Home Vacation Rentals By Owner In Germantown, NY

Showing 10 Of 10 Vacation Rentals
Slider Thumb

$140.4

/ Nightly
Condo

Sunny Victorian Studio in Pacific Heights

Germantown, New York, United States

Sunny second floor studio in 1886 Victorian five unit building in prestigious Pacific Heights. Main room has bay windows with southern exposure, queen bed and closet. The kitchen is in a separate room with large windows and a sitting area. Large bathroom with original tile and updated fixtures. High ceilings with original ornate crown mouldings, ceiling medallions and other original Victorian embellishments and hardwood floors throughout. Quiet street across from two private schools.brThe spacebrThe studio has been recently remodeled, updated and painted. It is located in a charming victorian building within walking distance of Union St., Fillmore St., Chestnut St. and the Marina. It is a bright, happy space in a quiet building on a quiet street (no buses).brGuest accessbrGuests will have access to the entire unit. The front door is shared by other condo owners and the stairs are shared with the occupant on the third floor. There is a shared utility room in the basement with a washer and dryer.
Bed 1

Bed

Bath 1

Bath

Sleep 2

Sleeps
Slider Thumb
Exceptional(43)

$230.53

/ Nightly
Cottage

Loblolly Cottage - Enchanting Retreat set among towering pines.

Germantown, New York, United States

Loblolly Cottage is a peaceful retreat set among towering pines on ourbrproperty in Germantown NY. This guest suite harkens back to an authentic 1930s Adirondack cabin that features a reclaimed barn wood interior with vaulted ceilings and antique beams. Outside enjoy our fantastic deck with a Cabana kitchen and fire pit. A short stroll will lead you to the heart of the hamlet where you will find an array of shops and restaurants. Loblolly Cottage is a unique one-of-a-kind vacation experience. brI'm new on VRBO, but I have over 150 Five Star Reviews on that other rentalbrplatform. Check them out there.
Bed 1

Bed

Bath 1

Bath

Sleep 2

Sleeps
Slider Thumb
Exceptional(3)

$2430.4

/ Nightly
Private Vacation Home

Holcroft On Hudson, 4 Br, Hudson River Manor on 65 acres, with pool

Germantown, New York, United States

Holcroft is a private, 65-acre country estate on the Hudson River in Columbia County, offering old-world charm and elegance, as well as spectacular sunsets over the Hudson and the Catskill Mountains. It provides a once-in-a-lifetime opportunity to spend a weekend, a week, or more in a secluded and country mansion, relaxing with family and friends.brbrThe house is located 7 miles from Bard College and is a perfect accommodation for families attending Bard College Graduations.brbrAccommodations include a master en-suite, a guest en-suite, and two bedrooms that share a full bath. Additional rooms upon request.brbrKitchen with gas range, and views of the Hudson River; pantry with dishwasher, washer/dryer. Large, 800 square foot drawing room with period furniture and portraits plus a fireplace, and a formal dining room with seating for 10.brbrPorch with marble table and outdoor shaded seating for 10, plus incomparable views of ocean-going and smaller watercraft on the ever-changing tidal currents of the Hudson River. In-ground, fenced pool with views of the Hudson and Catskills. Expansive lawns for croquet, frisbee, wiffle ball, and other outdoor pursuits. Professionally landscaped gardens throughout the property, walking paths to explore, including the mile-long driveway.
Bed 4

Bed

Bath 4

Bath

Sleep 8

Sleeps
Slider Thumb
Exceptional(11)

$172.48

/ Nightly
Cottage

Charming loft cottage in tranquil Germantown with WiFi, AC

Germantown, New York, United States

Make yourself at home in this welcoming 1-bedroom Germantown retreat. Just .3miles from Otto's Market (groceries and deli) and Universal Cafe (farm to table global inspired classics restaurant). This beautiful cottage features 1 queen bed and 1 sofa bed perfect for a cozy stay. Enjoy the amenities like AC, WiFi, radiant heating system, smart TV with a fire stick with access to Amazon Prime and Netflix and full kitchen with plenty of amenities. The bathroom offers a refreshing shower and hair dryer for your convenience. We're happy to assist with any questions while you stay at our cottage.
Bed 1

