Bloomington Holiday Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

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

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
12 Jun - 14 Jun
In two months
24 Jul - 26 Jul
In three months
21 Aug - 23 Aug
In four months
18 Sept - 20 Sept

Our top choices for Bloomington holiday rentals

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
Saugerties
8.0 out of 10, Very good, (47 reviews)
"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$979
HK$1,272 total
includes taxes & fees
31 May - 1 Jun
'A Place in the Woods' - Cabin on Chloe's Lake on 23 acres near Woodstock, NY
1 bedroom, free WiFi, bed sheets

Totally secluded Yurt surrounded by waterfalls, brooks, cliffs and forest

Totally secluded Yurt surrounded by waterfalls, brooks, cliffs and forest
Ulster Park
10.0 out of 10, Exceptional, (101 reviews)
"We had a fantastic and relaxing time in the Yurt. It’s so peaceful and welcoming."
United States
Zachary W.
Totally secluded Yurt surrounded by waterfalls, brooks, cliffs and forest
Interior

Esopus Creek modern Tiny house Retreat in Woodstock &Kingston Catskill area!

Esopus Creek modern Tiny house Retreat in Woodstock &Kingston Catskill area!
Kingston
9.6 out of 10, Exceptional, (79 reviews)
"A quick stop over to explore Kingston and the surrounding area. We had a very nice time, thank you!"
United States
Lee M.
The price is HK$1,191
HK$1,904 total
includes taxes & fees
3 Jun - 4 Jun
Esopus Creek modern Tiny house Retreat in Woodstock &Kingston Catskill area!
Private kitchen

Woods Cabin-Kingston/Woodstock, NY.

Woods Cabin-Kingston/Woodstock, NY.
Kingston
The price is HK$987
HK$1,457 total
includes taxes & fees
16 Jun - 17 Jun
Woods Cabin-Kingston/Woodstock, NY.
Outdoor dining

Umana's Cabin, cozy, comfy, 5+ acres of land

Umana's Cabin, cozy, comfy, 5+ acres of land
Saugerties
10.0 out of 10, Exceptional, (3 reviews)
"Secluded and private but just a short drive away from a little town with great bars, restaurants and music venues. "
United States
Paul
The price is HK$2,108
HK$3,949 total
includes taxes & fees
28 May - 29 May
Umana's Cabin, cozy, comfy, 5+ acres of land
Interior

Stunning 5-bedroom house with AC / Heat in charming Poughkeepsie NY

Stunning 5-bedroom house with AC / Heat in charming Poughkeepsie NY
Poughkeepsie
9.6 out of 10, Exceptional, (4 reviews)
"Great host"
United States
Lindsey F.
The price is HK$1,398
HK$4,015 total
includes taxes & fees
28 May - 29 May
Stunning 5-bedroom house with AC / Heat in charming Poughkeepsie NY
Interior

Campfire Cottage: Fireplace, fire pit & no chores!

Campfire Cottage: Fireplace, fire pit & no chores!
Kingston
10.0 out of 10, Exceptional, (31 reviews)
"The place was amazing! Very easy check in/out process and the host is very responsive. "
United States
Samuel M.
The price is HK$744
HK$2,212 total
includes taxes & fees
1 Jun - 2 Jun
Campfire Cottage: Fireplace, fire pit & no chores!
TV

NEW-Romantic Lake View Carriage House

NEW-Romantic Lake View Carriage House
Lake Hill
10.0 out of 10, Exceptional, (1 review)
"Beautiful place! The host was wonderful. We got in right before a snow storm and they were kind enough to shovel for us. View was beautiful. Very clean and relaxing."
United States
Kathryn H.
The price is HK$1,481
HK$3,115 total
includes taxes & fees
3 Jun - 4 Jun
NEW-Romantic Lake View Carriage House
Interior

Relaxed Mountain Living Near Minnewaska | Dream House in the Gunks

Relaxed Mountain Living Near Minnewaska | Dream House in the Gunks
Kerhonkson
10.0 out of 10, Exceptional, (37 reviews)
"I was very happy with the property. I shared the place with my adult children for a family wedding. It was wonderful to have some quality, screenfree, engaging time with them. We took full advantage of the games and cards provided. The bedding was sooo comfy that I came home and ordered the same pillows that were there. I would definitely add the fact that the water is “well water” to the listing so people know in advance to bring water. All in all a great experience."
United States
Kim
The price is HK$612
HK$1,375 total
includes taxes & fees
3 Jun - 4 Jun
Relaxed Mountain Living Near Minnewaska | Dream House in the Gunks
1 bedroom, free WiFi, bed sheets

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, (35 reviews)
"Instructions were clear. Accommodations were comfortable and clean. Lovely grounds. "
United States
Julia
The price is HK$881
HK$2,137 total
includes taxes & fees
7 Jun - 8 Jun
The Studio at the Inn at High Falls
Smart TV, video games, offices

Peaceful Cabin w/ Fire Pit & Creek Access

Peaceful Cabin w/ Fire Pit & Creek Access
Saugerties
9.8 out of 10, Exceptional, (16 reviews)
"The home was extremely clean and nicely appointed. Beds were very comfortable and kitchen was nicely equipped."
United States
Nancy B.
The price is HK$905
HK$2,452 total
includes taxes & fees
9 Jun - 10 Jun
Peaceful Cabin w/ Fire Pit & Creek Access
Smart TV, fireplace

