Luxury Vacation Rentals with a Private Pool in East Stroudsburg

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

Top-rated private pool vacation rentals in East Stroudsburg

Epic Poconos Pad: Pool, Hot Tub, Gym, Golf Sim

6 bedrooms•4.5 baths

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New

~$155 less than other sites

Modern Stream-front 4000 sf House

6 bedrooms•4 baths

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~$125 less than other sites

Modern Creek-front, Hot Tub, Volleyball court

6 bedrooms•4 baths

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~$125 less than other sites

Riverfront Lodge with Indoor Pool & Hot Tub

6 bedrooms•3 baths

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~$270 less than other sites

Amazing Modern Lakefront Chateau

6 bedrooms•5 baths

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~$125 less than other sites

Unique Estate with Heated Indoor Pool

8 bedrooms•5 baths

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~$255 less than other sites

Poconos Retreat: Hot Tub, Fire Pit, Game Room

4 bedrooms•2 baths

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New

~$90 less than other sites

Pocono Escape, Fire Pit + Game Room + Lake Access

3 bedrooms•3 baths

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New

~$95 less than other sites

Welcome to private poolside luxury in East Stroudsburg

Claim your own mountain escape with a sparkling pool to match. Wander offers luxury private-pool vacation rentals in East Stroudsburg that combine serene Pocono settings with the polish of a five-star stay.

Choose from modern mountain homes and wooded retreats designed for indoor and outdoor living, with heated pools, spa-worthy hot tubs, expansive patios, and cozy fire features. Inside, expect chef-ready kitchens, premium linens, dedicated workstations, and ultra fast WiFi. Every stay includes pristine cleaning and 24/7 concierge service, and our homes always look exactly like the photos.

Available soon in East Stroudsburg

Modern Stream-front 4000 sf House

6 bedrooms•4 baths

•

~$125 less than other sites

Modern Creek-front, Hot Tub, Volleyball court

6 bedrooms•4 baths

•

~$125 less than other sites

Amazing Modern Lakefront Chateau

6 bedrooms•5 baths

•

~$125 less than other sites

Unique Estate with Heated Indoor Pool

8 bedrooms•5 baths

•

~$255 less than other sites

Poconos Retreat: Hot Tub, Fire Pit, Game Room

4 bedrooms•2 baths

•

New

~$90 less than other sites

Pocono Escape, Fire Pit + Game Room + Lake Access

3 bedrooms•3 baths

•

New

~$95 less than other sites

Silverline Social Club, Pool, Gameroom, HT, Sauna

5 bedrooms•3 baths

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~$195 less than other sites

Featured private pool vacation rentals in East Stroudsburg

Unique Estate with Heated Indoor Pool

8 bedrooms•5 baths

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~$255 less than other sites

Highlights in East Stroudsburg

Discover the natural beauty of the Poconos with scenic waterfalls, outdoor adventures, and historic charm right at your doorstep.

Delaware Water Gap National Recreation Area

Bushkill Falls

Shawnee Mountain Ski Area

Quiet Valley Living Historical Farm

Smithfield Beach National Recreation Area

Pocono Snake & Animal Farm

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.

All homes in East Stroudsburg

Epic Poconos Pad: Pool, Hot Tub, Gym, Golf Sim

6 bedrooms•4.5 baths

•

New

~$155 less than other sites

Modern Stream-front 4000 sf House

6 bedrooms•4 baths

•

~$125 less than other sites

Modern Creek-front, Hot Tub, Volleyball court

6 bedrooms•4 baths

•

~$125 less than other sites

Riverfront Lodge with Indoor Pool & Hot Tub

6 bedrooms•3 baths

•

~$270 less than other sites

Amazing Modern Lakefront Chateau

6 bedrooms•5 baths

•

~$125 less than other sites

Unique Estate with Heated Indoor Pool

8 bedrooms•5 baths

•

~$255 less than other sites

Poconos Retreat: Hot Tub, Fire Pit, Game Room

4 bedrooms•2 baths

•

New

~$90 less than other sites

Pocono Escape, Fire Pit + Game Room + Lake Access

3 bedrooms•3 baths

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New

~$95 less than other sites

View all homes

Most popular amenities for private pool vacation rentals in East Stroudsburg

Exercise equipment (1)

More popular private pool destinations near East Stroudsburg

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Other popular amenities & vacation types in East Stroudsburg

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Pet-friendly vacation rentals in East Stroudsburg

Hot tub vacation rentals in East Stroudsburg

Discover more beyond the pool in East Stroudsburg

Set within the rolling ridgelines of the Pocono Mountains, East Stroudsburg delivers four-season scenery and fresh mountain air. The Delaware Water Gap offers dramatic overlooks and river adventures, while nearby trail networks wind through quiet forests and past cascading falls.

Winter brings skiing and snow tubing at local resorts. Summer means lake days, golf, and paddling on gentle stretches of the Delaware. Autumn lights up the valleys with brilliant foliage, and spring returns with wildflowers and cool breezes.

With convenient access from New York City and Philadelphia yet a true sense of escape, East Stroudsburg makes getting away effortless. This is why Wander’s luxury vacation rentals in East Stroudsburg are the perfect choice, whether you’re traveling for work or leisure.

FAQs: Vacation Rentals in East Stroudsburg

Why should I book a Wander in East Stroudsburg 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 East Stroudsburg 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 East Stroudsburg?

Some of our most popular private pool vacation rentals in East Stroudsburg include Epic Poconos Pad: Pool, Hot Tub, Gym, Golf Sim, Modern Stream-front 4000 sf House, and Modern Creek-front, Hot Tub, Volleyball court. 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 East Stroudsburg?

Wander offers 9 private pool vacation rentals in East Stroudsburg, 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 East Stroudsburg?

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

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

Yes. Every Wander home in East Stroudsburg 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.