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10+ Red Cottage Vacation Rentals We’re Eyeing for Summer 2025
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. Upstate New York: Classic Catskills + Hudson Valley Getaways 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. Birch & Buck — Leeds, NY 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. The Rye House — Craryville, NY 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 — Wassaic, NY ...
A Guide to Jeffersonville, NY
Tucked into the Western Catskills just over two hours from New York City, Jeffersonville is a small Sullivan County village with an evolving spirit. Surrounded by farmland and forest, its main street has grown into a hub of independent shops, bakeries, and quietly ambitious dining. Weekenders come for the balance – a place where you can sip cider with a view, hike above the Delaware River, or spend an afternoon with alpacas.
A Guide to New Paltz, NY
At the base of the Shawangunk Ridge, New Paltz brings together scenic trails, historic architecture, and a lively downtown rooted in its college town energy. Just 90 minutes from New York City, it’s a place where access to some of the Northeast’s best hiking and climbing sits just minutes from cafés, restaurants, bars, and local shops. Known for its creative streak and outdoorsy edge, New Paltz moves comfortably between nature and culture. Mornings can mean ridge-top hikes or farmers markets; evenings, live music and small plates on Main Street. Plan your visit with our guide to the best hikes, kayaking spots, restaurants, and places to relax in and around New Paltz.
A Guide to Hillsdale, NY
Water cascades through a rocky gorge at Bash Bish Falls, one of the Taconic Mountains’ most iconic destinations, set on the border between Massachusetts and New York. Photo: Escape Brooklyn EB's Top 5 in Hillsdale: • Kayaking on Copake Lake: Spend an entire day on the water by renting a kayak or paddleboard through Copake Lake Boat & Ski. Rentals are available by the hour or for the entire day, starting at $25/hr. • Flights at Roe Jan Brewing Co.: For an afternoon of beer tasting, build a flight of four beers to enjoy on the brewpub's back deck. Keep it light and fresh with the Pill Hill (American Pilsner), 22.5 (Juicy IPA), Harlem Valley (Kolsch), and Roeliff (Saison Ale). • Cross-State Hiking in Taconic State Park: In just under two miles, hike from New York into Massachusetts on the Bash Bish Falls Trail. The New York trailhead provides a more level path than the Massachusetts entrance, so park at the Bash Bish Lower Lot for a gentler start to the hike. • Brunch at Little Cat Lodge: While dinners at Little Cat Lodge impress, the brunch menu is equally noteworthy. Start with a mimosa, then dig into the Little Cat Benedict, which swaps the traditional English muffins with potato latkes. • A Day Trip to Hudson, NY: Just half an hour from Hillsdale, the thriving town of Hudson offers a more bustling environment. Check out the Escape Brooklyn Guide to Hudson to inspire this worthwhile day trip. Tucked where the Hudson Valley meets the Berkshires, Hillsdale and the neighboring town of Copake offer a rural retreat shaped by mountain air, wooded trails, and a quietly evolving food scene. Surrounded by protected parkland and dotted with lakes, farms, and small hamlets, this corner of Upstate NY feels both peaceful and purposeful – an ideal setting for long hikes, outings on the lake, and post-adventure libations. In summer, quiet trails lead to ridgelines and waterfalls, while Copake Lake offers a calm spot for swimming, paddling, or simply drifting dockside. Come winter, nearby Catamount Mountain Resort becomes the main draw, with ski trails and lodge-style dining that anchor the cold-weather season. Year-round, the towns’ compact centers provide a thoughtful mix of cafés, breweries, and restaurants, each one adding a layer to the area’s low-key appeal. Read on for our Hillsdale and Copake guide – including where to hike, ski, eat, and unwind in this scenic stretch of New York. What to Do in Hillsdale, NY: Exploring the Outdoors Start the morning with a stop at Twisted Sisters Coffee House in the center of town, before heading into the mountains. Just over the Massachusetts border, the Bash Bish Falls Trail offers a short, scenic hike to a dramatic waterfall. For more elevation gain, the Cedar Brook Trail in Taconic State Park climbs along its namesake stream before linking with the lengthy South Taconic Trail for broader access to the ridgeline. On Saturdays from May through ...