Mossy Moody Cabin in High Falls, NY

Mossy Moody Cabin in High Falls, NY
High Falls
9.8 out of 10, Exceptional, (19 reviews)
"Had a great fall weekend staying at the cabin. Cute place and the location was perfect for our activities in the nearby towns like Kingston and Accord."
United States
Steve H.
Mossy Moody Cabin in High Falls, NY
Fireplace, books

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
9.6 out of 10, Exceptional, (14 reviews)
"Charming and relaxing cottage. Perfect location for hiking or enjoying Lake Minnewaska or Mohonk Preserve. "
United States
Patrick S.
The price is HK$619
HK$1,382 total
includes taxes & fees
4 Jun - 5 Jun
Cozy Cottage Near Hiking, Infrared Sauna & Fireplace | 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
Gardiner
10.0 out of 10, Exceptional, (16 reviews)
"Great weekend getaway to reconnect with old friends!"
United States
Lisa D.
The price is HK$1,538
HK$2,389 total
includes taxes & fees
11 Jun - 12 Jun
Modern Zen Chalet at the Foot of Gunks w Mt. View and barrel outside sauna
Terrace/patio

Dog-Friendly Hudson Valley Escape with Hot Tub & Jacuzzi

Dog-Friendly Hudson Valley Escape with Hot Tub & Jacuzzi
Kingston
9.2 out of 10, Wonderful, (29 reviews)
"The beds were especially comfortable! "
United States
josh p.
The price is HK$917
HK$2,115 total
includes taxes & fees
28 May - 29 May
Dog-Friendly Hudson Valley Escape with Hot Tub & Jacuzzi
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!
Wallkill
10.0 out of 10, Exceptional, (81 reviews)
"great location and nice host"
United States
christopher s.
The price is HK$1,128
HK$2,123 total
includes taxes & fees
9 Jun - 10 Jun
Create Memories at our Modern Waterfront 1 BR Apartment: Hike, Sip Wine, Relax!
Living area

Hot Tub; Big Kitchen; 2 Blocks to Downtown Saugerties

Hot Tub; Big Kitchen; 2 Blocks to Downtown Saugerties
Saugerties
10.0 out of 10, Exceptional, (3 reviews)
"Very comfortable accommodation, beds and pillows are wonderful!"
United States
Danita K.
The price is HK$1,142
HK$4,088 total
includes taxes & fees
1 Jun - 2 Jun
Hot Tub; Big Kitchen; 2 Blocks to Downtown Saugerties
Smart TV, fireplace

Cozy Log Cabin with Hot-Tub, Firepit & Prime Catskills Location

Cozy Log Cabin with Hot-Tub, Firepit & Prime Catskills Location
Boiceville
9.8 out of 10, Exceptional, (10 reviews)
"Great place and very clean. Beds are very comfortable. Would definitely stay here again."
United States
Charles S.
The price is HK$2,194
HK$4,694 total
includes taxes & fees
28 May - 29 May
Cozy Log Cabin with Hot-Tub, Firepit & Prime Catskills Location
Smart TV, fireplace, books

NEW: SoulWood - Heart, Hearth and Hot-tub nr Woodstock

NEW: SoulWood - Heart, Hearth and Hot-tub nr Woodstock
Saugerties
The price is HK$3,189
HK$7,394 total
includes taxes & fees
23 Jun - 24 Jun
NEW: SoulWood - Heart, Hearth and Hot-tub nr Woodstock
Fridge, microwave, oven, stovetop

Welcome to New Paltz. Charming 3-bedroom house with AC, WIFI,

Welcome to New Paltz. Charming 3-bedroom house with AC, WIFI,
new paltz
8.6 out of 10, Excellent, (7 reviews)
"Very clean Good communication with host Close to town & hiking Recommend! "
United States
Jennifer E.
The price is HK$1,763
HK$5,502 total
includes taxes & fees
28 May - 29 May
Welcome to New Paltz. Charming 3-bedroom house with AC, WIFI,
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.
View all properties
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

Hyatt Place Poughkeepsie / Hudson Valley

Hyatt Place Poughkeepsie / Hudson Valley

6/10 Okay
"If you stay here make sure they don’t put you on the 1st floor. My family and I will never be staying at this hotel again. We were put on the 1st floor and our room floor had water coming up from the seems everywhere. I told the front desk and the man there came to see and gave me extra towels to put on the floor. It didn’t help because the towels got soaked within an hour and then were just walking on wet towels. I told the front desk that we were very upset so she said they would have management call me and they never did. Also, the shampoo dispenser in the shower was completely empty. I didn’t realize it until I was actually in the shower so it was too late to tell anyone. Very disappointing."
Teriann 1-night trip
Posted 4 hours ago
Hyatt Place Poughkeepsie / Hudson Valley

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?

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 Mid-Hudson Civic Center, or get outside and enjoy nature at Esopus Creek. Ulster Performing Arts Center and Kingston Point Beach 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.