Summer’s around the corner — and with Memorial Day just ahead, we’re officially in vacation-planning mode. Whether that means long weekends in the mountains, lazy days by the pool, or finding the perfect town to wander for a few days, we’re always on the lookout for special places to stay.

This season, we’re teaming up with Red Cottage — a premier platform for thoughtfully curated vacation rentals and property management across the Northeast. With a portfolio that spans the Catskills, Hudson Valley, Berkshires, Poconos, and Long Island, Red Cottage has earned a reputation for exceptional homes that blend style, setting, and comfort in all the right ways.
From modern cabins with fire pits to riverfront homes and coastal bungalows, we’ve handpicked 10+ standout properties — plus a little insider intel to help make the most of each one.

A mix of rugged trails, wooded privacy, and design-forward cabins defines this iconic part of the Northeast. Each of these five homes is perfect for a long weekend close to nature, with pools, firepits, and plenty of nearby adventure.

Tucked into the foothills of the Catskills, Birch & Buck’s pool deck features expansive, panoramic views of the mountain range.

Floating above 13 private acres with panoramic mountain views, Birch & Buck is a modern Catskills lodge with soft, elegant interiors and a showstopping deck built for golden hour. Inside, a glass-walled great room, chef’s kitchen, and four en-suite bedrooms set the tone for luxurious downtime. Outside, a heated pool, hammock grove, and firepit seating offer the kind of serenity rarely found this close to town.

A Community for Artists: Spend the day exploring the thriving town of Catskill, where art spaces like Foreland and galleries like Gallery 495 draw visitors from across the region.

Just twenty minutes from the shops, bars, and restaurants of Hudson, The Rye House feels worlds away – a secluded, picturesque retreat with easy access to one of Upstate’s most vibrant towns.

Sleek, private, and purpose-built for unplugging, The Rye House is a modern hillside escape designed for total immersion in nature — without leaving comfort behind. With a pool, built-in hot tub, and walls of glass framing panoramic views, this three-bedroom retreat invites guests to stock up on gourmet groceries, then settle in for a weekend of cooking, lounging, and doing absolutely nothing.

20 Minutes Away in Hudson, NY: Take a short morning drive to Hudson to pick up provisions (and coffee) at Talbott & Arding, followed by Grapefruit Wines for a bottle or two of natural wine. Then, spend the day snacking and drinking poolside.

Harlem Valley Hideout’s eclectic interiors stand out for design lovers, while amenities like a large pool, multiple fireplaces, and a chef’s kitchen make it equally appealing for group getaways and slow weekends upstate.

A joyful blend of bold design and mid-century charm, Harlem Valley Hideout is a two-bedroom (plus nursery) retreat made for creative families and design lovers alike. Bursting with color and playful patterns, the home pairs its vintage soul with thoughtful upgrades: a marble-accented kitchen, multiple lounge areas, and a fenced-in pool surrounded by sunny seating and herb gardens.

Creative Energy, Small-Town Charm: Spend the afternoon wandering The Wassaic Project, a boundary-pushing art space housed in a converted grain elevator just down the road. Come evening, grab a table at The Lantern Inn for wood-fired pizza, small plates, and live music that draws an eclectic crowd. Those looking to explore the nearby town of Millerton can head to Hunter Bee and the Millerton Antiques Center for vintage shopping, or can catch a film at The Moviehouse – an independent cinema housed in a beautifully restored 1903 theater.

Located in the Great Northern Catskills, West Kill Farmhouse’s impressive exteriors set the stage for days by the pool, al fresco meals on the deck, and evenings around the fire pit.

Tucked into 40 private acres in the Spruceton Valley, West Kill Farmhouse is a bold and luxurious five-bedroom retreat with floor-to-ceiling mountain views and serious lodge energy. A soaring great room centers around a fireplace and leather sectional, while outside, a pool, hot tub, fire pit, and outdoor shower set the stage for group hangs that stretch into the evening.

Spruceton Valley: Home to Epic Hikes + Our Favorite Catskills Brewery: Start the day hiking the challenging Diamond Notch Falls trail, then walk to West Kill Brewing for a pint from the taproom and a snack from the rotating food pop-ups before returning home.

Perfect for immersing in the outdoors, Spirit Cabin’s private lake frontage offers swimming and non-motorized boating just steps from the door.

