The best properties for your fall trip

Sep 7, 2021

Fall is right around the corner, and now’s the perfect time to plan a trip around the changing of the seasons. Whether you’re into leaf-peeping, pumpkin-flavored delicacies or simply the cool, brisk weather that permeates much of the country during autumn, there are an array of spots to visit.

Top destinations in the United States to experience the wonders of fall include New England, the Pacific Northwest and the Blue Ridge Mountain range in North Carolina. But wherever you decide to go for your fall trip, has the perfect property for you and your traveling companions — and with the Rewards program, you’ll collect stamps towards reward nights with each stay you book.

A reward night is easily within reach if you book your fall trip with, and for some inspiration, here are some of our favorite properties worth considering in top destinations across the U.S.

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Depending on what area of Vermont you’re visiting, fall foliage can be seen anywhere from late September through the end of October. Fall starts early in the north, while your best bet for seeing the changing of the seasons in southern Vermont would typically be closer to mid-October. Luckily, no matter what part of the state you’re visiting, you’ll find a great place to stay at

There’s so much to see and do in Vermont for history buffs as well.

Photo of the front of Windsor Mansion Inn
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Windsor Mansion Inn in Windsor, VT

Windsor, Vermont is known as the birthplace of Vermont, serving as the location for the signing of Vermont’s declaration of independence from the British Empire in 1771. Its location in the southeastern part of the state means that mid-October is a great time to visit if your goal is to witness fall colors. Once a successful trade and agricultural center, visitors can explore the history of innovation and industry at the American Precision Museum situated within walking distance from Windsor Mansion Inn.

Related: Attractions worthy of a family road trip in Vermont

Windsor Mansion Inn is a century-old mansion turned charming bed and breakfast. The historical home was originally built in the 1800’s and sits on a private, 14-acre estate featuring views of Lake Runnemede and Mount Ascutney. Nearby hiking and biking trails add to the allure of this ideally located accommodation for taking in the beauty of fall. Windsor Mansion Inn recently underwent a massive restoration project, returning it to its intended glory.

There are only 17 guest rooms, and continental breakfast, Wi-Fi and parking are included in your stay. As a VIP Access property, Gold and Silver members can enjoy 20% off food and beverage at the lounge or the coffee shop once per stay. In addition to this unique benefit, Gold members receive a two-hour, guaranteed late check out and a free room upgrade (subject to availability) at this property.

Rooms start at $175 per night in October — so a two-night stay would earn you two stamps valued at $175 each.

Photo of living area of mountain chalet near mount snow.
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Mountain chalet in West Dover, VT

West Dover is located in the southern part of the state and can be a worthwhile stop to add to any visit to New England thanks to its proximity to Mt. Snow, southern Vermont’s most popular ski resort. Dover is close to the Southern Vermont Natural History Museum as well as a conservation area protecting over 600 acres of forest. There are plenty of other places for visitors to see fall colors as well, including Green Mountain National Forest and Molly Stark State Park, both less than 14 miles from West Dover.

A spacious rental home near Mount Snow, this four-bedroom, three-bathroom mountain chalet can accommodate up to 9 guests and boasts a furnished, wrap-around deck and private hot tub —  perfect for avid hikers and outdoor enthusiasts to relax after a long day. Complimentary Wi-Fi is included in your stay as well as a fully-equipped kitchen, wood-burning fireplace and outdoor living area.

You can rent the entire cabin starting at $471 per night in early October, meaning that a two-night stay would earn you a pair of stamps valued at $471 each.

Photo of the property surrounding Manchester mountain home
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Manchester Mountain Home in Manchester, VT

Manchester, Vermont is a four-hour drive from New York City and two-hour drive from Boston, making it an ideal spot for a weekend getaway this fall. Best known as the home of the historic Equinox Hotel and Hildene, the estate of Abraham Lincoln’s son Robert Lincoln, there’s plenty to see and do in this town. There are dozens of restaurants to enjoy, harvest festivals to attend and history to explore — including a haunted hike in nearby Glastenbury Mountain.

