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Billings Holiday Rentals

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Check prices for these dates

In two weeks
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

Our top choices for Billings holiday rentals

A modern kitchen with a granite countertop, a built-in stove, and a dining area with a glass table and chairs.

1. 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, (5 reviews)
"Beautiful property with ample space for parking. Host was super nice and met all of our needs!"
United States
Nicole Y.
The price is HK$1,260
HK$3,406 total
includes taxes & fees
4 Oct - 5 Oct
Stunning 5-bedroom house with AC / Heat in charming Poughkeepsie NY
A white house with a steeply pitched roof and a small tower-like structure.

2. Charming 2-bedroom apartment on 2nd floor in Millbrook NY, right in the village

Charming 2-bedroom apartment on 2nd floor in Millbrook NY, right in the village
Millbrook
9.8 out of 10, Exceptional, (8 reviews)
"Lovely home in the heart of Millbrook."
United States
Marianne A S.
The price is HK$2,511
HK$3,852 total
includes taxes & fees
12 Oct - 13 Oct
Charming 2-bedroom apartment on 2nd floor in Millbrook NY, right in the village
A spacious living room with a large wooden dining table, a comfortable sofa, and a bookshelf filled with books and decorative items.

3. Steps to the Delightful Village of Millbrook ☆ Fun Family Getaway

Steps to the Delightful Village of Millbrook ☆ Fun Family Getaway
Millbrook
10.0 out of 10, Exceptional, (6 reviews)
"This is a charming, historic, well-maintained home on a beautifully landscaped lot. The updates in the home balance a respect for tradition while also providing modernization. The village of Millbrook is a quintessential twee New England village. The house felt very comfortable and homey and the caretaker was attentive and accommodating. We enjoyed our stay!"
United States
Beth E.
The price is HK$3,138
HK$6,595 total
includes taxes & fees
11 Oct - 12 Oct
Steps to the Delightful Village of Millbrook ☆ Fun Family Getaway
A farm sign for Clover Brooke Farm in Hyde Park, NY, with a barn and a building in the background.

4. Hudson Valley Farm Getaway- West/Llama Lover Lane

Hudson Valley Farm Getaway- West/Llama Lover Lane
Hyde Park
9.8 out of 10, Exceptional, (8 reviews)
"Great location not too far from the CIA."
United States
alexandra a.
The price is HK$1,352
HK$1,760 total
includes taxes & fees
6 Oct - 7 Oct
Hudson Valley Farm Getaway- West/Llama Lover Lane
An outdoor patio area with a covered seating area, a pool, and potted plants.

5. Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo

Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
Fishkill
9.2 out of 10, Wonderful, (78 reviews)
"It’s was nice, clean and the outdoor out area was really nice."
United States
Roger S.
The price is HK$2,050
HK$2,679 total
includes taxes & fees
8 Oct - 9 Oct
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
A compact kitchen with white cabinets, a microwave, a refrigerator, a sink, and a countertop.

6. 1 King Bed | Non-Smoking, Kitchen, Shower

1 King Bed | Non-Smoking, Kitchen, Shower
Fishkill
9.6 out of 10, Exceptional, (19 reviews)
"Great rooms and service,"
United States
Anonymous traveller
The price is HK$622
HK$704 total
includes taxes & fees
21 Oct - 22 Oct
1 King Bed | Non-Smoking, Kitchen, Shower
An aerial view of a lakeside property with a dock, a small building, and several outdoor seating areas.

7. Rustic Cabin in Fishkill!

Rustic Cabin in Fishkill!
Fishkill
10.0 out of 10, Exceptional, (5 reviews)
"Ideal cabin getaway. "
United States
Nadja E.
The price is HK$2,158
HK$3,282 total
includes taxes & fees
1 Nov - 2 Nov
Rustic Cabin in Fishkill!
A brick building with a sign reading 'Lobby' in front.

