Holiday houses in Stroudsburg

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Quick stats about holiday rentals in Stroudsburg

  • Total holiday rentals

    Explore 20 holiday rentals in Stroudsburg

  • Nightly prices starting at

    Stroudsburg holiday rentals start at $86 AUD per night before taxes and fees

  • Verified guest reviews

    Over 2,930 verified reviews to help you choose

  • Family-friendly holiday rentals

    10 properties offer extra space and kid-friendly amenities

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wi-Fi availability

    20 of Stroudsburg holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Gym, BBQ grill and Laptop-friendly workspace across Stroudsburg rentals

  • 4.8 Average rating

    Stroudsburg stays are highly rated by guests—averaging 4.8 out of 5!

Top-rated holiday rentals in Stroudsburg

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top Guest favourite
A modern bathroom features a glass shower with marble tiles, a freestanding tub beside a window, and plush towels hanging nearby. The light wood flooring complements the spacious layout and natural light filters through a skylight.
Townhouse in East Stroudsburg
4.93 out of 5 average rating, 155 reviews

Luxe 2-Bed/2.5-Bath: Sleeps 8, Breakfast/Ski/Views

Beautiful luxe townhouse for up to 8 guests, with 2 bedrooms, 2.5 baths, a full kitchen, office, loft, and a deck with a grill overlooking parklike shared grounds. Bright interiors, skylights, mountain views, and a marble master shower will take your breath away. Steps from Shawnee Mountain and a short drive to Shawnee Inn & Golf, Bushkill Falls, the Delaware Water Gap, outlets, and dining. Includes breakfast, snacks, and quality body care—ideal for families, couples, or groups. Decor available.

Guest favourite
An A-frame cabin is nestled among tall trees, illuminated by warm string lights. A cozy fire pit with glowing embers is positioned in front, creating a welcoming atmosphere. The cabin's porch features seating, inviting relaxation in a serene outdoor setting.
Chalet in Stroudsburg
4.94 out of 5 average rating, 140 reviews

Cozy Poconos A-Frame on Appenzell Creek

Charming A-frame cabin with modern amenities on 3.5 acres of private land. Appenzell Creek and its tributaries run through the property. Perfect for a relaxing getaway. Minutes from Delaware Water Gap, skiing, hiking, state parks, lakes, water parks, outlet shopping, breweries, wineries, great dining, resorts, casinos and more. Enjoy listening to the rushing creek while grilling on the deck, soaking in the hot tub, decompressing in the sauna or dipping your feet in the creek.*NOT a party house*

Top Guest favourite
Home in Penn Estates
5.0 out of 5 average rating, 253 reviews

Enchanted Forest Escape | Hot Tub | Movie Screen

A truly unique stay in the Pocono Mountains, home to rolling mountain terrain, breathtakingly beautiful waterfalls, thriving woodlands, + 170 miles of winding river. Created with the “ultimate night in" themed experience, guests can sip wine under the stars in a private hot tub, + enjoy movies on their own 135" movie screen equipped w/ the world's first LED 4K gaming projector. Enjoy themed bedrooms and experience a stay where the forest takes you away as you stay in ultimate comfort + luxury.

Top Guest favourite
An outdoor deck features comfortable lounge furniture in shades of blue, surrounded by lush greenery. A stock tank pool is seen, offering a relaxing spot. Soft gravel pathways lead to various seating areas, creating a serene outdoor retreat on the property.
Home in Stroudsburg
4.99 out of 5 average rating, 196 reviews

Simply Serene: Wild West City/Escape Room/4 Acres

✨IT'S ALL ABOUT FINDING THE CALM IN THE CHAOS ✨ & making memories .. 🌿4 ACRES OF PRIVACY, TRANQUILITY & WILD WEST CHARM 🌿4 COZY BEDROOMS • 3000+ SQ FT OF PURE FUN 🏡Unique Custom Designed Retreat in the Heart of the Poconos - Stunning Nature & Wildlife yet Minutes from All Major Poconos' Attractions 💖Perfect for Any Group Size - From Romantic Getaways, to Family Reunions, Special Occasions, OR Relaxing with Friends & Loved Ones ⭐Over 100 Indoor & Outdoor FUN Activities for All Ages ⭐

Guest favourite
A warmly decorated living area features a sectional sofa complemented by a plush ottoman. A natural wood accent wall houses a flat-screen TV above a fireplace. A potted plant adds a touch of greenery, while a patterned rug covers the wooden floor, enhancing the space's comfort.
Townhouse in East Stroudsburg
4.96 out of 5 average rating, 186 reviews

Serene Escape - Jacuzzi, mins from trails/skiing

Step into the comfort of this luxurious, 2 BR 2 Bath house with recently renovated spaces that make it feel like a home away from home. Situated in a serene residential area, the home promises a mountain retreat close to the best skiing, restaurants, stores, hiking, and amenities of the Poconos. Enjoy ski slope and mountain views from the deck. Contemporary design and an abundance of amenities will satisfy all your needs. ✔ 2 Comfortable BRs ✔ Fully Equipped Kitchen ✔ Jacuzzi Tub ✔ Smart TVs

