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Check prices for these dates

Next weekend
22 Aug - 24 Aug
In two weeks
29 Aug - 31 Aug
In one month
12 Sep - 14 Sep
In two months
10 Oct - 12 Oct

Browse Select Round Top Cottages

4 Mi to Dtwn Catskill: Mtn-view Home
House (4 Bedrooms) | Front of property

4 Mi to Dtwn Catskill: Mtn-view Home

3.0 star property
4 Mi to Dtwn Catskill: Mtn-view Home
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
Catskills Home, 5 Mins to Windham Mtn Resort!
House (2 Bedrooms) | Interior

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!
Catskill Mtn Home w/ Deck ~ 1 Miles to Zoom Flume!
House (3 Bedrooms) | Interior

Catskill Mtn Home w/ Deck ~ 1 Miles to Zoom Flume!

3.0 star property
Catskill Mtn Home w/ Deck ~ 1 Miles to Zoom Flume!
Catskills Cottage w/ Deck, 7 Mi to Hunter Mtn
Cottage (3 Bedrooms) | Front of property

Catskills Cottage w/ Deck, 7 Mi to Hunter Mtn

3.0 star property
Catskills Cottage w/ Deck, 7 Mi to Hunter Mtn
Private 7-acre Retreat: On-site Pond, Streams
House (3 Bedrooms) | Interior

Private 7-acre Retreat: On-site Pond, Streams

3.0 star property
Private 7-acre Retreat: On-site Pond, Streams
Grand Windham Retreat w/ Fire Pit & Game Room
House (2 Bedrooms) | Interior

Grand Windham Retreat w/ Fire Pit & Game Room

3.0 star property
Grand Windham Retreat w/ Fire Pit & Game Room
Charming Cottage w/ Yard - 2 Mi to Tinker St!
Cottage (2 Bedrooms) | Interior

Charming Cottage w/ Yard - 2 Mi to Tinker St!

3.0 star property
Charming Cottage w/ Yard - 2 Mi to Tinker St!
Catskill Park Farm by Avantstay Huge Yard, Fire Pit Near Windham Ski Resort
House (4 Bedrooms) | Interior

Catskill Park Farm by Avantstay Huge Yard, Fire Pit Near Windham Ski Resort

3.0 star property
Catskill Park Farm by Avantstay Huge Yard, Fire Pit Near Windham Ski Resort
Quaint Woodstock Escape - 2 Mi to Tinker St!
House (3 Bedrooms) | Interior

Quaint Woodstock Escape - 2 Mi to Tinker St!

3.0 star property
Quaint Woodstock Escape - 2 Mi to Tinker St!
Mtn Views + On-site Hiking Trails: Catskills Cabin
House (2 Bedrooms) | Front of property

Mtn Views + On-site Hiking Trails: Catskills Cabin

3.0 star property
Mtn Views + On-site Hiking Trails: Catskills Cabin
Retreat w/ Deck & Grill: 1 Mi to Hunter Mtn Resort
House (6 Bedrooms) | Interior

Retreat w/ Deck & Grill: 1 Mi to Hunter Mtn Resort

3.0 star property
Retreat w/ Deck & Grill: 1 Mi to Hunter Mtn Resort
7 Mi to Kaaterskill Falls: Home w/ Mountain Views!
House (2 Bedrooms) | Interior

7 Mi to Kaaterskill Falls: Home w/ Mountain Views!

3.0 star property
7 Mi to Kaaterskill Falls: Home w/ Mountain Views!
Secluded Elka Park Cabin: Hot Tub & Fire Pit!
House (2 Bedrooms) | Interior

Secluded Elka Park Cabin: Hot Tub & Fire Pit!

3.0 star property
Secluded Elka Park Cabin: Hot Tub & Fire Pit!
Saugerties Farmhouse: Sauna & Countryside Views
House (3 Bedrooms) | Interior

Saugerties Farmhouse: Sauna & Countryside Views

3.0 star property
10.0 out of 10, Exceptional, (1)
"My stay here was short—just three nights—but it was absolutely perfect. The house is beautiful and comfortable, equipped with everything I needed to feel welcome. I particularly loved the heated floor in the bathroom and the cozy ambiance throughout the entire house. My favorite part was sitting on the porch, enjoying coffee and watching the birds. I definitely plan to return for another stay. The house was easy to find and impeccably clean. Communication was seamless, and the instructions were...
Saugerties Farmhouse: Sauna & Countryside Views
Sleepy Hollow Lake Home w/ Deck, Pool Access!
House (3 Bedrooms) | Interior

Sleepy Hollow Lake Home w/ Deck, Pool Access!

3.0 star property
Sleepy Hollow Lake Home w/ Deck, Pool Access!
Cozy Catskills Home w/ Pond on 2 Acres!
House (2 Bedrooms) | Interior

Cozy Catskills Home w/ Pond on 2 Acres!

3.0 star property
10.0 out of 10, Exceptional, (2)
"Absolutely gorgeous property, the owner is awesome and can’t forget Leo the cat. "
Cozy Catskills Home w/ Pond on 2 Acres!
Fully Remodeled Saugerties Retreat on 7 Acres!
House (1 Bedroom) | Interior

Fully Remodeled Saugerties Retreat on 7 Acres!

3.0 star property
Fully Remodeled Saugerties Retreat on 7 Acres!
Woodstock Getaway w/ Hot Tub ~ 2 Mi to Dtwn!
House (4 Bedrooms) | Interior

Woodstock Getaway w/ Hot Tub ~ 2 Mi to Dtwn!

3.0 star property
Woodstock Getaway w/ Hot Tub ~ 2 Mi to Dtwn!
Updated/pet-friendly Cabin By Hikes and Woodstock!
House (2 Bedrooms) | Interior

Updated/pet-friendly Cabin By Hikes and Woodstock!

3.0 star property
8.0 out of 10, Very good, (1)
"This is a lovely small cottage in the middle of a forest. It has two bedrooms upstairs and bathroom downstairs. There was not enough linens and no bathroom appliances. "
Updated/pet-friendly Cabin By Hikes and Woodstock!
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
"Excellent "
Jennifer 2-night trip
Posted 6 hours ago
Holiday Inn Express & Suites Kingston-Ulster by IHG

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 112 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 travelling 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 favourite people.