Billings Holiday Rentals

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Check prices for these dates

In two weeks
20 Nov - 22 Nov
In two months
1 Jan - 3 Jan
In three months
29 Jan - 31 Jan
In four months
26 Feb - 28 Feb

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
9.8 out of 10, Exceptional, (6 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 NZ$846
includes taxes & fees
9 Nov - 10 Nov
Stunning 5-bedroom house with AC / Heat in charming Poughkeepsie NY
A rustic cabin with a chimney, surrounded by dense autumn foliage and a narrow road.

2. 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 NZ$473
includes taxes & fees
8 Nov - 9 Nov
Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park
A compact kitchen with white cabinets, a black refrigerator, and a microwave. There is a wooden dining table with a chair, and a sofa with a decorative pillow.

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

Hudson Valley Farm Getaway- West/Llama Lover Lane
Hyde Park
9.8 out of 10, Exceptional, (9 reviews)
"Great location not too far from the CIA."
United States
alexandra a.
The price is NZ$381
includes taxes & fees
6 Dec - 7 Dec
Hudson Valley Farm Getaway- West/Llama Lover Lane
A living room with a fireplace, two armchairs, a sofa, and a TV.

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

Mid Century Modern Studio w/ Full Kitchen - Newly Built
Kent
9.8 out of 10, Exceptional, (26 reviews)
"Very private, rural spot. Immaculate, thoughtfully furnished, lacking nothing"
United States
benjamin
The price is NZ$327
includes taxes & fees
9 Nov - 10 Nov
Mid Century Modern Studio w/ Full Kitchen - Newly Built
A white house with a steeply pitched roof and a small tower-like structure.

5. 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, (9 reviews)
"We had a wonderful time at this property. It was quaint and clean and right in the middle of town near everything. Thank you, Tanya."
United States
Laurie F.
The price is NZ$819
includes taxes & fees
8 Nov - 9 Nov
Charming 2-bedroom apartment on 2nd floor in Millbrook NY, right in the village
An aerial view of a lakeside property with a dock, a small building, and several outdoor seating areas.

6. Rustic Cabin in Fishkill!

Rustic Cabin in Fishkill!
Fishkill
9.8 out of 10, Exceptional, (6 reviews)
"Clean rooms, Diner down the block, family friendly, communication was prompt and clear"
United States
Joseph
The price is NZ$662
includes taxes & fees
13 Nov - 14 Nov
Rustic Cabin in Fishkill!
A room with a large bookshelf filled with books and DVDs, a bed, a small table with a lamp, and a window with blinds.

7. Mid-Century DJ’s Dream

Mid-Century DJ’s Dream
Staatsburg
10.0 out of 10, Exceptional, (61 reviews)
"Quiet clean accommodations in a central location for exploring the Hudson Valley."
United States
Alexandra R.
The price is NZ$410
includes taxes & fees
11 Nov - 12 Nov
Mid-Century DJ’s Dream
A brick building with a sign reading 'Lobby' in front.

8. Cozy Queen Suite, Nsmk Kitchen|Studio 6 Fishkill

Cozy Queen Suite, Nsmk Kitchen|Studio 6 Fishkill
Fishkill
9.0 out of 10, Wonderful, (21 reviews)
"Great place to stay,"
United States
Anonymous traveller
The price is NZ$163
includes taxes & fees
24 Nov - 25 Nov
Cozy Queen Suite, Nsmk Kitchen|Studio 6 Fishkill
A small, two-story house with a red and gray exterior, a front porch with blue chairs, and a table.

9. 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, (31 reviews)
"Everything was just as it was in our past stays. The place was clean, neat and organized very well. Communication with the host was very easy and almost immediate reply."
United States
Albert
The price is NZ$393
includes taxes & fees
8 Nov - 9 Nov
Cabin in the heart of the Hudson Valley, Cabin 4
A spacious living room with a large wooden dining table, a comfortable sofa, and a bookshelf filled with books and decorative items.

10. 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, (8 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 NZ$1,354
includes taxes & fees
15 Nov - 16 Nov
Steps to the Delightful Village of Millbrook ☆ Fun Family Getaway
A modern kitchen with white cabinets, a central island, and a view to the outside.

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

Pleasant 1-bedroom apartment in Staatsburg perfect for your getaway,
Staatsburg
9.6 out of 10, Exceptional, (13 reviews)
"We thoroughly enjoyed our stay. We would definitely come back! A fantastic location. And very good communication with the host, Alexander."
United States
elizabeth
The price is NZ$355
includes taxes & fees
11 Nov - 12 Nov
Pleasant 1-bedroom apartment in Staatsburg perfect for your getaway,
A compact living space with a kitchenette, a sofa, a bed, and a colorful rug.

