Six Shoulder Season Stays Worth the Trip

From a classy Inn in Vermont to a Midwest golf magnate to the California Coast, these accommodations are worth the trip

Shoulder season, often referred to as the travel industry’s best-kept secret, is an ideal time to embark on adventures. This transitional period between peak and off-peak seasons offers a harmonious blend of favorable weather, fewer crowds, and attractive prices. Travelers can revel in the beauty of destinations without the hustle and bustle of peak season crowds, allowing for a more immersive and authentic experience.


Whether it’s enjoying the vibrant fall foliage in New England or the temperate conditions of the California coast, this time of year is ideal for comfortable weather, serene landscapes and fewer people. Here are six places we recommend.


Woodstock Inn (for fall foliage and quintessential New England atmosphere)


Nestled in the picturesque town of Woodstock, Vermont, the Woodstock Inn is a luxurious, yet quintessential New England retreat that embodies timeless charm of the area. Surrounded by the natural beauty of the Green Mountains, this historic inn has been welcoming guests since 1793, offering a seamless blend of tradition and modern comfort.


The architectural elegance of the inn reflects the region’s colonial heritage, with its white-clapboard exterior, dormer windows, and inviting front porch. Inside, guests are greeted by a warm and welcoming atmosphere, featuring cozy fireplaces, comfortable furnishings, and tasteful decor that captures the essence of Vermont’s rustic elegance.



The inn boasts a range of accommodations to suit every traveler’s preference, from charming guest rooms to luxurious suites. One of the inn’s highlights is its commitment to culinary excellence. The Red Rooster Restaurant, located within the inn, showcases Vermont’s farm-to-table ethos. The menu features locally sourced ingredients that celebrate the flavors of the region, providing a true gastronomic experience for guests and visitors alike.


For those seeking relaxation, the Woodstock Inn’s spa offers a serene haven with a range of treatments designed to rejuvenate the mind, body, and spirit. Guests can also explore the surrounding area, where outdoor activities abound, including hiking, skiing, and exploring the charming town of Woodstock with its boutique shops, art galleries, and historic sites.

Throughout its rich history, the Woodstock Inn has retained its commitment to providing a welcoming and unforgettable experience. Whether savoring gourmet meals, unwinding in the spa, or simply enjoying the tranquility of the Vermont landscape, visitors to the Woodstock Inn can expect a stay that captures the essence of New England hospitality and natural beauty.



Ocean House (for luxury at a slightly discounted rate)


While Newport may get the majority of summer visitors to Rhode Island, Watch Hill—just over the boarder from Connecticut—has a quiet charm that many prefer over the towns further up the coast. It also has some of the best beaches in New England, with comfortable ocean temps—thanks to the guldfstream—well into the early fall.  And while you have views of both eastern Long Island (Montauk, The Hamptons) and Block Island it is open ocean.

Watch Hill has a few lodging options, but the best remains the Ocean House. In fact, the Ocean House might be the nicest resort in all of New England. CNN named it one of the “20 Most Beautiful Hotels in the US” (2016), Coastal Living named one of the “10 Best Beach Resorts in the World” and Travel+Leisure named one of the “10 Best Hotels in the Northeast” and “Top 100 in the World.” While the Ocean House is affordable to few during peak season, the offseason offers a little bit of financial respite.



Built in 1868, the Victorian mansion was a favorite summer retreat for the well heeled until it was torn down in 2005, before being rebuilt as nearly an exact replica—from the exterior at least. Preservationists were initially up in arms but the architects’ lovingly reconstructing of the landmark building—albeit at a smaller scale (but with a hefty $140 million price tag)—quelled a lot of those complaints. Guests can choose from 49 rooms (159 existed in the original structure) furnished in a British colonial style with colorful New England flourishes, all with dramatic views of the ocean. iPads are available for use and guests have access to other modern amenities, including flat panel TVs with multimedia connectivity.