8. 2 Full Beds | Non-Smoking, Kitchen

2 Full Beds | Non-Smoking, Kitchen
Fishkill
9.2 out of 10, Wonderful, (21 reviews)
"great place tostay"
United States
Anonymous traveller
The price is HK$747
HK$863 total
includes taxes & fees
5 Oct - 6 Oct
2 Full Beds | Non-Smoking, Kitchen
A deck with a red umbrella, wooden chairs, and a table with potted plants.

9. Mid-Century DJ’s Dream

Mid-Century DJ’s Dream
Staatsburg
10.0 out of 10, Exceptional, (60 reviews)
"Quiet clean accommodations in a central location for exploring the Hudson Valley."
United States
Alexandra R.
The price is HK$1,249
HK$2,026 total
includes taxes & fees
4 Oct - 5 Oct
Mid-Century DJ’s Dream
A modern living room with a sectional sofa, a coffee table, and a bar area with stools.

10. Private, Cozy, Clean apartment in lovely Hyde Park

Private, Cozy, Clean apartment in lovely Hyde Park
Hyde Park
10.0 out of 10, Exceptional, (2 reviews)
"The host was great, the place was really nice and cozy. I would definitely stay here again!!! "
United States
Janet M.
The price is HK$989
HK$1,527 total
includes taxes & fees
13 Oct - 14 Oct
Private, Cozy, Clean apartment in lovely Hyde Park
A stone house with a steeply pitched roof, surrounded by a well-maintained lawn and trees.

11. Hickory on Willow Lake

Hickory on Willow Lake
Fishkill
9.8 out of 10, Exceptional, (6 reviews)
"Clean, quiet and great location. Beautiful property."
United States
Sheila B.
The price is HK$3,021
HK$4,297 total
includes taxes & fees
1 Nov - 2 Nov
Hickory on Willow Lake
A rustic cabin with a chimney, surrounded by dense autumn foliage and a narrow road.

12. Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park

Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park
Hopewell Junction
9.4 out of 10, Exceptional, (13 reviews)
"Lovely space and situation, unique. Close to the AT, as well."
United States
Peter W.
The price is HK$1,326
HK$2,192 total
includes taxes & fees
5 Oct - 6 Oct
Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park
A kitchen with wooden cabinets, a black countertop, a sink, and a window with a view of trees.

13. "Country outside the city " 3 bedrooms 2 full bathrooms

"Country outside the city " 3 bedrooms 2 full bathrooms
Holmes
9.6 out of 10, Exceptional, (4 reviews)
"Great house! We had a fantastic weekend!! Thank you so much "
United States
pamela w.
The price is HK$1,568
HK$4,534 total
includes taxes & fees
13 Oct - 14 Oct
"Country outside the city " 3 bedrooms 2 full bathrooms
A small, two-story house with a red and gray exterior, a front porch with blue chairs, and a table.

14. Cabin in the heart of the Hudson Valley, Cabin 4

Cabin in the heart of the Hudson Valley, Cabin 4
Newburgh
9.2 out of 10, Wonderful, (28 reviews)
"Pet-friendly and easily accessible."
United States
Brigitte
The price is HK$902
HK$1,492 total
includes taxes & fees
5 Oct - 6 Oct
Cabin in the heart of the Hudson Valley, Cabin 4
A living room with a fireplace, two armchairs, a sofa, and a TV.

15. Mid Century Modern Studio w/ Full Kitchen - Newly Built

Mid Century Modern Studio w/ Full Kitchen - Newly Built
Kent
10.0 out of 10, Exceptional, (24 reviews)
"Very nice, great location in town"
United States
Lisa F.
The price is HK$1,301
HK$1,668 total
includes taxes & fees
5 Oct - 6 Oct
Mid Century Modern Studio w/ Full Kitchen - Newly Built
A compact living space with a kitchenette, a sofa, a bed, and a colorful rug.

