Round Top Holiday Rentals

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Holiday Rentals in Round Top

Property grounds
Streamside Cottage Walking Distance to Town of Woodstock
10.0 out of 10, Exceptional, (196)
"My sister and I needed a quick getaway from the world and found refuge in this sweet little cottage that is right on the creek. The cottage was pristine, fully eqipped, quiet and tastefully decorated. My communication with the owner, Jane, was "easy breezy". Our favorite part of our stay were the sights and sounds of the water! It was truly magnificent. We came to the cottage a little tired from the pressures of life but left rejuvenated and filled with peace. Our short stay was delightful. We...
The price is NZ$532
includes taxes & fees
16 May - 17 May
Streamside Cottage Walking Distance to Town of Woodstock
View from property
Where the Broadway Stars Vacation! Private Woodstock getaway & walk to town!
10.0 out of 10, Exceptional, (152)
"this was one of the most comfortable, easy to navigate vacation homes we have ever had. we used the grill, kitchen had everything you need, the deep sinks made washing dishes easy, (there was a dishwasher. but we didn't use it), windows allowed a 180 degree view of the back yard and forest beyond, where we saw a family of deer. Everyone slept like babies on mattresses that were heavenly! Or was super available and responsive to questions. A hannaford super market is 2.3 miles away. Bread Alone...
Where the Broadway Stars Vacation! Private Woodstock getaway & walk to town!
Terrace/patio
Best Mountain Views Triple level Deck /w Hot tub Brand New Home Sleeps 30!
10.0 out of 10, Exceptional, (7)
"House and location were great, would definitely come back."
Best Mountain Views Triple level Deck /w Hot tub Brand New Home Sleeps 30!
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Exterior
Junebug Cottage: peace, love and privacy a short walk to Woodstock village green
10.0 out of 10, Exceptional, (37)
"A perfect location and the cottage was set up with great attention to detail. Everything was very clean and comfortable. The property is beautiful too. John and Mollie are very responsive hosts and provided us with anything we needed. Could not ask for more. Highly recommend!"
Junebug Cottage: peace, love and privacy a short walk to Woodstock village green
Fridge, microwave, oven, stovetop
Charming Artist's Retreat
10.0 out of 10, Exceptional, (112)
"The property is lovely and the entire experience of working with Maureen was amazing. Looking forward to a return trip!"
Charming Artist's Retreat
Property grounds
Updated Cabin on the Esopus
10.0 out of 10, Exceptional, (17)
"The cabin was excellent, very clean, and they gave us everything we needed"
Updated Cabin on the Esopus
Property grounds
Cozy Relaxing Retreat in Saugerties, NY
10.0 out of 10, Exceptional, (30)
"It was a nice location to spend time with family."
Cozy Relaxing Retreat in Saugerties, NY
Exterior
HUGE KITCHEN 4 Private Acres, 7 Min to Town, WiFi, AC, Fireplace
10.0 out of 10, Exceptional, (27)
"This is our third stay in this property, and each time we had a fabulous time."
HUGE KITCHEN 4 Private Acres, 7 Min to Town, WiFi, AC, Fireplace
1 bedroom, free WiFi, bed sheets
Romantic Luxury Chalet With Private Pool
10.0 out of 10, Exceptional, (259)
"Richard was very kind and thoughtful. The stay was very comfortable and Richard provided many ideas for things to in the vicinity. We will definitely consider staying here again if we're back in the area."
Romantic Luxury Chalet With Private Pool
Property grounds
Dancing Horse Farm in Windham: Spectacular 9 Bedroom Home, 30 Acres, Near Hunter
10.0 out of 10, Exceptional, (131)
"We had a great time at Greg’s property. The house is huge and easily accommodated the 25 guests we had. It is very conveniently located for those that like to take advantage of skiing between Hunter and Windham mountains. Greg was extremely responsive and very easy to work with anytime we had questions arise. I would definitely recommend to others and will most certainly keep this place in mind for future trips! Thanks again!"
The price is NZ$2,958
includes taxes & fees
23 May - 24 May
Dancing Horse Farm in Windham: Spectacular 9 Bedroom Home, 30 Acres, Near Hunter
1 bedroom, iron/ironing board, free WiFi, bed sheets
Romantic sky loft with steam shower/giant tub. Minutes to the slopes.
10.0 out of 10, Exceptional, (10)
"All around excellent experience! Apologies for not checking in and out as instructed- Cell service wouldn't work for us, nor would WiFi calling (the WiFi worked well, however- Confident the issue was with our provider and nothing to do with the rental. Thank you for everything!"
Romantic sky loft with steam shower/giant tub. Minutes to the slopes.
Fridge, microwave, oven, stovetop
Your peaceful, private retreat to get away with friends & family!
10.0 out of 10, Exceptional, (22)
"The place and host were amazing. The property was well kept and well appointed for our stay. It is nicely secluded, and the hot tub was perfect for relaxing."
Your peaceful, private retreat to get away with friends & family!
Property grounds
7Bdr/5Bth, Amazing View, Lake,1/2 ml Hunter Mountain, Hot Tub/Sauna. Ski, Swim
10.0 out of 10, Exceptional, (208)
"House came with great amenities and host was very communicative and flexible"
The price is NZ$1,174
includes taxes & fees
22 May - 23 May
7Bdr/5Bth, Amazing View, Lake,1/2 ml Hunter Mountain, Hot Tub/Sauna. Ski, Swim
Exterior
Classic Catskills Estate, Amazing Location!
10.0 out of 10, Exceptional, (87)
"Beautiful location and view, extremely quiet. Room enough for everyone (we had 9 adults and 3 kids). We hosted an Easter dinner for 15, the kitchen and dining room had room to spare. We had beautiful spring weather so most time was spent on the huge porch or around the fire pit."
Classic Catskills Estate, Amazing Location!
Fridge, microwave, stovetop, dishwasher
Tannersville Retreat w/ Pool, 6 Mi to Hunter Mtn!
10.0 out of 10, Exceptional, (48)
"Loved the house and it was perfect for our old friends hiking weekend"
Tannersville Retreat w/ Pool, 6 Mi to Hunter Mtn!
The Cabin at Chichester in the Catskills Mountains
9.8 out of 10, Exceptional, (165)
"Very clean, good area"
The Cabin at Chichester in the Catskills Mountains
Outdoor dining
SOLAR ECLIPSE SPECIAL. Tuscan Year Round Beauty / Pickle Ball.
9.8 out of 10, Exceptional, (86)
"Stayed here with a group of friends, and loved it! We had terrible weather, but the house was the best place to be stuck inside. We made pizzas in the outdoor oven, and enjoyed the hot tub. Can't recommend enough! The property manager Alan was awesome."
SOLAR ECLIPSE SPECIAL. Tuscan Year Round Beauty / Pickle Ball.
Exterior
Beautiful House 0,5 Mile From Hunter Mountain
9.8 out of 10, Exceptional, (188)
"It was a great family time. Play and rest"
Beautiful House 0,5 Mile From Hunter Mountain
Property grounds
THE LAKEFRONT CHALET - SKI, RIDE, GOLF, BIKE, HIKE
9.8 out of 10, Exceptional, (80)
"Natalya was a great host! Property was very nice and great location to Hunter!"
The price is NZ$1,140
includes taxes & fees
16 May - 17 May
THE LAKEFRONT CHALET - SKI, RIDE, GOLF, BIKE, HIKE
Property grounds
Hamptons on the Hudson in South Saugerties
9.8 out of 10, Exceptional, (6)
"Rainy but had a great time at the Wool and Sheep Festival.The fall colors were beautiful."
Hamptons on the Hudson in South Saugerties
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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.

