Billings Holiday Rentals

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Holiday Rentals in Billings

The Farm at Hyde Park
9.8 out of 10, Exceptional, 48 reviews
"We thoroughly enjoyed our stay. It was a unique setting. Glen was very accommodating for our check in & out needs. Great location & central to everything we wanted to do & see. Definitely would come back."
The Farm at Hyde Park
Hudson River View Suite-idyllic getaway with fireplace & private deck-75 min NYC
10.0 out of 10, Exceptional, 36 reviews
"Very nice. A lot of attention to detail"
Hudson River View Suite-idyllic getaway with fireplace & private deck-75 min NYC
Cozy Countryside Cottage with Spa/Fireplace//Enclosed Yard/Fire Pits
9.6 out of 10, Exceptional, 35 reviews
"Three nights here as we toured the area. Check in was easy. We were able to access the VRBO app 30 minutes prior to our arrival. By the time we reached the driveway, Ruben had sent the access code.The road to the house is gravel and only wide enough for one car. We were glad we had arrived during the day.The house has an antique store vibe. Lots of books for a rainy day activity. FYI, the photos on the listing are a bit different from what we saw in the rooms. The dining table is larger with...
Cozy Countryside Cottage with Spa/Fireplace//Enclosed Yard/Fire Pits
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Lake Cottage 3 Private Beaches w/ Kayaks, 1 hour & 15 Minutes from NYC
9.4 out of 10, Exceptional, 75 reviews
"We had such an awesome stay! Check in process was easy! Amazing scenery amazing adventure we had with our two furr babies!"
Lake Cottage 3 Private Beaches w/ Kayaks, 1 hour & 15 Minutes from NYC
Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.
10.0 out of 10, Exceptional, 62 reviews
"Stayed for West Point graduation. Beautiful home, scenic views, and everything we needed."
Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.
Enjoy a cozy, quiet spot off the main roads but close to hiking/biking trails!
9.8 out of 10, Exceptional, 22 reviews
"place was great, exactly as described...ryan was great, no issues all was as described...however sent 2 notes via vrbo but rec'd no response and ryan apologized...so all good...if needed place up that way again would stay."
The price is NZ$463
per night
4 Jun - 5 Jun
Enjoy a cozy, quiet spot off the main roads but close to hiking/biking trails!
Cozy Countryside Barn with Spa/Fireplace/Enclosed YardFire Pits
9.8 out of 10, Exceptional, 35 reviews
"This is a cozy property in a very rural setting. The host is extremely responsive and very thorough. It is quiet and private. The furniture and bed are very comfortable. The wood burning stove is a pellet stove which provides enough heat to take the edge off. The hot tub could comfortably fit 4 people. The Village of Cold Spring is less than 10 minutes away, as is the Interstate 84 bridge across the Hudson. If you want to make your own food, bring it. There is no grocery store nearby."
Cozy Countryside Barn with Spa/Fireplace/Enclosed YardFire Pits
Studio near Millbrook, Poughkeepsie. Close to Polo Club w/ mini farm!
9.0 out of 10, Wonderful, 29 reviews
"Lovely stay! Comfortable accommodation and welcoming family."
Studio near Millbrook, Poughkeepsie. Close to Polo Club w/ mini farm!
Cozy country efficiency in the Hudson Valley
9.8 out of 10, Exceptional, 40 reviews
"This was a perfect hideaway located 15 minutes from Beacon where the wedding was. It was reasonably priced and had so many cute accents. The host was on top of all the details and very nice in person. Would definitely recommend. The only thing I would say just for an fyi it’s better for a couple as it’s a full size bed. I went with my teen daughter and it was too small for both of us in the bed so we alternated the couch. Not a minus at all but more an fyi. Thanks so much for hosting us."
The price is NZ$348
per night
4 Jun - 5 Jun
Cozy country efficiency in the Hudson Valley
Spectacular Log Home Estate North Wing Apt
10.0 out of 10, Exceptional, 25 reviews
"All as represented. Had everything we needed for a lovely home away from home!"
Spectacular Log Home Estate North Wing Apt
Lakeview Home 3 Private Beaches w/ Kayaks, on Squantz Pond
9.6 out of 10, Exceptional, 58 reviews
"Property manager was very kind and responsive. Greatly enjoyed the views of the pond and the basement pool and ping pong tables. Great time playing these games with mybson as the weather wasn't conducive for water activities."
Lakeview Home 3 Private Beaches w/ Kayaks, on Squantz Pond
Romantic Log Cabin on Privately-Owned Lake with Fireplace
9.8 out of 10, Exceptional, 70 reviews
"Fantastic, loved everytbing about it"
Romantic Log Cabin on Privately-Owned Lake with Fireplace
1 HR NYC Getaway Awesome Newly Renovated Home on 4 Acres, Stunning Views
9.0 out of 10, Wonderful, 21 reviews
