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Billings Vacation Rentals

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Check prices for these dates

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

Our top choices for Billings vacation 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 CA $300
CA $676 total
includes taxes & fees
Nov 9 - Nov 10
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 CA $236
CA $376 total
includes taxes & fees
Nov 10 - Nov 11
Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park
A farm sign for Clover Brooke Farm in Hyde Park, NY, with a barn and a building in the background.

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 CA $245
CA $302 total
includes taxes & fees
Dec 2 - Dec 3
Hudson Valley Farm Getaway- West/Llama Lover Lane
A two-story house with a dark blue exterior, a large arched window, and two garage doors.

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 CA $208
CA $257 total
includes taxes & fees
Nov 6 - Nov 7
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 CA $447
CA $631 total
includes taxes & fees
Nov 9 - Nov 10
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 CA $350
CA $520 total
includes taxes & fees
Nov 6 - Nov 7
Rustic Cabin in Fishkill!
A deck with a red umbrella, wooden chairs, and a table with potted plants.

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 CA $203
CA $326 total
includes taxes & fees
Nov 11 - Nov 12
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 CA $111
CA $128 total
includes taxes & fees
Nov 24 - Nov 25
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 CA $208
CA $310 total
includes taxes & fees
Nov 8 - Nov 9
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 CA $559
CA $1,064 total
includes taxes & fees
Nov 10 - Nov 11
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 CA $160
CA $280 total
includes taxes & fees
Nov 10 - Nov 11
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 CA $236
CA $386 total
includes taxes & fees
Nov 11 - Nov 12
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 CA $100
CA $113 total
includes taxes & fees
Dec 3 - Dec 4
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 CA $383
CA $482 total
includes taxes & fees
Nov 11 - Nov 12
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 CA $277
CA $733 total
includes taxes & fees
Nov 12 - Nov 13
"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 CA $297
CA $594 total
includes taxes & fees
Nov 6 - Nov 7
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 CA $259
CA $475 total
includes taxes & fees
Dec 3 - Dec 4
Cozy country efficiency in the Hudson Valley
A farm sign for Clover Brooke Farm in Hyde Park, NY, with a barn and a building in the background.

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 CA $245
CA $302 total
includes taxes & fees
Dec 1 - Dec 2
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 CA $307
CA $607 total
includes taxes & fees
Nov 6 - Nov 7
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 CA $363
CA $665 total
includes taxes & fees
Nov 11 - Nov 12
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

Best Western Fishkill Inn & Suites

Best Western Fishkill Inn & Suites

8/10 Good
"The room were really nice. The only complaint we had was the noise from people walking around on the floor above us.when the upstairs guest walked around it was very obvious in our first floor room."
Shannon 1-night trip
Posted 1 hour ago
Best Western Fishkill Inn & Suites

Find out more about Billings

Everything you need to know about Billings vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Billings vacation rental for you. At Expedia, you can take your pick from private vacation 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Billings vacation 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 vacation 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 vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Billings vacation rentals we have selected for you start as low as CA $113 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 vacation 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 vacation.

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 vacation rentals in Billings?

Yes, there are vacation rentals close to popular points of interest in Billings, or you can go with a more secluded option if you'd like a relaxing place to stay.

What are some of the best vacation rentals that Billings has to offer?

Lakehouse Boat Dock, Kayaks, Fire-Pit, Pool Table, Air Hockey, Hammock, King Bed: Visitors like this Billings vacation home rental. It offers a fireplace, a patio, and a barbecue grill 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 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 larger area, you’ll find Stormville Airport Antique Show & Flea Market and Vassar College.

What’s a vacation rental in Billings like?

A vacation rental is a private property where you can stay for several days or longer in Billings. Vacation rentals provide amenities such as kitchens and laundry facilities so you'll feel just like you're at home. If you're concerned about cleanliness, vacation rentals can provide a sense of safety away from public hotel elevators and lobbies bustling with people while still allowing you to travel. You'll also get more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is a popular option for family trips or small group gatherings.