Search Round Top Villa Rentals from CA $1,039

  • Plan, book, stay with confidence

    • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Next weekend
Mar 14 - Mar 16
In two weeks
Mar 21 - Mar 23
In one month
Apr 4 - Apr 6
In two months
May 2 - May 4

Browse Select Round Top Villas

Mountain-View Retreat @ Heart of Hudson with Decks, Designer Decor & Game
Terrace/patio

Mountain-View Retreat @ Heart of Hudson with Decks, Designer Decor & Game

Mountain-View Retreat @ Heart of Hudson with Decks, Designer Decor & Game
Log cabin with INDOOR POOL foot of hunter mountain
Fridge, microwave, oven, stovetop

Log cabin with INDOOR POOL foot of hunter mountain

9.0 out of 10, Wonderful, (4)
"This house had enough space for all 16 of us, with a wonderful pool house and sauna that kept the 9 teens entertained and having fun together swimming and playing games. We were located so close to the mountain that two even walked home from the ski mountain one day. We all enjoyed walking into town. Plenty of parking for our 7 cars. We had a terrific ski vacation and only wished for better snow!!!"
Log cabin with INDOOR POOL foot of hunter mountain
Beautiful Mountain Villa
Miscellaneous

Beautiful Mountain Villa

10.0 out of 10, Exceptional, (1)
Beautiful Mountain Villa
Custom Windham Mtn Villa w/ Pool, Theater & Views!
TV, fireplace

Custom Windham Mtn Villa w/ Pool, Theater & Views!

6.0 out of 10, (2)
"Visited Windham with family and luckily I came across this beautiful house to stay. This will be my to go place in Windham. The indoor pool was a plus, kids had a lot of fun. One thing I’ll mention is level of chlorine in the water, my kids had teary and itchy eyes and coughing after being in the pool for awhile. They got better the next day. I was told that it was the right amount in it and even lady showed up to make sure that it was fine. I appreciate for what they did. Maybe kids are not...
Custom Windham Mtn Villa w/ Pool, Theater & Views!
Catskill Villa/Pool with Hudson River View
Interior

Catskill Villa/Pool with Hudson River View

9.0 out of 10, Wonderful, (2)
"Really enjoyed our stay and the town."
Catskill Villa/Pool with Hudson River View
Luxury Catskill MNTN 5BR 3Bath Villa w Hot Tub next to Ski
Outdoor spa tub

Luxury Catskill MNTN 5BR 3Bath Villa w Hot Tub next to Ski

9.4 out of 10, Exceptional, (10)
"We had the best time in Prattvilla. this is our second time and we love it, the villa is spacious and comfortable ,the best amenities from the fire place to the game room with football, pingpong table, airhockey popcorn machine billiard table and the perfect backyard with large hot tub, BBQ and fire pit. the location is close to Hunter for Ski with many dining options. Thank you Gal our host who was always responsive. looking forward coming again next year. "
The price is CA $1,039
CA $1,920 total
includes taxes & fees
Mar 12 - Mar 13
Luxury Catskill MNTN 5BR 3Bath Villa w Hot Tub next to Ski
Catskills Cottage close to Windham and Hunter
Property grounds

Catskills Cottage close to Windham and Hunter

8.0 out of 10, Very good, (4)
"We had an excellent stay at the property. Communicating with Don, the property manager, was so easy and he was so helpful. We would definitely return to this property. "
Catskills Cottage close to Windham and Hunter
5k+ Sq Ft of Luxury Living on 54 Acres near Hudson
Property grounds

5k+ Sq Ft of Luxury Living on 54 Acres near Hudson

8.0 out of 10, Very good, (5)
"Property was perfect for our group trip. The house was clean, spread out, well air-conditioned during the summer, and provided a number of sleeping options (easily sleeping 10). The outside was perfect for our guys-trip - lots of space, nice patio with overhang, and the pool was incredible. Overall the house was great, and Gautam was a great host - easy to communicate with, providing additional air mattresses and towels in every room. The house is 15-20 minutes from Hudson/Catskill towns, and...
5k+ Sq Ft of Luxury Living on 54 Acres near Hudson
Secluded Art & Architecture in Nature Retreat - hi
Interior

Secluded Art & Architecture in Nature Retreat - hi

Secluded Art & Architecture in Nature Retreat - hi
Custom Windham Mtn Villa w/ Pool, Theater & Views!
Fireplace

Custom Windham Mtn Villa w/ Pool, Theater & Views!

3.0 star property
Custom Windham Mtn Villa w/ Pool, Theater & Views!
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.
Don't see what you're looking for?
See all available properties in Round Top
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Other property types in Round Top

Postcard Cabins Eastern Catskills
Exterior

Postcard Cabins Eastern Catskills

2.0 star property
8.0 out of 10, Very good, (4)
"We love our Bartow cabin, it was so cozy and relaxing for us. A perfect getaway from the city life. Will definitely stay again. "
The price is CA $254
CA $274 total
includes taxes & fees
Mar 11 - Mar 12
Postcard Cabins Eastern Catskills
Hamptons on the Hudson in South Saugerties
Terrace/patio

Hamptons on the Hudson in South Saugerties

10.0 out of 10, Exceptional, (14)
"We had an absolutely wonderful stay at this Vrbo! From the moment we arrived, everything was spotless, beautifully decorated, and thoughtfully equipped with everything we needed. The hosts went above and beyond to ensure a comfortable and seamless experience, providing clear instructions and even thoughtful touches that made us feel right at home.The location was perfect—close enough to attractions and restaurants but still peaceful and private. The beds were incredibly comfortable, the kitchen...
Hamptons on the Hudson in South Saugerties
Streamside Cottage Half Mile to Town of Woodstock
Aerial view

Streamside Cottage Half Mile to Town of Woodstock

10.0 out of 10, Exceptional, (228)
"We totally enjoyed our stay at the cottage! Exactly as advertised, except the views of the river from the home are are even better than pictured. We would definitely recommend!"
Streamside Cottage Half Mile to Town of Woodstock
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.

Frequently asked questions

Why book your villa in Round Top with Expedia?
Expedia makes it a breeze to find your dream villa in Round Top. Taking the kids on vacation? Take advantage of our filters to look for stays with a pool or free WiFi. If you’re on a budget, decide on how much you want to spend and the star rating of the property. We’ll help you find the perfect stay that suits your style and taste.
How can I find cheap villas in Round Top?
With Expedia’s useful filter tool, sourcing cheap villas in Round Top is a breeze. To discover properties that’ll make your wallet happy, narrow down your search by amenities, star rating and budget.
What is there to do near my villa in Round Top?
The ultimate travel accessory is a well-thought-out travel plan. Blackhead Mountain Country Club is a great place to kick off your sightseeing in Round Top.