Hillside Holiday Rentals

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Holiday Rentals in Hillside

Beautiful cottage with HOT TUB in Kingston/Woodstock Catskills, Hudson Valley
6.0 out of 10, (2)
"we where on tour with our band. we like to stay a few minutes from the venue. This was the perfect place only a few minutes to downtown woodstock. We would definitely book again, and the host the host are very awesome. That you again Stacey"
The price is AU$277
includes taxes & fees
7 July - 8 July
Beautiful cottage with HOT TUB in Kingston/Woodstock Catskills, Hudson Valley
The Farm at Hyde Park
9.8 out of 10, Exceptional, (49)
"We needed a central location for my daughter’s bridal shower. We could not have imagined a better place. It is beautiful and so natural. Glen was helpful and welcoming. He even came over to sweep off the expansive patio before our guests arrived and this was after he made sure everyone was awake. The house was well supplied with kitchen and dining items. The grounds were perfect - lawn chairs, picnic table, fire pit and free range chickens whose eggs we were able to enjoy. We would all stay here...
The Farm at Hyde Park
Streamside Cottage Walking Distance to Town of Woodstock
10.0 out of 10, Exceptional, (200)
"Very nice stay from start to finish. We stayed two nights after a busy conference and the space was clean and tranquil, with a gorgeous stream to relax us. "
The price is AU$546
includes taxes & fees
24 June - 25 June
Streamside Cottage Walking Distance to Town of Woodstock
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'A Place in the Woods' - Cabin on Chloe's Lake on 23 acres near Woodstock, NY
8.4 out of 10, Very good, (37)
"Our trip was amazing. We do it again again and again"
The price is AU$189
includes taxes & fees
19 June - 20 June
'A Place in the Woods' - Cabin on Chloe's Lake on 23 acres near Woodstock, NY
Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream
9.2 out of 10, Wonderful, (32)
"This is a great place to stay. Really loved the fire pit by the creek for evening cocktails and conversation."
The price is AU$462
includes taxes & fees
24 June - 25 June
Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream
Enjoy a cozy, quiet spot off the main roads but close to hiking/biking trails!
9.8 out of 10, Exceptional, (23)
"The backyard was really cool! Great features. Beautiful, peaceful, and private. We did not see or hear anyone else on the property during our stay. The apartment was very nice. Cozy, clean and comfortable, perfect for two. The host, Ryan was extremely responsive and friendly. We had an amazing stay would definitely recommend!"
The price is AU$437
includes taxes & fees
21 June - 22 June
Enjoy a cozy, quiet spot off the main roads but close to hiking/biking trails!
Studio near Millbrook, Poughkeepsie. Close to Polo Club w/ mini farm!
9.0 out of 10, Wonderful, (30)
"Very charming one room apartment with bathroom and kitchen area. Beautiful surrounding you with very pleasant hosts"
Studio near Millbrook, Poughkeepsie. Close to Polo Club w/ mini farm!
Sauna, Hot-tub, Private Pool, fire-pit, pet friendly, Mountain views!
9.6 out of 10, Exceptional, (163)
"The house was fantastic. Close to Hunter Mountain Ski Resort and a cute one street town. Peter and Lara had both wood burning stoves going for us when we arrived. The house is wonderful with a fun separate hang out place for the kids. Well equipped kitchen. Comfortable beds. Hot tub with wonderful views. All the firewood you could ever need. We will be back for sure!"
Sauna, Hot-tub, Private Pool, fire-pit, pet friendly, Mountain views!
Junebug Cottage: peace, love and privacy a short walk to Woodstock village green
10.0 out of 10, Exceptional, (39)
"Junebug Cottage was a top notch place to stay and we enjoyed every minute of it! It is clean, well kept, and has everything needed for your stay. John is very hospitable and easy to communicate with. We loved the space and even spent some time reading on the back patio. Definitely recommend this place!"
Junebug Cottage: peace, love and privacy a short walk to Woodstock village green
Exquisite Mtn Chalet 5 min to Woodstock's Best Scenic Walks, we have generator.
10.0 out of 10, Exceptional, (86)
"Everything was as described, instructions to the house were precise and the facility was exactly what we 2 couples) needed for a weekend of strolls in Woodstock and trails around. We cooked 2 dinners, kitchen and BBQ were great."
The price is AU$442
includes taxes & fees
20 June - 21 June
Exquisite Mtn Chalet 5 min to Woodstock's Best Scenic Walks, we have generator.
Charming Artist's Retreat
10.0 out of 10, Exceptional, (114)
"This is our second time staying at the cottage. What beautiful weather in such a beautiful setting. Incredible motorcycle ride through the mountains. Thank you Maureen. Robin & Bruce"
Charming Artist's Retreat
Riverfront property in the beautiful Hudson Valley with many outdoor activities.
9.4 out of 10, Exceptional, (41)
"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.
Romantic Log Cabin on Privately-Owned Lake with Fireplace
9.8 out of 10, Exceptional, (71)
"The cabin is really cute & has wind chimes & garden art all around it that integrates so perfectly with the natural oasis it is set in. This is a great place for a nature loving couple to enjoy. Singing birds, frogs, turtles chipmunks & fish in the lake, are the only neighbors you will notice o this beautiful property. Karen is a lovely gracious host and both she and the cabin are very welcoming & charming. Its a perfect spot go to with your soulmate & reconnect with nature."
Romantic Log Cabin on Privately-Owned Lake with Fireplace
Hamptons on the Hudson in South Saugerties
9.8 out of 10, Exceptional, (7)
"Really cute interior. Perfect for our stay while at the horse show "
Hamptons on the Hudson in South Saugerties
Spacious restored Victorian w/ wraparound porch
9.4 out of 10, Exceptional, (10)
"The property was gorgeous, the house large enough to accommodate our group. The kitchen was well stocked. We used the pool, hot tub, fire pit, and pool table. The indoor and outdoor speakers were a nice touch. I would definitely recommend this home I had to reach out to our host 2 days before check in to find out how to get in- usually that is communicated earlier than that. I had informed the host that we were going to have a luncheon for 10 additional people after the memorial service and was...
Spacious restored Victorian w/ wraparound porch
Campfire Cottage: Fireplace, fire pit & no chores!
10.0 out of 10, Exceptional, (16)
"An unassuming setting belies the well-appointed interior and thoughtful extras you’ll find within. Parking is tight but it is off-street and the location offers come-and-go convenience for exploring the area."
The price is AU$427
includes taxes & fees
25 June - 26 June
Campfire Cottage: Fireplace, fire pit & no chores!
Cozy Relaxing Retreat in Saugerties, NY
10.0 out of 10, Exceptional, (33)
"Pictures can fool anyone but as my son and I entered this property on our first day, he raised his hand with a genuine smile of joy, uttering that in renting this house, I made a very good choice. He was visiting me from Germany for his birthday, and I wanted to spend some days away from NYC, in quiet, conversation, and cooking. Being there for five days provided for us a wonderful framework to spend time together, and the house is as inviting as the pictures suggest. Our only criticism is a...
Cozy Relaxing Retreat in Saugerties, NY
The Cabin at Chichester in the Catskills Mountains
9.8 out of 10, Exceptional, (165)
"Very clean, good area"
The Cabin at Chichester in the Catskills Mountains
High Point Mtn House~Mother's Day on the Mountain~2 hrs to NYC ULTIMATE PRIVACY!
9.8 out of 10, Exceptional, (18)
"My recent weekend getaway to the Catskills was truly unforgettable, thanks to our wonderful host and their charming retreat nestled in the heart of this picturesque mountain region. From the moment we arrived, we were greeted with warm hospitality and a sense of tranquility that immediately set the tone for our stay. The accommodations were nothing short of perfect – cozy yet spacious, with rustic charm and modern amenities seamlessly blended together. Our host went above and beyond to ensure...
High Point Mtn House~Mother's Day on the Mountain~2 hrs to NYC ULTIMATE PRIVACY!
Sexiest Lil Cabin in Saugerties, NY
8.4 out of 10, Very good, (6)
"We loved our stay here, it was the perfect short getaway. Thanks Alexandria!"
The price is AU$189
includes taxes & fees
24 June - 25 June
Sexiest Lil Cabin in Saugerties, NY
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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 Hillside you may be interested in