Tucked into five private lakefront acres in the woods of Forestburgh, Spirit Cabin is a modern-rustic retreat with a Nordic twist. Designed for equal parts leisure and adventure, this design-forward three-bedroom blends clean-lined interiors with a full suite of wellness amenities — including a sauna, cold plunge, saltwater pool, and CrossFit-style gym. Mornings begin with yoga on the east-facing deck or boating on the lake; evenings wind down in the hot tub, by the fire pit, or in front of the outdoor movie screen.

Low-Key Nights and Local Favorites Near Forestburgh: Pick up wood-fired pizza from Forage to bring back for a low-key night in, or make the short drive to Livingston Manor for new Korean spot Threshold. When the weather turns, catch a show at the Forestburgh Playhouse — a local standby for rainy-day plans.

Think mountain air, wildflower fields, and cozy towns with great food scenes. These homes in the Berkshires and Poconos are set up for a little bit of everything: hiking, lounging, day trips, and stargazing from a hot tub.

Set on 80 private acres, enjoy complete privacy when taking dips in the pool – and for those seeking extra adventure, head to Red Rock Summit’s hidden swimming pond to enjoy a natural body of water.

Perched on 80 private acres in the rolling hills of East Chatham, Red Rock Summit is a contemporary mountain retreat designed to showcase panoramic views at every turn. Inside, airy, sun-filled interiors frame the landscape with floor-to-ceiling glass, while outside, a swimmable pond, fire pit, and pool with mountain views invite guests to slow down and soak it all in. With four bedrooms, four baths, and ample space for gathering or retreating, it’s a secluded escape that makes the most of every season.

Explore the Western Berkshires: Spend the afternoon hiking the Ooms Conservation trails, or explore the sculpture garden at Art Omi in the nearby town of Ghent. For dinner, grab pizza at Bimi’s Canteen, or opt for seasonal fare at The Bartlett House.

Valley View’s fully retractable glass doors blur the lines between indoor and outdoor spaces, creating an open feel throughout the living area.

Tucked into the rolling farmland of Copake, Valley View blends the character of a restored 19th-century cottage with the light-filled expanse of a striking contemporary addition. Set on 37 private acres with a serene pond, panoramic views, and a pool deck made for golden-hour lounging, this five-bedroom home is both grounded and elevated – designed for quiet mornings, group gatherings, and starry nights by the fire. From exposed beams and wide-plank floors to retractable glass walls and a fully equipped gym, it’s a home that balances heritage with modern comfort.

Waterfalls, Lake Days, and Drive-In Nights: Start the day hiking to Bash Bish Falls – a dramatic, multi-tiered waterfall accessed via a trail that straddles the New York–Massachusetts border – or paddling the calm waters of Copake Lake. In the evening, catch a movie at Four Brothers Drive-In, known for its elevated snack bar fare and retro setup – or stay in for a night swim under the stars at Valley View.

Start the day on the spacious sundeck, then head down to the cabin’s private riverfrontage for kayaking and swimming.

Set on three private acres along a quiet bend of the Delaware River, The Riverside Cabin includes both a striking A-frame and a separate two-bedroom cottage. Great for groups, the homes are outfitted with a wood stove, game room, fire pit, and kayaks for exploring the water.

Hikes, Floats, and Wine in the Western Catskills: Hike Jensen’s Ledges, tube, kayak, or canoe on the Delaware at Soaring Eagle Campground, then head into Callicoon for drinks at Callicoon Wine Merchant and dinner at Black Walnut.

Tamarack House’s open layout allows for easy movement between the kitchen, living, and dining spaces – ideal for gathering with friends and family.

Minimal and modern, Tamarack House is a two-bedroom cabin set on two private acres just minutes from Narrowsburg — one of the most charming towns on the Delaware River. Floor-to-ceiling windows bring the woods in, while a wood-burning stove and deck with outdoor dining make it a cozy year-round base.

Hit Main Street Narrowsburg: Spend an afternoon exploring downtown Narrowsburg, where a stretch of Main Street packs in some of the region’s best shopping. Dig through design-forward salvage and European finds at Maison Bergogne, flip through curated titles at One Grand Books, or hunt for vintage treasures at Moonriver Antiques. Stop for a riverside pizza at The Laundrette, then linger over dinner at The Heron – a longtime favorite for seasonal, locally sourced plates.

