Book Holiday Homes in Round Top

More Flash, Less Cash - Take advantage of our Price Pledge** (even on luxey stays)

We keep it easy with the option to pay now or later on select accommodation

Book up 'til the last second - millions of rooms to crash tonight^

Featured Holiday Homes in Round Top

Esopus Creek modern Tiny house Retreat!

Esopus Creek modern Tiny house Retreat!

Kingston
The price is NZ$396 per night from 1 Jan to 2 Jan
NZ$396
includes taxes & fees
1 Jan - 2 Jan 2025
Stay at this vacation home in Kingston. Enjoy free WiFi, an in-room coffeemaker, and air conditioning. Popular attractions Thorn Preserve - Catskill Center and ...
Esopus Creek modern Tiny house Retreat!
 Studio 3 BEDS-SLEEPS 3

Studio 3 BEDS-SLEEPS 3

Windham
The price is NZ$274 per night from 5 Jan to 6 Jan
NZ$274
includes taxes & fees
5 Jan - 6 Jan 2025
Stay at this vacation home in Windham. Enjoy patios, cable/satellite TV service, and an in-room coffeemaker. Popular attractions Windham Mountain Resort and ...
Studio 3 BEDS-SLEEPS 3
Hamptons on the Hudson in South Saugerties

Hamptons on the Hudson in South Saugerties

Glasco
Book a stay at this family-friendly vacation home in Glasco. Enjoy free WiFi, private pools, and a garden. Popular attractions Falling Waters Preserve and West ...
Hamptons on the Hudson in South Saugerties
Save an average of 15% on thousands of hotels when you're signed in
Lakefront Luxe: Private Dock, Game Rm, Near Hudson

Lakefront Luxe: Private Dock, Game Rm, Near Hudson

Athens
Book a stay at this family-friendly vacation home in Coxsackie. Enjoy free WiFi, a garden, and tennis courts. Popular attractions Sleepy Hollow Lake and Hudson ...
Lakefront Luxe: Private Dock, Game Rm, Near Hudson
Connect with mother nature and nurture your mind, body and soul!!

Connect with mother nature and nurture your mind, body and soul!!

Round Top
The price is NZ$1,870 per night from 23 Dec to 24 Dec
NZ$1,870
includes taxes & fees
23 Dec - 24 Dec
Stay at this vacation home in Round Top. Enjoy free WiFi, a sauna, and a pool table. Popular attractions Angelo Canna Town Park and Cairo Lockwood State Forest ...
Connect with mother nature and nurture your mind, body and soul!!
Dancing Horse Farm in Windham: Spectacular 9 Bedroom Home, 30 Acres,  Ski Lodge

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

Windham
Book a stay at this family-friendly vacation home in Windham. Enjoy free WiFi, a water park, and a fitness center. Our guests praise the helpful staff in our ...
Dancing Horse Farm in Windham: Spectacular 9 Bedroom Home, 30 Acres, Ski Lodge
SPECTACULAR CATSKILL OASIS with Hunter Mountain Views, INCREDIBLE LOCATION!!!

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

Hunter
Stay at this vacation home in Hunter. Enjoy free WiFi, a garden, and patios. Popular attractions Hunter Mountain and H Ski Lift are located nearby.
SPECTACULAR CATSKILL OASIS with Hunter Mountain Views, INCREDIBLE LOCATION!!!
Catskill Mountain Retreat -- private, beautiful views

Catskill Mountain Retreat -- private, beautiful views

Lexington
Book a stay at this family-friendly vacation home in West Kill. Enjoy a fitness center, a garden, and a pool table. Popular attractions Bearpen Mountain State ...
Catskill Mountain Retreat -- private, beautiful views
The Tipsy Gypsy

The Tipsy Gypsy

Hunter
The price is NZ$702 per night from 23 Dec to 24 Dec
NZ$702
includes taxes & fees
23 Dec - 24 Dec
Stay at this vacation home in Hunter. Popular attractions Hunter Mountain and Windham Mountain Resort are located nearby.
The Tipsy Gypsy
Don't see what you're looking for?
See all available properties in Round Top
View all properties
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.

Round Top Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Round Top vacation homes are the perfect way for you to wing it.

Holiday houses in Round Top let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Round Top in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Round Top adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Round Top with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Round Top vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Round Top Holiday Homes essential information

Accommodation
689 Holiday Homes
Lowest Price
NZ$217
Highest Price
NZ$1,870
Popular accommodation
Esopus Creek modern Tiny house Retreat!, Studio 3 BEDS-SLEEPS 3, Hamptons on the Hudson in South Saugerties, Lakefront Luxe: Private Dock, Game Rm, Near Hudson, Connect with mother nature and nurture your mind, body and soul!!, Dancing Horse Farm in Windham: Spectacular 9 Bedroom Home, 30 Acres, Ski Lodge, SPECTACULAR CATSKILL OASIS with Hunter Mountain Views, INCREDIBLE LOCATION!!!, Catskill Mountain Retreat -- private, beautiful views, The Tipsy Gypsy

Top trending hotels in Round Top

Hunter Lodge, a Bluebird by Lark

Hunter Lodge, a Bluebird by Lark

3 out of 5
7433 Main St, Hunter, NY
Fully refundableReserve now, pay when you stay
The price is NZ$400 per night from 6 Jan to 7 Jan
NZ$400
includes taxes & fees
6 Jan - 7 Jan 2025
Stay at this 3-star hotel in Hunter. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. ...
Hunter Lodge, a Bluebird by Lark
Hampton Inn Kingston

Hampton Inn Kingston

2.5 out of 5
1307 Ulster Ave, Kingston, NY
Fully refundableReserve now, pay when you stay
The price is NZ$217 per night from 5 Jan to 6 Jan
NZ$217
includes taxes & fees
5 Jan - 6 Jan 2025
Book a stay at this business-friendly hotel in Kingston. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
Hampton Inn Kingston
Courtyard by Marriott Kingston

Courtyard by Marriott Kingston

3 out of 5
500 Frank Sottile Blvd, Kingston, NY
Fully refundableReserve now, pay when you stay
The price is NZ$225 per night from 6 Jan to 7 Jan
NZ$225
includes taxes & fees
6 Jan - 7 Jan 2025
Stay at this 3-star business-friendly hotel in Kingston. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the ...
Courtyard by Marriott Kingston
Save an average of 15% on thousands of hotels when you're signed in
Hotel Vienna

Hotel Vienna

2.5 out of 5
107 State Route 296, Windham, NY
Fully refundableReserve now, pay when you stay
The price is NZ$266 per night from 1 Jan to 2 Jan
NZ$266
includes taxes & fees
1 Jan - 2 Jan 2025
Book a stay at this golf hotel in Windham. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. ...
Hotel Vienna
Don't see what you're looking for?
See all available properties in Round Top
View all properties
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.

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.