Top Guest favourite
The inviting living area features wooden beams and a stone fireplace, surrounded by comfortable seating arrangements. Large windows illuminate the space, showcasing rustic decor and a cozy sheepskin rug on warm-toned wooden floors. A dining table is visible in the background, enhancing the communal atmosphere.
Cabin in East Stroudsburg
4.93 out of 5 average rating, 450 reviews

Coziest Creek Cabin- Idyllic, Authentic, Poconos

Deep within our psyche lies a romantic image, that of a log cabin tucked into the woods perched above a babbling trout laden stream. Perhaps inside there's a sheepskin rug laid before a grand fireplace, a reading nook, and a child's dreamy hideaway loft. Or maybe you're out on the deck, a crisp morning bundled and sipping cocoa on a rocking chair, or nights soaking sore bones and soaking up the sounds of the stream & kids below roasting smores by the fire. Now make that dream a reality!

Guest favourite
A modern kitchen features a central island with seating for several, surrounded by dark wood cabinetry. The granite countertops reflect light, and stylish backsplash tiles add texture. Glass doors lead to an outdoor space, creating a bright, open atmosphere enhanced by recessed lighting.
Home in Stroudsburg
4.94 out of 5 average rating, 227 reviews

Luxury Rental in the Pocono Mountains Pa

Luxury in the Pocono Mountains. Equipped for long stays. This beautiful 3,200 sq.ft. home is only 90 minutes from NYC and located on a quiet and private lot. Guests can enjoy their stay year round do to the central Pocono location. Its just a short drive from Shawnee & Camelback Mountains, as well as the Kalahari Resort and Great Wolf Lodge. Shopping at the Crossings Premium Outlets, plenty of dining options, and a neighboring vineyard/winery and entertainment await you. 25 and over to book.

Top Guest favourite
A spacious two-story home features a rich red exterior and a welcoming front porch with steps leading up. Lush greenery surrounds the house, enhancing the tranquil setting. A gravel driveway and landscaped areas contribute to the inviting outdoor space.
Chalet in Stroudsburg
4.95 out of 5 average rating, 503 reviews

Dog-Friendly Chalet in the Heart of the Poconos

This comfortable home with a fully fenced yard is located in the heart of the Pocono Mountains. It is minutes from Camelback Mountain, The Crossings Premium Outlets, the Pocono Raceway, indoor and outdoor water parks, the Appalachian Trail, and some of Pennsylvania's best fishing and hunting. The property features a 1/3 acre fully fenced yard with deck access including a smaller fenced area for letting dogs out in a more contained space than the larger fenced yard. The house is pet friendly.

Guest favourite
An open-concept living area features a combination of wooden beams and white shiplap walls. A cozy seating area is positioned next to a stone fireplace. A modern kitchen with dark cabinetry is visible, along with a dining table set for four, complete with plates and a decorative centerpiece.
Chalet in East Stroudsburg
4.9 out of 5 average rating, 217 reviews

Enchanting River Chalet

Located Conveniently in the Pocono's, just 1 hour 30 minutes from Manhattan and under 2 hours from Philly! Our relaxing 100 year old cabin has been fully remodeled down to the finest detail. Just minutes from the most popular hiking destinations, waterfalls, and sits right on the Bushkill River for great fishing and relaxation. The bathroom features special stone imported from Italy along with a custom carved rock sink. Pets are welcome free of charge (:

Guest favourite
The cabin features a modern exterior with large windows and a dark finish, enhancing its rustic charm. A welcoming deck is accessed by steps, surrounded by natural landscaping. Warm lights are positioned above, providing subtle illumination for evening gatherings.
Cabin in Penn Estates
4.91 out of 5 average rating, 151 reviews

Gorgeous Lake Cabin in Poconos

The perfect escape from city life. Up winding mountain roads you'll land at your private cabin just a walk away from the beautiful lake. Enjoy our private hot tub or sit outside on our expansive deck & watch the wildlife. Gather around the firepit to make s'mores. If you're looking to be more active, there are basketball courts, tennis courts, & swimming all within our safe and peaceful gated community.

Guest favourite
The exterior of the rustic cottage features a wooden facade and two sets of French doors. Chairs are positioned on a stone path leading to the entrance, surrounded by a manicured garden area with pebbles and greenery. Nearby trees provide a natural backdrop.
Guesthouse in Stroudsburg
4.95 out of 5 average rating, 280 reviews

Cozy guest cottage with indoor fireplace

Take it easy at this unique getaway in the Poconos! This vintage one room cottage is the perfect space for soaking in nature, getting creative, or exploring the attractions of the Pocono Mountains. The cozy cottage is within 20 minutes of ski resorts, Kalahari, and the Delaware Water Gap national recreation park. Reach downtown Stroudsburg and it’s restaurants and nightlife within 7 minutes.

