A mountainous landscape with dense forests and a rocky cliff.

Round Top Vacation Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Oct 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

Our top choices for Round Top vacation homes

A bedroom with a bed, a desk, and a chair, a large window with a view of a forest, and a sliding glass door leading to a balcony with a chair.

1. Designer Private Catskills House + Fire Pit

Designer Private Catskills House + Fire Pit
Round Top
The price is CA $266
CA $764 total
includes taxes & fees
Sep 28 - Sep 29
Designer Private Catskills House + Fire Pit
A modern living room with a large sectional sofa, a potted plant, and a flat-screen TV mounted on the wall.

2. Catskills Escape! Hot Tub, Massage Chairs & Games

Catskills Escape! Hot Tub, Massage Chairs & Games
Round Top
10.0 out of 10, Exceptional, (11 reviews)
"Very nice house. The rooms were very clean and the host gets back to text messages very quickly."
United States
Sehan R.
The price is CA $919
CA $1,534 total
includes taxes & fees
Sep 27 - Sep 28
Catskills Escape! Hot Tub, Massage Chairs & Games
A cabin with a large deck, multiple windows, and a fire pit.

3. Modern Luxurious Cabin, Catskills - The Tiny Nook

Modern Luxurious Cabin, Catskills - The Tiny Nook
Catskill
10.0 out of 10, Exceptional, (12 reviews)
"We had an excellent experience. The place was wonderful. A real place to disconnect from everything. We Highly recommend it."
United States
Saul
The price is CA $252
CA $521 total
includes taxes & fees
Oct 20 - Oct 21
Modern Luxurious Cabin, Catskills - The Tiny Nook

4. Cozy Mountain Getaway - Hot Tub - Grill - Fire Pit

Cozy Mountain Getaway - Hot Tub - Grill - Fire Pit
Tannersville
8.8 out of 10, Excellent, (6 reviews)
"The house was great! We enjoyed shopping, hiking and going to local restaurants. The house was exactly as described. Very comfortable. Ivan was a great host. Will definitely stay again."
United States
Kathleen D.
The price is CA $223
CA $761 total
includes taxes & fees
Sep 28 - Sep 29
Cozy Mountain Getaway - Hot Tub - Grill - Fire Pit
A spacious living room with a sectional sofa, a coffee table, and a rug.

5. Spacious 3BR Home ~ Sleeps 6 ~ Near Catskill Mountains & Skiing ~ Yard ~ Parking

Spacious 3BR Home ~ Sleeps 6 ~ Near Catskill Mountains & Skiing ~ Yard ~ Parking
Catskill
10.0 out of 10, Exceptional, (3 reviews)
"Great place to stay!"
United States
Kristen C.
The price is CA $358
CA $573 total
includes taxes & fees
Sep 29 - Sep 30
Spacious 3BR Home ~ Sleeps 6 ~ Near Catskill Mountains & Skiing ~ Yard ~ Parking
A hotel room with a wooden headboard, a large bed with white and yellow bedding, a sliding glass door to the outside, and a window with an air conditioning unit.

6. Cozy Family Friendly home near Hunter Mt, Katerskill Falls & hiking trails

Cozy Family Friendly home near Hunter Mt, Katerskill Falls & hiking trails
Catskill
10.0 out of 10, Exceptional, (1 review)
"Great and funny time thanks owner you very kindly "
United States
Gabdulkarim Z.
The price is CA $313
CA $677 total
includes taxes & fees
Oct 27 - Oct 28
Cozy Family Friendly home near Hunter Mt, Katerskill Falls & hiking trails
A modern interior with a staircase, wooden flooring, a dining area, and a brick wall.

7. Catskill Cottage Walk to Downtown & River Views

Catskill Cottage Walk to Downtown & River Views
Catskill
10.0 out of 10, Exceptional, (30 reviews)
"Great little place to stay at right in downtown!!"
United States
Bryan S.
The price is CA $112
CA $236 total
includes taxes & fees
Sep 28 - Sep 29
Catskill Cottage Walk to Downtown & River Views
A modern kitchen with a stainless steel refrigerator, a dining area with a table and chairs, and a living room with a sofa and a lamp.

8. Cozy Waterfall Oasis + Firepit

Cozy Waterfall Oasis + Firepit
East Durham
9.6 out of 10, Exceptional, (18 reviews)
"Everything was perfect!"
United States
Jen C.
The price is CA $197
CA $471 total
includes taxes & fees
Sep 27 - Sep 28
Cozy Waterfall Oasis + Firepit
A spacious living room with a stone fireplace, large windows, and a cozy seating area.

9. Modern Chalet * Hot Tub * Game And Media Level

Modern Chalet * Hot Tub * Game And Media Level
Catskill
10.0 out of 10, Exceptional, (1 review)
"LOVE this house"
United States
Anya K.
The price is CA $345
CA $1,263 total
includes taxes & fees
Oct 27 - Oct 28
Modern Chalet * Hot Tub * Game And Media Level
A kitchen with a sink, a coffee maker, and a microwave.

10. Cozy Retreat - Walk to Shops, Hot Tub, Fenced Yard

Cozy Retreat - Walk to Shops, Hot Tub, Fenced Yard
Tannersville
The price is CA $205
CA $698 total
includes taxes & fees
Sep 30 - Oct 1
Cozy Retreat - Walk to Shops, Hot Tub, Fenced Yard
A living room with a fireplace, a sliding glass door, and a rug.