Visitors can swim in the open Atlantic and frolic on the dune-y beaches (Watch Hill Beach, Main Beach and Misquamicut Beach) which are some of the most pristine beaches on the east coast. Go for a sunset stroll and grab a drink along the way at Paddy’s Beach. Or grab a fishing pole and head to Block Island Sound. Surfers journey to Westerly or Narragansett. A number of good public and private golf courses exist in the area. The rates can’t be beat at Winnapaug Golf and Country Club, a public course in nearby Westerly. Bottom line, if you are looking for a classy beach resort in New England with all the comforts of a 5-star hotel, you cannot go wrong with The Ocean House. Since it’s 2010 renovation it has become the gold standard of New England beach resorts.


Foundry Hotel Asheville (for hip, mountain vibes)


The Foundry Hotel stands as a unique blend of industrial charm and modern luxury in the scenic mountains of western North Carolina. Housed in a former steel factory dating back to the 1920s, the hotel seamlessly marries its rich history with contemporary design and upscale amenities, offering guests an unforgettable stay.


The Foundry Hotel’s exterior pays homage to its industrial heritage, with weathered brick walls and steel accents that evoke a sense of authenticity and character. Upon entering, guests are greeted by an atmosphere that combines rustic elements with sleek sophistication, creating a welcoming ambiance that reflects Asheville’s eclectic spirit.


The hotel’s accommodations range from well-appointed guest rooms to spacious suites, each thoughtfully designed to provide comfort and elegance. High ceilings, exposed beams, and a blend of modern and vintage furnishings create a distinct sense of style that pays homage to the building’s past while catering to the needs of today’s travelers.


Dining at The Foundry Hotel is an experience in itself. The hotel boasts a renowned restaurant that showcases locally sourced ingredients and Southern-inspired cuisine. Guests can savor delectable dishes in a setting that fuses industrial aesthetics with a contemporary dining atmosphere.


The hotel’s commitment to relaxation is evident in its amenities, including a spa and wellness center that offer a range of treatments to soothe and rejuvenate. For those who wish to explore the vibrant city, The Foundry Hotel’s central location places guests within walking distance of Asheville’s art galleries, live music venues, and unique boutiques.


A stay at The Foundry Hotel is not only a chance to experience the allure of a bygone era brought to life, but also an opportunity to immerse oneself in Asheville’s vibrant culture. With its seamless blend of history, design, and hospitality, The Foundry Hotel invites guests to discover the dynamic spirit of Asheville while enjoying the comfort and luxury of a truly exceptional accommodation.


Big Cedar (for a Midwest golf magnate)



Nestled in the heart of the picturesque Ozark Mountains in southern Missouri, Big Cedar Lodge stands as a premier wilderness resort that offers a harmonious blend of nature’s beauty and luxurious comfort. Surrounded by the serenity of Table Rock Lake and the lush woodlands, this expansive resort provides an idyllic escape for those seeking a tranquil retreat.


Big Cedar Lodge captures the essence of rustic elegance with its charming cabins, lodges, and accommodations. The resort’s architecture and design pay homage to the region’s natural beauty, blending seamlessly into the landscape. From cozy cabins to spacious lodges, each accommodation is meticulously appointed with modern amenities while exuding a warm and inviting atmosphere.


The real allure of Big Cedar however, is undoubtedly the 4 world-class golf courses, including the Jack Nicklaus-designed Top of the Rock course. This par-3 course is renowned not only for its challenging design but also for its stunning vistas that showcase the Ozark Mountains and the pristine Table Rock Lake. Golfers are treated to an unparalleled experience as they navigate through meticulously designed holes, some of which are perched atop the cliffs, offering breathtaking panoramic views.


Beyond the Top of the Rock course, Big Cedar Lodge offers the Buffalo Ridge Springs course, designed by renowned architect Tom Fazio. This 18-hole championship course is known for its strategic layout, incorporating natural rock formations, water features, and lush fairways that seamlessly blend with the surrounding wilderness.