Bed

Bath 1

Bath

Sleep 2

Sleeps
Slider Thumb
Exceptional(1)

$2594.67

/ Nightly
Private Vacation Home

Historic Gilded Age Riverfront Mansion, Pool, Tennis, Sleeps 20+, 70ac on Hudson

Germantown, New York, United States

Built in 1885 and featured in Martha Stewart Living magazine, Midwood is one of the Hudson Valley's most storied private estates — a 12-bedroom Gilded Age mansion set on 70 acres of rolling riverfront land, 2.5 hours from New York City.brThis is not a vacation rental that happens to have history. History happened here. The estate was built by a descendant of Robert R. Livingston, who helped draft the Declaration of Independence. Franklin Delano Roosevelt rode the carriage road behind the Big House while courting Eleanor before their 1905 wedding. For the past 40 years, the property has been cared for by a family of artists, educators, and community builders. Every room reflects that.brThe Big Housebr12 bedrooms, most with private bathrooms, sleeping 20+ guests comfortably. Each room is richly furnished and full of character — original artwork, vintage furnishings, layered textures that reflect generations of creative life. No two rooms are alike.brThe shared spaces are made for gathering: a formal dining room that seats 16+, a double living room perfect for group evenings or lazy afternoons by the fire, and a fully equipped kitchen with a professional-grade stove and new refrigerator. Step out onto the west-facing porch and you'll understand why families keep coming back — the Hudson stretches wide before you, the Catskill Mountains rise on the far bank, and ships sail past day and night.brThe GroundsbrSwimming pool tucked in the woodsbrTennis courtbrPrivate waterfront and river accessbrCarriage road and walking trails across 70 private acresbrExpansive lawn for outdoor gatheringsbrParking for 14 vehicles on-sitebrWiFi, Nest heating, washer/dryer — everything you need to feel at homebrThe LocationbrMidwood sits in the heart of the Hudson Valley, centrally located between Hudson, Red Hook, and Rhinebeck. Two and a half hours from NYC by car; 20 minutes from Amtrak stops in Hudson and Rhinecliff. Nearby towns offer galleries, restaurants, farm stands, and markets — Rhinebeck and Hudson in particular are worth a full day each.brGood to KnowbrMidwood is newly listed on VRBO, and we're offering introductory pricing to welcome our first guests through the platform. The estate has been hosting family reunions, retreats, weddings, and gatherings for decades — you'll be in very good hands.brThe listed rate covers self-catered use of the house and grounds for groups of up to 20 guests. If you're planning a professionally catered event, additional fees and a separate agreement apply — reach out and we're happy to discuss. All prices shown include fees. No surprises at checkout.
Bed 12

Bed

Bath 10

Bath

Sleep 24

Sleeps
Slider Thumb

$511.3

/ Nightly
Private Vacation Home

Classic Greek Revival, 4 bedroom, light filled house with views of the Catskills

Germantown, New York, United States

19th century, light filled, house in charming Germantown, New York. Four bedrooms with five beds, two full baths, and two kitchens, a living room and den provide ample space to relax with plenty of privacy for families or small groups! Enjoy a drink on the deck as you watch the sunset over the Catskill mountains.
Bed 4

Bed

Bath 2

Bath

Sleep 8

Sleeps
Slider Thumb
Exceptional(4)