16. Cabin in the Heart of the Hudson Valley, Cabin 1

Cabin in the Heart of the Hudson Valley, Cabin 1
Newburgh
10.0 out of 10, Exceptional, (36 reviews)
"Great place! Nicely decorated with attention to detail. My wife and I would stay again if we are back in the area."
United States
Tim G.
The price is HK$981
HK$1,789 total
includes taxes & fees
5 Oct - 6 Oct
Cabin in the Heart of the Hudson Valley, Cabin 1
A modern kitchen with white cabinets, a central island, and a view to the outside.

17. Pleasant 1-bedroom apartment in Staatsburg perfect for your getaway,

Pleasant 1-bedroom apartment in Staatsburg perfect for your getaway,
Staatsburg
9.4 out of 10, Exceptional, (10 reviews)
"Nice stay for our quick overnight Comfortable space "
United States
jay c.
The price is HK$812
HK$1,549 total
includes taxes & fees
19 Oct - 20 Oct
Pleasant 1-bedroom apartment in Staatsburg perfect for your getaway,
A cozy living room with a sofa, a dining table, and a bed.

18. Cozy country efficiency in the Hudson Valley

Cozy country efficiency in the Hudson Valley
Newburgh
10.0 out of 10, Exceptional, (74 reviews)
"Comfy cozy weekend retreat"
United States
Michael M.
The price is HK$1,452
HK$2,771 total
includes taxes & fees
5 Oct - 6 Oct
Cozy country efficiency in the Hudson Valley
A living room with a fireplace, a painting, shelves with decorative items, and a television.

19. Grant - A Tranquil One Bedroom Steps from River

Grant - A Tranquil One Bedroom Steps from River
Newburgh
9.6 out of 10, Exceptional, (50 reviews)
"We enjoyed our stay, property was as described. It's convenient to many of the Hudson Valley small towns, including West Point."
United States
Mike W.
The price is HK$1,059
HK$2,308 total
includes taxes & fees
5 Oct - 6 Oct
Grant - A Tranquil One Bedroom Steps from River
A porch with white railings and multiple chairs.

20. Step into history & unwind at Spring apt a charming 🏡 at the❤️of NYHudson Valley

Step into history & unwind at Spring apt a charming 🏡 at the❤️of NYHudson Valley
Highland
10.0 out of 10, Exceptional, (2 reviews)
"Everyone was just right! The home is perfect for a photo shoot. We weren't there for that, but we thought the setting was unique and beautiful! Everything we needed!!"
United States
Rebecca D.
The price is HK$1,334
HK$3,023 total
includes taxes & fees
5 Oct - 6 Oct
Step into history & unwind at Spring apt a charming 🏡 at the❤️of NYHudson Valley
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 Billings Hotel Reviews

Hyatt Place Poughkeepsie / Hudson Valley

Hyatt Place Poughkeepsie / Hudson Valley

10/10 Excellent
"Helpful staff . Clean ."
Chhanda 2-night trip
Posted less than an hour ago
Hyatt Place Poughkeepsie / Hudson Valley

Find out more about Billings

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

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

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

Frequently asked questions

Are there holiday rentals in Billings?

Yes, there are holiday rentals close to the most popular sights in Billings, 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 Billings has to offer?

Lakehouse Boat Dock, Kayaks, Fire-Pit, Pool Table, Air Hockey, Hammock, King Bed: This holiday home rental outside of Billings offers a fireplace, a patio and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games.

What’s there to see and do in Billings?

Explore the area and family-friendly sights such as Mid-Hudson Civic Center, or get out into nature at a spot like Whaley Lake. In the wider area, you’ll find Stormville Airport Antique Show & Flea Market and Vassar College.

What’s a holiday rental in Billings like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Billings. Holiday rentals provide amenities like kitchens and laundry facilities so you'll have all the conveniences of home. If you're concerned about a clean environment, holiday rentals can offer a sense of privacy away from public hotel lifts and busy front desks while still allowing you the excitement and enjoyment of travel. You'll also find more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a great choice for a small group gathering.