Listen, as a Tennessee transplant living in New York, no matter how much love I feel for this city, the crowded subways and endless honking can just get… old. That said, a weekend away can work wonders.
And honestly, you don’t need to fly halfway across the country to make it feel like a true vacation. From cozy cabins in the Catskills to waterfront spots in Vermont, there are plenty of small-town gems just a few hours from New York City, and yes — they can be booked (or at least partially covered) with miles and points.
Below are three easy weekend trips from NYC: one by car, one by train, and one by air.
Each includes solid points hotel options, ideas for using free night certificates or travel credits, and a few of my personal recommendations once you’re all set up.
Cabin in the Catskills (by Car)
Getting to the Catskills
This one speaks to me on a spiritual level. If you’re craving a proper “leave-the-city-in-the-dust” type weekend, the Catskills are perfect. We’re talking fire pits, crisp mornings, and more trees than humans.
Driving from NYC is your best move here. It’s a scenic ride, and having a car gives you freedom to explore hiking trails, farm stands, and nearby towns.
How to Use Points and Perks in the Catskills
Stay with Points: The Postcard Cabins (which used to be called Getaway House) is now part of Marriott Bonvoy’s new Outdoor Collection. They’re super beautiful and modern cabins tucked away in the woods. And, they’re now bookable with Marriott points, or even free night certificates.
I stayed here a few years ago when it was still called Getaway House, and it remains one of my favorite and more unique stays — the perfect place to hit pause.
Photo courtesy of Marriott
The Eastern Catskills location will take you about 2.5 to 3 hours by car from the city, and nights start at 52,000 Marriott Bonvoy points and vary by season.
Recommended Cards:
Marriott Bonvoy Boundless® Credit Card — earn tons of extra points on your stay and work toward higher status
Capital One Venture X Rewards Credit Card — use the $300 travel credit to book directly and then cover the rest with miles
Chase Sapphire Reserve® or American Express Platinum Card® — earn extra points if you’re paying for your stay with cash
💡 Pro Tip: Outdoor Collection properties still earn elite night credit, so you can turn your cozy getaway into progress toward status.
What To Do in the Catskills
Hike Giant Ledge or Kaaterskill Falls
Visit a cider mill or a cute little roadside farm
Cozy up with a book by the fire and use this time to disconnect
Food Recs: Kitty’s Market, Silvia, Fellow Mountain Cafe, and Phoenicia Diner
Hudson Highlands (by Train)
If you want a quick trip without the stress of renting a car, Cold Spring is a super solid option. This riverfront town is charming, walkable, and surrounded by gorgeous hikes, and it’s just over an hour away by train.
Getting to Cold Spring
You can take the Metro-North Hudson Line from Grand Central to Cold Spring, and it should take you around an hour and twenty minutes. Step off the train and straight onto Main Street… no car required (yay!).
How to Use Points and Perks in the Hudson Highlands
Cold Spring itself is mostly home to small inns and Airbnbs, but just a few minutes away in Fishkill or Beacon, you’ll find plenty of chain hotels that are easy to book with points.
Hyatt House Fishkill/Poughkeepsie — nights start around 6,500 Hyatt points, which is super affordable for a weekend trip
Hampton Inn Fishkill — around 50k Hilton Honors points per night
Courtyard by Marriott Fishkill — nights starting at 19k Marriott Bonvoy points, but vary depending on the season
Courtyard by Marriott Fishkill / Photo courtesy of Marriott
Or, if you prefer something different, it’s an easy place to use your Venture X travel credit on a smaller, boutique stay.
Recommended Cards:
The World of Hyatt Credit Card — earn up to 9x points on Hyatt stays
Marriott Bonvoy Brilliant® American Express® Card — use your complimentary Platinum Elite status for perks like upgrades and other freebies
Sapphire Preferred — transfer to Hyatt and earn points back on travel
💡 Another Pro Tip: If you don’t want to rely on rideshares, Beacon has more hotel options and is just one stop north of Cold Spring on the same train line.