$808.0

/ Nightly
Private Vacation Home

Pool, Fireplace, Converted Barn! | Chic Barn House

Germantown, New York, United States

Summary:brbrThis extraordinary designer barn-house retreat is nestled along the scenic Hudson River in Germantown. A one-of-a-kind home to unwind in style; cathedral windows showcase the home’s unique architecture. Enjoy evenings by the fire pit, take a refreshing dip in the heated pool, or gather in the dining area for memorable meals.brbrbrbrPlease SEE: Other Things to NotebrbrFor Area Details, Please SEE: The Neighborhood & Getting Aroundbrbr*Pet Friendly, fee applies per pet.brbrbrbrThe Space:brbrChic Barn House, Home Features:brbr• 3 Bedroom, 2 Bath - Available for up to 11 Guests!brbr• Upstairs Primary Ensuite with WFH Deskbrbr• Heated Pool* & Outdoor BBQbrbr• Unique Converted Barnbrbr• Free WiFi & Smart TVbrbrbrbrSleeping Arrangements: brbr• Bedroom 1 - King Bed + Queen Sleeper Sofa (Upstairs)brbr• Bedroom 2 - 4 x Twin Beds (Upstairs Loft, Over Living Room)brbr• Bedroom 3 - 2 x Queen Beds (Downstairs)brbrbrbrStep into a sun-filled barn-house retreat in Germantown where the outdoor space is just as memorable as the home itself. In the summer months, cool off with a dip in the heated pool, then stretch out on the patio, sway in the hammock, and fire up the BBQ for an easy dinner outside. As the evening sets in, gather around the wood-burning fire pit under the stars and linger a little longer in the fresh Hudson Valley air.brbrbrbrInside, the home keeps the same easy, welcoming flow, with an open-concept living, dining, and kitchen space that’s perfect for coming together between adventures. Stream your favorites on the smart TV, then head to the fully equipped kitchen with stainless steel appliances, ample counter space, booth seating, and a dedicated workspace—ideal for everything from pool-day snacks to big group dinners.brbrbrbrWhen it’s time to rest, there’s space for everyone to spread out comfortably. Upstairs, the primary bedroom features a king bed plus a pull-out sofa sleeper, while downstairs offers a spacious bedroom with two queen beds. The loft rounds it out with four twin beds that are perfect for kids, cousins, or classic sleepover nights, and Casper mattresses throughout help everyone sleep cool and wake up refreshed.brbrbrbrThe best part is how effortlessly this home blends rustic character with modern comfort—original beams, sliding barn doors, and cathedral windows paired with renovated bathrooms, walk-in showers, and a private sauna for post-hike (or post-pool) recovery. Whether you’re here for sunny pool days, fire-lit evenings, or simply a place that makes it easy to be together, this one-of-a-kind Germantown barn-house is ready to host your next getaway.brbrbrbrbrbrPlease Note: There is no central Air Conditioning. We have 2 window units, but the loft may get hot during summer heatwaves. brbrPool Access: Available seasonally, closed in winter months. Pool is available June through August. Heating by request, $50/night fee applies.brbrbrbr• Winter Access Notice: The driveway and parking area is plowed in winter. During snowy conditions, a 4WD or AWD vehicle is strongly recommended for reaching the home. If you’re traveling without one, access may be difficult or not possible at times. Portoro Homes cannot be held responsible for weather-related access issues or provide assistance if a vehicle becomes stuck.brbrbrbrGuest Access:brbrPortoro Homes offers convenient self check-in. Check-in instructions will be sent by email and text prior to arrival with everything you need to access the home easily and on your schedule. You’ll also receive a digital Guest Guide for the home, packed with helpful tips, house info, and local recommendations to make the most of your stay.brbrbrbr• Early check-ins or late check-outs: Standard check-in time is 4:00 p.m. and standard check-out time is 11:00 a.m. If the home is ready earlier on the day of arrival, an early check-in may be available when confirmed with our main office. Late check-outs must be requested and confirmed by our main office prior to departure.brbrbrbrThe Neighborhood:brbrThe Hudson Valley and nearby Catskills are a favorite escape for travelers who want river views, mountain air, and small-town charm without sacrificing great food and culture. Days here can be as active or as slow as you want—waterfalls and trailheads, kayaking on the Hudson, antique shops and galleries, then a farm-to-table dinner that somehow tastes even better after a day outside. Fall is especially magical, when the hills turn into a sweep of color and every drive feels like a scenic route.brbrbrbrThis home is tucked into quiet Germantown, a pastoral pocket of the Hudson Valley known for its farmland, historic estates, and easy access to some of the region’s best day trips. From here, you’re close to the river and just a short drive to beloved towns like Hudson and Rhinebeck for shopping, cafés, and weekend markets. You’re also well-positioned for iconic Hudson Valley sights—like Olana and Clermont—and if you’re craving bigger hikes and waterfalls, the