Manchester Mountain Home’s prime location just minutes from Main Street makes it the ideal rental home for large groups visiting this southern Vermont town. The home has six bedrooms and three bathrooms and comfortably sleeps up to 12 people. Amenities include complimentary Wi-Fi, private catering or a chef as well as in-room massages and other concierge services.

This home can be rented in early October starting at $750 — and if you booked a three-night stay, that would earn you three stamps valued at $750 each.

Photo of the outside of Mountain Top Inn
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The Mountain Top Inn & Resort in Chittenden, VT

Just an hour north of Manchester is Chittenden, Vermont, the largest town in the state (by area). The town is actually split in half by a ridge of the Green Mountains, making an especially interesting place to view fall foliage, as only half of the town is settled.

The Mountain Top Inn & Resort is a waterfront property with views of the Green Mountains and miles of trails. The property has plenty of activities to enjoy in the fall — including fishing, kayaking and tennis. There are also horseback-riding trails and local markets nearby. The resort features a restaurant and bar on property, but other dining options are also available not far from the resort.

Room rates start at $400 per night in October — so booking a three-night stay would earn you three stamps, valued at $400 each.

Total value

If you book all four of the above options for a 10-day trip, you’d wind up with the following:

  • Two stamps valued at $175
  • Two stamps valued at $471
  • Three stamps valued at $750
  • Three stamps valued at $400

This means that your 10 nights would get you a reward night worth $474.20 — though note that this value can only be applied to the room rate, not taxes and fees.

And while not everyone can book a week-and-a-half-long getaway this fall, this serves to illustrate just how quickly you can collect stamps toward reward nights in the Rewards program.

Blue Ridge Mountains

With more than 4,000 species of plants and over 100 varieties of trees, the Blue Ridge Mountain range is one of the most botanically-diverse regions in the world. You can expect to see fall colors from late September all the way through early November, depending on where you are along the route that includes North Carolina, Tennessee, Virginia and North Georgia.

And just like Vermont, features a wide variety of accommodations for every type of fall traveler — along with the same rewarding way to collect stamps.

Photo of the front of Windsor Boutique Hotel.
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The Windsor Boutique Hotel in Asheville, NC

There’s plenty to see and do in Asheville, the largest city in western North Carolina. Located right in the Blue Ridge Mountains about two hours from Charlotte, Asheville is home to two historic sites — the Biltmore Estate and the Basilica of Saint Lawrence — as well as a thriving art and dining scene.

The Windsor Boutique Hotel in downtown Asheville has 14 guestrooms and a full-service spa. Guests receive complimentary Wi-Fi and onsite parking, concierge services and, as a VIP Access property, Gold and Silver members in the Rewards program will also receive one complimentary bottle of wine per stay. In addition to this perk, Gold members get two-hour, guaranteed late check out and free room upgrades (when available).

The hotel is also close to shops and restaurants and just under an hour’s drive from Great Smoky Mountains National Park.

Related: 4 road trips you can take from Charlotte, North Carolina

Rates starting at $429 per night October 4-6 — so a three-night stay would earn you three stamps valued at $429 each.

Photo of the living room at Bear Bottom Cabin.
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Bear Bottom Cabin in Horse Shoe, NC

Just outside of downtown Asheville is the next property on our list, one that offers the best of both worlds: quiet seclusion paired with easy access to the comforts of larger towns (both Asheville and Hendersonville are less than 30 minutes away). Bear Bottom Cabin is a three-bedroom rental home that comfortably sleeps eight but can accommodate up to 10 people.