What To Do in the Hudson Highlands
Hike Breakneck Ridge or Bull Hill for some Hudson Valley views
Stroll Main Street for coffee, antiques, and shops
Watch the sunset over the Hudson River
Food Recs: Stissing House (technically in Pine Plains), Raffaele, Taco District, Le Bouchon, Cold Spring Depot, and MooMoo Creamery
Lakefront in Burlington, Vermont (by Air)
If you want to get out of the city but still keep the cozy vibes going, Burlington is a perfect long-weekend option for you. It’s a college town with beautiful lake views, great restaurants, and two solid points hotels right near the water.
Getting to Burlington, Vermont
There are tons of nonstop flights to Burlington International Airport (BTV) from New York (JFK) on JetBlue and Delta Air Lines, all of which take less than two hours. This is also a solid option if you need to rock with a Friday night departure after work.
💡 Pro Tip: Roundtrip fares can be as low as $150, making this a great candidate for “pay with points” or a travel credit redemption.
How to Use Points and Perks in Burlington, Vermont
Hotel Champlain Burlington, Curio Collection by Hilton — redeem Hilton Honors points at this great location right by the lake, nights starting around 45k points
Courtyard Burlington Harbor — use Bonvoy points or free night certificates, nights hover around 50k points
Hotel Champlain Burlington / Photo courtesy of Hilton
Recommended Cards:
Hilton Honors American Express Card — earn points on stays and/or enjoy your complimentary Hilton Honors Silver status
American Express® Gold Card or Citi Strata Premier® Card — use either of these on dining to rack up more points
And, you could even cover flights with points from programs like Chase Ultimate Rewards or Capital One miles
What To Do in Burlington, Vermont
Walk or bike along the Lake Champlain waterfront trail
Explore Church Street Marketplace (and its excellent food scene)
Take a day trip to Stowe or hop on a ferry across the lake
Food Recs: Honey Road, Frankie’s, Poco, Santiago’s Cuban Cuisine, and Café HOT
Bonus Picks: Madison and Mystic, Connecticut (by Train or Car)
If you’re vibing with a coastal vacation, then Connecticut has some truly charming towns just a few hours from NYC. Both of these cities are train-friendly, making them great picks if you still want to ditch the car.
Madison, Connecticut
Madison is a relaxed beach town that’s easy to get to and even easier to love. You’ll get plenty of waterfront views, quiet boardwalk walks, and just an overall peaceful vibe.
Consider staying at the Madison Beach Hotel, Curio Collection by Hilton, which is bookable with Hilton Honors points (rates starting around 80k points per night).
How to Get There: Take Amtrak to New Haven, then transfer to Shore Line East. It’s about 2.5 to 3 hours total, or a super easy and fun drive.
💡 Pro Tip: Madison is especially great for summer weekend redemptions. Lock in Hilton award nights early before cash rates spike.
Mystic, Connecticut
Mystic is just a bit further up the coast and is hands down one of the most charming seaside towns in New England. We’re talking fresh seafood, beautiful streets (like Olde Mistick Village), museums, and plenty of waterfront views.
Points hotels are a little limited, but this is a great place to use your travel credits or cover a boutique inn stay with miles.
Here are a few cute options I found (that I’m personally bookmarking for the future): The Taber Inn, The Whaler's Inn Hotel of Mystic, and Delamar Mystic.
How to Get There: Take the Amtrak directly from NYC to Mystic, Connecticut, which should take about 2.5 to 3 hours.
💡 Pro Tip: Mystic is ideal for stacking travel credits. Use your Venture X or Sapphire Reserve travel credit, or book through a portal if the math looks good.
Pro Tips for Weekend Getaways
Book early with points — Small towns have limited spots, and award nights disappear fast, especially during peak seasons like fall and summer.
Stack travel credits and points — If a cash rate is better than the redemption value, use a credit and save your points for bigger redemptions.
Pack light — Especially for Cold Spring or Burlington. A carry-on makes train and plane travel much, much easier.
Check transfer bonuses — If you’re moving points to Marriott, Hyatt, or Hilton, you might be able to squeeze even more value.
Bottom Line
Weekend getaways don’t have to mean booking some crazy expensive flight to Europe. Whether it’s a cabin in the Catskills, a train ride to the Hudson Highlands, or a lakeside spot in Vermont, your points and travel credits can make these trips both easy and affordable.
So… who’s ready to leave the city for a few days? And maybe take me with you? 😌