Other types of properties in Round Top you may be interested in

Lobby sitting area
Hunter Lodge, a Bluebird by Lark
2.5 star property
9.4 out of 10, Exceptional, (358)
"Nice clean and the price was right "
The price is NZ$206
includes taxes & fees
27 May - 28 May
Hunter Lodge, a Bluebird by Lark
Premium bedding, down duvets, Tempur-Pedic beds, laptop workspace
AutoCamp Catskills
3.5 star property
9.2 out of 10, Wonderful, (269)
"Very unique experience as compared to a standard hotel room. Loved the fireplace!! "
The price is NZ$375
includes taxes & fees
27 May - 28 May
AutoCamp Catskills
Exterior
Courtyard by Marriott Kingston
3.0 star property
8.6 out of 10, Excellent, (820)
"👍"
The price is NZ$244
includes taxes & fees
27 May - 28 May
Courtyard by Marriott Kingston
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

Are there holiday rentals in Round Top?

Yes, there are holiday rentals close to the most popular sights in Round Top, or you can select a more secluded option if you're looking for a relaxing stay. Nature enthusiasts will enjoy the mountain landscape in Round Top. Make sure you have time to check out the ski areas and golf courses during your trip.

How many holiday rentals are there in Round Top?

Choose from 3 Expedia holiday rentals in Round Top for a memorable holiday.

What’s there to see and do in Round Top?

While exploring the area, visit family-friendly sights like Zoom Flume, or get outside and enjoy nature at Mountain Top Arboretum. In the wider area, you’ll find North-South Lake Campground & Day Use Area and Kaaterskill Falls.

What’s a holiday rental in Round Top like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Round Top. Holiday rentals feature extras like laundry facilities and kitchens so you'll feel right at home. If you're concerned about a sanitised environment, a holiday rental can provide a sense of safety away from shared hotel lifts and busy reception areas while still allowing you the experience of travel. You'll also have more space in a holiday rental than in a traditional hotel, which makes a holiday rental a popular option for small groups.