Bloomington holiday rentals

We found 381 holiday rentals — enter your dates for availability
Scroll through and select from holiday rentals in Bloomington to find one that's perfect for your trip. Whether you're travelling with family, friends or just your furry companion, holiday homes have the amenities that you expect for your stay, which might include Wi-Fi and a washer and dryer. You'll be able to choose a property to rent that has what everyone needs, including places that are non-smoking or accessible.

Holiday rentals with weekly discounts – Bloomington

Showing deals for:6 Nov - 13 Nov

Living area with wood burning fireplace,
Two ovens, two refrigerators, plate warmer & an enormous butcher block counter.
Main entrance.
High pitched ceiling dining room located next to the kitchen.
Exceptional
(48 reviews)

Spacious/Secluded Home w/Pool, Chefs Kitchen, Neighboring Farm Pastoral Views

High Falls

8% off
AU$11,624
for 7 nights, 1 home
AU$1,661 per night
includes taxes & fees
Spacious/Secluded Home w/Pool, Chefs Kitchen, Neighboring Farm Pastoral Views
Dining
Outdoor dining
Interior
Front Entry
Exceptional
(10 reviews)

Church Des Artistes a Hudson Valley retreat

Kingston

8% off
AU$17,308
for 7 nights, 1 home
AU$2,473 per night
includes taxes & fees
Church Des Artistes a Hudson Valley retreat
A cozy bedroom boasts a unique charm with its stone wall and wide plank flooring.  Queen size bed with luxury linens you'll find it hard to leave. For your comfort we installed a MiniSplit system for heating and AC.  Creating warm ambiance to enjoy.
Dining
For those moments when you prefer a more private escape, we've created a tranquil area in the front yard.
A Special Place for Your Special Times!  4 bedroom, 3.5 baths, Full Kitchen, Kitchenette, 2 Living Areas, 2 Dining Areas, Full access to backyard with dining area, fire pit with adirondack chairs, BBQ grill, hammock on 2 acres of land.
Exceptional
(25 reviews)

Spacious 4BD Country Gem - Fire Pit & Chill Vibes

Highland

7% off
AU$6,522
for 7 nights, 1 home
AU$932 per night
includes taxes & fees
Spacious 4BD Country Gem - Fire Pit & Chill Vibes
Terrace/patio
Exterior
Dining
Interior
Exceptional
(9 reviews)

Mohonk's Peaceful 5BR-3BA~Jacuzzi~Huge Deck~Right On Coxing Kill~ Private Road

High Falls

16% off
AU$6,897
for 7 nights, 1 home
AU$985 per night
includes taxes & fees
Mohonk's Peaceful 5BR-3BA~Jacuzzi~Huge Deck~Right On Coxing Kill~ Private Road
Dining
Interior
Private kitchen
.72 acres of lawns next to a 10 acre wood.
Exceptional
(45 reviews)

Mansion-on-the-hill elegance close to all the Hudson Valley has to offer.

Kingston

8% off
AU$10,095
for 7 nights, 1 home
AU$1,442 per night
includes taxes & fees
Mansion-on-the-hill elegance close to all the Hudson Valley has to offer.
Interior
Property grounds
Property grounds
Room
Exceptional
(17 reviews)

Hudson Valley’s Private Waterfront Camping Getaway

Lake Katrine

8% off
AU$2,305
for 7 nights, 1 unit
AU$329 per night
includes taxes & fees
Hudson Valley’s Private Waterfront Camping Getaway
Interior
Room
Property grounds
Interior
Exceptional
(84 reviews)

for the creative spirit, swimming dock on pond, horses to pet, Fire pit

Ulster Park

8% off
AU$3,266
for 7 nights, 1 home
AU$467 per night
includes taxes & fees
for the creative spirit, swimming dock on pond, horses to pet, Fire pit
Exterior
Living area
Living area
Room
Exceptional
(22 reviews)

Charming 2-bedroom cottage with large deck in beautiful Accord NY.

Accord

6% off
AU$2,707
for 7 nights, 1 cottage
AU$387 per night
includes taxes & fees
Charming 2-bedroom cottage with large deck in beautiful Accord NY.
Interior
Living area
Room
Interior
Exceptional
(9 reviews)

Indoor-Outdoor Retreat in the Heart of Uptown Kingston

Kingston

12% off
AU$4,439
for 7 nights, 1 home
AU$634 per night
includes taxes & fees
Indoor-Outdoor Retreat in the Heart of Uptown Kingston
Living area
Interior
Dining
Private kitchen
Exceptional
(26 reviews)

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

Lake Katrine

16% off
AU$2,703
for 7 nights, 1 home
AU$386 per night
includes taxes & fees
Brand New House with Huge patio overlooks Esopus Creek at Lake Katrine
Loft with TV
Exterior
Interior
Living room with TV
Exceptional
(16 reviews)

Cheerful 3 Bedroom Cottage by Rail Trail

New Paltz

7% off
AU$2,140
for 7 nights, 1 cottage
AU$306 per night
includes taxes & fees
Cheerful 3 Bedroom Cottage by Rail Trail
Entry
Porch in winter (floor to ceiling screens in summer)
Exterior
Backyard in Fall
Exceptional
(10 reviews)

Cozy modern home on 14 acres of woods

Accord

8% off
AU$5,035
for 7 nights, 1 home
AU$719 per night
includes taxes & fees
Cozy modern home on 14 acres of woods
Private kitchen
Terrace/patio
Living area
Dining
Exceptional
(28 reviews)

Cabin 85: 2 Bedrooms + 2 Lofts Perfect Retreat!