The home boasts a wrap-around porch and private hot tub as well as outdoor areas and a game room for kids. Bear Bottom Cabin is also just minutes from The Blue Ridge Parkway, a scenic byway that runs from Virginia to North Carolina and spans the southern and central Appalachians. Stops along the parkway include Linville Gorge, the deepest gorge east of the Grand Canyon, and Mount Mitchell, the highest peak in the eastern United States.

You can rent this cabin in early October starting at $287 per night, meaning that a three-night stay would get you three stamps valued at $287 each.

Photo of the front of Esmeralda Inn.
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The Esmeralda Inn in Chimney Rock, NC

Lake Lure is another idyllic location to enjoy the changing of the seasons. The man-made lake is surrounded by mountain tops, granite cliffs and the famous Chimney Rock — all within just under an hour’s drive from Asheville. In addition to hiking and activities on the lake, visitors can also go ziplining through the foothills of the Blue Ridge Mountains — providing a unique way to take in the foliage.

The Esmeralda Inn can offer an ideal place to stay when visiting the area. There are 17 cabins of varying sizes, including three-bedroom cabins with mountain views. There is also an on-site spa, and complimentary breakfast is served daily. A billiards room, hiking trails, and nearby fishing and kayaking round out the fun activities available at the property.

Room rates start at $319 per night in October — and a four-night stay would get you four stamps valued at $319 each.

Total value

By booking three nights at both the Windsor Boutique Hotel and Bear Bottom Cabin followed by four nights at the Esmeralda Inn (at the above prices), you’d earn a reward night worth $342.40.

Pacific Northwest

The beauty of fall isn’t limited to the eastern part of the United Status. The Pacific Northwest also offers an ideal spot for enjoying fall foliage — in some places beginning in early September. The best time to view fall leaves along Oregon’s Columbia River is anywhere between late September and mid-October with colors usually lasting about two weeks.

The following properties are either in or near Portland, Oregon, a great place to jumpstart any fall trip to the Pacific Northwest. Just don’t forget to sign up for the Rewards program to begin collecting those stamps toward reward nights.

Related: Your layover guide to Portland, Oregon (PDX)

Photo of the outside of the Benson Hotel in Portland, Oregon.
(photo courtesy of

The Benson Hotel in Portland, OR

While Portland is the largest city in Oregon, it’s also known for its funky, counter-culture vibe (“Keep Portland weird” is a common bumper sticker phrase). That said, the city is a popular foodie destination with a bevvy of outdoor activities nearby. Portland is just 90 minutes away from Mount Hood and roughly an hour from Columbia River Gorge, America’s largest national scenic area.

Conveniently located near Powell’s Bookstore, a must-see when visiting Portland, The Benson Hotel is in the middle of downtown within walking distance of numerous restaurants, museums and a waterfront park. As the largest of the accommodations featured on this list (287 rooms), the hotel comes with more of the amenities you’d expect from a traditional hotel — including a 24-hour fitness center, dry cleaning and laundry service.

As a VIP Access property, Gold and Silver members will enjoy complimentary valet parking during their stay. Gold members also have access to guaranteed late check out and complimentary, space-available room upgrades.

Room rates start at $707 per night in October — so a three-night stay would get you three stamps, each valued at $707.

Skamania Mountain Lodge great room with view of the mountain.
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Skamania Lodge in Stevenson, WA

Stevenson, Washington is considered the starting point for exploring a number of beautiful areas — including Beacon Rock State Park and Gifford Pinchot National Forest and Mount St. Helens. It’s also on the north side of the Columbia River, making it an ideal spot for activities like white water rafting, kayaking and windsurfing.

Skamania Lodge is located inside the Columbia River Gorge National Scenic Area, about an hour’s drive from Portland. Visitors can rent bicycles or enjoy the nearby trails by foot to take in all of the beauty of fall at this Pacific Northwest destination. The Columbia River is just a 20-minute walk from the property, and multiple dining options in downtown Stevenson are less than two miles away.

Room rates start at $179 per night in early October, meaning a three-night stay would earn you three stamps valued at $179 each.