11. Close to skiing and hiking, walk to main street

Close to skiing and hiking, walk to main street
Tannersville
9.2 out of 10, Wonderful, (15 reviews)
"Couldn't ask for a more perfect place to stay. Beautiful property, very quiet, and very comfy. You are on vacation but it feels like home. Definitely be staying here in the future!"
United States
Brandon M.
The price is CA $245
CA $640 total
includes taxes & fees
Sep 28 - Sep 29
Close to skiing and hiking, walk to main street
A cozy living room with a white brick fireplace, a round table with a board of cured meats and cheese, two glasses of red wine, and a few potted plants.

12. Cute Cozy Catskill Escape

Cute Cozy Catskill Escape
Tannersville
10.0 out of 10, Exceptional, (1 review)
"This was the most stunning relaxing weekend me and my family had for years. clean and beautiful cozy house beautiful neighbourhood and some nice attractions in the area and most of all the best host you can ever hope for, from making sure everything is alright being responsive right away and what not he had no problem with anything we asked for. It’s a well maintained house and a brand new fridge freezer grill dishwasher dishes everything just perfect so if you are looking for a wonderful time...
United States
Benjamin S.
The price is CA $541
CA $1,148 total
includes taxes & fees
Sep 27 - Sep 28
Cute Cozy Catskill Escape
A kitchen with a central island, bar stools, and pendant lighting.

13. Cozy Catskill Escape

Cozy Catskill Escape
Catskill
10.0 out of 10, Exceptional, (2 reviews)
"Very accommodating host. Great with last minute visits."
United States
Kevin P.
The price is CA $181
CA $383 total
includes taxes & fees
Oct 20 - Oct 21
Cozy Catskill Escape
A round table with a candle, a book, and a vase with dried flowers.

14. Spacious 5 BR w/Mountaintop Views-2 Min to Hunter

Spacious 5 BR w/Mountaintop Views-2 Min to Hunter
Tannersville
10.0 out of 10, Exceptional, (8 reviews)
"The property is located on incredible Landfield....the view is spectacular and everything around is nature."
United States
NANCY
The price is CA $332
CA $985 total
includes taxes & fees
Oct 27 - Oct 28
Spacious 5 BR w/Mountaintop Views-2 Min to Hunter
A single-story house with a porch, a chimney, and a well-maintained lawn.

15. Country House offers 2 bedrooms and a den, lots of parking.

Country House offers 2 bedrooms and a den, lots of parking.
Saugerties
The price is CA $191
CA $493 total
includes taxes & fees
Sep 28 - Sep 29
Country House offers 2 bedrooms and a den, lots of parking.
A modern living space with a kitchen area, a dining table, and a sofa.

16. Cabin Oasis near Town

Cabin Oasis near Town
Catskill
The price is CA $255
CA $458 total
includes taxes & fees
Oct 20 - Oct 21
Cabin Oasis near Town
A wooden deck leading to a cabin with a window and a door, surrounded by trees.

17. Modern cabin retreat

Modern cabin retreat
Catskill
The price is CA $197
CA $380 total
includes taxes & fees
Sep 27 - Sep 28
Modern cabin retreat
Two wooden Adirondack chairs on a covered patio with a wooden fence in the background.

18. Brand New 2 Bdr. Townhome Minutes from Windham Mtn

Brand New 2 Bdr. Townhome Minutes from Windham Mtn
Hensonville
10.0 out of 10, Exceptional, (11 reviews)
"This is a very cute, very clean condo near Windham. Perfect for our family of 4. Would definitely stay again. "
United States
Kimberly K.
The price is CA $255
CA $522 total
includes taxes & fees
Sep 27 - Sep 28
Brand New 2 Bdr. Townhome Minutes from Windham Mtn
A two-story cabin with a balcony and a chimney, surrounded by a snowy forest.

19. Pines Vignette • Modern 3BR Home in Windham

Pines Vignette • Modern 3BR Home in Windham
Windham
10.0 out of 10, Exceptional, (2 reviews)
"House is cozy and has everything you need. We enjoyed our stay."
United States
William H.
The price is CA $283
CA $765 total
includes taxes & fees
Sep 27 - Sep 28
Pines Vignette • Modern 3BR Home in Windham
A bedroom with a bed, bedside table, lamp, and a framed botanical print on the wall.

20. Catskills Stone Getaway - 6BR, Sleeps 14, Game Room, Firepit, Near Skiing

Catskills Stone Getaway - 6BR, Sleeps 14, Game Room, Firepit, Near Skiing
Purling
The price is CA $621
CA $741 total
includes taxes & fees
Sep 28 - Sep 29
Catskills Stone Getaway - 6BR, Sleeps 14, Game Room, Firepit, Near Skiing
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Round Top Hotel Reviews

Holiday Inn Express & Suites Kingston-Ulster by IHG

Holiday Inn Express & Suites Kingston-Ulster by IHG

8/10 Good
"We had a lovely time. Staff and room were great!"
Cindy 2-night trip
Posted 3 hours ago
Holiday Inn Express & Suites Kingston-Ulster by IHG

Find out more about Round Top

Round Top Vacation Homes information

Number of reviews
121
Accommodation
770 Vacation Homes
Lowest Price
CA $236
Highest Price
CA $1,534

Explore a world of travel with Expedia