Catskills are within reach for an easy adventure day before coming back to unwind in the calm of Germantown.brbrbrbrThings to See & Do:brbr-- Explore:brbr• Stroll Germantown and pop into local shops, galleries, and markets for an easy small-town afternoon.brbr• Spend a day in Hudson for antiques, bookstores, cafés, and a creative main-street scene.brbr• Head to Rhinebeck for charming boutiques, historic streets, and classic Hudson Valley dining.brbr• Take a scenic drive along Route 9G for Hudson River views and beautiful countryside.brbr• Make time for golden-hour river overlooks and spontaneous farm-stand stops.brbr-- Outdoor Adventures:brbr• Hike Kaaterskill Falls for one of the region’s most iconic waterfall trails.brbr• Kayak or canoe on the Hudson River for a peaceful, scenic paddle.brbr• Explore riverside paths and picnic spots throughout the area.brbr• Plan a Catskills day trip for bigger mountain views, deeper woods, and classic trail days.brbr-- Farms, Markets & Wine:brbr• Browse the Germantown Farmers’ Market for seasonal produce and local goods.brbr• Visit the Hudson Farmers’ Market for a lively weekend stop with regional vendors.brbr• Go wine tasting at nearby wineries like Hudson-Chatham Winery and Tousey Winery.brbr• Seek out local farm stands for fresh fruit, flowers, and Hudson Valley pantry staples.brbr-- Arts, Culture & Entertainment:brbr• Visit Olana State Historic Site for art, architecture, and sweeping Hudson River views.brbr• Tour Clermont State Historic Site for history, gardens, and a beautiful riverside setting.brbr• Check out Basilica Hudson for rotating art, music, and event programming.brbr• Explore Art Omi for an outdoor sculpture experience that feels like a hidden gem.brbr• Make a day trip to the Thomas Cole National Historic Site in Catskill.brbr-- Dining & Shopping:brbr• Book a meal at Gaskins for a Hudson Valley farm-to-table favorite.brbr• Stop by Otto’s Market for coffee, provisions, and local treats.brbr• Explore Hudson’s food scene with spots like Lil’ Deb’s Oasis, Swoon Kitchenbar, and The Spotty Dog Books & Ale.brbr• Antiques and vintage lovers will have plenty to do in Hudson, with shops and warehouses worth wandering.brbr-- Golf Courses:brbr• Copake Country Club (Copake Lake)brbr• Rip Van Winkle Country Club (Palenville)brbr• Red Hook Golf Club (Red Hook)brbr• Catskill Golf Club (Catskill)brbr-- Annual Festivals & Events:brbr• Hudson Winter Walk (Hudson, NY)brbr• Basilica SoundScape (Hudson, NY)brbr• Hudson Valley Garlic Festival (Saugerties, NY)brbr• Hudson Valley Wine & Food Fest (Rhinebeck, NY)brbr• Columbia County Fair (Chatham, NY)brbr• Hudson Jazz Festival (Hudson, NY)brbr• Seasonal riverfront and farmers’ market events (Germantown, NY)brbrbrbrGetting Around:brbrGetting around Germantown and the Hudson Valley is easy, scenic, and best done by car, especially from 516 Hover Avenue Extension. Having your own vehicle gives you the freedom to hop between river towns, farm stands, trailheads, and historic sites without feeling rushed, and most drives are calm and low-stress with well-maintained roads and minimal traffic. Parking is typically straightforward and often free, and even in popular nearby spots like Hudson or Rhinebeck, you’ll usually find public lots or metered spaces without much hassle.brbrbrbrSome of the most enjoyable routes in the area turn simple errands into mini road trips. Route 9G is a favorite for Hudson River views and historic stops, while Route 23 is a beautiful option when you want broader valley scenery and access to nearby towns. If you’re heading farther afield, the Taconic State Parkway offers classic upstate landscapes, and Route 28 is a great gateway when you’re aiming toward the Catskills. Cell service is generally reliable, but it’s still smart to download maps ahead of time if you plan to wander onto quieter back roads.brbrbrbrWildlife sightings are part of the experience—especially at dawn and dusk—so take it slow on darker stretches and keep an eye out for deer. Winter travel can be stunning but weather-dependent, so a well-equipped car and a little extra time go a long way. Rideshares exist in some areas, but availability can be limited outside the busier towns, making a personal vehicle the most convenient way to explore.brbrbrbrAirports:brbr• Albany International Airport (ALB): ~1 hour 15 minutesbrbr• Stewart International Airport (SWF): ~1 hour 30–1 hour 45 minutes depending on route/trafficbrbr• Hudson Valley Regional Airport (POU): ~1 hourbrbr• New York City Airports (JFK/LGA/EWR): ~2.5–3 hours depending on route/trafficbrbrbrbrPopular Landmarks:brbr• Clermont State Historic Site (Germantown, NY)brbr• Olana State Historic Site (Hudson, NY)brbr• Thomas Cole National Historic Site (Catskill, NY)brbr• Hudson River Skywalk (Catskill/Hudson area)brbr• Basilica Hudson (Hudson, NY)brbr• Walkway Over the Hudson (Poughkeepsie, NY)brbr• Montgomery Place Historic Estate (Annandale-on-Hudson, NY)brbr• Saugerties Lighthouse (Saugerties, NY)brbr• Kaaterskill Falls (Hunter, NY)brbr• Kingston Waterfront & Stockade District (Kingston, NY)
Bed 3

