Round Top Vacation Rentals

    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
    today icon
    Change your mind
    Book hotels with free cancellation

Vacation Rentals in Round Top

Micosta Leisure Inn
3.0 star property
9.0 out of 10, Wonderful, (83)
"The owner was fantastic! Super kind and accommodating. Very available for any help or questions. Well maintained, clean and quiet property. Would definitely stay there again! "
The price is CA $152
CA $164 total
includes taxes & fees
Oct 10 - Oct 11
Micosta Leisure Inn
'A Place in the Woods' - Cabin on Chloe's Lake on 23 acres near Woodstock, NY
8.4 out of 10, Very good, (41)
"We had a great time at the cabin! It was the perfect escape from the city. The view was gorgeous, and the cabin had everything we needed. We also tried to use the canoe but the padlock is stuck, it might be rusted/need to be replaced. Otherwise everything was perfect!"
The price is CA $168
CA $195 total
includes taxes & fees
Oct 2 - Oct 3
'A Place in the Woods' - Cabin on Chloe's Lake on 23 acres near Woodstock, NY
Streamside Cottage Half Mile to Town of Woodstock
10.0 out of 10, Exceptional, (216)
"This was our second time staying at this beautiful home and we will be back again! "
The price is CA $240
CA $434 total
includes taxes & fees
Oct 15 - Oct 16
Streamside Cottage Half Mile to Town of Woodstock
Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream
9.2 out of 10, Wonderful, (37)
"IT WAS IDYLLIC."
The price is CA $242
CA $376 total
includes taxes & fees
Oct 13 - Oct 14
Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream
Tuscan Year Round Beauty - Pickleball Court
10.0 out of 10, Exceptional, (94)
"Hard to decide where to begin…one of the nicest rental homes in the Windham area! Outside amenities are incredible - the firepit is amazing, the outdoor kitchen provides so many wonderful options (outdoor pizza oven was a hit) The inside provides fabulous space for all - even when the weather doesn’t cooperate. Rick and Alan were a pleasure to deal with. We look forward to a return trip!"
Tuscan Year Round Beauty - Pickleball Court
HUGE KITCHEN 4 Private Acres, 7 Min to Town, WiFi, AC, Fireplace
10.0 out of 10, Exceptional, (30)
"We had a wonderful time in this cabin in the woods. We saw fireflies, a bear, a fox and countless deer. The Wifi was great so the adults could work while the kids were at camp. "
HUGE KITCHEN 4 Private Acres, 7 Min to Town, WiFi, AC, Fireplace
Romantic sky loft with steam shower/giant tub. Minutes to the slopes.
10.0 out of 10, Exceptional, (13)
"We really enjoyed our stay at the loft! We went to see a show at the Bearsville Theater in Woodstock and this place was under 20 mins from the venue. Very comfortable king size bed, loved the rustic boho vibes. The bathroom was a dream, highly recommend indulging in the steam shower and doing a cold tub plunge afterwards! Overall this was a beautiful spot tucked in the mountains and we can’t wait to come back and check out the town that’s just a short walk down the road."
Romantic sky loft with steam shower/giant tub. Minutes to the slopes.
Dancing Horse Farm in Windham: Spectacular 9 Bedroom Home, 30 Acres, Near Hunter
10.0 out of 10, Exceptional, (140)
"Great stay. Come here every year."
Dancing Horse Farm in Windham: Spectacular 9 Bedroom Home, 30 Acres, Near Hunter
Beautiful House 0,5 Mile From Hunter Mountain
9.8 out of 10, Exceptional, (196)
"Very accommodating host! Thanks for the stay. Definitely consider staying again! Lovely layout, airy, roomy. Host generous with paper goods etc. Thanks for a great vacation!"
Beautiful House 0,5 Mile From Hunter Mountain
7Bdr/5Bth, Amazing View, Lake,1/2 ml Hunter Mountain, Hot Tub/Sauna. Ski, Swim
10.0 out of 10, Exceptional, (212)
"We had a fantastic stay in Valentyna's home. We had a large group of 16 at the home during labor day weekend. We found the house large, clean, updated and had plenty of space. The bedrooms are roomy, the living spaces are even larger than pictured, and the five different outdoor areas are fantastic. The house has every amenity you can ask for. Direct lake access is steps from the house and the house is close to Hunter for the winter months. We had a great time and would happily stay again. "
The price is CA $536
CA $1,065 total
includes taxes & fees
Sep 30 - Oct 1
7Bdr/5Bth, Amazing View, Lake,1/2 ml Hunter Mountain, Hot Tub/Sauna. Ski, Swim
THE LAKEFRONT RETREAT - SKI, RIDE, GOLF, BIKE, HIKE
10.0 out of 10, Exceptional, (85)
"Each year we go on vacation with our daughter, son in law and his family. We are a group of 12 and loved this lake house. We all want to make this our yearly trip. Great place"
The price is CA $537
CA $943 total
includes taxes & fees
Oct 15 - Oct 16
THE LAKEFRONT RETREAT - SKI, RIDE, GOLF, BIKE, HIKE
The Cabin at Chichester in the Catskills Mountains
9.8 out of 10, Exceptional, (169)
"That was the good stay. We enjoy it"
The Cabin at Chichester in the Catskills Mountains
Cozy Relaxing Retreat in Saugerties, NY
10.0 out of 10, Exceptional, (40)
"Great place, communicative host, and perfect location! Will definitely return!"
The price is CA $223
CA $455 total
includes taxes & fees
Oct 22 - Oct 23
Cozy Relaxing Retreat in Saugerties, NY
Charming Artist's Retreat
10.0 out of 10, Exceptional, (124)
"We had a lovely time relaxing at Maureen’e cottage for the weekend. Sitting in the garden, taking in the mountain view, and listening to the surrounding wildlife was the perfect respite from hectic city life. As artists, we felt right at home among the artwork and vintage treasures around the house. We enjoyed a hearty breakfast at the Village Diner, and loved exploring the Saugerties Lighthouse Trail - only ten minutes away! Thank you Maureen for a wonderful stay. - Dave and Alie"
Charming Artist's Retreat
LOCATION! Location! Walking distance to Hunter MT! Oktoberfest 3rd nt SPECIAL!
9.6 out of 10, Exceptional, (45)
"We really enjoyed our stay in Hunter. The house met our needs well for a large family gathering. The hot tub and game room were excellent. Beutiful inside.It is close to shopping and hiking trails in the area. We did a lot of cooking and could have used larger cutting boards and baking/roasting pans. Be aware that the house is right on the main road into Hunter. The pinball machine was frustrating at times because the ball would get stuck.Overall it was a great stay."
LOCATION! Location! Walking distance to Hunter MT! Oktoberfest 3rd nt SPECIAL!
Catskills Windham Hunter Mountain Cabin Getaway
9.2 out of 10, Wonderful, (24)
"Quiet stay in the mountains in the summer."
The price is CA $361
CA $864 total
includes taxes & fees
Oct 2 - Oct 3
Catskills Windham Hunter Mountain Cabin Getaway
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!"
Sexiest Lil Cabin in Saugerties, NY
Waterfront home w/swimming, kayaking and more; plus Hot Tub!!
9.8 out of 10, Exceptional, (70)
"My friends and I booked for a long weekend-we had so many plans outside of the house but when we got there we were so happy with the accommodations we hardly left! The swimming pond was amazing and the yard/deck/firepit kept us entertained the entire time. Beautiful property-definitely book!!"
Waterfront home w/swimming, kayaking and more; plus Hot Tub!!
NEW! Herb Cottage: Historic Artist's Cottage, Wood Stove, Walk to Town!
9.8 out of 10, Exceptional, (129)
"The location was perfect. The history of the residence fascinating. The hosts most accommodating. We had a problem that was quickly attended to and solved. Everything we needed was on hand and our dog loved walking about in the yard. Elder visitors alert: the top step is tough to negotiate, but we did."
NEW! Herb Cottage: Historic Artist's Cottage, Wood Stove, Walk to Town!
Sauna, Hot-tub, Private Pool, fire-pit, pet friendly, Mountain views!
9.6 out of 10, Exceptional, (168)
"Our late summer visit to the Catskill Mountains was very relaxing even with a 2-year-old. The kids enjoyed the pool the most and the property owners provided many pool toys for all. We enjoyed the hot tub also. There was plenty of room. WIFI was spotty, but no one had to work and that forces us to relax. Everyone reported they had a great time. Family time is the most important gift. Thank you Pete and Lara "
Sauna, Hot-tub, Private Pool, fire-pit, pet friendly, Mountain views!
Don't see what you're looking for?
See all available properties in Round Top
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.
Save an average of 15% on thousands of hotels when you're signed in

