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Compare 688 Vacation Homes in Round Top with updated reviews, rates, and availability.

Lakefront Luxe: Private Dock, Game Rm, Near Hudson & Ski/Tubing

10.0 out of 10, Exceptional, (128)
"Stayed at the house over Christmas with family. The house is well-appointed with excellent heat. Hosts were excellent at communicating with us when we had questions."
Lakefront Luxe: Private Dock, Game Rm, Near Hudson & Ski/Tubing

Quaint Cottage with Peloton Bike & Sauna near Skiing

9.8 out of 10, Exceptional, (8)
"Wonderful location close to Woodstock and hiking. Enjoyed the quiet solitude and this super cozy home with gleaming hardwood floors and comfy sofa. Very clean and neat. We Would stay again and there was an overnight snowfall that created a glistening storybook setting. So beautiful in winter and it was a fun birthday weekend! Cheers! Thank you to my hosts! "
The price is AED 345
AED 951 total
includes taxes & fees
26 Jan - 27 Jan
Quaint Cottage with Peloton Bike & Sauna near Skiing

Magical Home Located in Windham and Catskills

2.0 star property
10.0 out of 10, Exceptional, (8)
"Great location and clean and owner was generous. "
Magical Home Located in Windham and Catskills

The Tipsy Gypsy

9.8 out of 10, Exceptional, (20)
"Great location. Very clean and cozy. Very nice people to work with. My kids loved it as well."
The price is AED 826
AED 1,653 total
includes taxes & fees
26 Jan - 27 Jan
The Tipsy Gypsy

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 AED 569
AED 815 total
includes taxes & fees
24 Jan - 25 Jan
Esopus Creek modern Tiny house Retreat!

Studio 3 BEDS-SLP 3. Downtown Windham. Next to the Ski Resort. Close to Hunter

9.4 out of 10, Exceptional, (28)
"Wonderful coszy spot perfect location for singles and couples even family "
The price is AED 349
AED 533 total
includes taxes & fees
26 Jan - 27 Jan
Studio 3 BEDS-SLP 3. Downtown Windham. Next to the Ski Resort. Close to Hunter

Dancing Horse Farm in Windham: Spectacular 9 Bedroom Home, 30 Acres, Ski Lodge

10.0 out of 10, Exceptional, (148)
"We went with 3 families (kids 4-14) and had the best time !! Great house for a group. We were 18 total. Awesome location. The kids loved playing in the snow and visiting with the cows! The grounds were really beautiful. The house had plenty of room. The bunk rooms were awesome for kids. Upstairs master has a tiny room a one single bed off of it, perfect for a toddler or baby. Two living rooms for multiple sports game watching. Short drive to the mountain and restaurants. We even brought food...
Dancing Horse Farm in Windham: Spectacular 9 Bedroom Home, 30 Acres, Ski Lodge

SPECTACULAR CATSKILL OASIS with Hunter Mountain Views, INCREDIBLE LOCATION!!!

9.8 out of 10, Exceptional, (19)
"Really love the mountains and fall leaves and lots to do and see in the area, unlike some resort towns. The accommodations were very nice, thank you! "
The price is AED 878
AED 1,853 total
includes taxes & fees
18 Feb - 19 Feb
SPECTACULAR CATSKILL OASIS with Hunter Mountain Views, INCREDIBLE LOCATION!!!

Luxurious & Enchanting Log House in Heart of Hudson Valley/Catskills, Upstate NY

10.0 out of 10, Exceptional, (36)
"We rented this house for ourselves and our friends for our wedding weekend around the corner. It was the best decision, large group and we had plenty of places to sleep, the yard gave ample space for activities, the sound system kept us entertained, and the kitchen made hosting a large group a breeze. Yuri was amazing in making himself available and our stay memorable. Can’t wait to visit again!"
Luxurious & Enchanting Log House in Heart of Hudson Valley/Catskills, Upstate NY

Country Estate Outside Hudson - Heated Extra Large Pool w/ Outdoor Barrel Sauna

10.0 out of 10, Exceptional, (23)
"We stayed at the house with extended family for a ski trip weekend at Catamount. The drive was 30mins away and the house a wonderful place to relax together after a long day on the mountain. The house is spacious, bright, clean and tastefully decorated. The layout is comfortable and practical. The lovely, open-kitchen was well-equipped and allowed us all to gather and chat pre and post dinner. The sauna is a great perk with gorgeous views! Highly recommend! Would love to come back in the summer...
Country Estate Outside Hudson - Heated Extra Large Pool w/ Outdoor Barrel Sauna

Experience Woodstock charm while staying in a cozy cabin in the woods

9.8 out of 10, Exceptional, (22)
"Missy was a fantastic communicator from the beginning. Her place was perfect for two families of four. The house is well kept and the perfect distance from town, hiking, Opus 40 and much more. Highly recommend."
Experience Woodstock charm while staying in a cozy cabin in the woods

Charming cottage with lake access, wood burning fire place, and WiFi

2.0 star property
10.0 out of 10, Exceptional, (1)
"Oriana was awesome and I look forward to staying there again."
Charming cottage with lake access, wood burning fire place, and WiFi

Cozy Hudson River Waterfront, 3 Bdrm Pool/Quiet Street/Great Views/HITS 2 miles

2.0 star property
10.0 out of 10, Exceptional, (4)
"Great pool on the river! Loved watching th La ge barges go by! "
Cozy Hudson River Waterfront, 3 Bdrm Pool/Quiet Street/Great Views/HITS 2 miles

Inviting, Cozy Catskills Home - Primed for Fall!