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Poet’s Hill in Hudson, NY
Located on a quiet country road outside of Hudson, NY, Poets Hill was designed with serenity in mind. Rent one or both homes on-site: its pool house accommodates up to four guests in two bedrooms, while its tiny house accommodates two. At the pool house, take advantage of the expansive outdoor area, with a large deck that's home to a Viking grill/BBQ, sink, and large dining table for al fresco meals, poolside. Its 82 foot pool is open May through October 1, weather permitting.
Goldie Point in Barnegat Light, NJ
100 miles from NYC, midcentury beach getaway Goldie Point is wonderful year-round, but would like you to know about "Secret September" and "Summer’s Not Over October." Currently it's September, the weather is still hot, the water is warm, and the masses of tourists are totally gone. A few months later, experience what the owners call “Wes Anderson Winter,” where the season and stillness create the perfect environment for recovery and wellness at the beach — in total solitude.
Mountain Terrace in Parksville, NY
Perched on a hill and surrounded by tall trees, Mountain Terrace is akin to staying in a luxury treehouse. Three bedrooms sleeps six guests at this beautiful Airbnb in Parksville, NY with two floors, two bathrooms and two living rooms. At the heart of the home is Mountain Terrace's porch: wrap-around style, with west-facing views to watch the sunset each day. A grill and large dining table are perfect for meals al fresco, under the surrounding swaying treetops. At night, head to the bonfire for stargazing outside the private yoga studio, also available for guest use.
Moody Pond House in Warren, CT
Less than 100 miles from NYC, find the magical Moody Pond House: a brand new, modern home tucked away on 18.5 acres in the impossibility picturesque Warren, Connecticut. Named after the gorgeous pond on the property, the popular rental home offers a cushy, private retreat year-round.
Catskills Cloud House in Phoenicia, NY
This gorgeous farmhouse has just been renovated into the perfect rental – especially for those wanting a quick, easy getaway without a car. Hop on the Trailways Bus and arrive into the small town of Phoenicia, where the house is just a 5 minute walk from Main Street. Walk into town for meals, or prepare breakfast, lunch and dinner in the beautiful kitchen and dining area. The trailhead for the Tanbark Trail is walkable from the house, as is the beautiful Esopus River for fishing, tubing, or just taking a cool-off dip.
Cherry Hill in Accord, NY
Midcentury vacation rental Cherry Hill in Accord NY sits atop a hill with panoramic views of the Shawangunk Mountain ridge. Drink in the views from its large hot tub — or opt to watch sunset from the living room, whose large stone fireplace is adjacent to a wall of windows overlooking the mountains. Stunning oversized windows throughout, multiple dining spaces and patios, a well-equipped kitchen and two cozy fireplaces makes this home the perfect destination for a retreat from the city any time of year.
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Potter Mountain House in Gilboa, NY
Tucked into the northern Catskills, Potter Mountain House unfolds with a sense of arrival and quiet intention. Surrounded by 37 acres of wooded trails, meadows, and mountain views, the residence bridges past and present with uncommon clarity. What began as a nineteenth-century church has been reimagined as a refined country retreat — equal parts grounded and grand in its design.
Charming Vintage Farmhouse with Barn Apartment in Catskill, NY
Set in the heart of the Catskills, this early 20th-century farmhouse has been thoughtfully updated for modern living while preserving its historic charm. Inside, a warm material palette – painted wood paneling, exposed beams, wide-plank floors – pairs with a fluid layout designed for connection, comfort, and everyday ease. With layered outdoor spaces, a guest-ready barn apartment, and interiors that balance rustic character with considered details, the property is as well-suited to weekends away as it is to full-time country living.