Best Western Plus Kingston Hotel And Conference Center
2.5 star property
8.0 out of 10, Very good, (1002)
"token machine was broken, arcade games were iffy and vending machine was out of soda. But we still had a great time in the pool and the breakfast was great and the rooms comfy and clean. Didn't know how to turn on fan in bathroom.Love the courtyard!"
The price is AU$237
includes taxes & fees
23 June - 24 June
Best Western Plus Kingston Hotel And Conference Center
DoubleTree by Hilton Poughkeepsie
4.0 star property
8.2 out of 10, Very good, (983)
"Nice staff and beautiful room "
The price is AU$215
includes taxes & fees
30 June - 1 July
DoubleTree by Hilton Poughkeepsie
AutoCamp Catskills
3.5 star property
9.0 out of 10, Wonderful, (284)
"Good"
The price is AU$440
includes taxes & fees
1 July - 2 July
AutoCamp Catskills
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.

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

Hillside holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Hillside. 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 depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Hillside 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 Hillside holiday rentals we have selected for you start as low as AU$189 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Hillside rentals

At Expedia, we put the best Hillside 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 Hillside 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 Hillside 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 Hillside. 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 Hillside?

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

The Farm at Hyde Park: This holiday home rental outside of Hillside is located in a rural location, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. Kick off your shoes and enjoy yourself with a garden and a selection of games.

What’s there to see and do in Hillside?

While exploring the area, visit family-friendly sights like Hyde Park Station, or get outside and enjoy nature at Catskill Mountains. Esopus Creek and Ulster Performing Arts Center are a couple of places you'll find in the wider area.

What’s a holiday rental in Hillside like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Hillside. Holiday rentals feature extras such as kitchens and laundry facilities to help you enjoy your stay. If you're concerned about cleanliness, a holiday rental can provide a sense of security away from shared hotel lifts and busy front desks while still allowing you the experience of travel. You'll also get more space in a holiday rental than in a standard hotel, which makes a holiday rental an attractive choice for family trips or small group gatherings.

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