Bed

Bath 2

Bath

Sleep 11

Sleeps
Slider Thumb
Exceptional(11)

$224.09

/ Nightly
Apartment

Cozy Guest Suite At The Blue Ranch

Germantown, New York, United States

This hotel style suite is cozy yet modern. Larger than a typical hotel room the studio includes a living space, dining area, and private outdoor patio perfect for sipping a morning cup of joe or capping off the evening with a tasty glass of wine.brbrGuests have access to the suite via private entrance with a digital door code for entry. Please note the studio is connected to our private residence with shared parking but grants complete privacy.brbrEnjoy all the Hudson Valley has to offer at our inviting ranch. Location is minutes to amazing local farms, wineries, distilleries, & farm to table restaurants. 20 minutes from the Catskills Mountains, makes for great hikes, or mountain biking, as well as kayak or paddle boarding along the Hudson River. This suite is perfect for a couple or solo traveler who plans on enjoying local amenities as there is no kitchen located on site.br
Bed 1

Bed

Bath 1

Bath

Sleep 2

Sleeps
Slider Thumb

$253.17

/ Nightly
Cabin

Modern Cabin, Sauna, EV Charger, Forest Escape, Close to Tivoli, Germantown, RH

Germantown, New York, United States

The Grove is a one-bedroom cabin set on 50 wooded acres in Germantown, designed as a quiet refuge for creatives, founders, and anyone looking to step away and reset. Tucked into the landscape but thoughtfully outfitted, it offers the rare combination of privacy, design, and access to everything that makes the Hudson Valley so magnetic.brInside, the space is calm and functional. A queen bedroom anchors the cabin, with a comfortable sofa bed in the living area for additional guests. The bathroom is clean and modern with a walk-in shower and essentials provided. It’s well heated in the colder months and cool in summer, making it an easy, year-round stay.brStep outside and the experience opens up. A wood-fired sauna offers a true reset at the end of the day. There are outdoor dining and entertaining areas set within the trees, perfect for slow mornings or long evenings. A Tesla charger is available on-site for convenience.brGuests have access to the broader property, including a shared in-ground pool, tennis court, and private river access reached by foot. The 50 acres of woods, trails, and open space create a sense of quiet that’s increasingly hard to find.brThe Grove is ideally positioned for exploring the Hudson Valley. Tivoli, Germantown, Hudson, Red Hook, and Rhinebeck are all a short drive away, offering restaurants, shops, galleries, and weekend markets. Whether you’re here for a quick reset or a longer stay, everything feels close, but never intrusive.brThis is also an ideal home base for wedding guests and event attendees in the area. Close to many of the region’s top venues, it offers a more private, design-forward alternative to traditional accommodations. For influencers, creatives, and those documenting their time in the Hudson Valley, the setting provides a natural backdrop that feels both elevated and effortless.brThe Grove works just as well for a quiet solo retreat as it does for a weekend away with a partner or small group. It’s a place to unplug, host a simple meal, take a sauna, walk the property, and settle into a slower pace.brPrivate, grounded, and thoughtfully designed, it’s the kind of stay people return to.
Bed 1