Four bedroom, six bathroom farmhouse | 2,851 square foot home on 1.9 acres | Full length front porch | Chef’s kitchen with soapstone and butcher block countertops, an eat-in island, and breakfast nook | Wood-burning stove | Gas log fireplace | Covered back deck with wood stove and dining space | Breezeway with back deck access | Large primary suite with spa-like ensuite bathroom | Upstairs sitting room with balcony | Pea gravel patio with stone firepit | Enclosed garden | Four RV hookups | Heated barn-style two-car garage with one-bedroom apartment | Asking $1,285,000
Listed by Richard Vizzini and Emily Wagner at The Wolf Team Catskills at Cocoran Country Living. For showings or inquiries, email richvrealtor@gmail.com or emily.wagner@corcorancl.com, or call/text 845-389-7879 (Richard) or 845-532-2923 (Emily)
From the farmhouse’s front porch, enter into the foyer, where penny tile floors and painted wood paneling create balance between early 1900s craftsmanship and contemporary refinement. To the left, the dining and living rooms open beneath exposed beams, with wide-plank floors and a gas fireplace anchoring the space. A wall of windows and sliding glass doors frames views of the backyard and offers a seamless flow to the covered deck, designed for easy indoor-outdoor entertaining. A cased opening reconnects the living area with the foyer, where a breezeway at the rear adds a subtle point of connection and contrast. Glass-paned doors on one side of the breezeway lead out to the back deck, while an adjacent set opens onto a quaint covered porch.
In the home’s right wing, the kitchen blends farmhouse practicality with updated warmth. Butcher block and soapstone countertops, a copper apron-front sink, and stainless steel appliances bring texture and functionality to the space, while a built-in banquette defines the breakfast nook. A brick hearth with a wood-burning stove anchors the eat-in island and adjoining seating area, creating a cozy gathering spot that invites lingering conversations and slow mornings.
Upstairs, a bright landing gives way to a second-level sitting room with oversized windows, vaulted ceilings, and a set of French doors that open onto a Juliet balcony. To the right of the sunroom, the primary suite offers a sense of calm and refinement, with a walk-in closet, integrated laundry, and abundant natural light. The ensuite bath features vintage farmhouse cabinetry, black-and-white finishes, a rainfall shower, a deep soaking tub with views of the grounds, and a double-faucet sink set in a classic apron-front basin. The second level also includes two …
Custom-Built Modern Home in Saugerties, NY
Set on a quiet road just outside Woodstock, this striking modern home is defined by its clarity of design and connection to the surrounding landscape. Clean lines and minimalist design meet native grasses and towering trees, creating a thoughtful balance of structure and landscape that feels distinctly Upstate.
Four bedroom, three bathroom modern home | 3,035 square foot home on 3.6 acres | Open layout | Floor-to-ceiling windows | Sleek floating fireplace with | Chef’s kitchen with eat-in island, stainless steel appliances, and Italian cabinetry | Primary suite with ensuite bath, double vanity, walk-in shower, and outdoor access | Guest suite with ensuite bath with soaking tub | Lower level yoga studio with potential to finish additional rooms | Bluestone patios | Heated in-ground saline pool | Hot tub | Additional land parcel available | Asking $1,795,000
Listed by Richard Vizzini and Emily Wagner at The Wolf Team Catskills at Corcoran Country Living. For showings or inquiries, email richvrealtor@gmail.com or emily.wagner@corcorancl.com, or call/text 845-389-7879 (Richard) or 845-532-2923 (Emily)
Through a set of glass doors, the home’s main foyer opens directly into a dramatic living space, defined by soaring ceilings, a floating space-age fireplace, and a wall of floor-to-ceiling windows. These windows extend into the open dining area, where a centered skylight brings in natural light throughout the day. From here, the layout flows easily into the kitchen, anchored by a sleek eat-in island and outfitted with custom Italian cabinetry and stainless steel appliances.
A wall of windows frames the home’s living space, creating a backdrop for evenings gathered around the space-age fireplace. Photos: Will Nainis
Tucked beside the kitchen, a private corridor leads to two guest bedrooms, a sunlit office, and the primary suite, where oversized glass doors frame the landscape and open directly to the outdoors. The ensuite bath features a double vanity, walk-in shower, and a separate entrance for easy access to the patio and pool. On the opposite wing, a guest suite with its own bath adds flexibility for hosting. Downstairs, the lower level – currently staged as a yoga studio – offers additional potential to expand guest quarters or create a second living area.
High ceilings and oversized glass doors allow light to fill the primary suite, creating a breezy feeling throughout.
Outside, the grounds echo the home’s clean lines and strong connection to nature. Bluestone patios wrap the exterior, offering space for lounging, dining, and entertaining. A heated saline pool and hot tub are set into the lawn, surrounded by native grasses and towering trees. Set well off the road, with the option for additional acreage, the property offers a rare balance of architectural precision and natural beauty, made for slow mornings, golden afternoons, and starry nights beneath the Catskills.
