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Check prices for these dates

Next weekend
21 Saf. - 23 Saf.
In two weeks
28 Saf. - 2 Rab. I
In one month
14 Rab. I - 16 Rab. I
In two months
11 Rab. II - 13 Rab. II

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

Charming Cottage in Private Lake Community (Pet-Friendly!)
Welcome to White Bunny Cottage

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

9.8 out of 10, Exceptional, (27)
"Our family (7 adults and 2 dogs) stayed over the Christmas holiday. The house was just perfect for our group. It was clean, comfortable and cozy! The hosts were responsive and super nice to deal with. We would definitely go back for any future stays in the area. "
Charming Cottage in Private Lake Community (Pet-Friendly!)
20 Miles to Windham Mountain Cozy Getaway: King bed/ Game Room
Game room & futon

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

9.0 out of 10, Wonderful, (14)
"The house was beautiful and comfy."
20 Miles to Windham Mountain Cozy Getaway: King bed/ Game Room
Streamside Cottage Half Mile to Town of Woodstock
Front Entrance to Cottage

Streamside Cottage Half Mile to Town of Woodstock

10.0 out of 10, Exceptional, (228)
"OVERALL, EVERYTHING WAS FANTASTIC. IF I WANTED TO BE REAL PICKY...THE KITCHEN WAS SMALL EVENTHOUGH IT HAD ALMOST EVERYTHING AND THE TV WAS IN THE LIVINGROOM ONLY, NONE IN THE BEDROOM. WE WOLD DEFINATELY STAY THERE AGAIN."
Streamside Cottage Half Mile to Town of Woodstock
Charming Artist's Retreat
enchanted setting among cedar trees

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

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

9.4 out of 10, Exceptional, (80)
"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.
The Cabin at Chichester in the Catskills Mountains
The Cottage at Chichester

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

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

10.0 out of 10, Exceptional, (7)
"The pipes were frozen at the original place, but they were kind enough to upgrade our stay. The mountain view was gorgeous, and the staff were extremely nice."
The price is SAR 413
SAR 654 total
includes taxes & fees
17 Feb - 18 Feb
Country Cottage with beautiful views and easy access to Catskills activities.
Catskills Cottage w/ Deck, 7 Mi to Hunter Mtn
Elka Park Vacation Rental | 3BR | 2BA | 1,200 Sq Ft | Step-Free Entry

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
Private Woodstock cottage. Don't forget your dog!
Living area

Private Woodstock cottage. Don't forget your dog!

10.0 out of 10, Exceptional, (8)
"Irene was wonderful! Will return!"
Private Woodstock cottage. Don't forget your dog!
NEW! Herb Cottage: Historic Artist's Cottage, Wood Stove, Walk to Town!
View of Herb Cottage from the 'show off' herb garden

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

9.8 out of 10, Exceptional, (132)
"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!
Cozy Mountain Getaway | Hot Tub | Grill | Fire Pit | 5 Min to Kaaterskills Falls
Outdoor dining

Cozy Mountain Getaway | Hot Tub | Grill | Fire Pit | 5 Min to Kaaterskills Falls

10.0 out of 10, Exceptional, (1)
"The place was clean, the area was adorable and close to everything, and the communication with the owner was quick and painless. Would stay again. "
Cozy Mountain Getaway | Hot Tub | Grill | Fire Pit | 5 Min to Kaaterskills Falls
TOP RATED Romantic rustic luxury + flowing stream + walk to town = Brook Cottage
The loft also overlooks the spacious living room…

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
Hot Tub and Barn Movie Theater at Route 22 Retreat

Hot Tub and Barn Movie Theater at Route 22 Retreat

10.0 out of 10, Exceptional, (2)
"About 20 minutes from the mountain, my friends and I were very cozy and entertained by amenities. Comfortable and clean and owner very responsive."
The price is SAR 822
SAR 1,343 total
includes taxes & fees
11 Mar - 12 Mar
Hot Tub and Barn Movie Theater at Route 22 Retreat
Saugerties Cottage - relaxing home in nature, close to downtown, HITS & hikes
Living room with L shaped couch + love seat (not featured)

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
Living area

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

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

The price is SAR 1,087
SAR 2,062 total
includes taxes & fees
17 Feb - 18 Feb
Charming Retreat 5 Minute Walk to Main Street & 7 Minutes to Hunter Mountain
Charming 2-bedroom cottage with WiFi and AC in fabulous Phoenicia
Exterior

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
Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream
Teahouse

Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream

9.2 out of 10, Wonderful, (40)
"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 1,035 total
includes taxes & fees
23 Feb - 24 Feb
Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream
Romantic cottage w/hot tub . Close to skiing and breweries . Pet friendly!
Living area

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

10.0 out of 10, Exceptional, (11)
"Short vacation for us to escape the city. This place is very nice and quite, we love it! Thank you!"
Romantic cottage w/hot tub . Close to skiing and breweries . Pet friendly!
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, (59)
"The cottage is adorable and clean and recently renovated. Location is close to town and yet tucked away and peaceful. I have never experienced such wonderful hosts who truly go above and beyond. I'm so thankful I reserved Junebug Cottage for my stay in Woodstock."
Junebug Cottage: peace, love and privacy a short walk to Woodstock village green
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

Micosta Leisure Inn
Terrace/patio

Micosta Leisure Inn

3.0 star property
9.2 out of 10, Wonderful, (93)
"Second time I’ve stayed. Nice place. Owner very communicative. Good prices. "
The price is SAR 487
SAR 526 total
includes taxes & fees
2 Mar - 3 Mar
Micosta Leisure Inn
Hamptons on the Hudson in South Saugerties
Pool

Hamptons on the Hudson in South Saugerties

10.0 out of 10, Exceptional, (14)
"Great property overlooking Hudson River. Close to Woodstock and Rheinbeck. Very good local restaurants for brunch and dinner. Host was great and responded quickly with all questions "
Hamptons on the Hudson in South Saugerties
True Ski On - Ski Off Four Seasons Luxury Mountain Retreat!
Living area

True Ski On - Ski Off Four Seasons Luxury Mountain Retreat!

2.0 star property
9.8 out of 10, Exceptional, (28)
"Great place and location. We have been staying at different condo places for the past 3 Winter Ski season. This is by far the best. Matt is great. "
The price is SAR 589
SAR 1,016 total
includes taxes & fees
5 Mar - 6 Mar
True Ski On - Ski Off Four Seasons Luxury Mountain 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?
You can expect to pay between SAR 413 and SAR 1,087 per night for cottages in Round Top. No matter your budget, an excellent stay is only a few clicks away on Expedia. 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?
Take your pick of 166 cottages in Round Top. Whether you’re taking a trip with the little ones or planning a weekend escape with close friends, Expedia will help you find the ideal space to reacquaint yourself with nature.
Why book your cottage in Round Top with Expedia?
We think that vacays should be simple, so if you’re searching for cottages in Round Top at a great price, Expedia delivers. Keep costs down and choose an economical option far away from the downtown buzz, or splurge on a 5-star cottage to spoil the ones you love most.
How can I find cheap cottages in Round Top?
Expedia is here to help you easily track down cheap cottages in Round Top. To lock in a fantastic stay in a matter of clicks, simply use our convenient filter tool to refine your search results by budget, amenities and star rating.