Other types of properties in Round Top you may be interested in

Hunter Lodge, a Bluebird by Lark
3.0 star property
9.4 out of 10, Exceptional, (476)
"Room was huge. Really clean, beautiful view of hunter's mountain. "
The price is CA $200
CA $245 total
includes taxes & fees
Oct 2 - Oct 3
Hunter Lodge, a Bluebird by Lark
Howard Johnson by Wyndham Saugerties
2.0 star property
7.4 out of 10, Good, (1002)
"The beds were very comfortable and the room was clean . The bathroom shower was a different story . "
The price is CA $138
CA $154 total
includes taxes & fees
Oct 8 - Oct 9
Howard Johnson by Wyndham Saugerties
AutoCamp Catskills
5.0 star property
9.0 out of 10, Wonderful, (324)
"We loved the concept—it's really cool. We're already thinking about where we can go next with Auto Camp. It's perfect for those of us who want a camping experience but don't want to buy and do all the work "real" camping requires. "
The price is CA $196
CA $267 total
includes taxes & fees
Oct 16 - Oct 17
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.

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?

HUGE KITCHEN 4 Private Acres, 7 Min to Town, WiFi, AC, Fireplace: This vacation home rental outside of Round Top is located in the mountains and has a fireplace, a patio, and a barbecue grill 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 books.

How many vacation rentals are there in Round Top?

Choose from 6 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 Hunter Mountain and North-South Lake Campground & Day Use Area.

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.