A mountainous landscape with dense forests and a rocky cliff.

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Check prices for these dates

In two weeks
Oct 2 - Oct 4
In two months
Nov 13 - Nov 15
In three months
Dec 11 - Dec 13
In four months
Jan 8 - Jan 10

Our top choices for Round Top cottages

Terrace/patio

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, (20 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.
$278 nightly
The price is $300
Sep 22 - Sep 23
Total with taxes and fees
Warm cozy country cottage nestled beneath the mountains, woodstove, Catskill
Exterior

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.
$468 nightly
The price is $506
Sep 18 - Sep 19
Total with taxes and fees
Cozy 2-bedroom cottage in enchanting Catskill Mountains
Exterior

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.
$304 nightly
The price is $340
Sep 18 - Sep 19
Total with taxes and fees
Charming Cottage in the Heart of Catskill & Pet Friendly
Interior

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, (14 reviews)
"great location, clean & good communication with host."
United States
Kanna S.
$235 nightly
The price is $263
Sep 23 - Sep 24
Total with taxes and fees
Charming loft cottage in tranquil Germantown with WiFi, AC
Property grounds

5. Streamside Cottage Half Mile to Town of Woodstock

Streamside Cottage Half Mile to Town of Woodstock
Woodstock
10.0 out of 10, Exceptional, (298 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.
$276 nightly
The price is $309
Sep 27 - Sep 28
Total with taxes and fees
Streamside Cottage Half Mile to Town of Woodstock
Outdoor dining

6. 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
$518 nightly
The price is $559
Sep 20 - Sep 21
Total with taxes and fees
Close to skiing in Windham and Hunter, hiking, lakes, 20+restaurants
Terrace/patio

7. Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream

Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream
woodstock
8.8 out of 10, Excellent, (48 reviews)
"A gem just minutes from the heart of Woodstock!"
United States
Susannah H.
$278 nightly
The price is $311
Sep 21 - Sep 22
Total with taxes and fees
Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream
Terrace/patio

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

Boho Hot Tub Cottage | Pet-Friendly | Hudson Valley
Stottville
$361 nightly
The price is $404
Oct 13 - Oct 14
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

Hotel Vienna

Hotel Vienna

10/10 Excellent
"Very nice property with nice rooms and friendly staff. Breakfast could have been a little better. Also, would be helpful to start the breakfast time earlier."
Virender 1-night trip
Posted 3 hours ago
Hotel Vienna

Find out more about Round Top

Round Top Cottages information

Number of reviews
407
Accommodation
186 Cottages
Lowest Price
$263
Highest Price
$559

Frequently asked questions

How much do cottages in Round Top cost?
Cottages in Round Top range between $263 and $559 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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