In + Around Woodstock, NY: Our Local Recommendations
Surrounded by forested hills and winding backroads, …
Juniper Woods in Woodstock, NY
Just over 100 miles from New York City, Juniper Woods is a custom-designed home set on four private, wooded acres in the heart of the Hudson Valley. With more than 3,000 square feet of living space, the three-bedroom, three-bathroom residence offers a rare balance of architectural refinement and natural quiet — where vaulted ceilings, curated materials, and a thoughtful layout support both ease and retreat.
Three-bedroom, three-bathroom contemporary home | 3,076 square foot home on 4.08 acres | Vaulted ceilings | Oversized wood-framed windows | Three-sided fireplace | Chef’s kitchen with Miele appliances, eat-in island, and breakfast nook | Sunroom with direct pool access | First-floor primary suite | Lofted second level | Landscaped gardens | In-ground saline pool | Asking $1,825,000
Listed by Victoria Stent and Leslie Foti at Coldwell Banker Village Green. For showings or inquiries, contact Victoria at vickistent01@gmail.com or 609-356-2275, and Leslie at leslie@upstateabodes.com or 917-670-8509
Enter through the front door into a light-filled, open-concept first floor. At its center, a three-sided fireplace anchors the main living spaces, creating a natural flow between rooms. The living area is framed by oversized windows and vaulted ceilings, drawing in views of the lush grounds and surrounding forest. Just beyond, the kitchen is outfitted with Miele appliances, a generous eat-in island, and a breakfast nook that opens into the formal dining room — a layout designed to gather and move with ease. Off the dining space, a sunroom offers an additional place to lounge and direct access to the patio and pool.
Juniper Woods’ open floor plan allows for easy movement between living spaces, making the layout ideal for hosting and entertaining.
The first-floor primary suite is tucked into its own wing, complete with a quiet bedroom, study, walk-in closet, and a spacious bath with a steam shower and soaking tub. Upstairs, a lofted landing overlooks the living space below and offers additional room for seating, creating a transitional space between two well-proportioned bedrooms.
Set on four wooded acres, the grounds are both cultivated and secluded, defined by mature trees and layered plantings. An in-ground saline pool extends from the main terrace, framed by stonework and soft landscaping that lend a sense of quiet enclosure. The surrounding patio offers ample space to lounge or dine outdoors, with open lawn stretching beyond for recreation or seasonal planting. Designed for ease and immersion, the outdoor areas echo the home’s architectural clarity — considered, refined, and deeply connected to the landscape.
In + Around Woodstock, NY: All Our Local Recommendations
Start the day with coffee and a pastry from Bread Alone – or opt for a sit-down brunch at Garden Cafe, a plant-based restaurant in the heart of Woodstock. From there, explore the town’s deep artistic roots at the Woodstock Artists Association & Museum and Elena Zang Gallery, or take the twenty-minute drive south to see the
Slide Mountain Chalet in Big Indian, NY
Tucked into the high peaks of the Northern Catskills, Slide Mountain Chalet is a character-filled Bavarian retreat perched atop the summit of its namesake mountain. Set on 1.9 wooded acres that neighbor protected state land, the property offers easy access to swimming holes, hiking trails, and skiing, less than three hours from New York City. Balancing alpine charm with backcountry access, this mountaintop chalet is a rare find in one of the most scenic corners of the Catskills.
Two bedroom, one bathroom Bavarian-style chalet | 960 square foot home on 1.9 acres | Vaulted ceilings with exposed beams | Hardwood floors and rich wood paneling | Wood-burning stove with stone hearth | Playful architectural details | Open-concept kitchen with custom vintage cabinetry and stainless appliances | Lofted bonus space with projector screen | Renovated bath with soaking tub and walk-in rainfall shower | Expansive deck and screened porch | Mossy fire pit area | Asking $379,000
Listed by Robin Jones at Anatole House. For showings or inquiries, email robin@anatolehouse.com or call/text 845-943-4177
Open house Saturday, May 31 from 12:00 pm to 2:00 pm at 1636 Frost Valley Road, Big Indian, NY 12410. Please contact the listing agent to RSVP.
