Search Round Top Cottage Rentals from CA $249

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Check prices for these dates

Next weekend
May 9 - May 11
In two weeks
May 16 - May 18
In one month
May 30 - Jun 1
In two months
Jun 27 - Jun 29

Browse Select Round Top Cottages

Streamside Cottage Half Mile to Town of Woodstock
Aerial view

Streamside Cottage Half Mile to Town of Woodstock

10.0 out of 10, Exceptional, (234)
"Beautiful stream right behind the property"
Streamside Cottage Half Mile to Town of Woodstock
Private Home ~ All Yours ~ In town ~ fenced in yard ~ Hot Tub ~ Pets welcome!
Banquet hall

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

9.8 out of 10, Exceptional, (112)
"This house couldn’t be closer to town - literally steps from our favorite restaurant. Perfect for our family of three (plus our dog) but would also work well for two couples (with a loft area that could sleep a kid or two on the couch or an air mattress). Great communication with our host who was super responsive and accommodating. All the amenities we needed and the hot tub was a great bonus. We’d stay again in a heartbeat! "
Private Home ~ All Yours ~ In town ~ fenced in yard ~ Hot Tub ~ Pets welcome!
TOP-RATED! Pristine style+romantic luxury+firepit+walk to town=Brook Cottage Too
Outdoor dining

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

10.0 out of 10, Exceptional, (118)
"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
Romantic cottage w/hot tub . Close to skiing and breweries . Pet friendly!
Terrace/patio

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

10.0 out of 10, Exceptional, (13)
"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!
ADORABLE CREEK COTTAGE Charming Original Details, Fireplace, Near Town, WiFi
Outdoor dining

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

10.0 out of 10, Exceptional, (79)
"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
Exterior

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

10.0 out of 10, Exceptional, (61)
"We had a great stay. The property was perfectly located just outside the town center. "
Junebug Cottage: peace, love and privacy a short walk to Woodstock village green
Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream
Property grounds

Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream

9.0 out of 10, Wonderful, (42)
"This is a great place to stay. Really loved the fire pit by the creek for evening cocktails and conversation."
The price is CA $249
CA $429 total
includes taxes & fees
May 4 - May 5
Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream
The Cabin at Chichester in the Catskills Mountains

The Cabin at Chichester in the Catskills Mountains

9.8 out of 10, Exceptional, (181)
"Really clean property and amazing manager"
The Cabin at Chichester in the Catskills Mountains
NEW! Herb Cottage: Historic Artist's Cottage, Wood Stove, Walk to Town!
TV, DVD player, books, video library

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

9.8 out of 10, Exceptional, (133)
"We had a marvelous visit!"
NEW! Herb Cottage: Historic Artist's Cottage, Wood Stove, Walk to Town!
Charming Artist's Retreat
Fridge, microwave, oven, stovetop

Charming Artist's Retreat

10.0 out of 10, Exceptional, (134)
"Enjoyed our stay!"
Charming Artist's Retreat
Charming Cottage in Private Lake Community (Pet-Friendly!)
Fridge, microwave, oven, stovetop

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

9.8 out of 10, Exceptional, (27)
"Very nice and cozy and comfortable! "
Charming Cottage in Private Lake Community (Pet-Friendly!)
Catskills Cottage w/ Deck, 7 Mi to Hunter Mtn
TV, books

Catskills Cottage w/ Deck, 7 Mi to Hunter Mtn

9.6 out of 10, Exceptional, (16)
"We loved the stay at this cabin."
Catskills Cottage w/ Deck, 7 Mi to Hunter Mtn
Stream Come True! Ski, hike, spa, flow, relax...
2 bedrooms, free WiFi, bed sheets

Stream Come True! Ski, hike, spa, flow, relax...

10.0 out of 10, Exceptional, (5)
"Tranquil sounds of flowing water all day was very relaxing. Property was just as described. Thank you!"
Stream Come True! Ski, hike, spa, flow, relax...
Charming Retreat 5 Minute Walk to Main Street & 7 Minutes to Hunter Mountain
Interior

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

10.0 out of 10, Exceptional, (3)
"Matched the pictures and responsive host. Really good location for skiing and town."
Charming Retreat 5 Minute Walk to Main Street & 7 Minutes to Hunter Mountain
Loblolly Cottage - Enchanting Retreat set among towering pines.
1 bedroom, desk, free WiFi, bed sheets

Loblolly Cottage - Enchanting Retreat set among towering pines.

10.0 out of 10, Exceptional, (37)
"My wife and I had a wonderful stay. Super cozy, romantic and accommodating. We had a wonderful time and William was very responsive. Would highly recommend and stay again. "
Loblolly Cottage - Enchanting Retreat set among towering pines.
Cozy Mountain Getaway | Hot Tub | Grill | Fire Pit | 5 Min to Kaaterskills Falls
Outdoor spa tub

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

10.0 out of 10, Exceptional, (2)
"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. "
The price is CA $279
CA $804 total
includes taxes & fees
May 1 - May 2
Cozy Mountain Getaway | Hot Tub | Grill | Fire Pit | 5 Min to Kaaterskills Falls
Hits Adjacent | Pet Friendly | Caraway Cottage
TV, fireplace, offices

Hits Adjacent | Pet Friendly | Caraway Cottage

10.0 out of 10, Exceptional, (5)
"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 CA $278
CA $578 total
includes taxes & fees
May 4 - May 5
Hits Adjacent | Pet Friendly | Caraway Cottage
Spacious Cozy Getaway in the Catskills: King bed/ Game Room
Miscellaneous

Spacious Cozy Getaway in the Catskills: King bed/ Game Room

9.2 out of 10, Wonderful, (15)
"The house was beautiful and comfy."
Spacious Cozy Getaway in the Catskills: King bed/ Game Room
Saugerties Cottage - relaxing home in nature, close to downtown, HITS & hikes
Property grounds

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
Private kitchen

Modern Country Cottage

10.0 out of 10, Exceptional, (2)
Modern Country Cottage
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
Exterior

Postcard Cabins Eastern Catskills

2.0 star property
8.6 out of 10, Excellent, (10)
"We always live these cabins & we've been coming for years!"
The price is CA $242
CA $314 total
includes taxes & fees
May 1 - May 2
Postcard Cabins Eastern Catskills
Micosta Leisure Inn
Balcony

Micosta Leisure Inn

3.0 star property
9.2 out of 10, Wonderful, (96)
"Third or fourth time staying. Always a pleasure "
The price is CA $180
CA $194 total
includes taxes & fees
May 13 - May 14
Micosta Leisure Inn
Esopus Creek modern Tiny house Retreat!
Outdoor dining

Esopus Creek modern Tiny house Retreat!

9.8 out of 10, Exceptional, (25)
"Had a fantastic stay for a quick overnight trip to ski."
The price is CA $214
CA $338 total
includes taxes & fees
May 6 - May 7
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.