10.0 out of 10, Exceptional, (2)
"Very nice house conveniently located on Rt28. We enjoyed our stay there for a weekend. Unfortunately the fireplace did not work but the living room was cozy anyway. "
Inviting, Cozy Catskills Home - Primed for Fall!

Modern Cabin CLOSE to skiing, w/mountain & pond views, Hot Tub, games and more!!

9.8 out of 10, Exceptional, (73)
"We had a great time. Nice house. Quiet and comfortable. Thank you. "
Modern Cabin CLOSE to skiing, w/mountain & pond views, Hot Tub, games and more!!

Beautiful new house 3/4 mile from Hunter Mountain

9.6 out of 10, Exceptional, (126)
"Great location! Perfect size house for a large family. Had a great time!"
Beautiful new house 3/4 mile from Hunter Mountain

7Bdr/5Bth, Amazing View, Lake,1/2 ml Ski Hunter Mountain, Hot Tub/Sauna. Swim

10.0 out of 10, Exceptional, (212)
"We had a fantastic stay in Valentyna's home. We had a large group of 16 at the home during labor day weekend. We found the house large, clean, updated and had plenty of space. The bedrooms are roomy, the living spaces are even larger than pictured, and the five different outdoor areas are fantastic. The house has every amenity you can ask for. Direct lake access is steps from the house and the house is close to Hunter for the winter months. We had a great time and would happily stay again. "
The price is AED 1,833
AED 3,302 total
includes taxes & fees
4 Feb - 5 Feb
7Bdr/5Bth, Amazing View, Lake,1/2 ml Ski Hunter Mountain, Hot Tub/Sauna. Swim

Beautiful House 1 Mile From Hunter Mountain

9.6 out of 10, Exceptional, (121)
"My family really enjoyed their stay at this house. The kids were super excited about the game room. The house is very clean and in a perfect location for the activities you want to do. They have everything you need to make your vacation as enjoyable as possible. Communication with the host was excellent, he was an accessible person. Highly recommended."
Beautiful House 1 Mile From Hunter Mountain

Cortland by AvantStay | Charming Heritage Estate w/ Private Lake & Pool

9.4 out of 10, Exceptional, (13)
"We had a lovely stay for our family of 5 during the week before xmas. The home was well appointed, with all the normal needs we have to cook, etc... The house was very quiet despite 5 of us being there. Everyone had their own space. Very cozy. Loved that there were games to play, we had a great family round of monopoly!The property manager was so responsive. We felt very supported and attended to. Despite the cold weather the house stayed plenty warm as well!We highly recommend this home and...
Cortland by AvantStay | Charming Heritage Estate w/ Private Lake & Pool

River House by AvantStay | Historic & Secluded Estate on the Hudson River w/Pool

9.8 out of 10, Exceptional, (13)
"This place had enough room for family of 24. Lots of space to hangout at. Will book again"
River House by AvantStay | Historic & Secluded Estate on the Hudson River w/Pool
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

3.0 star property
9.2 out of 10, Wonderful, (92)
"Second time I’ve stayed. Nice place. Owner very communicative. Good prices. "
The price is AED 477
AED 515 total
includes taxes & fees
6 Feb - 7 Feb
Micosta Leisure Inn

'A Place in the Woods' - Cabin on Chloe's Lake on 23 acres near Woodstock, NY

8.2 out of 10, Very Good, (42)
"We had a great time at the cabin! It was the perfect escape from the city. The view was gorgeous, and the cabin had everything we needed. We also tried to use the canoe but the padlock is stuck, it might be rusted/need to be replaced. Otherwise everything was perfect!"
The price is AED 459
AED 533 total
includes taxes & fees
26 Jan - 27 Jan
'A Place in the Woods' - Cabin on Chloe's Lake on 23 acres near Woodstock, NY

Dancing Horse Farm in Windham: Spectacular 9 Bedroom Home, 30 Acres, Ski Lodge

10.0 out of 10, Exceptional, (148)
"We went with 3 families (kids 4-14) and had the best time !! Great house for a group. We were 18 total. Awesome location. The kids loved playing in the snow and visiting with the cows! The grounds were really beautiful. The house had plenty of room. The bunk rooms were awesome for kids. Upstairs master has a tiny room a one single bed off of it, perfect for a toddler or baby. Two living rooms for multiple sports game watching. Short drive to the mountain and restaurants. We even brought food...
Dancing Horse Farm in Windham: Spectacular 9 Bedroom Home, 30 Acres, Ski Lodge
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.