Bloomington Holiday Rentals

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Holiday Rentals in Bloomington

Esopus Creek modern Tiny house Retreat!

Kingston
9.8 out of 10, Exceptional, (60)
"The property was beautiful. Quiet area but close enough to all the places we wanted to go. Our hosts were very gracious, attentive and friendly. Enjoyed our weekend retreat. "
United States
Rebecca
The price is NZ$459
includes taxes & fees
5 Dec - 6 Dec
Esopus Creek modern Tiny house Retreat!

Hamptons on the Hudson in South Saugerties

Glasco
10.0 out of 10, Exceptional, (33)
"The entire process and stay were flawless. We had a rush booking and every request we had was accommodated. I give the highest recommendation and will hopefully being staying here again."
United States
Gordon V.
Hamptons on the Hudson in South Saugerties

The Farm at Hyde Park

Staatsburg
9.8 out of 10, Exceptional, (84)
"We enjoyed our stay...lots to do in the area. Glen was very friendly and accommodating. "
United States
Robert W.
The Farm at Hyde Park

Luxurious Woodstock Home Rental Catskill Mountains Views & Private Retreat

Bearsville
10.0 out of 10, Exceptional, (123)
"As roomy as promised, and one of the quietest places I've ever been. May return for our annual gathering next year."
United States
Tony G.
Luxurious Woodstock Home Rental Catskill Mountains Views & Private Retreat

Hot Tub - Fire Pit - BBQ - Hammock - Colonial

Kingston
9.4 out of 10, Exceptional, (22)
"We came down with our dog. We work a lot and needed a break. The place is cozy and comfy and the outdoor space is so lovely. Good mix of sunny space and shaded space.Our dog very much enjoyed the backyard and we loved the small businesses within walking distance "
United States
Heather H.
The price is NZ$417
includes taxes & fees
18 Nov - 19 Nov
Hot Tub - Fire Pit - BBQ - Hammock - Colonial

Groovy 1 Bedroom Apartment in Woodstock - AC & WiFi!

Woodstock
8.0 out of 10, Very good, (7)
"The location cannot be beat, right in the center of Woodstock where you can walk to all the shops and restaurants. The apartment is furnished with all that you need for a short stay and well appointed. What people have not mentioned in their reviews is: 1) The whole building looks hundreds of years old---including the very warped wooden floors which you will notice when walking. Beware if you have mobility issues. 2) 1 flight of stairs to get to the apartment 3) Worst of all the noise---you...
United States
Maria
The price is NZ$493
includes taxes & fees
18 Nov - 19 Nov
Groovy 1 Bedroom Apartment in Woodstock - AC & WiFi!

'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)
"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."
United States
Eileen F.
The price is NZ$287
includes taxes & fees
23 Nov - 24 Nov
'A Place in the Woods' - Cabin on Chloe's Lake on 23 acres near Woodstock, NY

The Studio at the Inn at High Falls

High Falls
8.0 out of 10, Very good, (32)
"Lovely!"
United States
Julia H.
The price is NZ$479
includes taxes & fees
15 Nov - 16 Nov
The Studio at the Inn at High Falls

Streamside Cottage Half Mile to Town of Woodstock

Woodstock
10.0 out of 10, Exceptional, (258)
"Very cozy cottage with everything you need, close to town, and a beautiful stream right in the backyard that we loved listening to."
United States
Kevin M.
Streamside Cottage Half Mile to Town of Woodstock

Dog-Friendly Hudson Valley Escape with Hot Tub & Jacuzzi

Kingston
9.6 out of 10, Exceptional, (25)
"A lovely place and Seth is always so helpful."
United States
Lynn L.
The price is NZ$432
includes taxes & fees
11 Nov - 12 Nov
Dog-Friendly Hudson Valley Escape with Hot Tub & Jacuzzi

Sioux Tipi on Chloe's Lake

Saugerties
9.8 out of 10, Exceptional, (6)
"This was such a cool experience Id love to go back! "
United States
Brandon
The price is NZ$257
includes taxes & fees
9 Nov - 10 Nov
Sioux Tipi on Chloe's Lake

A Spectacular 50 Mile View of the Hudson Valley in all seasons

Saugerties
9.8 out of 10, Exceptional, (94)
"Secluded yet conveniently located."
United States
Richard G.
A Spectacular 50 Mile View of the Hudson Valley in all seasons

Mid-Century DJ’s Dream

Staatsburg
10.0 out of 10, Exceptional, (42)
"Great place to stay! Close to many attractions by car - most 10-15 minutes. Clean and comfortable. Kevin has lots of great suggestions on places to go and restaurants."
United States
Anonymous traveller
The price is NZ$345
includes taxes & fees
15 Nov - 16 Nov
Mid-Century DJ’s Dream

Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream

woodstock
9.0 out of 10, Wonderful, (45)
"This is a great place to stay. Really loved the fire pit by the creek for evening cocktails and conversation."
United States
Paul H.
The price is NZ$552
includes taxes & fees
7 Dec - 8 Dec
Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream

Spacious A-Frame w/ Game Room, Fire Pit & Modern Comforts in Hudson Valley

New Paltz
10.0 out of 10, Exceptional, (8)
"The house exceeded expectations. Extremely clean especially considering small dogs are allowed. The bedrooms are spacious. Everything is furnished beautifully, and the basement game room was a winner. Although there was snow, the kids still loved playing in the yard and morning coffee on the deck cannot be beat. The only thing that caused us trouble was the stove but I’m not used to a convection rangtop. "
United States
Mary M.
The price is NZ$1,741
includes taxes & fees
10 Nov - 11 Nov
Spacious A-Frame w/ Game Room, Fire Pit & Modern Comforts in Hudson Valley

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

Ulster Park
10.0 out of 10, Exceptional, (94)
"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."
United States
David W.
Totally secluded Yurt surrounded by waterfalls, brooks, cliffs and forest

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

2.0 star property
New Paltz
9.4 out of 10, Exceptional, (24)
"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."
United States
Leyla S.
The price is NZ$930
includes taxes & fees
12 Nov - 13 Nov
Scenic New Paltz Escape: River Views, Hot Tub & Deck | Dream House in the Gunks

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

2.0 star property
Kingston
3.0 out of 10, (2)
"Never let me know the property wasnt available tillnday of. Ended up going home. Ruinjng stay"
United States
Patricia
The price is NZ$439
includes taxes & fees
30 Nov - 1 Dec
Minutes to Saugerties & HITS Horse show. Above garage w/ own private entrance.

NEW Spectacular Views & Private space on a Scenic Mountain 40ft Salt Water Pool

Ulster Park
10.0 out of 10, Exceptional, (132)
"The house was comfortable for a large group, beautiful setting, private, clean, etc. We enjoyed our stay."
United States
mary r.
NEW Spectacular Views & Private space on a Scenic Mountain 40ft Salt Water Pool

Charming 2-bedroom house in fabulous Kingston close to everything

Kingston
10.0 out of 10, Exceptional, (1)
"House was spotless. Hosts were very responsive and helpful. "
United States
Lawrence R.
Charming 2-bedroom house in fabulous Kingston close to everything
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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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 favorite 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 depends 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 NZ$257 per night. Entering your travel dates in the search wizard you might find 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.