
"Just wasn't our cup of tea. Quiet location, close to attractions, and easy to find. "
United States
William K.
The price is HK$875
HK$2,094 total
includes taxes & fees
29 Dec - 30 Dec
The Studio at the Inn at High Falls
Exterior
'A Place in the Woods' - Cabin on Chloe's Lake on 23 acres near Woodstock, NY

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

'A Place in the Woods' - Cabin on Chloe's Lake on 23 acres near Woodstock, NY
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 HK$972
HK$1,263 total
includes taxes & fees
28 Dec - 29 Dec
'A Place in the Woods' - Cabin on Chloe's Lake on 23 acres near Woodstock, NY
Property grounds
Cozy Apartment with Sauna in Historic Stone Ridge

Cozy Apartment with Sauna in Historic Stone Ridge

Cozy Apartment with Sauna in Historic Stone Ridge
Stone Ridge
9.0 out of 10, Wonderful, (15)
"Clean cozy will be staying again"
United States
Michael C.
The price is HK$455
HK$1,212 total
includes taxes & fees
4 Jan - 5 Jan 2026
Cozy Apartment with Sauna in Historic Stone Ridge
Terrace/patio
Dog-Friendly Hudson Valley Escape with Hot Tub & Jacuzzi

Dog-Friendly Hudson Valley Escape with Hot Tub & Jacuzzi

Dog-Friendly Hudson Valley Escape with Hot Tub & Jacuzzi
Kingston
9.6 out of 10, Exceptional, (25)
"Very clean very comfortable beds."
United States
Millgate F.
The price is HK$840
HK$2,038 total
includes taxes & fees
4 Jan - 5 Jan 2026
Dog-Friendly Hudson Valley Escape with Hot Tub & Jacuzzi
Property grounds
Charming 2-bedroom cabin on 25 acres with loft space and full basement

Charming 2-bedroom cabin on 25 acres with loft space and full basement

Charming 2-bedroom cabin on 25 acres with loft space and full basement
Hyde Park
10.0 out of 10, Exceptional, (3)
"Beautiful house, very cozy, plenty of stuff to keep the kids busy and Zack was very helpful with everything."
United States
James S.
The price is HK$1,944
HK$3,017 total
includes taxes & fees
30 Dec - 31 Dec
Charming 2-bedroom cabin on 25 acres with loft space and full basement
Smart TV, fireplace, books, stereo
Secluded Couples Spa Sanctuary with HotTub!

Secluded Couples Spa Sanctuary with HotTub!

Secluded Couples Spa Sanctuary with HotTub!
Kerhonkson
9.2 out of 10, Wonderful, (9)
"We had a great stay at Fern Pond. The property offers a relaxing, quiet detox from the city. It is about 20-30 minutes from a grocery store but there’s also a bunch of Farm stands in between. The yard was great for our pup as well. Excellent stay, we will be back! "
United States
Ashley J.
The price is HK$1,594
HK$4,536 total
includes taxes & fees
15 Jan - 16 Jan 2026
Secluded Couples Spa Sanctuary with HotTub!
Fridge, microwave, oven, stovetop
The Meyer: spacious family home with hot tub minutes to downtown New Paltz

The Meyer: spacious family home with hot tub minutes to downtown New Paltz

The Meyer: spacious family home with hot tub minutes to downtown New Paltz
New Paltz
10.0 out of 10, Exceptional, (12)
"Clean environment, quiet, family friendly and was well equipped. Our family enjoyed staying and the host was available for any questions. "
United States
Awa Malicka B.
The price is HK$762
HK$2,717 total
includes taxes & fees
8 Jan - 9 Jan 2026
The Meyer: spacious family home with hot tub minutes to downtown New Paltz
Exterior
Container Cabin in the Catskills

Container Cabin in the Catskills

Container Cabin in the Catskills
Saugerties
10.0 out of 10, Exceptional, (2)
"Super fun little cabin you can spend all day in. Has everything that someone needs to enjoy themselves. Takes a little work to get some things going but everything is provided so its really no issue. Will be back again."
United States
John W.
The price is HK$1,516
HK$2,508 total
includes taxes & fees
1 Jan - 2 Jan 2026
Container Cabin in the Catskills
TV, fireplace, offices
Hits Adjacent | Pet Friendly | Caraway Cottage

Hits Adjacent | Pet Friendly | Caraway Cottage

Hits Adjacent | Pet Friendly | Caraway Cottage
Saugerties
9.8 out of 10, Exceptional, (16)
"Great location, comfortable beds, clean and updated space."
United States
Carolyn S.
The price is HK$1,866
HK$3,607 total
includes taxes & fees
23 Jan - 24 Jan 2026
Hits Adjacent | Pet Friendly | Caraway Cottage
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

Residence Inn by Marriott Kingston

Residence Inn by Marriott Kingston

10/10 Excellent
"Staff was very kind and courteous "
Natasha 1-night trip
Posted 2 days ago
Residence Inn by Marriott Kingston

Find out more about Bloomington

Search for holiday rentals in Bloomington on Expedia! You can easily find your home rentals, villas, holiday apartments in Bloomington using one of the methods below:

  • View our selection of featured holiday rentals in Bloomington
  • Use the map to find apartments and other holiday homes in the Bloomington neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Bloomington while they last

Look no further and take a look at our great range of rental properties in Bloomington!

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 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.