Round Top Vacation Rentals

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Check prices for these dates

In two weeks
Dec 19 - Dec 21
In two months
Jan 30 - Feb 1
In three months
Feb 27 - Mar 1
In four months
Mar 27 - Mar 29

Vacation Rentals in Round Top

Property grounds
Beautiful Mountain Villa

Beautiful Mountain Villa

Round Top
9.0 out of 10, Wonderful, (6)
"The property managers were the nicest people & very quick to respond. Couldn’t be happier about that. However, the house is in dire need of a deep cleaning & a refresh of bed linens. "
United States
Judy L.
Beautiful Mountain Villa
Balcony
Micosta Leisure Inn

Micosta Leisure Inn

3.0 star property
Hudson
9.2 out of 10, Wonderful, (131)
"Clean, pet friendly , just an overall super nice place to stay "
United States
Gail
$133 nightly
The price is $150
Dec 4 - Dec 5
Total with taxes and fees
Micosta Leisure Inn
Property grounds
Streamside Cottage Half Mile to Town of Woodstock

Streamside Cottage Half Mile to Town of Woodstock

Woodstock
10.0 out of 10, Exceptional, (261)
"Jane was very nice and accommodating, the cottage was very clean and comfortable, a very relaxing and calming place "
United States
Scott
$346 nightly
The price is $388
Dec 13 - Dec 14
Total with taxes and fees
Streamside Cottage Half Mile to Town of Woodstock
Exterior
'A Place in the Woods' - Cabin on Chloe's Lake on 23 acres near Woodstock, NY

'A Place in the Woods' - Cabin on Chloe's Lake on 23 acres near Woodstock, NY

Saugerties
8.2 out of 10, Very Good, (46)
"We had an amazing peaceful time at this property. Check in was seamless and we got lots of great recommendations from our hosts that we really enjoyed! It was very private and cozy and really helped us relax and renew! We will definitely be returning. "
United States
Josh M.
$145 nightly
The price is $162
Dec 3 - Dec 4
Total with taxes and fees
'A Place in the Woods' - Cabin on Chloe's Lake on 23 acres near Woodstock, NY
Terrace/patio
Hamptons on the Hudson in South Saugerties

Hamptons on the Hudson in South Saugerties

Glasco
10.0 out of 10, Exceptional, (34)
"Beautiful home and fantastic pool. Responsive and friendly host. Our whole family had a great time! "
United States
Courtney W.
Hamptons on the Hudson in South Saugerties
Exterior
A Spectacular 50 Mile View of the Hudson Valley in all seasons

A Spectacular 50 Mile View of the Hudson Valley in all seasons

Saugerties
9.8 out of 10, Exceptional, (95)
"Enjoyed our stay!"
United States
Mike T.
A Spectacular 50 Mile View of the Hudson Valley in all seasons
Children's area
Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream

Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream

woodstock
9.0 out of 10, Wonderful, (45)
"I was in town for a few days to get some writing done and see friends. The cabin is beautiful and perfect for one or two people and a dog. The location is also perfect; it's in walking distance (or a very short drive) to town, but the main draw is that it's located on a beautiful stream. The rooster crowing in the background and the deer who visited the property were welcome. "
United States
Shannon F.
$279 nightly
The price is $312
Dec 7 - Dec 8
Total with taxes and fees
Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream
Outdoor dining
Esopus Creek modern Tiny house Retreat!

Esopus Creek modern Tiny house Retreat!

