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Check prices for these dates

In two weeks
12 Sep - 14 Sep
In one month
26 Sep - 28 Sep
In two months
24 Oct - 26 Oct
In three months
21 Nov - 23 Nov

Cottages in Round Top

Streamside Cottage Half Mile to Town of Woodstock
Property grounds

Streamside Cottage Half Mile to Town of Woodstock

10.0 out of 10, Exceptional, (249)
"A beautiful quiet setting! "
The price is AED 547
AED 1,189 total
includes taxes & fees
2 Sep - 3 Sep
Streamside Cottage Half Mile to Town of Woodstock
Junebug Cottage: peace, love and privacy a short walk to Woodstock village green
Exterior

Junebug Cottage: peace, love and privacy a short walk to Woodstock village green

10.0 out of 10, Exceptional, (73)
"We were in Woodstock for a wedding. Junebug Cottage was perfect for our stay! "
Junebug Cottage: peace, love and privacy a short walk to Woodstock village green
NEW! Herb Cottage: Historic Artist's Cottage, Wood Stove, Walk to Town!
TV, DVD player, books, video library

NEW! Herb Cottage: Historic Artist's Cottage, Wood Stove, Walk to Town!

9.8 out of 10, Exceptional, (135)
"We had a marvelous visit!"
NEW! Herb Cottage: Historic Artist's Cottage, Wood Stove, Walk to Town!
TOP RATED Romantic rustic luxury + flowing stream + walk to town = Brook Cottage
Exterior

TOP RATED Romantic rustic luxury + flowing stream + walk to town = Brook Cottage

10.0 out of 10, Exceptional, (167)
"Great holiday weekend. Hiked, ate, shopped and enjoyed music at Levon’s. "
TOP RATED Romantic rustic luxury + flowing stream + walk to town = Brook Cottage
Charming Cottage in Private Lake Community (Pet-Friendly!)
Fridge, microwave, oven, stovetop

Charming Cottage in Private Lake Community (Pet-Friendly!)

10.0 out of 10, Exceptional, (33)
"We enjoyed ourselves,relaxed,visited had a very enjoyable bisit"
Charming Cottage in Private Lake Community (Pet-Friendly!)
The Cabin at Chichester in the Catskills Mountains

The Cabin at Chichester in the Catskills Mountains

9.8 out of 10, Exceptional, (186)
"This is a great little cottage! It’s super clean and has everything you need and plenty of space inside and out. Host was terrific to deal with and made the process seamless and simple. Would definitely stay here again as a great place to stay while enjoying all the area has to offer!! "
The Cabin at Chichester in the Catskills Mountains
Cedar Cottage with hot tub as seen in New York Times escape section.
Exterior

Cedar Cottage with hot tub as seen in New York Times escape section.

9.4 out of 10, Exceptional, (84)
"Diana’s property was the perfect spot to reconnect with old friends. We enjoyed the art, food and music of Woodstock and a side trip to Bethel to check out the Woodstock Museum. Diana’s home was a comfortable place to retreat to after our days of exploring. We would love to make it an annual event. "
Cedar Cottage with hot tub as seen in New York Times escape section.
TOP-RATED! Pristine style+romantic luxury+firepit+walk to town=Brook Cottage Too
Exterior

TOP-RATED! Pristine style+romantic luxury+firepit+walk to town=Brook Cottage Too

10.0 out of 10, Exceptional, (120)
"The property was lovely, and the perfect location. Chelsea was great to work with!"
TOP-RATED! Pristine style+romantic luxury+firepit+walk to town=Brook Cottage Too
Rose Cottage
Outdoor dining

Rose Cottage

9.0 out of 10, Wonderful, (7)
"It's so peaceful there. It was lovely."
Rose Cottage
Private Woodstock cottage. Don't forget your dog!
Interior

Private Woodstock cottage. Don't forget your dog!