A hot tub on a deck.
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Mountain cabin in Welches, OR

Welches, Oregon is located along the Mount Hood Scenic Byway, home to a now-dormant volcano and the state’s highest point. Mt. Hood is home to 12 glaciers and the source for five rivers that pour in the larger Columbia River. Welches is a small resort town where you can ski, golf and enjoy live music. There are also plenty of kid-friendly hiking options.

Welches mountain cabin offers a dog-friendly rental home that features a hot tub and a sauna — perfect for relaxing after a long day of hiking. The two-bedroom, two-bathroom home sleeps up to six guests and is within walking distance to the 33-mile Salmon River and Cascade Mountain Range, which stretches from Northern California all the way to British Columbia.

Room rates start at $159 per night — so a four-night stay would get you four stamps, each valued at $159.

Total value

With this example 10-day trip — three nights in the first two properties and four nights in the final one — you’d earn a reward night valued at $329.40. rewards program

It’s easy to earn rewards at either for stays booked through the website or by spending with the® Rewards Visa® Credit Card (rates & fees).

The information for the Card has been collected independently by The Points Guy. The card details on this page have not been reviewed or provided by the card issuer. 

Rewards at are called stamps, and you earn one stamp for every paid night you book and stay through either their website or mobile app (stamps are awarded within 72 hours of checking out). The stamps are worth the price of the paid night. After collecting 10 stamps, you get one reward night worth the average cost of the 10 nights you’ve previously booked.

Here’s an example:

  • You pay for five nights at $250 per night (earning five stamps worth $250 each).
  • You pay for five nights at $150 per night (earning five stamps worth $150 each).
  • You’ll then earn a reward night worth $200 (the average of the value of all 10 stamps).

Read more: The complete guide to the Rewards program

Your progress toward reward nights can accelerate with the credit card. Cardholders earn one stamp for every $500 spent on the card, and each stamp is worth $110. You would earn the 10 stamps needed for one reward night — worth $110 — after spending $5,000 on the card.

You can also earn reward nights through a combination of paid hotel stays and credit card spending. Here’s an example of what that could look like:

  • You pay for five nights on at $250 per night (earning five stamps worth $250 each).
  • You earn five stamps after spending $2,500 on your credit card (earning five stamps worth $110 each).
  • You’ll then earn a reward night worth $180 (the average of the value of the 10 stamps).

Related: Top 5 reasons to get the credit card

In addition to earning stamps towards rewards nights, frequent customers can earn Silver status after collecting 10 stamps in a calendar year and reach Gold status after collecting 30 stamps in a year. ​​And as you saw with some of the locations mentioned above, Silver and Gold members get even more if they look out for VIP Access properties.

VIP Access properties consistently receive the highest guest reviews from customers and meet stringent standards of quality — in addition to offering exclusive benefits to Silver and Gold members. Just look out for the VIP badge when you book.

Finally, collecting stamps towards reward nights isn’t the only reason to join the Rewards program. All members can also unlock instant savings through the site — simply look for the “Your Secret Price” designation when you’re searching for properties.

These savings can be up to 10% off, and you’ll still collect stamps on these stays — a great way to double dip through

Bottom line

Fall is right around the corner, and now is the perfect time to plan your fall trip to see the changing of the seasons. And if you want a wide selection of accommodations plus a rewarding loyalty program, has you covered.

The site offers 1 million properties where you can collect stamps toward reward nights, and 500,000 of those locations allow members to redeem reward nights — with no blackout dates. From luxury hotels to local inns to an array of vacation rentals, you’ll have no trouble finding accommodations to suit every style and budget.

In short, you can’t go wrong with

The best time to see fall foliage varies from one destination to the next — though September to early November is generally when you can expect to catch the most vibrant colors. But wherever you decide to vacation this fall, be sure to make one of your first stops in your trip-planning process.

Featured photo by Dillon Austin/Unsplash

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