Kingston
9.8 out of 10, Exceptional, (61)
"The property was beautiful. Quiet area but close enough to all the places we wanted to go. Our hosts were very gracious, attentive and friendly. Enjoyed our weekend retreat. "
United States
Rebecca
$216 nightly
The price is $241
Dec 3 - Dec 4
Total with taxes and fees
Esopus Creek modern Tiny house Retreat!
Fridge, microwave, oven, stovetop
Luxurious Woodstock Home Rental Catskill Mountains Views & Private Retreat

Luxurious Woodstock Home Rental Catskill Mountains Views & Private Retreat

Bearsville
10.0 out of 10, Exceptional, (124)
"A beautiful house on a stunning property. Looking forward to coming back!"
United States
A. M.
Luxurious Woodstock Home Rental Catskill Mountains Views & Private Retreat
Outdoor dining
Sexiest Lil Cabin in Saugerties, NY

Sexiest Lil Cabin in Saugerties, NY

Saugerties
9.0 out of 10, Wonderful, (13)
"A little piece of paradise!"
United States
Christi L.
Sexiest Lil Cabin in Saugerties, NY
Exterior
THE LUXURY LODGE - SKI, RIDE, GOLF, BIKE, HIKE

THE LUXURY LODGE - SKI, RIDE, GOLF, BIKE, HIKE

Hunter
10.0 out of 10, Exceptional, (271)
"House was great. Plenty of beds, great kitchen and large table for all. Kitchen was well stocked. "
United States
Sarah A.
$909 nightly
The price is $982
Dec 10 - Dec 11
Total with taxes and fees
THE LUXURY LODGE - SKI, RIDE, GOLF, BIKE, HIKE
Smart TV, fireplace, DVD player, foosball
Catskill Mountain Getaway - minutes to Hunter, Windham and Belleayre Skiing

Catskill Mountain Getaway - minutes to Hunter, Windham and Belleayre Skiing

West Kill
9.8 out of 10, Exceptional, (151)
"This is a fantastic place- lots of space and beautiful. Really enjoyed the hot tub"
United States
Evan S.
Catskill Mountain Getaway - minutes to Hunter, Windham and Belleayre Skiing
Fridge, microwave, oven, stovetop
LOCATION! Location! Walking distance to Hunter MT! FALL 3rd nt SPECIAL!

LOCATION! Location! Walking distance to Hunter MT! FALL 3rd nt SPECIAL!

Hunter
9.6 out of 10, Exceptional, (51)
"Comfortable stay with plenty of room and very close to Hunter Mountain for skiing. Views of the slopes from the hot tub were fantastic "
United States
Chris S.
LOCATION! Location! Walking distance to Hunter MT! FALL 3rd nt SPECIAL!
Exterior
Sioux Tipi on Chloe's Lake

Sioux Tipi on Chloe's Lake

Saugerties
9.8 out of 10, Exceptional, (6)
"This was such a cool experience Id love to go back! "
United States
Brandon
Sioux Tipi on Chloe's Lake
Terrace/patio
Sleeps 27/Pickleball Court/Game Room/Hot Tub/Pool/Batting Cage/Beach

Sleeps 27/Pickleball Court/Game Room/Hot Tub/Pool/Batting Cage/Beach

Coxsackie
10.0 out of 10, Exceptional, (168)
"Had an absolutely amazing time here! Jody was very prompt with responding to any questions we had during the duration of our stay. The house was so perfect. 5 Stars!!"
United States
Steve B.
Sleeps 27/Pickleball Court/Game Room/Hot Tub/Pool/Batting Cage/Beach
Exterior
Cozy Catskill Cabin w/ 10-minute Walk to Downtown Catskill

Cozy Catskill Cabin w/ 10-minute Walk to Downtown Catskill

Catskill
9.8 out of 10, Exceptional, (33)
"Very nice cabin lots of property space "
United States
Martin Z.
$305 nightly
The price is $330
Dec 3 - Dec 4
Total with taxes and fees
Cozy Catskill Cabin w/ 10-minute Walk to Downtown Catskill
Outdoor dining
Private Pickleball Ct - Indoor Hot Tub - Spa Room - Lift Tkts

