Luxury Vacation Rentals in Montgomery

Never book a bad vacation home again. Every Wander comes with hotel-grade amenities, inspiring views, pristine cleaning and 24/7 concierge service.

We found 1 vacation rentals – enter your dates for availability.

Top-rated vacation rentals in Montgomery

Home in Montgomery

6 bedrooms•4 baths

Welcome to Montgomery

Set your getaway in the Hudson Valley with Wander’s collection of luxury vacation rentals in Montgomery, New York. Tucked along quiet country lanes near the Wallkill River, these private homes offer peaceful acreage, fresh air, and sweeping pastoral views.

Inside, expect designer finishes, chef-ready kitchens, plush bedroom suites, and generous spaces for gathering or unwinding. Select homes feature pools or hot tubs and expansive decks, all supported by ultra fast WiFi for effortless work and play. Every stay includes pristine cleaning, hotel-grade linens, and 24/7 concierge service so you can arrive, exhale, and enjoy.

Destinations near Montgomery

Featured vacation rentals in Montgomery

Home in Montgomery

6 bedrooms•4 baths

All homes in Montgomery

Home in Montgomery

6 bedrooms•4 baths

View all homes

Highlights in Montgomery

Discover historic charm, scenic county parks, and craft cider tastings in the heart of the picturesque Hudson Valley.

Angry Orchard Innovation Cider House

Winding Hills Park

Orange County Firefighters Museum

Hill-Hold Museum

Baldwin Vineyards

IT'S A VACATION HOME, BUT BETTER

The Wander difference

Wander is different because we combine the quality of a luxury hotel with the comfort of a private vacation home. Your best trip ever is just a few clicks away.

Only the best homes

We’ll never not look like the pictures. Every Wander is beautiful and expertly operated, so you can leave any stress at the door.

Hotel-grade amenities

We’ll never leave you with nothing to do. From ultra fast WiFi to gyms and pools, our homes make it easy to blend work and play.

24/7 concierge service

We’ll never leave you hanging. Our chat-based Concierge is always available to help – from trip questions to special requests.

Inspiring and stunning views

We’ll never leave you uninspired. Every Wander has stunning views to refresh and inspire your soul. Adventure awaits.

Meticulous cleaning

We’ll never have you check in to a dirty house. Our cleaning teams are meticulous, and there are no chores at checkout.

Safety and security

We’ll never pass you off to a stranger. Every Wander location meets our industry-leading safety standards to give you peace of mind.

Most popular amenities for vacation rentals in Montgomery

Other popular amenities & vacation types in Montgomery

Pet-friendly vacation rentals in Montgomery

Large group vacation rentals in Montgomery

Discover more of Montgomery

Montgomery blends countryside calm with easy access to Hudson Valley culture. Historic mills and brick storefronts frame the village, while farms roll toward the Shawangunk Ridge. The Wallkill River threads it all together.

Autumn brings orchards and brilliant foliage, winter is quiet and crisp, and warm months invite time at Storm King Art Center, hikes on Minnewaska trails, and boutique shopping at Woodbury Common. City Winery Hudson Valley adds concerts and seasonal events close by, and country roads reveal scenic overlooks at every turn.

It is an elegant base for a refined escape, which is why Wander's luxury vacation rentals in Montgomery, New York are the perfect choice, whether you're traveling for work or leisure.

FAQs: Vacation Rentals in Montgomery

Why should I book a Wander in Montgomery over other vacation rentals?

Wander offers a level of consistency and quality you won’t find with most vacation rentals.

Every home in Montgomery delivers the quality of a luxury hotel, paired with the comfort and space of a private vacation home. You get hotel-grade amenities, meticulous cleaning, stunning views, and 24/7 concierge support in every stay. Why would you want to stay anywhere else?

Which are Wander’s most popular vacation rentals in Montgomery?

Some of our most popular vacation rentals in Montgomery include New Farmhouse-Hot Tub, King Beds, Golf Sim, Game Room & View and New Farmhouse-Hot Tub, King Beds, Golf Sim, Game Room & View. Guests love the quality of a luxury hotel, the comfort of a private vacation home, and the consistently exceptional experience Wander is known for. Explore the full collection to find the perfect home for your next stay.

How many different vacation rentals does Wander have available in Montgomery?

Wander offers 1 vacation rentals in Montgomery, each carefully designed and expertly operated. Browse the full collection to see what’s available for your trip.

What time is check-in and check-out at Wander’s vacation rentals in Montgomery?

You can check-in to Wander vacation rentals in Montgomery after 4.00pm and check-out before 10.00am.

Do Wander’s vacation rentals in Montgomery have WiFi access?

Yes. Every Wander home in Montgomery has ultra fast, reliable WiFi so you can stay connected throughout your stay.

What is Wander’s cancellation policy?

You can cancel your reservation within 24 hours of booking for a full refund.

For stays of less than 15 nights, you can cancel or reschedule up to 14 days before check-in for a full refund. For stays of 15 nights or longer, the cancellation window is 60 days.

For some homes, a 30-day deadline applies; this will be clearly shown before you book.