A mountainous landscape with dense forests and a rocky cliff.

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Check prices for these dates

In two weeks
Jul 24 - Jul 26
In two months
Sep 4 - Sep 6
In three months
Oct 2 - Oct 4
In four months
Oct 30 - Nov 1

Our top choices for Round Top cottages

House (4 Bedrooms) | Interior

'the Mountain House:' Windham Retreat w/ Hot Tub!

'the Mountain House:' Windham Retreat w/ Hot Tub!
3.0 star property
Windham
'the Mountain House:' Windham Retreat w/ Hot Tub!
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

Kaatskill Mountain Club & Condos by Vail Resorts

Kaatskill Mountain Club & Condos by Vail Resorts

10/10 Excellent
"I enjoyed my stay,will be coming back.It was very peaceful and everything in my room help make my stay more enjoyable."
Alicia 2-night trip
Posted 1 hour ago
Kaatskill Mountain Club & Condos by Vail Resorts

Find out more about Round Top

Round Top Cottages information

Number of reviews
Accommodation
198 Cottages
Lowest Price
Highest Price

Frequently asked questions

How much do cottages in Round Top cost?
Cottages in Round Top range between and 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 198 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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