The Best Historic Hotels in Maine You Can Book With Points

Take a walk on the boutique side of things.
A view of the Maine coastline


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Maine is a funny little place. It’s so often passed over as a major tourist destination but overwhelmingly adored by everyone who goes there. Its breathtakingly rugged coastlines and national parks beg for adventure while its marvelous cities and small towns add historic relevance far beyond the average state. It’s much more than a good lobster dinner. 

And it’s the history we’re honing in on in this article. With so many colorfully historic hotels in Maine, it’d be a shame to opt for a cookie-cutter franchise property. To help, we’ve found some of the best historic hotels in Maine you can book with points.

Best historic hotels in Maine you can book with points: Hyatt

Kennebunkport Captains Collection

The exterior of one of the Kennebunkport Captains Collection in Maine
Photo: Tripadvisor

Location: Kennebunkport, ME
Price: 24,750 points/$282+
Vibe: Historic and homey
The rundown: Its spectacularly cool name aside, all the stays featured in the Kennebunkport Captains Collection are the kind of places you keep coming back to. From the outside, they’re prototypical historic homes: beautiful, but you’ve seen it before. Inside, however, you discover a modern comfort paradise. It’s painstakingly renovated with artsy flourishes to bring it forward to the 21st century.

This is a new addition to the World of Hyatt program, transferred in with the new partnership between the hotel giant and Mr and Mrs Smith, the independent boutique hotel platform. As such, rates don’t match the same World of Hyatt award chart we’re used to, but it’s still possible to book one of the homes for a reasonable 24,750 points.

Best historic hotels in Maine you can book with points: Marriott

The Press Hotel, Autograph Collection

A balcony at the The Press Hotel, Autograph Collection
Photo: Tripadvisor

Location: Portland, ME
Price: 52,000+ points/$343+
Vibe: Luxury worth reading all about
The rundown: The Press Hotel is a renovation done right. So many historic buildings have been condemned to mediocrity, but not this one. Once the home of the Portland Press Herald, the state’s largest newspaper, it’s been transformed into a modern ode to its past. Rooms are stylish and modern but boast regular nods to the print industry without becoming tacky. Think: old typewriters in the hallways and printing stamps adorning the check-in wall.

It’s part of Marriott’s Autograph Collection and bookable at rates starting at 52,000 points a night. You’ll either need a Marriott co-branded card or an American Express card with a big bonus to grab those points. The Platinum Card® from American Express is a good call in this situation. Otherwise, you’re looking at around $343 for arguably the coolest of the historic hotels in Maine.

The Platinum Card® from American Express

80,000 Membership Rewards® Points

after you spend $8,000 on purchases in your first 6 months of card membership

Annual Fee: $695  |  Terms Apply  |  Rates & Fees

Westin Portland Harbor View

The communal lounge in the Westin Portland Harbor View overlooking Portland Maine
Photo: Tripadvisor

Location: Portland, ME
Price: 45,000+ points/$215+
Vibe: Historic hotel, modern amenities
The rundown: Marriott had their eye on historic hotels in Maine, obviously. The Westin Portland Harbor View was originally opened in the 1920s as the Eastland Park Hotel. It’s been fully renovated into a chic modern space but retains the elegance and style of the early 20th century everyone adores. Opt for a high-floor room if possible to take advantage of the stunning views over the city.

The best rate we could find on the Westin was 45,000 points, with rates rising from there depending on the date. That’s not terrible, and using the same Platinum card mentioned above, you’d be only 2,000 points short of a two-night stay after hitting the $8,000 spending threshold required to earn the 80,000 points.

Best historic hotels in Maine you can book with points: Chase Travel℠ portal

Cliff House

An aerial view of the Cliff House in Maine
Photo: Tripadvisor

Location: Cape Neddick, ME
Price: 1.25 or 1.5 cents per point (rooms start at $650)
Vibe: Cliffside classic
The rundown: We don’t always recommend using credit card travel portals, but historic hotels in Maine are predominantly independent so opting to use Chase or American Express’ own sites makes for a good alternative. Chase in particular offers good value depending on whether you have the Chase Sapphire Preferred® Card or the Chase Sapphire Reserve®. If it’s the latter, you’ll get 1.5 cents per point when redeeming hotels on the portal.

With that in mind, the Cliff House makes for an excellent choice. The stunning resort is perched atop a dramatic cliffside, with many rooms offering excellent sea views. Rooms are expansive and bright, and the onsite restaurant is a winner according to the reviews. It’s been in operation since 1872, so you can trust they know what they’re doing.

Chase Sapphire Reserve®

60,000 Bonus Points

after you spend $4,000 on purchases in the first 3 months from account opening. That’s $900 toward travel when you redeem through Chase Travel℠.

Annual Fee: $550  |  Terms Apply  |  Rates & Fees

Best historic hotels in Maine you can book with points: American Express Travel portal

Old Winterport Commerical House

The exterior of the Old Winterport Commerical House in Maine
Photo: Tripadvisor

Location: Winterport, ME
Price: 27,000 points+/$195+
Vibe: Live-in history
The rundown: If you’re looking for historic hotels in Maine, you can’t get much more historic than the Old Winterpoint Commerical House. Impossibly cozy, the B&B was built in the 1830s as a stagecoach stop. Nowadays, it has five unique rooms and a quirky little antique store on the bottom floor. It looks amazing from the outside, too.

This property is found on the American Express Travel portal. Unlike Chase’s version, you’ll only get 1 cent per point here, so we’d only recommend booking here if you’re desperate to save some cash and can’t find a stronger points deal elsewhere. The cash rates hover around $195, so it’s not too expensive.

Pentagoet Inn & Pub

The quirky interior of the Pentagoet Inn & Pub
Photo: Tripadvisor

Location: Castine, ME
Price: 1 cent per point/ $220+
Vibe: Vino-Victorian 
The rundown: Another masterclass in updating a hotel without losing its soul, this Victorian hotel was built in the late 1800s and features all the hallmarks of the times: three atmospheric turrets and an adorable little porch begging to be lounged around in in the late afternoon.

Its pub, Mister’s Pub, is an absolute highlight for anyone who stays. Decked out in Victorian antiques from around the world, there’s a massive wine list, excellent cocktails, and some wonderful supper options. It’s another American Express Portal option, so you’ll be looking to get that same 1 cent per point rate. The same advice from the previous hotel applies.

Editorial Disclaimer: Opinions expressed here are the author’s alone. This post contains references to products from one or more of our partners and we may receive compensation when you click on links to those products.

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