Deals on vacations and trips to Round Top

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Round Top flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
Wylder Hotel Windham

Wylder Hotel Windham

3.5 out of 5
Price was $1,039, price is now $866 per person
$866
per person
Oct 30 - Nov 3
found 7 hours ago
Roundtrip flight included
Grand Rapids (GRR) to Hudson (HCC)
This hotel features a restaurant, an outdoor pool, and a bar/lounge. Guests will appreciate free perks like free self parking and WiFi in public areas. A coffee shop, a lobby fireplace, and a communal living room are also on offer.
Mountainview - Guest House by Avantstay Heated Pool + Hot Tub + Games Lake + Cannoe Near Hunter Mountain

Mountainview - Guest House by Avantstay Heated Pool + Hot Tub + Games Lake + Cannoe Near Hunter Mountain

3 out of 5
Save 100% on your flight
Price was $4,967, price is now $3,482 per person
$3,482
per person
Oct 23 - Oct 26
found 7 hours ago
Roundtrip non-stop flight included
San Juan (SJU) to Hudson (HCC)
Free WiFi in public areas is available at this cottage. Take advantage of the free self parking.
Mountainview Estate - Main House by Avantstay Pool + Hot Tub + Canoe + Outdoor Dining + Game Room Near Windham Mountain

Mountainview Estate - Main House by Avantstay Pool + Hot Tub + Canoe + Outdoor Dining + Game Room Near Windham Mountain

3 out of 5
Save 100% on your flight
Price was $5,133, price is now $3,680 per person
$3,680
per person
Oct 23 - Oct 26
found 7 hours ago
Roundtrip non-stop flight included
San Juan (SJU) to Hudson (HCC)
An outdoor pool, free self parking, and barbecue grills are featured at this cottage. WiFi in public areas is free. A terrace is also provided.
Secluded Retreat w/ Pool, Hot Tub, Fire Pit, Views Windham Mountain House

Secluded Retreat w/ Pool, Hot Tub, Fire Pit, Views Windham Mountain House

3 out of 5
Save 100% on your flight
Price was $2,256, price is now $1,671 per person
$1,671
per person
Oct 23 - Oct 26
found 7 hours ago
Roundtrip non-stop flight included
San Juan (SJU) to Hudson (HCC)
This cottage doesn't skimp on freebies - guests receive free WiFi and free self parking. An outdoor pool and barbecue grills are also provided.
Eastwind Windham

Eastwind Windham

3.5 out of 5
Price was $1,104, price is now $991 per person
$991
per person
Oct 30 - Nov 3
found 7 hours ago
Roundtrip flight included
Grand Rapids (GRR) to Hudson (HCC)
This hotel features a restaurant and 2 bars/lounges. Enjoy the sauna and perks like free self parking and free WiFi. A lobby fireplace, a communal living room, and a picnic area are also on offer.

Top Round Top hotels deals

Hunter Lodge, a Bluebird by Lark

Hunter Lodge, a Bluebird by Lark

3 out of 5
7433 Main St Hunter NY
$155 nightly
The price is $168 total per night
$168 total
Sep 29 - Sep 30
Total with taxes and fees
A restaurant and a bar/lounge are featured at this hotel. There's no skimping on freebies - guests receive free breakfast, free WiFi, and free self parking. A lobby fireplace, a communal living room, and a library are also on offer.
Breakfast included
Pet friendly
Pocketbook Hotel and Bath

Pocketbook Hotel and Bath

2 out of 5
549 Washington Street Hudson NY
$234 nightly
The price is $264 total per night
$264 total
Sep 22 - Sep 23
Total with taxes and fees
This smoke-free hotel features 3 indoor pools, a restaurant, and a bar/lounge. Enjoy the steam room and perks like free valet parking and free WiFi. Free self parking, a coffee shop, and a garden are also offered.
Pool
Spa
Courtyard by Marriott Kingston

