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Compare 166 Cottages in Round Top with updated reviews, rates, and availability.

Streamside Cottage Half Mile to Town of Woodstock

10.0 out of 10, Exceptional, (228)
"We totally enjoyed our stay at the cottage! Exactly as advertised, except the views of the river from the home are are even better than pictured. We would definitely recommend!"
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

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. "
The price is SAR 521
SAR 1,261 total
includes taxes & fees
12 Mar - 13 Mar
Experience Peace in this Beautiful country cottage nestled beneath the mountains

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!)

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

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

9.8 out of 10, Exceptional, (109)
"Great location and responsive host."
Private Home ~ All Yours ~ In town ~ fenced in yard ~ Hot Tub ~ Pets welcome!

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 1,047 total
includes taxes & fees
16 Mar - 17 Mar
Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream

The Cabin at Chichester in the Catskills Mountains

9.8 out of 10, Exceptional, (179)
"Very nice cottage that is well kept and clean. Easy 7 min to Phoenicia and 20 min to Belleayre. The manager is very attentive and responsive to messages and questions. Very nice heat for the winter. Good kitchen for a small family. Also had a nice time running the dog in the yard."
The Cabin at Chichester in the Catskills Mountains

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.

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 2-bedroom cottage with WiFi and AC in fabulous Phoenicia

10.0 out of 10, Exceptional, (2)
"The house was well taken care of and suzanne was a very accomadating host"
Charming 2-bedroom cottage with WiFi and AC in fabulous Phoenicia

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

10.0 out of 10, Exceptional, (163)
"Our stay was ideal. Our third time staying at Brooks Cottage. The home is spacious and cozy, the kitchen very well equipped and the setting beautiful and all just a quick walk to the center of Woodstock. Highly recommend for those wanting to be "in town" yet in a very private and quite setting."
TOP RATED Romantic rustic luxury + flowing stream + walk to town = Brook Cottage

LAKE FRONT COTTAGE - YEAR ROUND HOT TUB

9.4 out of 10, Exceptional, (40)
"came here with my partner to celebrate my birthday. it was the perfect place to relax & wind down from living in the city. i would love to come back during warmer months!"
LAKE FRONT COTTAGE - YEAR ROUND HOT TUB

Hits Adjacent | Pet Friendly | Caraway Cottage

10.0 out of 10, Exceptional, (3)
"We had a lovely stay, and wish we had stayed longer. The house was warm, spacious, clean, comfortable. Will definitely be back!"
The price is SAR 559
SAR 1,369 total
includes taxes & fees
14 Mar - 15 Mar
Hits Adjacent | Pet Friendly | Caraway Cottage

20 Miles to Windham Mountain Cozy Getaway: King bed/ Game Room

9.2 out of 10, Wonderful, (15)
"Alex had a great property and was very communicative throughout the whole process. Amazing cabin with tons of amenities"
20 Miles to Windham Mountain Cozy Getaway: King bed/ Game Room

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

Country Cottage with beautiful views and easy access to Catskills activities.

10.0 out of 10, Exceptional, (8)
"Cozy little spot for a quick getaway. Very clean, quiet location. Easy check-in. "
The price is SAR 413
SAR 654 total
includes taxes & fees
16 Mar - 17 Mar
Country Cottage with beautiful views and easy access to Catskills activities.
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 657
SAR 709 total
includes taxes & fees
12 Mar - 13 Mar
Postcard Cabins Eastern Catskills

Streamside Cottage Half Mile to Town of Woodstock

10.0 out of 10, Exceptional, (228)
"We totally enjoyed our stay at the cottage! Exactly as advertised, except the views of the river from the home are are even better than pictured. We would definitely recommend!"
Streamside Cottage Half Mile to Town of Woodstock

Esopus Creek modern Tiny house Retreat!

9.8 out of 10, Exceptional, (23)
"Great little house for the holidays. We were looking for a place nearby or family where we could have our own space but still be close by. "
The price is SAR 581
SAR 840 total
includes taxes & fees
12 Mar - 13 Mar
Esopus Creek modern Tiny house Retreat!
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 SAR 413 and SAR 675 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 166 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.
How can I find cheap cottages in Round Top?
With Expedia’s handy filter tool, booking cheap cottages in Round Top has never been simpler. To view properties that are very pocket friendly, tailor your search results by star rating, amenities and budget.