Dream Weekend Trip: How I Booked Fall Break in the Berkshires With Amex Points

I’ve always wanted to do a classic fall getaway — think crisp air, colorful leaves, and a winding scenic drive through gorgeous hills.

When I saw that peak foliage in the Berkshires region would line up perfectly with a free weekend in October, I jumped on the opportunity. Fortunately, I had just earned a massive welcome bonus offer on The Business Platinum Card^® from American Express.

Keep reading to find out how I booked my entire Berkshires family vacation with Amex points, including flights and the hotel.

Earning 180,000 Amex Membership Rewards Points

I’ve had the Amex Business Platinum card for years, but I recently applied for a second one for another business I own. This is the current publicly available welcome offer for eligible applicants:

• Earn 150,000 points after spending $20,000 in eligible purchases within the first 3 months.

Fortunately, I had some estimated quarterly tax payments due, so I knew I could easily meet the minimum spend requirement. By charging exactly $20,000 to cover my tax bill, I earned 1.5x points per $1 on purchases of $5,000 or more through the Amex Business Platinum card’s bonus category (up to $2 million of these purchases per calendar year), which added 30,000 points to the welcome bonus offer.

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The Business Platinum Card^® from American Express

U.P. Rating 

The rating for this card has been determined by our own industry experts who know the ins and outs of credit card products. Bonuses, rewards as well as rates and fees are all taken into account. Compensation from the issuer does not affect our rating. We only recommend products we either use ourselves or endorse.

This card is ideal for business travelers who enjoy luxury travel and are looking for a card loaded with benefits!

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The Business Platinum Card^® from American Express

This card is ideal for business travelers who enjoy luxury travel and are looking for a card loaded with benefits!

Welcome Offer

Earn 150,000 Membership Rewards^® points after you spend $20,000 in eligible purchases on the Card within the first 3 months of Card Membership.

150,000 points

UP's Offer Valuation*:

Up to $3,300

Annual Fee

$695

APR

18.49% - 29.24% Variable

Credit Recommended

Upgraded Points credit ranges are a variation of FICO^®Score 8, one of many types of credit scores lenders may use when considering your credit cardapplication.

Good to Excellent

Why We Like This Card

The Business Platinum Card^® from American Express is a premium travel rewards card tailored toward business owners who are frequent travelers with a high number of annual expenses.

When you factor in the large number of perks that the card offers like the best airport lounge access at over 1,400 lounges, along with tons of annual credits, it’s easy to see why this card can is a top option for frequent traveling business owners.

Pros & Cons

Pros

• 5x Membership Rewards points per $1 on eligible travel purchases like flights, prepaid hotels, and prepaid short-term rentals booked through AmexTravel.com
• Access to over 1,400 worldwide airport lounges as part of the American Express Global Lounge Collection (as of 10/2024).
• Get 50% more Membership Rewards points (1.5 points per $1) on eligible purchases in key business categories, as well as on purchases of $5,000 or more (on up to $2 million per calendar year)

Cons

• High annual fee of $695 (rates & fees)
• Airline fee credit does not cover airfare, only incidentals like checked bags

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Card Highlights

• Welcome Offer: Earn 150,000 Membership Rewards^® points after you spend $20,000 in eligible purchases on the Card within the first 3 months of Card Membership.
• The American Express Global Lounge Collection^® can provide an escape at the airport. With complimentary access to more than 1,400 airport lounges across 140 countries and counting, you have more airport lounge options than any other credit card issuer on the market as of 10/2024.
• Unlock over $2,000 in statement credits with business and travel benefits annually* on the Business Platinum Card. Terms apply. Learn more. *After meeting qualifying spend thresholds
• New! Enroll and get up to $150 in statement credits on U.S purchases directly with Dell Technologies on the Business Platinum Card and an additional $1,000 statement credit after you spend $5,000 or more on that same Card per calendar year.
• New! Enroll and get a $250 statement credit after you spend $600 or more on U.S. purchases directly with Adobe per calendar year on the Business Platinum Card.
• Fly like a pro with a $200 Airline Fee Credit. Select one qualifying airline to receive up to $200 back per year on baggage fees and other incidentals.
• Make the Business Platinum Card^® work even harder for you. Hilton For Business members get up to $200 back per calendar year when you make an eligible purchase at Hilton properties across the globe. Benefit enrollment required.
• 5X points on flights and prepaid hotels booked on AmexTravel.com
• 1.5X points (that’s an extra half point per dollar) on purchases at US construction material & hardware suppliers, electronic goods retailers and software & cloud system providers, and shipping providers, as well as on each eligible purchase of $5,000 or more, up to $2 million of these purchases per calendar year. Purchases eligible for multiple additional point bonuses will only receive the highest eligible bonus.
• 1X points on other eligible purchases
• Use the Business Platinum Card^® and get up to $209 back per calendar year on your CLEAR^® Plus Membership (subject to auto-renewal).
• $695 Annual Fee.
• Terms Apply.