"This house has an ideal location to see lots of local sites of interest in the Hyde Park and Poughkeepsie area. Easy trip from there to West Point, Hyde Park and the Culinary Institute from the location, and great restaurant, Tiramasu, is very close. The house is immaculate! The beds were very comfortable, linens were provided, the bathrooms were spacious and the five of us had plenty of room for our toiletries. The house has steps to its multiple levels for all essential rooms, not accessible....
1 HR NYC Getaway Awesome Newly Renovated Home on 4 Acres, Stunning Views
Oversized Country house, Quiet Retreat & Gathering space ~NEW !!!
10.0 out of 10, Exceptional, 13 reviews
"We really enjoyed our stay! We had a large group of 24 friends, and the house met all of our needs. It was very clean, had enough bedrooms for everyone, and a large dining table that accommodated everyone for big dinners. We spent a lot of time throughout the weekend outside playing lawn games and sitting by the fire. The place was close enough to grab amenities or go to a grocery store, but off the beaten path and quiet. It was exactly what was listed and made for a where enjoyable time....
Oversized Country house, Quiet Retreat & Gathering space ~NEW !!!
Lakefront New York Abode w/ Deck, Grill & Fire Pit
9.6 out of 10, Exceptional, 4 reviews
"we were able to have all 3 of our children, with 2 of their spouses and bridal party for my daughter stay with us for the weekend. There were plenty of things to entertain during downtime. Rooms were comfortable and location was convenient to wedding activities."
Lakefront New York Abode w/ Deck, Grill & Fire Pit
Spacious restored Victorian w/ wraparound porch
9.6 out of 10, Exceptional, 8 reviews
"We enjoyed our stay very much!"
Spacious restored Victorian w/ wraparound porch
Log Cabin On A Lake With Private Dock & Beach! One Hour from NYC!
10.0 out of 10, Exceptional, 168 reviews
"If you need a relaxing few days in the winter, very good place. Great views and quiet is the key."
Log Cabin On A Lake With Private Dock & Beach! One Hour from NYC!
Riverfront property in the beautiful Hudson Valley with many outdoor activities.
9.4 out of 10, Exceptional, 41 reviews
"The house is decorated beautifully, and the view of the river is great. The beds and linens were soo comfortable. Would love to return in warmer weather to enjoy the outdoors 😀"
Riverfront property in the beautiful Hudson Valley with many outdoor activities.
Spectacular Short Term Vacation Rental in Kent
9.6 out of 10, Exceptional, 74 reviews
"For the groomsman it was perfect crazy fun."
Spectacular Short Term Vacation Rental in Kent
ValleyView-Ultimate 3BR Getaway w/Inground Pool by Fahnestock/Appalachian Trail
10.0 out of 10, Exceptional, 18 reviews
"We had a very pleasant stay! We came for our son’s graduation from West Point. Pat was a gracious host and made sure that we had up to date info. There were lots of thoughtful amenities, the beds and couches were very comfortable, we used the grill and sat on the deck which overlooks a wooded hill. The location is peaceful and in the country just down the street from a horse pasture. You can hear the brook bubbling across the way. The WiFi worked great and although there is just a window air...
The price is NZ$516
per night
5 Jun - 6 Jun
ValleyView-Ultimate 3BR Getaway w/Inground Pool by Fahnestock/Appalachian Trail
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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.

Other types of properties in Billings you may be interested in

HYATT house Fishkill/Poughkeepsie
3.0 star property
8.6 out of 10, Excellent, 1,003 reviews
"N/A"
The price is NZ$258
per night
16 Jun - 17 Jun
HYATT house Fishkill/Poughkeepsie
Best Western Fishkill Inn & Suites
3.5 star property
8.6 out of 10, Excellent, 482 reviews
"We enjoyed very much our stay here, the outdoor pool was the best for my kids:) everything was with a very short distance from food to shopping . Close to the outlets. We love it. "
The price is NZ$214
per night
1 Jul - 2 Jul
Best Western Fishkill Inn & Suites
DoubleTree by Hilton Poughkeepsie
4.0 star property
8.2 out of 10, Very good, 974 reviews
"Overall was great"
The price is NZ$241
per night
9 Jun - 10 Jun
DoubleTree by Hilton Poughkeepsie
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.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Billings holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Billings. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Billings. Seeing all the best attractions is bound to make you fall in love with Billings. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Billings short-term rentals, that won’t be hard to do.

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’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 Walkway Over the Hudson State Historic Park. 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.

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