Family-friendly holiday rentals in Stroudsburg

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.

Simply Serene: Wild West City, 4 acres of privacy

✨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 ⭐

Pocono Castle w/ Dungeon Escape Room &Private Pond

Sleep in a Fairy Tale at Pocono Castle! Live the dream in this 2,300 sq. ft storybook retreat, where you’ll sleep like royalty in a real fairy tale castle. Unwind in luxury with a bubbling hot tub, a cedar sauna, and endless magical touches. Dress up as Kings, Queens, or Knights and explore the grounds, featuring a private one-acre pond & maybe you’ll catch a Golden Fish! With enchanting bedrooms, outdoor adventures, and unforgettable charm, this is the OMG getaway you’ve been waiting for!

Cottage in the Woods | Pocono Mountains

Cabin vibes & luxury touches make the ⇛Cottage in the Woods⇚ an amazing place for our guests! Come escape to the Cottage nestled deep in the woods in a peaceful and quiet area. Connect with nature watching roaming deer and woodland views from the 4 season sunroom. Enjoy an evening fireside at the firepit with friends and family. *YoutubeTV included* We invite you to our Cottage with cabin vibes & luxury touches. 90min from NYC and 2hrs from Philadelphia. Welcome to the Pocono Mountains!

DWG Mountain Oasis-Private Apt w/Frog Pond

Private family apartment built for relaxing comfort and views of nature 2 miles from Mount Tammany, Mount Minsi, and the Appalachian Trail Walk to a private brookside trail and a winery Private deck Includes: Bread, eggs, pancake mix, coffee, tea, milk, bananas, s'mores kit, and more AWARDS: Top 1% of all Airbnb & #1 "Most Hospitable NJ Host" in 2021 Little or no host interaction – your choice Host lives on-site and can provide customized recommendations for food and things to do

Private Wellness Suite • Infrared Sauna • Views

Relax in a private, spa-inspired suite designed for simple luxury, wellness, and grounding. Located in the walk-out basement of our home, it features a private entrance and large patio with serene mountain views. Enjoy hotel-style touches, a 3-person infrared sauna with color therapy and Bluetooth, heated bathroom floors, and surround sound. Pet-friendly, set on a peaceful 3-acre property with hosts usually nearby. Ideal for wellness escapes, romantic getaways, or longer stays.

Cassie's Cozy Cottage - Poconos Near Shawnee

Welcome to Cassie's Cozy Cottage! Enjoy a peaceful stay suited for two people. Located near various outdoor recreational activities like skiing/snowboarding, hiking trails, river activities, golf courses, and also shopping outlets. Shawnee Mountain-3.7 miles, Camelback Mountain-12 miles, Delaware River Access- (Smithfield beach) 4.6 miles (Bushkill Access) 14 miles, Bushkill Falls- 10 miles. The Crossings Premium Outlets- 10 miles, ...and many more areas to visit close by.

Eclectic Pocono Retreat Ideal for groups, walkable

Perfect location for friends and family to unwind and breathe. Sleeps 10 with spacious rooms, fast Wi-Fi, board games and a dedicated Art Studio for rainy-day fun. 4 bedrooms, full kitchen, dedicated workspace, soaking tub and peaceful backyard space all in town. 3-Season Bonus! Cozy up on our enclosed porch with a glamping cot designed for 2 outdoor lovers. -Free parking four cars -Smart TV & streaming -Crib & family-friendly gear -5-star Superhost, rapid replies

Stroudsburg - Poconos: Nice 1 bedroom

You will be staying within walking distance of many local shops and restaurants when you book this unit for your stay. You will be located in Stroudsburg which is very convenient and you will love the fact you will not have to search for parking. The apartment has everything you need to offer you a great experience. As your host, we make sure to offer you a comfortable place as well as respond quickly to any concerns or help you may need.

Adorable Farm Cottage

This memorable place is anything but ordinary. The cottage is located on an organic farm. We have a staff onsite that is always buzzing around and happy to help you answer any questions you may have. We have a Wood Fire brick oven bakery on site as well. This is not just any Farm anyone who visits will understand the love that surrounds us! This cottage is not just a place to stay but an AMAZING experience as well!

Secluded Suite outside of town.

A small suite located above the town of Jim Thorpe. I am really geared towards couples looking for a weekend getaway. The space is smaller but very easily accomadates two people. A big step up from any hotel room/suite. The rental is not located in the town of Jim Thorpe. I am located about 10 minutes outside of town and about 5 minutes away from Penns Peak. The rental is connected to home but completely seperate.

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.