Bloomington Holiday Rentals

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Holiday Rentals in Bloomington

Hamptons on the Hudson in South Saugerties

10.0 out of 10, Exceptional, (14)
"We had an absolutely wonderful stay at this Vrbo! From the moment we arrived, everything was spotless, beautifully decorated, and thoughtfully equipped with everything we needed. The hosts went above and beyond to ensure a comfortable and seamless experience, providing clear instructions and even thoughtful touches that made us feel right at home.The location was perfect—close enough to attractions and restaurants but still peaceful and private. The beds were incredibly comfortable, the kitchen...
Hamptons on the Hudson in South Saugerties

Streamside Cottage Half Mile to Town of Woodstock

10.0 out of 10, Exceptional, (228)
"We totally enjoyed our stay at the cottage! Exactly as advertised, except the views of the river from the home are are even better than pictured. We would definitely recommend!"
Streamside Cottage Half Mile to Town of Woodstock

Spacious New Luxurious holiday house in lovely Hudson Valley

9.8 out of 10, Exceptional, (8)
"The house had room for all of us, spacious and comfortable with modern amenities. We enjoyed the large open kitchen, well equipped for making big meals, and especially loved the walk in pantry with sink, oven and coffee bar. The beds were comfy, the bathrooms deluxe. Large couch and huge TV in living room with cozy gas fireplace for us to gather and relax. Located on a quiet cul de sac, easy to get to local attractions. We enjoyed every minute of our stay."
The price is AU$1,290
includes taxes & fees
1 Mar - 2 Mar
Spacious New Luxurious holiday house in lovely Hudson Valley

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

10.0 out of 10, Exceptional, (172)
"This was an incredible place to stay for a snowy weekend with the family. The house is huge and and just beautiful. The hosts even had the long driveway plowed and stairs/walkway shoveled for us, would definitely recommend staying here. "
Where the Broadway Stars Vacation! Private Woodstock getaway & walk to town!

Hidden Charm in Hudson Valley In Dutchess County

2.0 star property
10.0 out of 10, Exceptional, (13)
"thank you to the host, she was responsive, the home was amazing, clean, secluded, perfect size for our family and the property was beautiful. we loved having 2 beds on the main floor, as my mom is elderly, so no stairs was incredibly convenient. house had all the supplies we needed to cook/clean, so it was just terrific!! Thank you!"
Hidden Charm in Hudson Valley In Dutchess County

Brand New House with Huge patio overlooks Esopus Creek at Lake Katrine

10.0 out of 10, Exceptional, (8)
"My family and I had a lovely stay! The home is beautiful and comfortable with all the amenities that we needed, including a crib as we were traveling with a newborn. Not much in the immediate vicinity but a short drive to Kingston. Smooth communication and easy checkin/checkout process."
The price is AU$543
includes taxes & fees
4 Mar - 5 Mar
Brand New House with Huge patio overlooks Esopus Creek at Lake Katrine

Esopus Creek modern Tiny house Retreat!

9.8 out of 10, Exceptional, (23)
"Great little house for the holidays. We were looking for a place nearby or family where we could have our own space but still be close by. "
The price is AU$357
includes taxes & fees
24 Feb - 25 Feb
Esopus Creek modern Tiny house Retreat!

Cedar Cottage with hot tub as seen in New York Times escape section.

9.4 out of 10, Exceptional, (81)
"This was our fifth time staying at the cabin and as always it was perfect. We stayed the week of Thanksgiving and cooked a full feast easily with the appliances and cookware found in the kitchen. We even woke up to snow a few times that week. We enjoyed the hot tub at night and the fireplace each day. Beds are comfy, rooms are cozy and location is ideal. With close proximity to Woodstock, Tannersville and West Kill we were able visit some of our favorite places in the mountains. We’ll be back....
Cedar Cottage with hot tub as seen in New York Times escape section.

Beautiful Private Stone Home in the Hudson Valley

10.0 out of 10, Exceptional, (139)
"We had a wonderful time together. Room for everyone. We were 11. Clean and spacious. We would stay there again."
Beautiful Private Stone Home in the Hudson Valley

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

2.0 star property
10.0 out of 10, Exceptional, (1)
"My husband and I had an amazing time. Absolutely beautiful home, great location, and overall amazing experience. "
The price is AU$626
includes taxes & fees
10 Mar - 11 Mar
Scenic New Paltz Escape: River Views, Hot Tub & Deck | Dream House in the Gunks

Mid-Century DJ’s Dream

10.0 out of 10, Exceptional, (27)
"The property is beautiful, we wish we would've had enough time to see everything. The rental place was spotless clean, the bed was comfortable, and the temperature control was efficient and adjustable. The property is located near a rural road and for the time of our stay I counted only 3 cars driving by, with a decent speed limit. Kevin, the host, was very accommodating, we appreciate the choice of coffee and the possibility do not do the dishes. Overall, our stay was perfect and we wish to...
The price is AU$278
includes taxes & fees
26 Feb - 27 Feb
Mid-Century DJ’s Dream

Lily Cottage - a cozy accomodation moments from the beautiful Ashokan reservoir

10.0 out of 10, Exceptional, (28)
"We had a wonderful stay in this quiet gem. Clean, comfortable, cute, and cozy. Highly recommended! "
Lily Cottage - a cozy accomodation moments from the beautiful Ashokan reservoir