Hurley

12% off
AU$2,679
for 7 nights, 1 cabin
AU$383 per night
includes taxes & fees
Cabin 85: 2 Bedrooms + 2 Lofts Perfect Retreat!
Stairs to second floor
Property grounds
Enclosed front porch
Second floor hallway
Exceptional
(51 reviews)

Cozy Hudson Valley 3-bedroom home

Ulster Park

16% off
AU$2,794
for 7 nights, 1 home
AU$399 per night
includes taxes & fees
Cozy Hudson Valley 3-bedroom home
Property grounds
Time flies in Cloud house~
Looks small but actually very spacious~ Come and check it out~
Exterior detail
Exceptional
(10 reviews)

Cloud House -1 Bd & 2 baths in New Paltz

New Paltz

7% off
AU$2,065
for 7 nights, 1 apartment
AU$295 per night
includes taxes & fees
Cloud House -1 Bd & 2 baths in New Paltz
Dining
Living area
Private kitchen
Living area
Exceptional
(7 reviews)

Charming 2-bedroom apartment in lovely Rosendale, just off the rail trai.

Kingston

8% off
AU$3,184
for 7 nights, 1 apartment
AU$455 per night
includes taxes & fees
Charming 2-bedroom apartment in lovely Rosendale, just off the rail trai.
Interior
Property grounds
Room
Exterior
Exceptional
(151 reviews)

Many perfect sunsets at the magical house on the lake

Rifton

8% off
AU$3,392
for 7 nights, 1 home
AU$485 per night
includes taxes & fees
Many perfect sunsets at the magical house on the lake
  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support
  • More quality time

    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more
  • More for less

    More space, more privacy, more amenities — more value

Book a holiday rental for your Bloomington getaway

Learn about the unique charm of Bloomington with a stay in a holiday home rental. This city has something for everyone. Whether you're planning a family holiday, a trip with friends or a romantic retreat, HomeAway has a great selection of holiday homes. Many rentals come with a full kitchen and separate dining area, perfect if you need a space for entertaining.

Activities and attractions in Bloomington

Are you hoping to find things to do while you're in the area? Venture out of your cosy holiday rental and check out everything that makes Bloomington a one-of-a-kind holiday spot. Here are some of the major attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • Mohonk Golf Course (8.4 mi / 13.4 km)
  • Whitecliff Vineyard (15.5 mi / 24.9 km)
  • New Paltz Golf Course (8.1 mi / 13.1 km)
  • Apple Greens Golf Course (11.1 mi / 17.8 km)
  • Robibero Winery (12.9 mi / 20.7 km)
  • Red Hook Golf Club (12.9 mi / 20.8 km)

Exploring the natural features in Bloomington

Whether you're an adventurous traveller or just want to appreciate the scenery, Bloomington is a great place to get outside. These are a few of the area's most enchanting features, all within 30 miles (48.2 km) of the city centre:

  • Esopus Creek (4.4 mi / 7 km)
  • Ashokan Rail Trail- Woodstock Dike Trailhead (8.3 mi / 13.4 km)
  • Mohonk Lake (9.7 mi / 15.7 km)
  • Opus 40 (11.8 mi / 19 km)
  • Mohonk Preserve Visitor Center (12.4 mi / 19.9 km)
  • Walkway Over the Hudson State Historic Park (12.6 mi / 20.3 km)

Travelling to and around Bloomington

Fly into Newburgh, NY (SWF-Stewart Intl.), the closest airport, located 26.3 mi (42.3 km) from the city centre.

Frequently asked questions

What is the most popular type of holiday home accommodation in Bloomington?
Cottages are the most popular style of holiday home in Bloomington, according to our data. Even if you've got a different idea in mind, Stayz has properties in many shapes and sizes. Take a look at our options to find your ideal fit.
How much does it cost to rent a holiday home in Bloomington?
Property type, length of stay and time of year are some of the conditions that can influence the price of a holiday home. Simply click on your travel dates to find your ideal escape. From cosy cabins to expansive luxury villas, all Stayz holiday homes provide amazing value.
How much does it cost to rent a beach house in Bloomington?
The average price for a holiday home by the beach in Bloomington depends on when you're going and the type and size of property you're looking for. You can find prices easily and quickly on Stayz by entering the dates you'll be travelling. Then use our handy filter tool to select the number of bedrooms and amenities that you need, like a pool, WiFi and air conditioning.
What are popular home amenities in Bloomington?
Nearby museums, a firepit and a nearby river rank as the most popular home amenities in Bloomington. Whether you're taking a trip alone, with your significant other or a group of friends, Stayz will help you find a holiday home that suits your tastes with all the conveniences you're looking for.
What are the top attractions for families in Bloomington?
Keeping the kiddos entertained during your stay in Bloomington is easy with these cool family-friendly attractions:
  • Hudson River Maritime Museum
  • Kingston Point Beach
  • Trolley Museum of New York
How old do you have to be to rent a holiday home in Bloomington?
The minimum age requirements can vary across properties on Stayz, so be sure to look at the rules of the holiday home in Bloomington you want. But usually, it's 16, 18 or 21.
How long can I rent a holiday home in Bloomington for?
It really depends on the Bloomington property. To browse available options offering extended stays, just type your dates and number of guests into Stayz's search page. Enjoy having the place to yourself, along with amenities such as air conditioning, a kitchen and a backyard to play in. Be on the lookout for any long-term stays that offer weekly or monthly discounts.