Luxury Pet-Friendly Vacation Rentals in Hillsdale

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 6 pet-friendly vacation rentals – enter your dates for availability.

Top-rated pet-friendly vacation rentals in Hillsdale

Home in Hillsdale

4 bedrooms•2 baths

Luxury

Home in Copake

3 bedrooms•2 baths

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Home in Egremont

3 bedrooms•1.5 baths

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New

Home in Craryville

6 bedrooms•5 baths

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Home in Craryville

3 bedrooms•3 baths

•

Luxury

Wander Hillsdale Lakeside

3 bedrooms•4 baths

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Welcome to pet-friendly Hillsdale

Set amid rolling hills and forested ridgelines, Wander brings luxury pet-friendly vacation rentals in Hillsdale to travelers who refuse to leave their companions behind. Enjoy the polish of a luxury hotel paired with the comfort and privacy of a beautifully operated home.

Expect sunlit living spaces, plush bedding, fully equipped kitchens, and smooth indoor-outdoor flow to patios, lawns, and lounging areas that make quick walks and playtime effortless. Every Wander includes inspiring views, pristine cleaning, ultra fast WiFi, and 24/7 concierge service so work and relaxation stay perfectly in balance.

Book a modern retreat with room to breathe and space for pets, and arrive to a home that looks exactly like the photos.

Featured pet-friendly vacation rentals in Hillsdale

Home in Craryville

6 bedrooms•5 baths

•

All homes in Hillsdale

Home in Hillsdale

4 bedrooms•2 baths

Luxury

Home in Copake

3 bedrooms•2 baths

•

Home in Egremont

3 bedrooms•1.5 baths

•

New

Home in Craryville

6 bedrooms•5 baths

•

Home in Craryville

3 bedrooms•3 baths

•

Luxury

Wander Hillsdale Lakeside

3 bedrooms•4 baths

•

View all homes

Highlights in Hillsdale

Experience the perfect blend of outdoor adventure, scenic state parks, and local charm nestled in the historic Taconic Hills.

Catamount Mountain Resort

Taconic State Park - Copake Falls Area

Bash Bish Falls State Park

Roeliff Jansen Park

Harlem Valley Rail Trail

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 pet-friendly vacation rentals in Hillsdale

Exercise equipment (1)

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Discover more pet-friendly spots in Hillsdale

Hillsdale sits where Columbia County meets the Berkshires, framed by open meadows and the Taconic Range. The scenery shifts with the seasons, from snow-draped valleys to wildflower fields, inviting slow mornings and unhurried sunsets.

Adventure comes easy here. Carve turns at Catamount Mountain Resort, hike to Bash Bish Falls from Taconic State Park, or glide along the Harlem Valley Rail Trail through farmland and forest. Nearby towns like Hudson and Great Barrington add galleries, boutiques, and a creative buzz to round out the trip.

For a gateway to nature with effortless access to culture, this is why Wander’s luxury pet-friendly vacation rentals in Hillsdale are the perfect choice, whether you’re traveling for work or leisure.

FAQs: Vacation Rentals in Hillsdale

Why should I book a Wander in Hillsdale over other pet-friendly vacation rentals?

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

Every home in Hillsdale 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 pet-friendly vacation rentals in Hillsdale?

Some of our most popular pet-friendly vacation rentals in Hillsdale include Breezy Hill, Private upstate home nestled in the Hudson Valley, and Rose Cottage. 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 pet-friendly vacation rentals does Wander have available in Hillsdale?

Wander offers 6 pet-friendly vacation rentals in Hillsdale, 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 pet-friendly vacation rentals in Hillsdale?

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

Do Wander’s pet-friendly vacation rentals in Hillsdale have WiFi access?

Yes. Every Wander home in Hillsdale 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.