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Check prices for these dates

Next weekend
16 May - 18 May
In two weeks
23 May - 25 May
In one month
6 Jun - 8 Jun
In two months
4 Jul - 6 Jul

Compare 890 Vacation Homes in Round Top with updated reviews, rates, and availability.

Esopus Creek modern Tiny house Retreat!
Outdoor dining

Esopus Creek modern Tiny house Retreat!

9.6 out of 10, Exceptional, (28)
"Had a fantastic stay for a quick overnight trip to ski."
The price is AED 569
AED 897 total
includes taxes & fees
6 May - 7 May
Esopus Creek modern Tiny house Retreat!
HOT TUB w/ POOL, STREAM on 7 Acres, JUST 2 MINUTES FROM TOWN
Terrace/patio

HOT TUB w/ POOL, STREAM on 7 Acres, JUST 2 MINUTES FROM TOWN

10.0 out of 10, Exceptional, (95)
"The 3 bedrooms house is located on a small stream. We saw multiple deer around the property. The town is a short drive away with lots of shops. We spent the weekend relaxing in the hot tub and playing games. I would definitely recommend this place"
HOT TUB w/ POOL, STREAM on 7 Acres, JUST 2 MINUTES FROM TOWN
Hamptons on the Hudson in South Saugerties
Terrace/patio

Hamptons on the Hudson in South Saugerties

9.8 out of 10, Exceptional, (19)
"Beautiful home and great location . "
Hamptons on the Hudson in South Saugerties
Beautiful new house 3/4 mile from Hunter Mountain
Exterior

Beautiful new house 3/4 mile from Hunter Mountain

9.6 out of 10, Exceptional, (128)
"Great location! Perfect size house for a large family. Had a great time!"
Beautiful new house 3/4 mile from Hunter Mountain
Luxurious Woodstock Home Rental Catskill Mountains Views & Private Retreat
Fridge, microwave, oven, stovetop

Luxurious Woodstock Home Rental Catskill Mountains Views & Private Retreat

10.0 out of 10, Exceptional, (118)
"super easy - we'll be back"
Luxurious Woodstock Home Rental Catskill Mountains Views & Private Retreat
SPECTACULAR Hunter Mountain Views, INCREDIBLE LOCATION-2 minutes to slopes !!
Smart TV, fireplace, computer monitors

SPECTACULAR Hunter Mountain Views, INCREDIBLE LOCATION-2 minutes to slopes !!

9.6 out of 10, Exceptional, (25)
"Had a great 2 night stay. Location is close to Hunter. "
SPECTACULAR Hunter Mountain Views, INCREDIBLE LOCATION-2 minutes to slopes !!
A'Neils Windham Ski Lodge & Family Retreat
Outdoor dining

A'Neils Windham Ski Lodge & Family Retreat

10.0 out of 10, Exceptional, (28)
"A wonderful space for a family reunion ski get away. Enough personal space for each while also offering great shared space for warm gatherings and meals. Host was very accommodating and easily available. We would definitely stay again!"
A'Neils Windham Ski Lodge & Family Retreat
7Bdr/5Bth, Amazing View, Lake/Swim. 1/2 ml Ski Hunter Resort, Hot Tub/Sauna.Golf
Outdoor spa tub

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

10.0 out of 10, Exceptional, (217)
"Excellent communication. Cozy home. Really enjoyed our stay. "
The price is AED 1,466
AED 3,126 total
includes taxes & fees
6 May - 7 May
7Bdr/5Bth, Amazing View, Lake/Swim. 1/2 ml Ski Hunter Resort, Hot Tub/Sauna.Golf
Brand New House with Huge patio overlooks Esopus Creek at Lake Katrine
Private kitchen

Brand New House with Huge patio overlooks Esopus Creek at Lake Katrine

10.0 out of 10, Exceptional, (11)
"Immaculate house beautiful furnishings Very comfortable Everything you need for a relaxing stay Fully equipped"
The price is AED 544
AED 1,362 total
includes taxes & fees
13 May - 14 May
Brand New House with Huge patio overlooks Esopus Creek at Lake Katrine
Quaint Cottage w/ Peloton & Sauna near Hiking
Property grounds

Quaint Cottage w/ Peloton & Sauna near Hiking

9.6 out of 10, Exceptional, (17)
"Once you connect to the wifi you can use your phone. The landlord as well as property manager are helpful and actually respond. Property is very peaceful!"
Quaint Cottage w/ Peloton & Sauna near Hiking
Cozy Retreat w/ Hot Tub, on Sleepy Hollow Lake!
TV, fireplace, books

Cozy Retreat w/ Hot Tub, on Sleepy Hollow Lake!

