A mountainous landscape with dense forests and a rocky cliff.

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Check prices for these dates

In two weeks
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

Our top choices for Round Top cottages

A covered porch with a wooden bench, a wicker chair, and a sofa with cushions.

1. Warm cozy country cottage nestled beneath the mountains, woodstove, Catskill

Warm cozy country cottage nestled beneath the mountains, woodstove, Catskill
Catskill
9.8 out of 10, Exceptional, (21 reviews)
"The property was just as described, very private and cozy. We enjoyed the large balcony as well as the yard. There were also several nice hiking trails close by. Overall we were very happy with our stay."
United States
Ryan P.
The price is NZ$539
includes taxes & fees
5 Oct - 6 Oct
Warm cozy country cottage nestled beneath the mountains, woodstove, Catskill
A single-story house with a dark exterior, a chimney, and a small window.

2. Cozy 2-bedroom cottage in enchanting Catskill Mountains

Cozy 2-bedroom cottage in enchanting Catskill Mountains
Catskill
10.0 out of 10, Exceptional, (2 reviews)
"The property is great. Easy check-in and communication with host. Large property and comfortable beds."
United States
Robert G.
The price is NZ$899
includes taxes & fees
7 Oct - 8 Oct
Cozy 2-bedroom cottage in enchanting Catskill Mountains
A single-story house with a black front door, two windows on either side, and two black trash bins in front.

3. Charming Cottage in the Heart of Catskill & Pet Friendly

Charming Cottage in the Heart of Catskill & Pet Friendly
Catskill
10.0 out of 10, Exceptional, (26 reviews)
"Everything was great! The house is in a great location and is very clean, modern and cozy. I would highly recommend staying here! "
United States
Dave P.
The price is NZ$676
includes taxes & fees
31 Oct - 1 Nov
Charming Cottage in the Heart of Catskill & Pet Friendly
A kitchen with white cabinetry, granite countertops, and a window with blinds.

4. Charming loft cottage in tranquil Germantown with WiFi, AC

Charming loft cottage in tranquil Germantown with WiFi, AC
Germantown
10.0 out of 10, Exceptional, (16 reviews)
"great location, clean & good communication with host."
United States
Kanna S.
The price is NZ$453
includes taxes & fees
13 Oct - 14 Oct
Charming loft cottage in tranquil Germantown with WiFi, AC
A wooden deck with a white railing, surrounded by lush green trees.

5. Close to skiing in Windham and Hunter, hiking, lakes, 20+restaurants

Close to skiing in Windham and Hunter, hiking, lakes, 20+restaurants
Maplecrest
10.0 out of 10, Exceptional, (24 reviews)
"Great stay, lovely place, friendly host. Everything was perfect!"
United States
Taylor
The price is NZ$989
includes taxes & fees
1 Oct - 2 Oct
Close to skiing in Windham and Hunter, hiking, lakes, 20+restaurants
A wooden cabin surrounded by lush greenery and trees.

6. Streamside Cottage Half Mile to Town of Woodstock

Streamside Cottage Half Mile to Town of Woodstock
Woodstock
10.0 out of 10, Exceptional, (301 reviews)
"It was the perfect place for a weekend away from home! The location was only a few minutes from town and was the perfect size for a couple. Would definitely reccomend!"
United States
Kristen S.
The price is NZ$612
includes taxes & fees
20 Oct - 21 Oct
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.
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Top Round Top Hotel Reviews

Holiday Inn Express & Suites Saugerties - Hudson Valley by IHG

Holiday Inn Express & Suites Saugerties - Hudson Valley by IHG

8/10 Good
"The continental breakfast was typical. The coffee was fantastic though - freshly ground beans and brewed by the cup. The shower water pressure and temperature were average at best. Beautiful view if your room is on the back side of the building. Easy to locate and park."
Deborah 2-night trip
Posted 16 hours ago
Holiday Inn Express & Suites Saugerties - Hudson Valley by IHG

Find out more about Round Top

Round Top Cottages information

Number of reviews
366
Accommodation
186 Cottages
Lowest Price
NZ$453
Highest Price
NZ$989

Frequently asked questions

How much do cottages in Round Top cost?
Cottages in Round Top range between NZ$453 and NZ$989 per night. These retreats offer a chance to reconnect with nature — at a price you can afford. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
How many cottages are there in Round Top?
Choose from 186 cottages in Round Top. Whether you're taking a trip with the little ones or planning a retreat with your closest amigos, Expedia will help you find the ideal space to reconnect with nature.
What is there to do in Round Top near my cottage?
If you're eager to discover the sights of Round Top, check out Blackhead Mountain Country Club. It's a hit with locals and visitors alike.