Search Round Top Cottage Rentals from CA $218

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Browse Select Round Top Cottages

"A beautiful quiet setting! "

CA $463 total

includes taxes & fees

Sep 2 - Sep 3

Set amidst a serene wooded area, this two-story house offers a retreat with a well-manicured lawn and a small deck.

"We were in Woodstock for a wedding. Junebug Cottage was perfect for our stay! "

Experience the charm of Pinewood Inn, featuring a covered porch and a cozy gazebo.

"cute fun place. loved the hot tub "

Experience rural living at this serene farmstead, surrounded by open fields and a simple, functional architecture.

"We enjoyed ourselves,relaxed,visited had a very enjoyable bisit"

Escape to a serene cabin nestled in a wooded area, surrounded by lush greenery and a charming front porch.

"It's so peaceful there. It was lovely."

Cozy cabin nestled in a dense forest, offering a serene retreat with a central window and small porch area.

"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. "

Traditional architecture meets serene gardens in this charming two-story building with a welcoming porch.

"We had a marvelous visit!"

Set amidst a tranquil forest, this charming home features a two-story facade with a welcoming yellow door and a picket fence.

"The location was exceptional, close to restaurants and shops, quiet neighborhood, comfortable bed and the house was well stocked with everything you’d need."

CA $994 total

includes taxes & fees

Aug 23 - Aug 24

Situated in a serene landscape, this charming home offers a peaceful retreat.

"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!! "

Enjoy a peaceful retreat with a view of the lush forest from this outdoor deck, featuring a table, chairs, and potted plants.

"This is a great place to stay. Really loved the fire pit by the creek for evening cocktails and conversation."

CA $423 total

includes taxes & fees

Aug 24 - Aug 25

"Enjoyed our stay!"

Relax in this stylish room with a large bed, sofa, and dining table, perfect for unwinding and enjoying your stay.

"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."

Enjoy al fresco dining on the deck with a barbecue grill and comfortable seating.

"We loved the stay at this cabin."

Enjoy outdoor dining or relaxation on the upper-floor balcony overlooking a beautifully maintained garden.

"The hosts had thought of everything to make our stay comfortable - lovely bright rooms, well stocked kitchen, plush linens and towels, within walking distance of all restaurants and shops and a beautiful stream and lawn outside! Excellent!"

Escape to a secluded cabin surrounded by tall trees and a gravel path, offering a peaceful retreat.

"This was just what we were looking for. The host was very quick to respond to any of my questions. We enjoyed the location and all the amenities. The outdoor grill, outdoor firepit and inside fireplace were enjoyed and it was a nice bonus that there was plenty of firewood."