Bobby’s Bookings: 6 Perfect Fall Getaways (That Are Just a Short Drive Away)

Photo: The Maker

Summer may be vacation season, but we think Fall is an equally ideal time to get away. With leaves changing and chilly nights made for getting cozy by a fire, it’s a great time to escape for a weekend. And we’ve got 6 stylish spots you can stay (that are just a short drive away from LA, NYC, and Chicago).

Whether you prefer a totally relaxing couples retreat or a family (and pet) friendly getaway, we’ve got a place that will appeal to you. From hip hotels, awesome Airbnbs – and even an airstream trailer – these lodgings are perfect for a quick escape to enjoy all that fall has to offer, or enjoy doing nothing at all! So to help you plan your next trip, we’ve got 6 options with all the details you need – including a link for each property to make it even easier to book. *Note that all the properties listed are compiling with social distancing and recommended procedures to keep you safe during your stay.

 

Keep scrolling to see all our picks – and plan your weekend getaway now!

 

 

Want to see all our other favorite hotels and rentals? Check out Bobby’s Bookings: 6 Last-Minute Places to Stay This Weekend and Bobby’s Bookings: 6 (Romantic) Places to Stay For Valentine’s Day

A Weekend With Wineries

 

NAME: SKYVIEW

 

LOCATION: LOS ALAMOS, CALIFORNIA (2.5 Hours from los Angeles)

 

ACCOMmODATIONS: 33 Room HOTEL

 

PRICE: starting at $179/ night

 

SUGGESTED AUTUMN ACTIVITY: BIKING TO LOCAL WINERIES, FOLLOWED BY GETTING COZY AROUND THE FIREPIT

 

Located in the sleepy town of Los Alamos, Skyview is a 1950s roadside hotel that’s been thoughtfully renovated, while retaining plenty of its mid-century charm (like velvet platform beds and wood beam ceilings). And while there’s lots to enjoy on the property – including an on-site restaurant, pool, and places to relax around a fire pit – we recommend venturing out to local wineries and tasting rooms to get a real taste of this idyllic region. Book here.

 

Photo: The Maker

Upstate New York Elegance 

 

NAME: the maker

 

LOCATION: hudson, new york (2.5 Hours from NYC)

 

ACCOMmODATIONS: 11 Room boutique hotel

 

PRICE: Starting at $275/ night

 

SUGGESTED AUTUMN ACTIVITY: reading by the fireplace and an evening cocktail in the lounge

 

For an escape that feels like stepping back in time, book a room at The Maker, a boutique property in Hudson, New York. With rooms named “The Architect” and “The Writer, this hotel channels a creative spirit, and uses rich fabrics, patterned wallpaper, and wood molding to create spaces that are perfect for curling up with a good book (there’s a full library to choose from too). And after an evening drink in the lounge, you’ll definitely want to head to your room for a relaxing soak in your clawfoot tub. Book here.

Photo: The Maker
Photo: The Maker

Laid Back Lakeside 

 

NAME: lake shore resort

 

LOCATION: SAGATUCK, MICHIGAN (2 Hours From Chicago)

 

ACCOMmODATIONS: 30 ROOM HOTEL

 

PRICE: STARTING AT $195/ NIGHT

 

SUGGESTED AUTUMN ACTIVITY: KAYAKING ON LAKE MICHIGAN and watching the sunset

 

Whether you prefer to bike, boat, or just breathe in nature, Lake Shore Resort has an option for you. Situated directly on Lake Michigan, the hotel features clean and modern guestrooms and ample outdoor space (including a private dock) to enjoy a gorgeous sunset lakeside. You’re also just a short drive from the town of Saugatuck, full of small-town charm, art galleries, and restaurants. Book here.

 

 

Rustic Retreat 

 

NAME: CEDAR LAKE ESTATES

 

LOCATION: PORT JERVIS, New York (2.5 Hours from NYC)

 

ACCOMmODATIONS: COTTAGES & CABINS

 

PRICE: starting at $325/ night (3 Night minimum AS OF OCTOBER 5TH)

 

SUGGESTED AUTUMN ACTIVITY: An AFTERNOON canoeing in the lake followed by a nature hike to see fall foliage

 

To really get away from it all, take a rustic retreat to Cedar Lake EstatesJust 2 hours west of NYC (and ideal for families), this 500-acre property feels like a world away, surrounded by thick forest and a pair of private lakes. There’s a variety of accommodations to choose from, ranging from cottages to cabins to the main farmhouse, and interiors that blend rustic and modern in a neutral color palette. With a restaurant serving locally grown foods, and plenty of outdoor activities like boating, fishing, and hiking, you can do as much – or as little – as you like. Book here.

 

Photo: Les Cactus

Desert Delight

 

NAME: LES CACTUS

 

LOCATION: PALM SPRINGS, CALIFORNIA (2 Hours from Los Angeles)

 

ACCOMmODATIONS:  BOUTIQUE HOTEL

 

PRICE: STARTING AT $199/ night

 

SUGGESTED AUTUMN ACTIVITY A MORNING HIKE AT TAhqUITZ CANYON FOLLOWED BY BREAKFAST BY THE POOL

 

Fall in the desert isn’t quite the same as other parts of the country, but it’s still got plenty of appeal for a weekend away from home – especially a stay at Les Cactus. With interiors that mix mid-century, boho, and southwestern (with lots of pale pink and green), this hotel has got plenty of personality. And you’ll definitely want to take advantage of lounging in a hammock by the pool or indulging in a massage. Book here.

 

Photo: Les Cactus
Photo: Les Cactus
Photo: Airbnb

Modern In Michigan

 

NAME: Wayfarer Treehouse

 

LOCATION: LAKE LEELANAU, MICHIGAN (5 Hours from chicago)

 

ACCOMmODATIONS: 3 bedroom HOME

 

PRICE: starting at $467/ night

 

SUGGESTED AUTUMN ACTIVITY: A WALK AROUND THE LAKE AND PICKING UP A BOTTLE OF WINE FROM A LOCAL VINEYARD

 

A bit of modern Scandinavian style in the midst of the Michigan forest, the Wayfarer Treehouse is the perfect place to unplug. With vaulted ceilings in the open kitchen and living room, plus 3 simply furnished bedrooms, the space was made for a family that appreciates comfort and style.  During your stay, you can pop over to the nearby lake for boating, or hike through the cherry orchards just outside your front door. Book here.

 

Photo: Airbnb
Photo: Airbnb

  1. I can attest to how magical the Wayfarer Treehouse is. We went up 2 years ago during the winter to explore the dunes at Sleeping Bear. The host is the kindest, and most stylish. The house hit all the feels of great design, comfort and a relaxing getaway from Chicago. The upstairs shower has a cedar shower mat inside that smells of a spa while you wash. The downstairs Primary stand alone bath is nestled under the windows to give your morning the perfect relaxing start to your day. We can’t wait to go back, they have 2 other must stay properties too!

    1. Thanks for sharing your stay at the Wayfarer Treehouse. It sounds really lovely and glad it was a relaxing getaway! xx -B