Large Family Group Holiday Esopus Creek-front Arcade Saugerties 5br

10.0 out of 10, Exceptional, (1)
"The town is a bit weird, but the house was great. We had a good time."
The price is AU$1,663
includes taxes & fees
23 Feb - 24 Feb
Large Family Group Holiday Esopus Creek-front Arcade Saugerties 5br

Mountain View escape

10.0 out of 10, Exceptional, (46)
"Can’t wait to go back, if I could move this home to Myrtle Beach I would. Fantastic communication with homeowner, great location. Homeowner keeps the home stocked with goodies, extra plus! Very cozy and Quiet it’s a 10 Star "
Mountain View escape

Luxurious & Enchanting Log House in Heart of Hudson Valley/Catskills, Upstate NY

10.0 out of 10, Exceptional, (36)
"We rented this house for ourselves and our friends for our wedding weekend around the corner. It was the best decision, large group and we had plenty of places to sleep, the yard gave ample space for activities, the sound system kept us entertained, and the kitchen made hosting a large group a breeze. Yuri was amazing in making himself available and our stay memorable. Can’t wait to visit again!"
Luxurious & Enchanting Log House in Heart of Hudson Valley/Catskills, Upstate NY

A-Frame of Mind

10.0 out of 10, Exceptional, (48)
"What has become a regular winter Woodstock retreat turned into something magical with the beauty, warmth and smart comfort of Nick’s home. His friendly affect and many small touches made this one of the best home-bases for me in my decades of solo retreats. Secluded, woodsy with beautiful A-Frame design but 10 minutes to either Woodstock or Saugerties. Great cooking kitchen, treadmill, great sound and entertainment or quiet nooks for writing and reading. Good heat and warm floors. Bathtub....
A-Frame of Mind

Luxurious Woodstock Home Rental Catskill Mountains Views & Private Retreat

10.0 out of 10, Exceptional, (110)
"super easy - we'll be back"
Luxurious Woodstock Home Rental Catskill Mountains Views & Private Retreat

Cortland by AvantStay | Charming Heritage Estate w/ Private Lake & Pool

9.4 out of 10, Exceptional, (13)
"We had a lovely stay for our family of 5 during the week before xmas. The home was well appointed, with all the normal needs we have to cook, etc... The house was very quiet despite 5 of us being there. Everyone had their own space. Very cozy. Loved that there were games to play, we had a great family round of monopoly!The property manager was so responsive. We felt very supported and attended to. Despite the cold weather the house stayed plenty warm as well!We highly recommend this home and...
Cortland by AvantStay | Charming Heritage Estate w/ Private Lake & Pool

NEW! Gated 21 Acre Modern Luxury Estate Heated Pool Hot Tub Gym Movie Theater.

9.6 out of 10, Exceptional, (51)
"Our family enjoyed our time at the property- it was a great place for us all to gather. The property managers were incredibly helpful and responsive to the few things that needed attention during our stay. The pool area is the shining star of this home. You can expect the house/ furnishings to be in mostly good shape and as photographed-. The layout of the bedrooms/ shared bathrooms did surprise us a bit despite careful review of photos and listing video tour. Overall great stay!"
NEW! Gated 21 Acre Modern Luxury Estate Heated Pool Hot Tub Gym Movie Theater.

Bluming Fields - A private home on a 150-acre horse farm.

9.6 out of 10, Exceptional, (14)
"This was a great large property to have separate areas for different family members and close proximity to my wife’s uncles family in Ellenville. The kids loves the horses and with a bit of snow they were able to create a snowman in the yard."
The price is AU$1,021
includes taxes & fees
22 Feb - 23 Feb
Bluming Fields - A private home on a 150-acre horse farm.
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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Other types of properties in Bloomington you may be interested in

Best Western Plus Kingston Hotel And Conference Center

2.5 star property
8.0 out of 10, Very good, (1002)
"clean hotel "
The price is AU$214
includes taxes & fees
4 Mar - 5 Mar
Best Western Plus Kingston Hotel And Conference Center

Wildflower Farms, Auberge Resorts Collection

5.0 star property
9.4 out of 10, Exceptional, (46)
"Every aspect of this resort is top notch. We had a magical stay. "
The price is AU$1,186
includes taxes & fees
6 Mar - 7 Mar
Wildflower Farms, Auberge Resorts Collection

Inn at Bellefield / Hyde Park, Residence Inn by Marriott

3.0 star property
9.8 out of 10, Exceptional, (263)
"Lovely and convenient place to stay when visiting Hyde Park. My only complaint was our first night the people above us could be easily heard. Not sure if they were just loud or this is a design flaw. "
The price is AU$254
includes taxes & fees
16 Mar - 17 Mar
Inn at Bellefield / Hyde Park, Residence Inn by Marriott
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.

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?

Hamptons on the Hudson in South Saugerties: This holiday home rental outside of Bloomington is located on a river, and has an outdoor pool, a fireplace and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a balcony, a garden and a selection of games so that you can immerse yourself in your holiday.

How many holiday rentals are there in Bloomington?

Expedia has 3 holiday rentals for your stay in Bloomington.

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.