Whether you’re a passionate golfer or simply looking to appreciate the artistry of the sport amidst stunning scenery, Big Cedar Lodge’s commitment to providing exceptional golf experiences makes it a destination that truly stands out on the map of golf resorts.


Post Ranch Inn (for nature, nurture and nourishment)


Perched on the dramatic cliffs of Big Sur, the Post Ranch Inn is a captivating retreat that offers a harmonious blend of luxury and natural beauty. With its innovative architecture and eco-conscious design, the inn seamlessly integrates into its stunning coastal surroundings. Guests are treated to breathtaking Pacific Ocean views from exquisite accommodations that include treehouses and ocean-view suites.


These retreats boast a blend of indoor and outdoor spa tubs, inviting wood-burning fireplaces, sumptuous leather furniture, elegant wooden ceilings, and expansive king-size beds. Beyond the comfort, each abode treats guests to majestic vistas of either the rolling surf or the grandeur of the mountains.


On the southern expanse of the property, the Cliff Houses, Peak Houses, and Pacific Suites beckon with their unique allure. Constructed using reclaimed lumber, they boast floor-to-ceiling windows that frame the breathtaking panorama. The Peak Houses even feature cantilevered terraces, offering an immersive connection with the surroundings. The accommodations afford a sense of seclusion, as if the sprawling land extends solely for your enjoyment.


The Post Ranch Inn’s dedication to preserving the environment is intrinsic to its philosophy. Using natural and sustainable building materials, minimizing wattage in lighting, and safeguarding rare and endangered species, the inn ensures that its luxurious offerings harmonize with the surroundings without compromising the integrity of the ecosystem.


While the mesmerizing views from your terrace are captivating, the resort presents a spectrum of activities to engage in throughout the day. Guided nature walks lead you through the enchanting redwood and oak forest, while evenings bring cosmic wonder through the eyes of the resident astronomer and the electronic telescope that unveils the night sky’s brilliance. Moreover, the inn’s proximity to central coast wineries allows for captivating wine journeys.


Within the resort, the acclaimed Sierra Mar restaurant garners recognition in esteemed publications like Food & Wine. Dinner offers a seasonal, shared experience that changes daily and is inspired by the harvest from our dynamic Chefs Garden. To complement these delights, an extensive wine list features California’s finest varietals, rounding out the culinary experience with finesse.


Ojai Valley Inn Spa (for relaxation, recreation, and rejuvenation)


Surrounded by the Topatopa Mountains and embraced by the vibrant energy of the Ojai Valley, this iconic resort offers a captivating blend of relaxation, recreation, and rejuvenation—a luxurious haven where natural beauty meets refined elegance.


Accommodations at the Ojai Valley Inn and Spa are a testament to comfort and sophistication. From cozy rooms and suites to luxurious private villas, each space is meticulously designed to embrace the region’s Spanish colonial heritage while providing modern amenities and serene views of the surrounding landscape.


The inn’s crown jewel is its award-winning spa, a sanctuary of serenity that embraces the spirit of the Ojai Valley. Indulge in a plethora of treatments and therapies that draw inspiration from the local flora, ensuring a harmonious connection with the environment. The Kuyam, a unique treatment inspired by Native American traditions, offers a communal journey of purification and rejuvenation.


The culinary offerings at the Ojai Valley Inn and Spa are a celebration of farm-to-table excellence. The Oak, the resort’s signature restaurant, sources ingredients locally to craft a menu that showcases the region’s bounty. Guests can savor delectable dishes in an inviting atmosphere that captures the essence of Ojai’s relaxed sophistication.


Beyond its remarkable amenities, the Ojai Valley Inn and Spa fosters a sense of community and connection. The Artist Cottage and Apothecary provides a space for creative exploration, while the resort’s dedication to sustainability and environmental stewardship reflects its commitment to preserving the natural beauty that envelops it.


From the invigorating spa experiences to the world-class golfing and the culinary delights, the Ojai Valley Inn and Spa offers an unparalleled escape where guests can immerse themselves in the serenity of the Ojai Valley while enjoying the pinnacle of luxury and hospitality.