The Barn’s warm wood interiors strike a balance between rustic charm and modern ease, wrapping the space in a sense of lived-in comfort.

A soaring post-and-beam structure from 1863 sets the stage for this unforgettable escape. Thoughtfully converted into a 4,100-square-foot home, The Barn  @Doodletown unfolds across three dramatic levels, with cathedral ceilings, plank floors, and a wood-burning stove anchoring the main living space. On 11 private acres next to the 690-acre Doodletown Wildlife Management Area, it’s a retreat that leans into both adventure and stillness, offering chef-grade kitchen amenities, indoor-outdoor flow, and a layout that’s ideal for group stays or quiet creative resets.

Lake Life by Day, Tavern Dining by Night: Spend the day at Lake Taghkanic State Park, where calm waters and forested shores offer a classic Upstate escape. Swim from the sandy beach, rent a kayak or paddleboard to explore the lake, then head back to the barn to freshen up before driving south to Stissing House – a beautifully restored tavern serving wood-fired fare in a candlelit dining room that feels both timeless and transportive.

Mountain View’s screened porch frames distant mountain vistas and sets the scene for al fresco dinners, even when summer rainstorms roll in.

Tucked into a quiet hillside clearing with wide-open vistas, Mountain View is a serene, design-forward retreat where the Catskills unfold just beyond your windows. This three-bedroom, multi-level home was built for slow mornings and long dinners, with wide decks, a screened porch, and cozy gathering spaces that all center around the view. Inside, clean lines and natural textures create a sense of calm, while outside, birdsong and meadow breezes are your background soundtrack.

Coffee, Hike, Beer, Repeat: Start your morning with coffee and a breakfast sandwich at Twisted Sisters Coffee House before heading out for a hike in Taconic State Park. For a challenge, take the South Taconic Trail to Andler Mountain and cross into Massachusetts, or opt for the gentler route to Sunset Rock for big views with less effort. Afterward, settle in for a beer flight at Roe Jan Brewing Co., or head to Little Cat Lodge for cocktails and alpine-inspired fare.

For those craving salt air and sun-soaked patios, these two Hamptons picks deliver laid-back luxury with style to spare. Great design, beach access, and space to spread out — summer starts here.

Framed by clean lines and bathed in natural light, Cape Lane’s modern design creates a serene backdrop for coastal getaways. 

Tucked into the woods just ten minutes from town, Cape Lane is a modern East Hampton gem that delivers on both luxury and laid-back living. A striking glass facade welcomes guests into a clean-lined, design-forward interior, where four bedrooms, curated furnishings, and walls of windows frame the surrounding nature preserve. Outside, a private oasis unfolds with a pool, fire pit, hammock, and outdoor shower — perfect for slow summer days.

Sun, Surf, and Savory Finds in East Hampton: Spend the afternoon on the sand at one of East Hampton Village’s guarded beaches – from the wide, dune-backed stretch of Main Beach to the more tucked-away Georgica or Two Mile Hollow. After a swim or a long walk at the water’s edge, swing by Cavaniola’s Gourmet in Sag Harbor to pick up wine and cheese to enjoy fireside back at Cape Lane.

Inspired by beachfront bungalows, this spacious, modern take on Long Island’s classic beach house blends laid-back coastal style with contemporary architecture.

With eclectic interiors, vintage touches, and a laid-back outdoor setup, Barnes Bungalow brings beachy charm to the Hamptons without sacrificing style. Located in Barnes Landing between East Hampton and Amagansett, the four-bedroom home features a white-brick fireplace, a cozy TV room, and sliding doors that open to a private backyard with a heated pool, fire pit, and paddleboards ready for adventure.

A Dreamy Day in Montauk: Take the short drive to Montauk to climb the Montauk Point Lighthouse for exceptional panoramic views of the Atlantic Ocean. Afterward, grab brunch at Bird On the Roof before heading out to shop in downtown Montauk (we love Wyld Blue, The 8th Drifter, and Road to Nowhere). End the day with dinner at Mavericks Montauk, then head back to Barnes Bungalow to enjoy an evening dip in the pool.