Private Pickleball Ct - Indoor Hot Tub - Spa Room - Lift Tkts

Windham
10.0 out of 10, Exceptional, (105)
"Rick has an incredible property to share and is a gracious host. A sure place to spend time with friends and family - cant wait to come back again."
United States
Chris R.
Private Pickleball Ct - Indoor Hot Tub - Spa Room - Lift Tkts
Smart TV
PERFECT ESCAPE For Total Privacy, Rustic Modern Cabin, 15 Pvt. Ac, WiFi, Heat/AC

PERFECT ESCAPE For Total Privacy, Rustic Modern Cabin, 15 Pvt. Ac, WiFi, Heat/AC

Mt. Tremper
9.6 out of 10, Exceptional, (10)
"The cabin is beautiful,clean and private all the amenities are there and if you feel like venturing out the town of Woodstock is close by "
United States
Edward C.
$438 nightly
The price is $490
Dec 3 - Dec 4
Total with taxes and fees
PERFECT ESCAPE For Total Privacy, Rustic Modern Cabin, 15 Pvt. Ac, WiFi, Heat/AC
Terrace/patio
ELEGANT LOG CABIN.PRIVATE, QUIET. Great wi-fi, Clean. Heaven.

ELEGANT LOG CABIN.PRIVATE, QUIET. Great wi-fi, Clean. Heaven.

Shandaken
9.8 out of 10, Exceptional, (105)
"Nice cabin in the woods. "
United States
RD
ELEGANT LOG CABIN.PRIVATE, QUIET. Great wi-fi, Clean. Heaven.
Exterior detail
Nature Mountain Retreat with Outdoor Hot Tub and Sauna Spa Experience

Nature Mountain Retreat with Outdoor Hot Tub and Sauna Spa Experience

West Hurley
10.0 out of 10, Exceptional, (5)
"very relaxing and comfortable place to stay!"
United States
Tilson
$771 nightly
The price is $864
Dec 3 - Dec 4
Total with taxes and fees
Nature Mountain Retreat with Outdoor Hot Tub and Sauna Spa Experience
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 Round Top Hotel Reviews

voco James Newbury Hudson Valley by IHG

voco James Newbury Hudson Valley by IHG

10/10 Excellent
"Beautiful room and very clean"
Mariam 1-night trip
Posted 2 days ago
voco James Newbury Hudson Valley by IHG

Find out more about Round Top

Everything you need to know about Round Top 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 Round Top vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 Round Top vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Round Top vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Round Top. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Round Top in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $143 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Round Top rentals

At Expedia, we put the best Round Top 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 Round Top 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 Round Top 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 Round Top. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

Frequently asked questions

Are there vacation rentals in Round Top?

Yes, we have vacation rentals near the most popular local attractions in Round Top, or you can choose a more secluded option if you're looking for relaxation. Nature enthusiasts will enjoy the mountain landscape in Round Top. Make sure you have time to check out the ski areas and golf courses during your trip.

What's the top vacation rental that Round Top has to offer?

Luxurious Woodstock Home Rental Catskill Mountains Views & Private Retreat: This vacation home rental outside of Round Top is located in the mountains and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 5 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Make the most of the selection of games in this rental home to help you unwind.

How many vacation rentals are there in Round Top?

Choose from 9 Expedia vacation rentals in Round Top for a memorable vacation.

What’s there to see and do in Round Top?

While exploring the area, visit family-friendly sights like Zoom Flume, or get outside and enjoy nature at Kaaterskill Falls. In the larger area, you’ll find Catskill State Park and Hunter Mountain.

What’s a vacation rental in Round Top like?

Vacation rentals are private properties where you can stay for a couple of days or more in Round Top. Vacation rentals feature amenities such as kitchens and laundry facilities so you'll have all the conveniences of home. If you're concerned about cleanliness, vacation rentals can provide a sense of privacy away from shared hotel elevators and busy front desks while still allowing you the experience of travel. You'll also have more space in a vacation rental than in a traditional hotel, which makes a vacation rental an attractive choice for a family getaway.