12. 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 NZ$481
includes taxes & fees
16 Nov - 17 Nov
Cabin in the Heart of the Hudson Valley, Cabin 1
A hotel lobby with a reception desk, seating area, and a fire extinguisher on the wall.

13. 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 NZ$143
includes taxes & fees
3 Dec - 4 Dec
1 King Bed | Non-Smoking, Kitchen, Shower
An outdoor patio area with a covered seating area, a pool, and potted plants.

14. 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, (81 reviews)
"The property was as advertised and met our needs for our trip."
United States
Sara
The price is NZ$608
includes taxes & fees
11 Nov - 12 Nov
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
A kitchen with wooden cabinets, a black countertop, a sink, and a window with a view of trees.

15. "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 NZ$933
includes taxes & fees
11 Nov - 12 Nov
"Country outside the city " 3 bedrooms 2 full bathrooms
A porch with white railings and multiple chairs.

16. 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 NZ$744
includes taxes & fees
6 Nov - 7 Nov
Step into history & unwind at Spring apt a charming 🏡 at the❤️of NYHudson Valley
A cozy living room with a sofa, a dining table, and a bed.

17. Cozy country efficiency in the Hudson Valley

Cozy country efficiency in the Hudson Valley
Newburgh
10.0 out of 10, Exceptional, (75 reviews)
"Lovely cottage in a beautiful setting with everything you need to rest, relax, and enjoy this lovely part of New York state. Highly recommend!"
United States
Frances N.
The price is NZ$599
includes taxes & fees
1 Dec - 2 Dec
Cozy country efficiency in the Hudson Valley
Terrace/patio

18. Hudson Valley Farm Getaway-East/Alpaca Lane-Apt 1

Hudson Valley Farm Getaway-East/Alpaca Lane-Apt 1
Hyde Park
8.6 out of 10, Excellent, (4 reviews)
"Great spot if you’re looking for a quiet rural area ! Seeing the llamas made the stay more fun. We weren’t there when the store was open so it was a bit disappointing we couldn’t see more of what the farm offers. We’d definitely go again."
United States
Meg H.
The price is NZ$381
includes taxes & fees
1 Dec - 2 Dec
Hudson Valley Farm Getaway-East/Alpaca Lane-Apt 1
A wooden porch with white rocking chairs and a hanging flower basket.

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

Step into history & unwind at Elixir apt a charming 🏡 at the❤️of NYHudson Valley
Highland
9.6 out of 10, Exceptional, (11 reviews)
"Would definitely stay again"
United States
Laurie G.
The price is NZ$763
includes taxes & fees
6 Nov - 7 Nov
Step into history & unwind at Elixir apt a charming 🏡 at the❤️of NYHudson Valley
A rustic cabin surrounded by a forest with a stream in the foreground.

20. Creek Side Cabin with Wood Fired Hot Tub and Fire Pit

Creek Side Cabin with Wood Fired Hot Tub and Fire Pit
New Milford
10.0 out of 10, Exceptional, (3 reviews)
"Great little house, our favorite part was the gorgeous creek. Absolutely would recommend to pet lovers and those looking for peaceful nature :)"
United States
Kristine W.
The price is NZ$808
includes taxes & fees
22 Nov - 23 Nov
Creek Side Cabin with Wood Fired Hot Tub and Fire Pit
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

An outdoor seating area with stone walls, a fire feature, and yellow chairs.
Home2 Suites By Hilton Poughkeepsie

Home2 Suites By Hilton Poughkeepsie

Home2 Suites By Hilton Poughkeepsie
Poughkeepsie

8/10 Good

Clean property, friendly staff. Perfect for overnight stay, only negative is breakfast offerings, we travelled with college sports team…only one bagel, told an hour wait for bread to defrost! Could’ve have been better prepped for catering otherwise no issues.
Australia
Bridget
Reviewed March 23, 2026
Home2 Suites By Hilton Poughkeepsie

Find out more about Billings

Everything you need to know about Billings 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 Billings 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 Billings holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Billings holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Billings. 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 Billings 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 Billings holiday rentals we have selected for you start as low as NZ$143 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Billings rentals

At Expedia, we put the best Billings 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 Billings 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 Billings 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 Billings. 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

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.