10.0 out of 10, Exceptional, (10)
"The property was Great! It was close to town, but far enough away for a little peace and quiet. The place itself was very clean, comfortable, and great for a couples weekend retreat."
Private Woodstock cottage. Don't forget your dog!
Charming Cottage in the Heart of Catskill & Pet Friendly
Outdoor dining

Charming Cottage in the Heart of Catskill & Pet Friendly

10.0 out of 10, Exceptional, (14)
"Really enjoyed my stay! Very thoughtful host. "
Charming Cottage in the Heart of Catskill & Pet Friendly
Catskills Home, 5 Mins to Windham Mtn Resort!
House (2 Bedrooms) | Front of property

Catskills Home, 5 Mins to Windham Mtn Resort!

3.0 star property
10.0 out of 10, Exceptional, (4)
"This place was awesome. Very clean, nicely appointed, very welcoming. Highly recommend and would definitely stay again. Only downside is that it is a second floor unit and the stairs are a little steep but still totally worth it "
Catskills Home, 5 Mins to Windham Mtn Resort!
Private Home ~ All Yours ~ In town ~ fenced in yard ~ Hot Tub ~ Pets welcome!
Banquet hall

Private Home ~ All Yours ~ In town ~ fenced in yard ~ Hot Tub ~ Pets welcome!

9.8 out of 10, Exceptional, (116)
"The location was exceptional, close to restaurants and shops, quiet neighborhood, comfortable bed and the house was well stocked with everything you’d need."
Private Home ~ All Yours ~ In town ~ fenced in yard ~ Hot Tub ~ Pets welcome!
4 Mi to Dtwn Catskill: Mtn-view Home
House (4 Bedrooms) | Interior

4 Mi to Dtwn Catskill: Mtn-view Home

3.0 star property
4 Mi to Dtwn Catskill: Mtn-view Home
Experience Peace in this Beautiful country cottage nestled beneath the mountains
Property grounds

Experience Peace in this Beautiful country cottage nestled beneath the mountains

10.0 out of 10, Exceptional, (6)
"Nice house, well stocked and nice outdoor area/deck."
The price is AED 516
AED 1,184 total
includes taxes & fees
7 Sep - 8 Sep
Experience Peace in this Beautiful country cottage nestled beneath the mountains
Charming 2-bedroom cottage with WiFi and AC in fabulous Phoenicia
Outdoor spa tub

Charming 2-bedroom cottage with WiFi and AC in fabulous Phoenicia

10.0 out of 10, Exceptional, (4)
"Very kind and can tell they put a lot of effort in hosting"
Charming 2-bedroom cottage with WiFi and AC in fabulous Phoenicia
Private hot tub + Modern Cottage
1 bedroom, desk, iron/ironing board, travel crib

Private hot tub + Modern Cottage

9.8 out of 10, Exceptional, (7)
"The property had everything we needed. We enjoyed our stay immensely."
Private hot tub + Modern Cottage
Cozy Catskills Cabin - 12 Mi to Windham Mountain!
House (2 Bedrooms) | Interior

Cozy Catskills Cabin - 12 Mi to Windham Mountain!

3.0 star property
10.0 out of 10, Exceptional, (1)
"It was great. Place was as advertised. Great place to stay, can't wait to book it again! Place was clean, easy to get in, has everything you would need for a long weekend getaway to the catskills."
Cozy Catskills Cabin - 12 Mi to Windham Mountain!
Hits Adjacent | Pet Friendly | Caraway Cottage
TV, fireplace, offices

Hits Adjacent | Pet Friendly | Caraway Cottage

10.0 out of 10, Exceptional, (11)
"We enjoyed our stay, nice location "
The price is AED 918
AED 1,804 total
includes taxes & fees
7 Sep - 8 Sep
Hits Adjacent | Pet Friendly | Caraway Cottage
Catskills Mtn Retreat w/ Panoramic View & Fire Pit
House (3 Bedrooms) | Interior

Catskills Mtn Retreat w/ Panoramic View & Fire Pit

3.0 star property
Catskills Mtn Retreat w/ Panoramic View & Fire Pit
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

Explore a world of travel with Expedia

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Frequently asked questions

How much do cottages in Round Top cost?
Cottages in Round Top range between AED 516 and AED 918 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 196 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.