Financial Snapshot

• APR: 18.49% - 29.24% Variable
• Foreign Transaction Fees: None

Rewards Center

American Express Membership Rewards

That gave me a total of 180,000 Amex Membership Rewards points to put toward my Berkshires trip — enough to cover flights for my family of 5 and hotel.

Booking Flights With Amex Points

While I usually redeem Amex Membership Rewards points for business class or other high-value redemptions, this trip was a bit different. The best (and only direct) booking for this trip was a JetBlue flight from Fort Lauderdale (FLL) to Albany (ALB) — super convenient for a family of 5.

Since the Berkshires are a bit spread out, travelers might also consider Hartford’s Bradley Airport (BDL) or Westchester County (HPN) outside New York City, depending on where they’re coming from.

What really caught my eye was the number of points required. I needed to book 5 round-trip tickets, and I found seats for less than 10,000 points per person and $11.20 in taxes and fees for my dates in October.

The transfer ratio from Amex to JetBlue TrueBlue is 5:4 isn’t ideal, but I felt it was a fair trade-off given the convenience of a nonstop flight. I usually transfer Amex points to airline partners for high-value redemptions through programs like Aeroplan, Flying Blue, and Virgin Atlantic Flying Club — but for this trip, the JetBlue transfer just made sense.

So, I transferred just 58,000 Membership Rewards points to JetBlue and booked all 5 round-trip tickets. That came out to a little over 11,000 points round-trip per person, which I was happy to pay to avoid connections and long travel days, especially when traveling with a toddler.

Booking a Stay in the Berkshires With Points

When it came time to book lodging for our family trip to the Berkshires, I quickly realized that the region isn’t exactly overflowing with points hotels — especially ones that are both well-reviewed and family-friendly.

But after some searching, I found a solid option: the Courtyard Lenox Berkshires, which stood out for its spacious rooms with 2 queen beds, perfect for accommodating my family of 5 comfortably.

The hotel is located just over an hour from Albany International Airport, making it a convenient base for exploring the Berkshires. At 55,000 Marriott Bonvoy points per night, it wasn’t a screaming deal by points standards — but it worked for us.

Since Amex Membership Rewards transfers to Marriott Bonvoy at a 1:1 ratio, I transferred 110,000 points to cover our 2-night stay.

Now, if you’re a points optimizer, you might question this redemption. We value Amex points at 2.2 cents each and Marriott Bonvoy points at around 0.7 cents each, so this isn’t what I’d call a high-value transfer on paper.

But this trip was never about maximizing every last cent of value — it was about using ~180,000 points Membership Rewards points to cover meaningful parts of our trip.

With cash rates running $468 per night, I ended up getting 0.85 cents per point, slightly above Marriott’s average but still well below the potential value of Amex points.

Still, the hotel had the space we needed, the location we wanted, and availability that lined up with our plans — and honestly, sometimes that’s what matters most when traveling with a family.

For the remaining 3 nights, we switched things up and booked a cozy Airbnb. It offered more of a homey feel — plus it had a full kitchen, backyard space, and multiple rooms that gave us some breathing room and made our stay that much more comfortable.

While I couldn’t book it directly with points, we used a credit card that earns transferable points — specifically, the Capital One Venture X Business Card*×Information collected independently. Not reviewed by Capital One., which earns 2 miles per $1 on every purchase, including Airbnb stays. I opted for this card over my Amex Business Platinum card, which only earns 1x on Airbnb, to make sure I maximized rewards on this part of the trip.

Final Thoughts

A trip to the Berkshires for iconic fall colors, peaceful countryside, and charming small towns has long called to me.

Thanks to the generous welcome bonus from the Amex Business Platinum card, I had more than enough Membership Rewards to cover flights for my family of 5, plus 2 nights at a comfortable Marriott hotel. These award redemptions covered a huge chunk of our trip costs and honestly saved me a ton of money to put toward other parts of the vacation and just made the whole experience way more affordable.

While not every redemption had the absolute highest value per point, the convenience and ease of the bookings made the whole experience smooth and stress-free, which is priceless when traveling with kids. If you’ve been thinking about a similar getaway or want to learn how to maximize travel rewards for your next family trip, this story shows how even a mid-tier redemption can unlock big travel goals.