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Check prices for these dates

In two weeks
27 Mar - 29 Mar
In two months
8 May - 10 May
In three months
5 June - 7 June
In four months
3 July - 5 July

Our top choices for Round Top cottages

Interior

Cottage in Germantown

Charming loft cottage in tranquil Germantown with WiFi, AC
10.0 out of 10, Exceptional, (10 reviews)
"Very clean, comfortable, good location, great communication with host. "
United States
Lisa B.
The price is AU$305
includes taxes & fees
16 Mar - 17 Mar
Charming loft cottage in tranquil Germantown with WiFi, AC
Exterior

Cottage in Catskill

Warm cozy country cottage nestled beneath the mountains, woodstove, Catskill
9.8 out of 10, Exceptional, (13 reviews)
"Very comfortable home"
United States
Holly
The price is AU$459
includes taxes & fees
14 Mar - 15 Mar
Warm cozy country cottage nestled beneath the mountains, woodstove, Catskill
Exterior

Cottage in Catskill

Charming Cottage in the Heart of Catskill & Pet Friendly
10.0 out of 10, Exceptional, (22 reviews)
"Really comfortable and cozy"
Canada
Lynne H.
The price is AU$489
includes taxes & fees
21 Mar - 22 Mar
Charming Cottage in the Heart of Catskill & Pet Friendly
Outdoor dining

Cottage in Shandaken

Modern Cottage 2 (The Lorca, Catskills) - 10 min to Belleayre, 25 min to Windham
10.0 out of 10, Exceptional, (1 review)
"10/10 experience. beautiful cabin, super cozy"
United States
Hunter W.
The price is AU$291
includes taxes & fees
23 Mar - 24 Mar
Modern Cottage 2 (The Lorca, Catskills) - 10 min to Belleayre, 25 min to Windham
Exterior

Cottage in Bearsville

Little red house just outside of Woodstock
9.0 out of 10, Wonderful, (2 reviews)
"The house is cute, well decorated but very small "
United States
Harry
The price is AU$794
includes taxes & fees
15 Mar - 16 Mar
Little red house just outside of Woodstock
Terrace/patio

Cottage in woodstock

Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream
9.0 out of 10, Wonderful, (46 reviews)
"A gem just minutes from the heart of Woodstock!"
United States
Susannah H.
The price is AU$441
includes taxes & fees
15 Mar - 16 Mar
Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream
Terrace/patio

Cottage in Stottville

Pet-Friendly Hudson Escape w/ Hot Tub
The price is AU$460
includes taxes & fees
12 Apr - 13 Apr
Pet-Friendly Hudson Escape w/ Hot Tub
Outdoor dining

Cottage in Maplecrest

Close to skiing in Windham and Hunter, hiking, lakes, 20+restaurants
10.0 out of 10, Exceptional, (22 reviews)
"We had a wonderful stay at the cottage. Place was perfect and met all our needs. The cottage was lovely and cozy, truly home away from home. The host, Agnes, was kind and very helpful. Will definitely be back."
United States
Carmela L.
The price is AU$786
includes taxes & fees
15 Mar - 16 Mar
Close to skiing in Windham and Hunter, hiking, lakes, 20+restaurants
Property grounds

Cottage in Ashland

Tiny House on Walnut Grove
4.0 out of 10, (2 reviews)
"Many problems with this listing, first the fire alarm was low on battery, I had to physically climb to reach the smoke detector to detach and remove the battery, a sharp beeping noise went off every 90 seconds and we wouldn’t have been able to sleep without stopping it. There were no spare batteries to change. There were spiders everywhere. My friend used the shower and saw 11 of them moving around the ceiling. They were in the main bed and on the counter and sink as well. The tenant was nice...
United States
Trevor C.
The price is AU$400
includes taxes & fees
19 Mar - 20 Mar
Tiny House on Walnut Grove
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

Woodstock Way Hotel

Woodstock Way Hotel

10/10 Excellent
"I recently stayed at Woodstock Way Hotel and had a lovely experience. The property feels calm, charming, and thoughtfully designed — a perfect place to unwind in Woodstock. Room: We stayed in a King Premium Suite with a balcony. The room was spacious and modern, the bed was extremely comfortable, and the heated bathroom floors were the highlight of the stay. The minibar with complimentary snacks and drinks was also a nice touch. Location: The hotel is perfectly located within walking distance of great spots like Shelter Woodstock, Allison Restaurant, and Yum Yum Noodle Bar. Service: Check-in was seamless and the staff were kind, attentive, and welcoming. Parking was also very easy and convenient. Overall, a wonderful stay — peaceful, comfortable, and perfectly located. I look forward to returning. "
Karen 2-night trip
Posted 10 hours ago
Woodstock Way Hotel

Find out more about Round Top

Round Top Cottages information

Number of reviews
118
Accommodation
181 Cottages
Lowest Price
AU$291
Highest Price
AU$794

Frequently asked questions

How much do cottages in Round Top cost?
Cottages in Round Top range between AU$291 and AU$794 per night. These stays offer a chance to get reacquainted with nature — at a price you can afford. This price was 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.
What is there to do in Round Top near my cottage?
Round Top has enough experiences and sights to keep you on the hop for weeks, starting with Hunter Mountain. Kaaterskill Falls, Bailiwick Ranch and Discovery Zoo and Indian Head Mountain are other fantastic attractions. If you have more time, Blackhead Mountain Country Club and Platte Clove Preserve - Catskill Centre are worthwhile additions to your itinerary.