Through a set of sliding glass doors, enter the chalet’s open layout living space, where exposed beams, hardwood floors, and original wood paneling frame a warm, inviting interior. To the right, a cozy living space is anchored by a wood-burning stove set on a stone hearth. To the left, there is a quaint kitchen and dining space with vintage cabinetry, butcher block countertops, and modern stainless steel appliances.
Oversized windows and high ceilings create an airy contrast to the chalet’s cozy wood stove and warm finishes. Photo: Zach Hyman
Off the living space, a flight of stairs adorned with a carved Bavarian railing leads to a vaulted loft that adds flexibility to the home. Currently set up as a home theater, the loft can be easily converted to a library, studio, or bonus guest space. Back downstairs, two quiet bedrooms share a recently updated bathroom, which features a walk-in rainfall shower and deep tub, ideal for soaks after days spent hiking or skiing.
Outside, the full-length deck acts as an open-air extension of the home, ideal for mountain-side meals or morning coffee. A screened porch with interior and exterior access sits at one end of the deck, creating space for storm watching or unwinding with a book on a slow summer afternoon. On the moss-covered grounds, a fire pit set against a backdrop of evergreen hemlocks offers a space to gather beneath the stars. The nearly two-acre lot adds room to roam, with a mix of boulders, forest, and natural clearings to explore.
Through the seasons, enjoy the Catskill Mountain air from the breezy screened porch.
In + Around Big Indian, NY: Our Local Recommendations
Tucked into a quiet corner of the Slide Mountain Wilderness, the chalet offers direct access …
The Robin’s Nest in Red Hook, NY
110 miles from NYC, The Robin’s Nest is a graceful home with historic roots where timeless design meets natural serenity. Nestled beneath mature trees and overlooking open farmland, the property offers a rare balance of privacy, elegance, and connection to the outdoors. Framed by sweeping views and quietude, the home’s classic architecture and refined interiors create a sense of calm that’s both grounded and elevated, ideal for those seeking a slower pace of living in the heart of the Hudson Valley.
Three-bedroom, one-and-a-half-bathroom Colonial Revival | 2,556-square-foot home on 1.35 acres | Wood-burning fireplace | Built-in shelves and cabinets | Country kitchen with marble countertops, stainless steel appliances, and farmhouse sink | Hardwood floors | Oversized windows | Primary bedroom with Juliet balcony | Brick-paved patio | Expansive lawn | Two parcels of land included in sale | Asking price $899,000
Listed by Leslie Foti at Coldwell Banker Village Green. For showings or inquiries, email leslie@upstateabodes.com or call/text 917-670-8509
Open house on May 25th from 12:00 pm – 2:00 pm at 293 Linden Avenue, Red Hook, NY 12571. Contact listing agent to RSVP.
Through the front door, The Robin’s Nest opens into a bright and flowing interior where space feels both open and grounded. To the right, the home’s main living space is anchored by a wood-burning fireplace, while oversized windows and a set of French doors leading to a patio frame views of the surrounding landscape. Modern design elements contrast with the home’s historic roots, creating a warm, timeless feel throughout.
From the living room, a set of French doors opens onto the home’s brick-paved patio. Photos: Shelter Upstate
In the left wing of the first level, a classic country kitchen—updated with marble counters, high-end appliances, and custom cabinetry—serves as the heart of the home. It opens directly to an elegant dining area, equally suited to large gatherings or quiet evenings. Just off the dining room, a bonus space with warm terracotta tiles and a large picture window creates an intimate seating area, thoughtfully tucked away from the main living spaces. The intuitive layout continues with a convenient first-floor bathroom and laundry, positioned discreetly just off the main living areas.
The Robin Nest’s country kitchen features stainless steel appliances, marble countertops, a farmhouse sink, and custom cabinetry.
Upstairs, two cozy bedrooms complement a generously sized primary, where glass-paned doors open to a Juliet balcony overlooking the property. Painted hardwood floors in soft white lend a clean, airy feel throughout. The renovated bathroom blends vintage charm with modern updates, including a walk-in shower with scalloped tile, a rainfall showerhead, and a classic pedestal sink. A palette of peach, black, and white adds a playful yet refined touch, echoing the home’s thoughtful balance of character and comfort.
Outdoors, a brick-paved patio off the main living room opens to a lush, tree-framed yard with wide views across neighboring farmland. Included with …