Round Top Vacations from $595
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Your Round Top Vacation
Come and discover this captivating city for yourself with a Round Top vacation package. Consider spending some time in the neighborhood of Jefferson Heights, which is great for golfing and walking, and your time here is sure to be unforgettable. Fill your spare time with tours of Kaaterskill Falls, North-South Lake Campground & Day Use Area and Mountain Top Arboretum, some of the top attractions you simply have to see during a trip to Round Top. Expedia will help you escape the everyday. Tailor your vacation to Round Top to match your travel style, whatever that may be.
The Latest Round Top Vacation Packages
- Wylder Hotel Windham
Dec 11 - Dec 14Wylder Hotel Windham + Flight
Windham3 nights3.5 star property9.0/10 - Wonderful (135 reviews)"Room super clean and beautiful property!"Reviewed November 2, 2026Roundtrip • Orlando (MCO) - Hudson (HCC)MCO - LGA • Nonstop EWR - MCO • Nonstop$700$595found 1 day agoper traveler - Mountainview Estate - Main House by Avantstay Pool + Hot Tub + Canoe + Outdoor Dining + Game Room Near Windham Mountain
Dec 19 - Dec 24Mountainview Estate - Main House by Avantstay Pool + Hot Tub + Canoe + Outdoor Dining + Game Room Near Windham Mountain + Flight
Hensonville5 nights3.0 star propertyRoundtrip • San Juan (SJU) - Hudson (HCC)SJU - ALB • 1 stop ALB - SJU • 2 stops$6,077$4,712found 1 day agoper traveler - Mountainview - Guest House by Avantstay Heated Pool + Hot Tub + Games Lake + Cannoe Near Hunter Mountain
Dec 11 - Dec 14Mountainview - Guest House by Avantstay Heated Pool + Hot Tub + Games Lake + Cannoe Near Hunter Mountain + Flight
Hensonville3 nights3.0 star propertyRoundtrip • Orlando (MCO) - Hudson (HCC)MCO - LGA • Nonstop EWR - MCO • Nonstop$3,204$2,555found 1 day agoper traveler - Windham NY Escape
Dec 11 - Dec 14Windham NY Escape + Flight
Hensonville3 nights3.0 star property10/10 - Exceptional (3 reviews)Roundtrip • Orlando (MCO) - Hudson (HCC)MCO - LGA • Nonstop EWR - MCO • Nonstop$893$815found 1 day agoper traveler - Eastwind Windham
Dec 11 - Dec 14Eastwind Windham + Flight
Windham3 nights3.5 star property9.2/10 - Wonderful (122 reviews)"Loved the stay here as well as the friendly staff. Jamie who had helped us check in was very friendly, helpful and made us feel welcome. Location was very dog friendly. Our room was very clean, quiet and had a beautiful scene of nature. Nice place to choose for a quiet get away stay."Reviewed October 20, 2026Roundtrip • Orlando (MCO) - Hudson (HCC)MCO - LGA • Nonstop EWR - MCO • Nonstop$704$654found 1 day agoper traveler
Where to stay near Round Top
Hudson
For travelers seeking a blend of culture and outdoor adventure, Hudson is an ideal base for exploring the picturesque region surrounding Round Top. This charming city offers attractions like the historic Olana State Historic Site, the serene Sleepy Hollow Lake, and the vibrant Hudson Opera House, ensuring a memorable experience year-round. Located about 16 miles away by car, Hudson provides convenient access to nature and arts, making it a smart choice for your next vacation getaway.
Catskill
Plan your stay in Catskill, a top-rated choice for outdoor enthusiasts and culture seekers looking for a vibrant mix of adventure and scenic beauty. With stunning attractions like the Olana State Historic Site, the breathtaking Kaaterskill Falls, and the serene Dutchman’s Landing park, Catskill offers plenty to explore year-round. Located about 11 miles by car from Round Top, this charming city makes for an ideal getaway for those wanting a memorable retreat.
