What are the Best Luxury Fall Vacation Rentals This Year?

If you’re thinking of taking a vacation this fall – in this COVID-19 era – you may be looking exclusively for private rental properties with plenty of social distance from the neighbors. Whether you’re thinking of a cabin beside a lake or a rustic-chic cottage with a prime view of the autumn leaves, what are the best luxury vacation rentals available this fall? Our ace correspondent Julie Chang Murphy has curated  a list of 30 of the best luxury home vacation rentals to consider this fall. Whether it’s just your family, or you and your pod, here are a few ways to get out of Dodge and revel in the splendors of autumn safely this year.

What are the best luxury vacation rentals this fall?

Once Fall is officially here, we will have spent over half a year social distancing and in various degrees of quarantining. During this time, many people have re-discovered the sights and sounds of our own states and regions.

According to Airbnb, rentals within 300 miles of home have proven to be the most popular with guests. We are among those who contributed to these stats. And we gotta say: it wasn’t that bad!

In fact, for us taking a driving-distance vacation achieved all the same things a jet-setting vacation to Europe might bring. Family time, relaxation, and the wonder and appreciation that comes with a change of scenery. While we will always look forward to vacationing in far-flung locales, we have a newfound appreciation for the good old-fashioned road trip and living our best wood nymph life hiking and creek stomping in the woods.

Whatever the season brings – a “second wave” or maybe, even a vaccine, being out in nature will continue to be our destination of choice. Maybe you’re dreaming of cozying up in a bucolic farm house, surrounded by fiery fall foliage. Or, migrating south to soak up one more week of sun, sea and sand. Whatever you’re dreaming of, there’s a luxurious vacation rental worthy of traveling to. We’ve combed through the listings and are featuring 20 of our favorite finds below. Grab it before someone else does!

What are the best luxury vacation rentals this fall?

THE NORTHEAST 

There is no better region to take in the fall foliage (and eat and drink pumpkin flavored everything) than in the Northeast. It’s also prime apple-picking and s’mores by the fire season. Don’t forget that flannel plaid shirt!

1. Hudson Pool House in Hudson Valley, New York 

    (4 guests/ 2 bedrooms/ 2 baths)

This stunningly modern and rustic retreat has floor to ceiling windows throughout the house for inspiring valley views. It also features a seasonal heated lap pool and year round hot tub.

For those who want access to civilization, no worries. The artsy town of Hudson filled with antique shops, boutiques and plentiful dining options is only 5 minutes away.

2. Woodstock Mediterranean Retreat in Woodstock, New York

(10 guests/ 4 bedrooms/ 3 baths)

Recently renovated, this ranch style home is super stylish with 16-foot-high cathedral ceilings and exposed beams, salt-water in-ground pool, 2000sf outdoor deck with BBQ grill, basketball court, and a large tranquil garden.

The picturesque village of Woodstock is just 4 minutes away or just gather around the firepit in the backyard in Adirondack chairs, overlooking the mature pine and oak trees.

3. Magical Country Home on 17 Acres in Olivebridge, New York 

    (8 guests/ 4 bedrooms/ 3 baths)

This one-of-a-kind farmhouse is full of character and charm. When you’re not breathing in the crisp, fall air on the property’s 17 rolling acres or soaking in the year round hot tub, the well-appointed interiors are the perfect setting for reading a mystery by one of the four fireplaces.

Explore the area’s numerous farm stands, orchards and hike and bike until your heart’s content- all 2 hours from NYC.

4. Expansive Modern Farmhouse in Collegeville, Pennsylvania

    (16 guests/ 6 bedrooms/ 6.5 baths)

This immaculate estate cannot be beat if you are looking to spend time in nature but are not quite ready to camp in the woods. It sits on 8 acres and backs up to over 3,300 acres of state park that includes 26 miles of trails in the park and fishing.

The spacious interiors are done in a sophisticated, transitional style and perfect for hosting a long-awaited family get-together.

5. “The Quonset” Dome House in Tiverton, Rhode Island

    (10 guests/ 4 bedrooms/ 2 baths)

In the 1940s, the Quonset hut on the property was used during the war to store ammunition. The owners have a passion for saving historic coastal Rhode Island homes and restored the house to its former glory – minus the ammunition.