Courtyard by Marriott Kingston

3 out of 5
500 Frank Sottile Blvd Kingston NY
Free Cancellation
Reserve now, pay when you stay
$127 nightly
The price is $142 total per night
$142 total
Sep 20 - Sep 21
Total with taxes and fees
This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Free parking, a coffee shop, and a terrace are also offered.
Pool
Parking included
Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

2.5 out of 5
282 Cairo Junction Rd Catskill NY
$201 nightly
The price is $217 total per night
$217 total
Sep 21 - Sep 22
Total with taxes and fees
This cabin features a virtual front desk. Take advantage of the free self parking.
Kitchen
Pet friendly
AutoCamp Catskills

AutoCamp Catskills

5 out of 5
882 NY-212 Saugerties NY
Free Cancellation
Reserve now, pay when you stay
$182 nightly
The price is $204 total per night
$204 total
Oct 7 - Oct 8
Total with taxes and fees
A restaurant and a bar/lounge are featured at this holiday park. Guests will appreciate free perks like free self parking and WiFi in public areas. A grocery/convenience store, a lobby fireplace, and a communal living room are also on offer.
Residence Inn by Marriott Kingston

Residence Inn by Marriott Kingston

3 out of 5
800 Frank Sottile Boulevard Kingston NY
Free Cancellation
Reserve now, pay when you stay
$143 nightly
The price is $160 total per night
$160 total
Sep 20 - Sep 21
Total with taxes and fees
This hotel doesn't skimp on freebies - guests receive free buffet breakfast, free WiFi, and free self parking. Business travelers can take advantage of the 24-hour business center. There's a 24-hour gym on site, and a 24-hour front desk and dry cleaning are also provided.
Breakfast included
Pet friendly
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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.

Frequently asked questions

How much are vacation packages to Round Top?
Your travel fantasies can all come true in Round Top from an impressive $866. Our package deals include flights and hotels, and they'll make booking your trip nice and easy. The only thing you'll have to focus on is having an incredible time.
How long should my Round Top vacation be?
Your Round Top getaway can be as long as you like, but the majority of people stay around 2 nights. Eager to get out and uncover some hidden treasures? Lock in a couple more nights and see a different side of this destination.
Where can I get the best vacation package deals for Round Top?
Grabbing the perfect package deal to Round Top is easy with Travelocity. With as many as 400 air carriers and 1,000,000 properties worldwide, you'll have loads of choice when selecting your hotels and flights.
Why should I book my Round Top vacation bundle with Travelocity?
We have experiences for every type of globetrotter, top-notch service and round-the-clock customer support. And the icing on the cake is we'll match any cheaper price you happen to find with our Price Match Guarantee.
Will I save money on my Round Top car rental if I combine it with a hotel or flight?
Certainly — bundle your hotel, flight and car into a Round Top vacation package and you'll save a handsome sum. With so many places to explore in the Round Top area, that rental car will come in handy. Once you're in the driver's seat, put the stereo on and make tracks to Times Square, a top sight about 100 mi from Round Top.
Which airport is best for Round Top?
You have two options for landing at Round Top, the first being Albany Intl. Airport (ALB). It's around 35 mi from the center of the city, while Stewart Intl. Airport (SWF) is 50 mi away from central Round Top.
What is there to do in Round Top?
Blackhead Mountain Country Club is one of the superb sights that make Round Top a popular place to visit. But give yourself enough time to discover the city's lesser-known attractions too. This is often where the best memories are created.
Where should I stay when visiting Round Top?
If you're searching for someplace comfortable to lay your head, have a look at the Crystal Brook Resort & Mountain Brauhaus. It's the top pick for many visitors.

Photos of local treasures

Browse Round Top vacation photos for more inspiration

A mountainous landscape with dense forests and a rocky cliff.
A person lying on a hay bale in a field with multiple hay bales and trees in the background.
A girl sitting on a hay bale in a field with hay bales and trees in the background.