Hunter
Adventure seekers will love Hunter, known for its stunning natural beauty and outdoor activities. With attractions like Kaaterskill Falls, Catskill State Park, and the majestic Catskill Mountains, it’s a perfect destination for those seeking skiing and sports experiences. Located about 24 miles by car from Round Top, Hunter offers a blend of family-friendly adventures and breathtaking landscapes. Choosing Hunter for your stay ensures you’re in the heart of nature's playground, making it an excellent hotel booking choice.
Windham
Windham stands out as a prime spot for travelers seeking a weekend getaway, family fun, and nature adventures. Here, visitors can explore stunning destinations like Kaaterskill Falls, enjoy outdoor activities at Huntersfield State Forest, and unwind at Ashland Park. With about an 18-mile drive from Round Top, accessing Windham is easy, making it an ideal choice for a memorable vacation. Whether you're hitting the slopes or soaking in the scenery, Windham offers a delightful retreat for every traveler.
Saugerties
Travelers seeking a weekend getaway will find Saugerties to be the ideal base for their vacation, featuring a rich blend of nature and culture. Explore the local charm at Bard College and immerse yourself in outdoor activities near the scenic lake and mountains. With ski resorts and equestrian events at HITS-on-the-Hudson, there's something for everyone. Located about 18 miles by car from Round Top, Saugerties offers a perfect mix of adventure and relaxation for your stay.
Round Top Hotel Deals
Crystal Brook Resort & Mountain Brauhaus
Crystal Brook Resort & Mountain Brauhaus"We did n"
Hunter Lodge, a Bluebird by Lark
Hunter Lodge, a Bluebird by Lark"Really enjoyed my overall experience and stay. Clean room and amenities and nice location in the Hudson Valley near a lot of hiking trails"
Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy
Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy
"Everything else was in the $350 range that weekend, so we went a little further out to budget our money. I couldn't figure out if the heater worked or not. No coffee. Just a place to rest our heads. It is what it is."
"The grounds and rooms and decor are very upscale Catskill and nice. I really enjoyed the many amenities available all day, including: games; coffee and tea; s'more kits; the fire pit that was well tended (and there was also an outdoor fireplace), the gas fireplace in the room and the small touches even in terms of encouraging a relaxing shower and the noise-cancelling machine in room - just very thoughtful touches everywhere."
Frequently Asked Questions
How much does a Round Top vacation package cost?
You'll find cheap prices from $595 on Expedia for your Round Top escape. However, factors like the length of stay, the season and your choice of hotel will determine how much your vacation to Round Top costs.
What are the cheapest months to go to Round Top?
If you'd like to snag a cheap Round Top vacation package, consider traveling in February, March and October. You'll typically find lower rates on accommodations and flights during these months — perfect for a budget-friendly getaway.
How many days is enough for Round Top?
The ideal duration for your Round Top vacation depends on what you'd like to do and see. Typically, a handful of days to a week will give you plenty of time to visit all the leading sights and explore some hidden gems along the way.
How to find the best Round Top package deals?
Use Expedia's handy filters to find some terrific Round Top package deals. When you begin your search, just set your maximum budget and then sort the results by "Price: low to high." If you want to save, plan your break for midweek, or browse for Round Top package deals in the off-peak season. Switch up your travel dates and you may land even better discounts. As a rule of thumb, it's typically best to lock in your vacation package well in advance.
Is it cheaper to book a Round Top vacation as a package?
Expedia vacation packages are designed to give you more bang for your buck. Bundle your hotel, car rental and flight into one great-value price and enjoy significant savings. You'll usually get a better deal than booking each component individually. And you'll still get the flexibility to create a personalized Round Top vacation by choosing your favorite type of stay, airline and car class.
When to book a vacation package to Round Top?
If you're planning an impromptu Round Top vacation, check out our last-minute deals that can be booked up to one week before you take off. Prefer not to wait until the last minute? You can score sensational deals on your hotels and flights by booking well in advance.
Does Expedia offer Book Now, Pay Later Round Top vacation packages?
Your Round Top getaway should be a relaxing escape from your busy life, not a reason for money worries. So to give you that extra flexibility, we've teamed up with online lender Affirm to bring you our Book Now, Pay Later vacations. Pick one of our vacation packages with payment plans and split up the cost over 3, 6 or 12 months. Plus, there are no late payment fees or hidden costs to worry about.