Aspiring chefs will love the oversized kitchen and design aficionados will appreciate the unique and stylish touches throughout the rooms. It comes equipped with kayaks and bikes for vacationers to enjoy the beach, a short distance away.

6. Luxurious Residence in Newton, Massachusetts 

    (10 guests/ 5 bedrooms/ 5.5 baths)

The state of Massachusetts peaks in the fall with its collegiate ambience and its historic associations with pilgrims and the founding of America.

This gorgeous residence is tastefully decorated in a traditional style with Asian antiques from the owner’s travels. It comes with an impressive gourmet kitchen and media room for at home entertaining.

7. The Rabbit Hole Luxury Cabin in Stowe, Vermont 

    (13 guests/ 5 bedrooms/ 2 baths)

This mountain getaway has an eclectic and relaxed vibe, located in the heart of Stowe.

In the front, you can relax near the peaceful pond or chill out on the boho-chic deck in the back with hot tub and fire pit. The homey touches make this Vermont retreat perfect for a cozy fall sojourn.

8. Modern Luxury Farmhouse in Rochester, Vermont

    (6 guests/ 3 bedrooms/ 3.5 baths)

Set on a pristine 25 acres, this sun-drenched house with undisturbed mountain views is the perfect site for unplugging and recharging. The interior is decorated in a serene Scandinavian style with a gracious living area and modern, updated bathrooms and amenities.

The town of Rochester has plenty of small town Vermont charm and fly fishing, hiking, and berry picking opportunities for outdoorsy fun.

9. Lake House with Private Beach in Casco, Maine

    (12 guests/ 4 bedrooms/ 3.5 baths)

It doesn’t get more picturesque than this waterfront Maine estate. The setting- a private beach on Crescent Lake with almost 500 feet of exclusive waterfront property.

It’s elegantly furnished with spacious rooms set up for game nights or meals around the table that go on all night. For freshwater enthusiasts, the house comes with two kayaks and a canoe.

THE SOUTH 

If you’re all about squeezing in a few more beach days – and who could blame you- make like a bird and get down south. The humidity has mostly abated and it’s still warm enough to rock that swimsuit and finish up that summer beach reading list.

1. 11 Grey Widgeon in Hilton Head Island, South Carolina

    (12 guests/ 5 bedrooms/ 5.5 baths)

Steps away from the beach, this property comes with ample indoor and outdoor living areas renovated in a modern, coastal aesthetic. Sit by the deck with a cocktail while the kids swim in the pool.

On cooler evenings, the fire pit is a perfect gathering spot. Shops and dining are plentiful whether in Harbourtown or down at the South Beach Marina Village.

2. Sea Oats in Captiva, Florida 

    (16 guests/ 9 bedrooms/ 9.5 baths)

This premier coastal estate is nestled on 4 acres between the Gulf of Mexico and one of Florida’s pristine wildlife preserves.

In addition to breathtaking views of Captiva Island’s famous sunsets, guests can take advantage of the tennis and basketball court and kayak and paddle board through the bay estuaries. The beach chic interiors are bright and soothing with direct access to the balcony that overlooks the courtyard pool.

3. Villa Sunrise in Coral Gables, Florida 

    (8 guests/ 4 bedrooms/ 5.5 baths)

This glamorous contemporary colonial style home is surrounded by swaying palm trees will transport you to another era.

Far from boring, every room is a conversation starter with an eclectic collection of patterns, textures, and contemporary works of art. The outdoor cabanas are perfect for happy hour and just lounging and napping the day away.

4. Setai Oceanfront Townhouse in Miami Beach, Florida 

    (6 guests/ 3 bedrooms/ 3 baths)

Here’s to the high life! Featuring 3,650 square feet of visionary living space, this incomparable rental is one of the finest private residences in Miami Beach. The luminous space has floor to ceiling windows overlooking the ocean and the kind of decor that just makes you feel like you’re part of the in-crowd.

This townhouse is co-located within the Setai Hotel where guests on premise can enjoy the hotel’s world-class cuisine, celebrated spa, and waterfront infinity pools. Or, just step outside and you’re on the beach.

