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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

Compare 158 Cottages in Ruby with updated reviews, rates, and availability.

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
Relaxing Catskill Mountain Cottage.
TV, fireplace, stereo

Relaxing Catskill Mountain Cottage.

10.0 out of 10, Exceptional, (48)
"We really enjoyed our time here"
Relaxing Catskill Mountain Cottage.
Reset and Relax in Luxury Cottage
Property grounds

Reset and Relax in Luxury Cottage

10.0 out of 10, Exceptional, (32)
"Amazing floors, bathroom showers (wow!), and an awesome kitchen."
Reset and Relax in Luxury Cottage
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 $310
includes taxes & fees
$277 per night
May 4 - May 5
Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream
Lily Cottage - a cozy accomodation moments from the beautiful Ashokan reservoir
Fridge, microwave, oven, stovetop

Lily Cottage - a cozy accomodation moments from the beautiful Ashokan reservoir

10.0 out of 10, Exceptional, (31)
"We had a wonderful stay in this quiet gem. Clean, comfortable, cute, and cozy. Highly recommended! "
Lily Cottage - a cozy accomodation moments from the beautiful Ashokan reservoir
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
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 $582
includes taxes & fees
$539 per night
May 1 - May 2
Cozy Mountain Getaway | Hot Tub | Grill | Fire Pit | 5 Min to Kaaterskills Falls
Leggett Cottage, High Falls, NY.

Leggett Cottage, High Falls, NY.

10.0 out of 10, Exceptional, (72)
"Very comfortable, relaxing and clean. Great space. Will be back Thank you very much - Patricia"
Leggett Cottage, High Falls, NY.
A Cozy Farmstead Cottage Amidst Two Barns in Hudson Valley
Exterior

A Cozy Farmstead Cottage Amidst Two Barns in Hudson Valley

9.8 out of 10, Exceptional, (52)
"Very beautiful property! Beautiful night sky views and excellent nature, perfect place for a romantic weekend"
A Cozy Farmstead Cottage Amidst Two Barns in Hudson Valley
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 Ruby

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 $227
includes taxes & fees
$210 per night
May 1 - May 2
Postcard Cabins Eastern Catskills
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 $249
includes taxes & fees
$222 per night
May 1 - May 2
Esopus Creek modern Tiny house Retreat!
Catskills Cabin with Hot Tub near Hiking located Minutes to Belleayre Mountain
Exterior

Catskills Cabin with Hot Tub near Hiking located Minutes to Belleayre Mountain

8.6 out of 10, Excellent, (14)
"My first time staying in a log cabin during the winter. Such a cute and cozy vibe, loved the decor and the quiet scenery. "
Catskills Cabin with Hot Tub near Hiking located Minutes to Belleayre Mountain
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.