Bed

Bath 1

Bath

Sleep 4

Sleeps
Slider Thumb
Exceptional(6)

$539.72

/ Nightly
Private Vacation Home

Hudson Valley Cabin

Germantown, New York, United States

Cape Farmhouse with modern touches, on nearly 3 acres backing up to a stream and an expansive backyard with far reaching country views . The house is bright, sun-filled and unique. brbrYou enter the house on the first floor with living, dining, kitchen, a bedroom and full bath. There are two additional bedrooms on the 2nd floor. The lower floor has the master bedroom, full bath and a spacious 2 story family room flooded with natural light and a brand new 65” TV for those rainy or snowy days.
Bed 4

Bed

Bath 2

Bath

Sleep 7

Sleeps

Home Most popular vacation rentals in Germantown

Slider Thumb
Exceptional(6)

$172.48

/ Nightly
Cottage

Charming loft cottage in tranquil Germantown with WiFi, AC

Germantown, New York, United States

Bed 1

Bed

Bath 1

Bath

Sleep 2

Sleeps
Slider Thumb
Exceptional(6)

$224.09

/ Nightly
Apartment

Cozy Guest Suite At The Blue Ranch

Germantown, New York, United States

Bed 1

Bed

Bath 1

Bath

Sleep 2

Sleeps
Slider Thumb
Exceptional(6)

$230.53

/ Nightly
Cottage

Loblolly Cottage - Enchanting Retreat set among towering pines.

Germantown, New York, United States

Bed 1

Bed

Bath 1

Bath

Sleep 2

Sleeps
Slider Thumb
Exceptional(6)

$808.00

/ Nightly
Private vacation home

Pool, Fireplace, Converted Barn! | Chic Barn House

Germantown, New York, United States

Bed 3

Bed

Bath 2

Bath

Sleep 11

Sleeps
Slider Thumb
Exceptional(6)

$2430.40

/ Nightly
Private vacation home

Holcroft On Hudson, 4 Br, Hudson River Manor on 65 acres, with pool

Germantown, New York, United States

Bed 4

Bed

Bath 4

Bath

Sleep 8

Sleeps
Slider Thumb
Exceptional(6)

$2594.67

/ Nightly
Private vacation home

Historic Gilded Age Riverfront Mansion, Pool, Tennis, Sleeps 20+, 70ac on Hudson

Germantown, New York, United States

Bed 12

Bed

Bath 10

Bath

Sleep 24

Sleeps
Slider Thumb
Exceptional(6)

$539.72

/ Nightly
Private vacation home

Hudson Valley Cabin

Germantown, New York, United States

Bed 4

Bed

Bath 2

Bath

Sleep 7

Sleeps
Slider Thumb
Exceptional(6)

$140.40

/ Nightly
Condo

Sunny Victorian Studio in Pacific Heights

Germantown, New York, United States

Bed 1

Bed

Bath 1

Bath

Sleep 2

Sleeps
Slider Thumb
Exceptional(6)

$253.17

/ Nightly
Cabin

Modern Cabin, Sauna, EV Charger, Forest Escape, Close to Tivoli, Germantown, RH

Germantown, New York, United States

Bed 1

Bed

Bath 1

Bath

Sleep 4

Sleeps
Slider Thumb
Exceptional(6)

$511.30

/ Nightly
Private vacation home

Classic Greek Revival, 4 bedroom, light filled house with views of the Catskills

Germantown, New York, United States

Bed 4

Bed

Bath 2

Bath

Sleep 8

Sleeps

Most Popular Cities in New York