5. “The Odessa” in Seagrove Beach, Florida 

    (12 guests/ 4 bedrooms/ 7 baths)

With unobstructed Gulf views and private beach access, this luxurious property seems like a mirage. Three master suites make it easy for all guests to live in maximum comfort while the four built-in bunks cater to memorable sleepovers for the kids.

The calming and upscale interiors make staying in a pleasure. And nearby state parks and bike trails provide ample opportunity for nature lovers.

6. “Out of the Blue” in Santa Rosa Beach, Florida

    (6 guests/ 3 bedrooms/ 3 baths)

A little off the beaten path, this European-inspired villa has a charming indoor courtyard along with imported architectural elements that provide old world charm.

Situated in the heart of Old Blue Mountain Beach, it is steps away from the gulf’s pristine beach and crystal clear waters. There are restaurants, coffee shops and ice cream parlors all within walking distance.

THE WEST COAST

Autumn on the West Coast can be just as dramatic and stunning with its beaches, mountainous landscapes and vineyards. We are hoping the fires are extinguished soon in California and Colorado and when they are, those local communities will need the support of tourists even more.

1. Vickerys Vantage in Breckenridge, Colorada

    (16 guests/ 5 bedrooms/ 4.5 baths)

This handsome chalet rises from the hillside with multiple common spaces perfect for any get-together. Floor-to-ceiling windows and a hot tub on the deck provide expansive views of the mountains.

Thoughtful and luxurious amenities like radiant flooring, wet bar, and exercise room will please even the most discerning guests.

2. Villa Harrah in Glenbook, Nevada 

    (16 guests/ 6 bedrooms/ 7.5 baths)

Overlooking Lake Tahoe, this zen-like villa has a generous terrace that leads to a pool, sandy beach, private pier, and balconies that seem endless. But that’s not where the extravagance ends.

The designer furnishings and decor are sure to impress but the property also boasts a full cinema, wet bar, and deluxe spa with a sauna, hot tub and salt room.

3. Mansion Del Sol in Cabo San Lucas 

    (12 guests/ 4 bedrooms/ 4.5 baths)

Take a stroll on your very own Cabo del Sol private beach or stay in the mansion lapping up the luxury in the infinity pool and private spa. This dreamy mansion has character and grandeur for days.

A world-renowned Jack Nicklaus Signature golf course surrounds the property and guests have access to The Clubhouse for meals and cocktails, complete with stunning views of the Baja coastline. Or, stay in and whip up a meal in the outdoor kitchen while the sun sets.

4. Hacienda House in Salinas, California 

    (14 guests/ 6 bedrooms/ 4 baths)

This impeccably maintained estate is set on 20 acres of grounds that includes an organic vineyard and olive orchard. Separate wings give members of the group alone time when needed while multiple common rooms, including a soaring great room and chef’s kitchen, naturally induce a convivial atmosphere.

The Mediterranean style home was designed by famed architect Richard Rhodes in the late 90’s and has been equipped with all the modern amenities, combining Old World beauty with modern luxury.

5. Camp Howard in Leavenworth, Washington

    (6 guests/ 2 bedrooms/ 2 baths)

Need an enchanting bungalow for a romantic getaway? Here it is. This newly built home sits 2000 feet above sea level, perched on top of 5 acres of ponderosa forest in the foothills of Cashmere mountain.

Whether it’s a quiet morning sipping coffee on the deck or snuggling in bed with an unbeatable view, this base will make you feel at one with nature.

What are the best luxury vacation rentals this fall?

There you have it- 20 luxurious fall rentals for a brag-worthy North American escape! Where are you headed this fall?

join our community

For access to insider ideas and information on the world of luxury, sign up for our Dandelion Chandelier Newsletter here. And see luxury in a new light.

Crediting her training as a cultural anthropologist at Wellesley College, Julie has immersed herself in various industries in the last 15 years including fashion design, event planning, and fitness. Julie lives in New York where she loves trying every ramen and dumpling restaurant with her husband and three children. She finds joy in bold prints, biographies of fierce women, kickboxing. And spending way too long finding the perfect polish color to express her mood.

Forward This Article