Regional Road Trips: 5 Amazing Places to Stay Using Points in New England

These properties are worthy stopping points on a regional road trip through New England.

Erin HurdJune 4, 2020

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Steeped in history and natural beauty, New England is composed of six diverse states: Connecticut, Maine, Massachusetts, New Hampshire, Rhode Island and Vermont. In the spring and summer you’ll find temperate weather and blooming flowers galore. Fall brings the famous, brilliantly colored foliage, and winter features skiing and cozy fireplaces.

While there are many airports that service the region with wide coverage, loading up the car and taking a good ol’ road trip is the best way to truly see New England. Here are five great properties across different travel rewards programs that you can book with points on your New England road trip.

Wentworth by the Sea Hotel and Spa

Oozing with charm, this historic Victorian property is known for its stunning grounds and luxurious spa. The sprawling Wentworth was an architectural feat in its day, modeled after elegant ocean liners and dubbed The Ship Building.

Even though the property dates back to 1874 and holds a place on the Historic Hotels of America register, it’s been updated into a full-service Marriott hotel. This seaside resort is located on the island of New Castle, New Hampshire, close to Portsmouth and just over an hour's drive from Boston.

Wentworth by the Sea is a Marriott category 7 hotel, which means it goes for between 50,000 and 70,000 Marriott Bonvoy points per night (depending on whether you’re staying during peak, standard or off-peak dates). It’s not uncommon to find a mixture of award night date classifications within the same month and even the same week.

For example, if you booked a standard king room for these five nights in August, some nights fall under the standard price of 60,000 points per night, while others are classified as peak pricing. When you book with Marriott Bonvoy points, you’ll always get the fifth night free… but the free night will be the lowest priced night.

The Wentworth by the Sea has several spacious suites that you can book if you’d like an upgrade from a standard room — you’ll still be able to book with points, but you’ll pay a cash upgrade fee. The cash price can run anywhere from a couple hundred to a couple thousand dollars, depending on the size of the suite and the peak/off-peak classification. Or, if you have Marriott Suite Night Awards, you can try to apply those for a free upgrade.

Nerd tip: You can earn Suite Night Awards when you reach 50 qualifying nights with Marriott and choose them as your annual choice benefit. Keep in mind that each award is good for one night, not one stay. You won’t know if your request to redeem your suite award will be honored until five nights before arrival, at the earliest.

Club Wyndham Inn on the Harbor

The idyllic town of Newport, Rhode Island — Gilded Age playground of the rich and famous — is a quintessential New England must-see. Take a stroll past the fabled Vanderbilt mansions on the Cliff Walk, relax on the beautiful Atlantic beaches or wander around the waterfront town and admire the yachts while you enjoy homemade ice cream from Kilwin’s.

Right in the heart of it all, you’ll find the Club Wyndham Inn on the Harbor. With a rooftop deck where guests can sip a sunset cocktail and watch the sailboats glide in, the Club Wyndham is an all-condo property, meaning your room comes complete with a kitchenette. You can book a one-bedroom suite for 15,000 Wyndham points per night.

Wyndham Rewards are a bit harder to earn than other hotel loyalty programs. That’s because even though Wyndham does have co-branded credit cards, the welcome bonuses are generally lower than those offered on co-branded cards from IHG or Hilton.

You can also transfer Capital One miles to Wyndham at a ratio of 2:1.5. That means that for every 1,000 Capital One miles you transfer, you’ll get 750 Wyndham Rewards. While that’s not the best redemption value you can get for your Capital One miles, it’s a good option if you need to top off your Wyndham account to make a redemption.

Kimpton Taconic Hotel

Nested in the Green Mountains of Southern Vermont lies the picturesque town of Manchester, with a population of just over 4,000. Hiking? Check. Skiing? Check. Rustic charm, historic buildings and a growing farm-to-table food scene? Check, check and check.

Take a drive to Manchester, where in the heart of the historic village you’ll find the Kimpton Taconic Hotel. A boutique hotel with quintessential Vermont farmhouse decor, the Taconic has all the charm of a classic bed and breakfast, but with modern amenities like in-room spa services and daily organic coffee and tea service.

Kimpton is a playful, boutique brand of hotels that was acquired several years ago by the InterContinental Hotel Group, so that means that you can book these fun properties with your IHG points.

You can find a charming King Deluxe room at the Kimpton Taconic Hotel for 45,000 points per night (plus taxes and a $33 resort fee). In this example, the cash rate for that room is $373, giving you a value of 0.82 cent per point — right on par with NerdWallet’s value for IHG points.

Hyatt Place Portland

Gorgeous waterfront, cobblestoned historic Old Port, a bustling art scene, beaches, lighthouses and killer lobster rolls — Portland, Maine, has something for everyone. Dubbed “Vacationland,” Maine is a wonderful place to visit year-round for gorgeous scenery and outdoor activities.

Perched on prime real estate right in the heart of the quaint Old Port district is the Hyatt Place Portland hotel. Although Hyatt Place properties aren’t full-service luxury hotels, they’re known for their spacious and comfortable rooms complete with a sleeper sofa and mini fridge. World of Hyatt members will receive a free hot breakfast when booked on an eligible rate (points redemption stays are eligible).

The Hyatt Place Portland is a Category 4 property, which means you can book a room for 15,000 World of Hyatt points per night. If you’ve earned a Hyatt free night award good for any Category 1-4 hotel, you could redeem it here.

Madison Beach Hotel

Connecticut’s only beachfront boutique resort and spa is a Four Diamond property that is sure to wow you on your New England road trip. Every room at the Madison Beach Hotel includes an ocean view that you can enjoy from your private furnished patio.

The private beach right outside the front doors of the Madison is lined with complimentary chairs, umbrellas and towels, and you can choose to have an attendant bring lunch and a cocktail right to you. Inside, you can dine at the award-winning Wharf Restaurant for delicious New England sea-to-table delicacies.

Hilton has what’s referred to as a dynamic pricing program for its Honors points. That means that instead of having a fixed award chart, the cost in points is tied to the cash rate of the room, and will fluctuate.

In peak season, you’ll find standard reward rooms go for around 80,000 Hilton Honors points per night. That sounds like a lot of points (and it is), but when you compare it to the cash price of $625 per night, you see that you’re getting a value of 0.78 cent per point. That’s 0.28 cent higher than our NerdWallet valuation of Hilton points.

The bottom line

There’s truly something for everyone in New England. While Boston is an incredible world-class city worth visiting time and again, there’s much more to see in the Northeast. Load up the family truckster, come hungry for lobstah and be ready for adventure as you wander the winding roads. Check out these hotels in your travels, and book on points so you can use your cash for delicious food and souvenirs.

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