Luxury Vacation Rentals with a Private Pool in Easton

Luxury Vacation Rentals with a Private Pool in Easton

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 2 private pool vacation rentals – enter your dates for availability.

Top-rated private pool vacation rentals in Easton

Easton Riverfront property photo 1

Easton Riverfront

3 bedrooms•4 baths
New
Easton Neck property photo 1

Easton Neck

6 bedrooms•3 baths
New
Welcome to private poolside luxury in Easton

Welcome to private poolside luxury in Easton

Settle into a refined escape with our luxury private-pool vacation rentals in Easton, Maryland. Wander pairs the consistency of a five-star hotel with the privacy of a beautifully appointed home, so every arrival feels effortless and every space looks exactly as promised.
Spread out in light-filled living areas designed for gathering, then step outside to your own pool and landscaped patio for unhurried afternoons. Expect chef-ready kitchens, fast WiFi with dedicated work zones, plush bedding, and thoughtful smart-home touches that make work and play flow with ease.
Every stay includes pristine cleaning, hotel-grade amenities, and 24/7 concierge service for anything you need.

Featured private pool vacation rentals in Easton

Easton Neck property photo 1

Easton Neck

6 bedrooms•3 baths
New

All homes in Easton

Easton Riverfront property photo 1

Easton Riverfront

3 bedrooms•4 baths
New
Easton Neck property photo 1

Easton Neck

6 bedrooms•3 baths
New
View all homes

Highlights in Easton

Discover Easton's historic charm, vibrant arts scene, and scenic Eastern Shore waterways, offering a perfect blend of culture and coastal relaxation.
Historic Downtown Easton
Avalon Theatre
Academy Art Museum
Pickering Creek Audubon Center
Chesapeake Bay Maritime Museum

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 private pool vacation rentals in Easton

Jacuzzi (2)
Hot tub (2)
Gym (2)
Outdoor pool (2)
Sauna (1)
Boat dock (1)
Kayaks (1)
Bicycle (1)
Garden (2)
Fire place (2)
Balcony (2)
Dryer (2)
Oven (2)
Washer (2)
Hammock (1)
Patio (1)

Other popular amenities & vacation types in Easton

Family vacation rentals in Easton
Large group vacation rentals in Easton
Discover more beyond the pool in Easton

Discover more beyond the pool in Easton

Graceful Eastern Shore living defines Easton, where Federal-era architecture, leafy streets, and a vibrant arts scene create a town that feels both cultured and relaxed. Weekends bring performances at the Avalon Theatre and a calendar full of festivals, yet the pace remains unhurried.
Water is never far. The Tred Avon and Miles rivers frame classic Chesapeake vistas of marsh and big sky, perfect for time on the water or along the shore. With nearby St. Michaels and Oxford adding easy day-trip appeal, Easton shines in every season. This is why Wander's luxury private-pool vacation rentals in Easton are the perfect choice, whether you're traveling for work or leisure.

FAQs: Vacation Rentals in Easton

Why should I book a Wander in Easton over other private pool vacation rentals?

Wander offers a level of consistency and quality you won’t find with most private pool vacation rentals.
Every home in Easton 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 private pool vacation rentals in Easton?

Some of our most popular private pool vacation rentals in Easton include Wander Easton Riverfront, Wander Easton Neck, and Wander Easton Riverfront. 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 private pool vacation rentals does Wander have available in Easton?

Wander offers 2 private pool vacation rentals in Easton, 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 private pool vacation rentals in Easton?

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

Do Wander’s private pool vacation rentals in Easton have WiFi access?

Yes. Every Wander home in Easton 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.