9.0 out of 10, Wonderful, (22)
"We had a great time staying at this house. It was quiet and relaxing. We would stay again!"
Cozy Retreat w/ Hot Tub, on Sleepy Hollow Lake!
◆DREAM Modern Cabin in the Woods ◆ Hot tub + Sauna
Outdoor dining

◆DREAM Modern Cabin in the Woods ◆ Hot tub + Sauna

9.6 out of 10, Exceptional, (5)
"Property is beautiful - hot tub, sauna, heated toilet seats, abundant spaces to meet and hang out. Only drawback was uneven temperatures in house - heaters in every room but it was cold almost everywhere. "
◆DREAM Modern Cabin in the Woods ◆ Hot tub + Sauna
TOWNHOUSE-Slp 8 Mt View/6 BEDS. Downtown Windham. Walk to restaurants and stores
Aerial view

TOWNHOUSE-Slp 8 Mt View/6 BEDS. Downtown Windham. Walk to restaurants and stores

9.2 out of 10, Wonderful, (44)
"Really lovely place right in the heart of town. Owner and manager were great."
The price is AED 404
AED 726 total
includes taxes & fees
11 May - 12 May
TOWNHOUSE-Slp 8 Mt View/6 BEDS. Downtown Windham. Walk to restaurants and stores
Gorgeous Hudson River Estate-with Pool and Winter Jacuzzi
Outdoor pool, a heated pool

Gorgeous Hudson River Estate-with Pool and Winter Jacuzzi

10.0 out of 10, Exceptional, (47)
"We had the most wonderful time! The views are unbelievable - sitting in the pool or hot tub or around the fire pit, watching the barges sail by was so special! We can’t wait to come back!"
Gorgeous Hudson River Estate-with Pool and Winter Jacuzzi
Experience Woodstock charm while staying in a cozy cabin in the woods
Interior

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

9.8 out of 10, Exceptional, (26)
"We had a wonderful long weekend experience — beautiful house, perfect heated pool and a very responsive host. "
Experience Woodstock charm while staying in a cozy cabin in the woods
Country Estate Outside Hudson - Heated Extra Large Pool w/ Outdoor Barrel Sauna
Fridge, microwave, oven, stovetop

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

10.0 out of 10, Exceptional, (24)
"Great house that has everything for the family vacation "
Country Estate Outside Hudson - Heated Extra Large Pool w/ Outdoor Barrel Sauna
HUGE KITCHEN 4 Private Acres, 7 Min to Town, WiFi, AC, Fireplace
Exterior

HUGE KITCHEN 4 Private Acres, 7 Min to Town, WiFi, AC, Fireplace

10.0 out of 10, Exceptional, (35)
"Absolutely loved the property and its proximity to the Bearsville Theatre where we had a 2-day concert. We only wish we could have stayed longer than a quick weekend trip!"
HUGE KITCHEN 4 Private Acres, 7 Min to Town, WiFi, AC, Fireplace
Game Room + Deck: Secluded Catskills Retreat
Fridge, microwave, stovetop, dishwasher

Game Room + Deck: Secluded Catskills Retreat

10.0 out of 10, Exceptional, (4)
"Another great stay at this beautiful home!"
Game Room + Deck: Secluded Catskills Retreat
The Best 3-bedroom house in Tivoli
Outdoor pool, a heated pool

The Best 3-bedroom house in Tivoli

The Best 3-bedroom house in Tivoli
Cozy Hudson River Waterfront, 3 Bdrm Pool/Quiet Street/Great Views/HITS 2 miles
Terrace/patio

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
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 AED 551
AED 734 total
includes taxes & fees
11 May - 12 May
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 AED 477
AED 515 total
includes taxes & fees
19 May - 20 May
Micosta Leisure Inn
Esopus Creek modern Tiny house Retreat!
Outdoor dining

Esopus Creek modern Tiny house Retreat!

9.6 out of 10, Exceptional, (28)
"Had a fantastic stay for a quick overnight trip to ski."
The price is AED 569
AED 897 total
includes taxes & fees
6 May - 7 May
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.