A mountainous landscape with dense forests and a rocky cliff.

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    We are not like the others - we include taxes and fees

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 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.
$268 nightly
The price is $289
Sep 28 - Sep 29
Total with taxes and fees
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, (1 review)
"The property is great. Easy check-in and communication with host. Large property and comfortable beds."
United States
Robert G.
$443 nightly
The price is $479
Sep 28 - Sep 29
Total with taxes and fees
Cozy 2-bedroom cottage in enchanting Catskill Mountains
A kitchen with white cabinetry, granite countertops, and a window with blinds.

3. 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, (14 reviews)
"great location, clean & good communication with host."
United States
Kanna S.
$219 nightly
The price is $245
Sep 30 - Oct 1
Total with taxes and fees
Charming loft cottage in tranquil Germantown with WiFi, AC
A single-story house with a black front door, two windows on either side, and two black trash bins in front.

4. 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.
$300 nightly
The price is $336
Sep 28 - Sep 29
Total with taxes and fees
Charming Cottage in the Heart of Catskill & Pet Friendly
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
$490 nightly
The price is $529
Sep 28 - Sep 29
Total with taxes and fees
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, (299 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.
$268 nightly
The price is $300
Sep 28 - Sep 29
Total with taxes and fees
Streamside Cottage Half Mile to Town of Woodstock
An outdoor patio with a fire pit, a grill, and outdoor furniture.

7. Boho Hot Tub Cottage | Pet-Friendly | Hudson Valley

Boho Hot Tub Cottage | Pet-Friendly | Hudson Valley
Stottville
$319 nightly
The price is $357
Sep 28 - Sep 29
Total with taxes and fees
Boho Hot Tub Cottage | Pet-Friendly | Hudson Valley
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 Kingston-Ulster by IHG

Holiday Inn Express & Suites Kingston-Ulster by IHG

10/10 Excellent
"Staff was very friendly and responsive"
Marie 1-night trip
Posted 12 hours ago
Holiday Inn Express & Suites Kingston-Ulster by IHG

Find out more about Round Top

Round Top Cottages information

Number of reviews
361
Accommodation
186 Cottages
Lowest Price
$245
Highest Price
$529

Frequently asked questions

How much do cottages in Round Top cost?
Cottages in Round Top range between $245 and $529 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.
Why book your cottage in Round Top with Expedia?
We think that traveling should be hassle-free, so if you're looking for cottages in Round Top at a competitive price, Expedia has got your back. Keep costs down and choose a cheap option far from the rush of the city, or splurge on a luxury cottage to really pamper your favorite people.
How can I find cheap cottages in Round Top?
With Expedia's handy filter tool, booking cheap cottages in Round Top has never been simpler. To view properties that are very pocket friendly, tailor your search results by star rating, amenities and budget.
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.

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