Guest favourite
Large windows allow natural light to illuminate the open living space, featuring a sectional leather sofa, a round wooden coffee table, and a stone fireplace with a wood stack. A dining area with an elegant table is visible in the background, framed by greenery.
Chalet in Penn Estates
4.96 out of 5 average rating, 224 reviews

Hot tub | Pool | King Bed | Lakes | Pickleball

Welcome to Blue Forest Chalet! This newly remodeled Pocono retreat blends chic design with woodsy charm. Unwind in the art-filled bath with a Japanese soaking tub or relax in your private hot tub. Summer guests enjoy access to 2 pools, 3 lakes, pickleball, game room & playgrounds (optional add-on pass)! Minutes from hiking, skiing, and waterparks. Your ultimate escape awaits!

Popular amenities for Stroudsburg holiday rentals

When is the best time to visit Stroudsburg?

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Frequently Asked Questions

  • What are the best places to stay in Stroudsburg?

    Vacation rentals in downtown and nearby neighborhoods are often favored for easy access to restaurants, galleries, and parks. Rural stays around the Pocono foothills provide a quieter setting.

  • What are the best things to do in Stroudsburg with kids?

    Kids enjoy interactive museums, local parks with play areas, and family programs at community centers. Seasonal festivals and hands-on art workshops are frequently suggested for younger visitors.

  • What are some of the best things to do in Stroudsburg?

    Explore galleries and boutiques downtown, catch a show at Sherman Theater, or stroll through local parks. The area often features farmers markets and seasonal events that draw both locals and visitors.

  • How is the weather in Stroudsburg?

    Stroudsburg experiences cold winters around 22–38°F (-6–4°C), with snowfall, and warm summers reaching 65–86°F (18–30°C) with frequent rain. Spring and autumn bring milder temperatures and colorful scenery.

  • When is the best time to visit Stroudsburg?

    Late spring and early autumn are often recommended for comfortable temperatures and vibrant landscapes. Summer draws many visitors for outdoor activities and frequent cultural events.

  • What are the best places to visit in Stroudsburg?

    Sherman Theater is frequently suggested for performances, while galleries and vintage shops line Main Street. Nearby parks make a great spot to explore local nature.

  • What are some hiking trails in Stroudsburg?

    Stroudsburg has wooded trails in area parks, and nearby sections of the Appalachian Trail can be explored for longer hikes. Local nature reserves provide pathways for leisurely walks and birdwatching.

  • What are some family activities we can do in Stroudsburg?

    Families often enjoy interactive museums, local parks with playgrounds, and occasional outdoor adventures such as tubing or mini golf. Seasonal arts programs and farmers markets are frequently suggested for all ages.

  • What are some of the best day trip ideas from Stroudsburg?

    Explore scenic parks in the Pocono Mountains, visit regional museums, or discover historic towns around the area. Many guests spend time on nature trails or browse local antique shops for unique finds.

  • Are there any pet friendly accommodations available in Stroudsburg?

    Many accommodations near downtown and in nearby neighborhoods welcome pets, making it convenient to travel with animal companions. Local parks and trails are inviting spots for walks.

  • What are some local tips for visiting Stroudsburg?

    Locals suggest exploring early in the day for a quieter experience and checking community bulletin boards for event updates. Bring layers due to changing weather, and sample locally roasted coffee when you visit downtown.

  • What is Stroudsburg known for?

    Stroudsburg is known for its vibrant downtown, mix of arts and culture, and access to the natural beauty of the Pocono Mountains. Local music and food scenes often reflect the town’s creative spirit.

  • What are the best hidden gems to explore in Stroudsburg?

    Art spaces tucked along quieter side streets, small vintage shops, and locally run bakeries are often described as hidden gems. Nature trails around the outskirts invite peaceful exploration away from crowds.

  • What are the best foods to try in Stroudsburg?

    Guests frequently suggest local farm-to-table dishes, Pennsylvania Dutch classics, and wood-fired pizza. Baked goods from independently owned shops and craft beers are popular treats.

  • What should I bring for a trip to Stroudsburg?

    Pack layers to adjust for fluctuating temperatures, sturdy shoes for exploring town and trails, and rain gear if visiting during spring or summer. Adding a reusable water bottle is also a good idea for outdoor activities.

  • What is the nightlife in Stroudsburg like?

    Stroudsburg has lively bars, local breweries, and venues with live music, especially near Main Street. Guests often explore casual restaurants with late-night menus and occasional community events in the evening.

  • What are the most popular events or festivals in Stroudsburg?

    StroudFest draws crowds to Main Street each Labor Day weekend, and the town often hosts seasonal farmers markets, music events, and holiday parades. The Sherman Theater is known for live performances and community gatherings.

  • Are there family friendly vacation rentals in Stroudsburg?

    The area has a range of family-friendly vacation rentals, including larger homes and apartments near parks and central amenities. Flexible spaces often feature amenities for children and group gatherings.