Search Cottages in Round Top

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Compare Cottages in Round Top with updated reviews, rates, and availability.

Streamside Cottage Half Mile to Town of Woodstock

10.0 out of 10, Exceptional, (230)
"The house was just as advertised. It is cozy and clean, on a gorgeous stream, and close to town. We'll definitely be back!"
Streamside Cottage Half Mile to Town of Woodstock

ADORABLE CREEK COTTAGE Charming Original Details, Fireplace, Near Town, WiFi

10.0 out of 10, Exceptional, (77)
"This was perfect place to spend time with friends!"
ADORABLE CREEK COTTAGE Charming Original Details, Fireplace, Near Town, WiFi

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

10.0 out of 10, Exceptional, (60)
"We stayed in Junebug Cottage for a long weekend getaway this winter, and it was everything we could have asked for in a quick couple’s getaway. From initial booking, John & Mollie were incredibly communicative and made sure we felt welcomed and had all the information we needed about the space and the area.The cottage is beautiful, immaculately kept and so clean. It has everything you could need for a weekend stay. We had a bad snow/ice storm the weekend we were there, and the cottage was so...
Junebug Cottage: peace, love and privacy a short walk to Woodstock village green

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

9.8 out of 10, Exceptional, (27)
"We enjoyed ourselves,relaxed,visited had a very enjoyable bisit"
Charming Cottage in Private Lake Community (Pet-Friendly!)

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

9.8 out of 10, Exceptional, (111)
"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!

Experience Peace in this Beautiful country cottage nestled beneath the mountains

10.0 out of 10, Exceptional, (4)
"This stay was exactly what we needed—quiet, cozy, and super relaxing. The house was well stocked for a comfortable visit, and the outdoor space was amazing for both us and our pup to explore. Bridget was so easy to communicate with, which made everything stress-free, and we loved the thoughtful honey gift—it made for the best tea moments. Highly recommend. "
Experience Peace in this Beautiful country cottage nestled beneath the mountains

The Cabin at Chichester in the Catskills Mountains

9.8 out of 10, Exceptional, (180)
"My son and I enjoyed staying at the house while on a trip for ski racing at Belleayre. The house was clean and set up well. It seems like it would be very nice in the warm months. There is no cell service anywhere nearby or even down"
The Cabin at Chichester in the Catskills Mountains

Romantic cottage w/hot tub . Close to skiing and breweries . Pet friendly!

10.0 out of 10, Exceptional, (13)
"Would recommend to anyone. "
Romantic cottage w/hot tub . Close to skiing and breweries . Pet friendly!

Charming Artist's Retreat

10.0 out of 10, Exceptional, (133)
"This super cozy cabin is perfectly located and close to major Catskills towns. Yet, Maureen has done an amazing job at creating a space that feels far away from every thing. Town and groceries are less than 10mins away. We visited Kingston and Woodstock - also nearby. The nearby trail options are endless too.This home is exemplar of what VRBO stands for. Thank you, Maureen! "
Charming Artist's Retreat

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

10.0 out of 10, Exceptional, (116)
"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

Loblolly Cottage - Enchanting Retreat set among towering pines.

10.0 out of 10, Exceptional, (37)
"Was a wonderful little cottage , we both enjoyed our stay and had a gracious host"
Loblolly Cottage - Enchanting Retreat set among towering pines.

Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream

9.2 out of 10, Wonderful, (41)
"2 nights in a delightful cottage. It is small but delightfully appointed. The highlight was this clean, warm little cottage is perched directly on swft stream. We left the backdoor open at night!"
The price is SAR 675
SAR 1,028 total
includes taxes & fees
30 Mar - 31 Mar
Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream

Catskills Cottage w/ Deck, 7 Mi to Hunter Mtn

9.6 out of 10, Exceptional, (16)
"I had a wonderful weekend stay at this lovely cabin! It is beautiful and cozy, all necessities provided. The check in and check out processes were easy, the guest contact was easy to contact and pleasant to speak with. The views are gorgeous, and the neighbors are so kind. Loved being here and definitely plan to come back! Will tell all my friends! Thank you!"
Catskills Cottage w/ Deck, 7 Mi to Hunter Mtn

Charming Retreat 5 Minute Walk to Main Street & 7 Minutes to Hunter Mountain

10.0 out of 10, Exceptional, (2)
"Matched the pictures and responsive host. Really good location for skiing and town."
The price is SAR 473
SAR 1,388 total
includes taxes & fees
25 Mar - 26 Mar
Charming Retreat 5 Minute Walk to Main Street & 7 Minutes to Hunter Mountain

Charming Cottage in the Heart of Catskill & Pet Friendly

10.0 out of 10, Exceptional, (12)
"Really enjoyed my stay! Very thoughtful host. "
Charming Cottage in the Heart of Catskill & Pet Friendly

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

10.0 out of 10, Exceptional, (164)
"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!"
TOP RATED Romantic rustic luxury + flowing stream + walk to town = Brook Cottage

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

9.8 out of 10, Exceptional, (133)
"The cottage was a great place to stay with great easy access to downtown Woodstock, Kingston, and Rhineback. Lots of attention to detail by the owner. For example, there are plenty of kitchen utensils and dishes and tons of books and DVD's. The DVD's are displayed in alphabetical order and there are multiple heat zones that enabled the bathroom to independently be very warm while keeping the remaining zones more temperate. The place has everything you need for a cozy stay. The only...
NEW! Herb Cottage: Historic Artist's Cottage, Wood Stove, Walk to Town!

Saugerties Cottage - relaxing home in nature, close to downtown, HITS & hikes

10.0 out of 10, Exceptional, (5)
"quiet sanctuary close to Woodstock and saugerties"
Saugerties Cottage - relaxing home in nature, close to downtown, HITS & hikes

Modern Country Cottage

10.0 out of 10, Exceptional, (2)
"We were looking for a quiet getaway and found it! The house is updated, immaculate and fully appointed. It is well laid out with very comfortable furniture. There is a deck with a forest and a pond in the backyard, and a short walk through the forest to a creek. Very peaceful, with things to do in the area."
Modern Country Cottage

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

9.2 out of 10, Wonderful, (82)
"This was our fifth time staying at the cabin and as always it was perfect. We stayed the week of Thanksgiving and cooked a full feast easily with the appliances and cookware found in the kitchen. We even woke up to snow a few times that week. We enjoyed the hot tub at night and the fireplace each day. Beds are comfy, rooms are cozy and location is ideal. With close proximity to Woodstock, Tannersville and West Kill we were able visit some of our favorite places in the mountains. We’ll be back....
Cedar Cottage with hot tub as seen in New York Times escape section.
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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Other property types in Round Top

Postcard Cabins Eastern Catskills

2.0 star property
8.0 out of 10, Very Good, (4)
"We love our Bartow cabin, it was so cozy and relaxing for us. A perfect getaway from the city life. Will definitely stay again. "
The price is SAR 750
SAR 810 total
includes taxes & fees
25 Mar - 26 Mar
Postcard Cabins Eastern Catskills

Micosta Leisure Inn

3.0 star property
9.2 out of 10, Wonderful, (94)
"Lovely caring owner. Beautiful room Hope to stay there again!"
The price is SAR 487
SAR 526 total
includes taxes & fees
7 Apr - 8 Apr
Micosta Leisure Inn

Streamside Cottage Half Mile to Town of Woodstock

10.0 out of 10, Exceptional, (230)
"The house was just as advertised. It is cozy and clean, on a gorgeous stream, and close to town. We'll definitely be back!"
Streamside Cottage Half Mile to Town of 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.

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 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?
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