Holiday rentals in Penn Estates

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Penn Estates

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

%{current} / %{total}1 / 1
Guest favourite
The cozy outdoor area features a fire pit surrounded by several Adirondack chairs. Soft lighting from string lights enhances the inviting atmosphere of the cabin, which is illuminated from within, showcasing a spacious deck and large windows that reflect the night sky.
Chalet in East Stroudsburg
4.99 out of 5 average rating, 164 reviews

Poconos Treetop Lakehouse: Lakefront/Spa/Sauna

Accessible, dog-friendly, waterfront A-line with breathtaking views only 50 ft from lake. Stepless entry/shower, elevator. Newly renovated & stylishly furnished w/ 4 bedrooms, 3 full bathrooms, hot tub, sauna, gourmet kitchen, 12 person custom dining table, coffee bar, fireplace, game room w/ billiards/foosball/arcade, many outdoor games, 3 outdoor decks, Big Green Egg grill, fire pit, fire table, hammocks, many types of boats, fishing poles, work desk, high speed WiFi, 5 Smart TV’s, EV charger.

Top guest favourite
The spacious living area features a large green sofa, two cozy accent chairs, and a rustic coffee table made from natural wood. A stone fireplace adds warmth, while soft lighting and large windows enhance the inviting atmosphere.
Home in East Stroudsburg
5 out of 5 average rating, 207 reviews

Themed| Lake | Pool | 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" experience in mind, 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
A castle-style retreat is showcased, featuring a whimsical dragon statue and a large chess set in the foreground. A tranquil pond with a fountain is visible, alongside a magnificent castle structure designed with classic stone elements and a welcoming entrance, all set amidst lush greenery.
Castle in East Stroudsburg
4.99 out of 5 average rating, 412 reviews

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!

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 East Stroudsburg
4.96 out of 5 average rating, 195 reviews

The Blue Forest Chalet: Hot tub/Firepit/Hike/Kayak

Welcome to the Blue Forest Chalet! This newly remodeled home perfectly blends chic with woodsy for the ultimate Pocono Retreat. Whether you come for adventure or just to relax, we have you covered. Unwind and indulge in an art-filled bathroom with a Japanese soaking tub or sit outside and watch the deer roam by from your private hot tub. Located in the heart of the Poconos, just minutes from excellent Hiking, Skiing, Swimming, Kayaking, Fishing, Shopping, Restaurants, Waterparks, and more.

Guest favourite
An inviting living area features a comfortable white sofa adorned with decorative cushions. A plush armchair in dark purple contrasts with warm wood flooring. The kitchen, visible in the background, includes wooden cabinetry and modern appliances. Natural light brightens the space through a window.
Guest suite in Bangor
4.94 out of 5 average rating, 341 reviews

Modern Cozy Oasis-Mountains Retreat

Relax in a Modern, Cozy Apartment on a Scenic 3-Acre Retreat Unwind in this stylish and comfortable apartment set on 3-acre property with stunning mountainside views. Whether you're walking, jogging, or simply relaxing, the spacious yard offers the perfect setting to reconnect with nature. In the evenings, gather around the fire pit and enjoy the peaceful sounds of the outdoors. 5 mins to historic Bangor 25 mins to Poconos, Kalahari, ski resorts & Delaware Water Gap Escape & unwind!

Superhost
An outdoor retreat is surrounded by lush greenery, featuring a hot tub under a gazebo and an inviting fire pit area. Soft, glowing string lights create a warm ambiance. The space is framed by towering trees, offering a sense of privacy and tranquility.
Home in East Stroudsburg
4.9 out of 5 average rating, 101 reviews

Huge Private Serenity Hot Tub, Fire Pit, Game Room

A STUNNING home, conveniently located just minutes away from all the natural attractions that the Poconos has to offer (lakes, hiking, & more!), you will have all the amenities & entertainment you could need right at home. Hot tub, fire pit, jungle gym, pool table, arcade games, and much more! 15 min - Delaware Water Gap, Downtown Stroudsburg 20 min - Kalahari Resort, Shawnee Mountain, Big Pocono State Park 30 min - Bushkill Falls Experience The Poconos With Us & Learn More Below!

Top guest favourite
A cozy living area features warm wooden paneling and a plush sofa with light-colored cushions. A wooden coffee table holds two water bottles and a binder, while a stone fireplace adds character. Natural light streams in through large windows, enhancing the inviting atmosphere.
Farm stay in Cresco
4.96 out of 5 average rating, 176 reviews

The Thoroughbred Cottage at Pleasant Ridge Farm

The Thoroughbred Cottage is the quintessential, early 1900s Pocono vacation cottage. Located on our commercial horse farm, the cottage has been entirely renovated but has kept its unique original details. Views include our upper pastures and wooded hillside of the state game lands beyond. The cottage is set back on our private lane, but is close to all major Pocono attractions and wedding venues. A perfect, cozy little getaway for couples. Not suitable for infants or children

Superhost
The living room features a spacious wrap-around couch and a coffee table, creating an inviting area for relaxation. Large windows allow natural light to fill the space, while views of the surrounding trees are visible. A dining area and kitchen can be seen in the background.
Home in East Stroudsburg
4.91 out of 5 average rating, 139 reviews

Poconos Mountain Retreat 4BR 3BA 15 Min Camelback

Newly renovated Poconos Mountain Retreat home! House contains 4 bedrooms and 3 full bathrooms with plenty of back and side decks. The home is equipped with a new central ac and heating system with vents in each room! About a 15 minute drive to Camelback. Close to Shawnee Mountain, Tannersville Outlets, Sunset Shooting Range, Great Wolf Lodge, and all the major attractions. Less than a 12 min drive from 24 hour grocery stores, as well as bars and restaurants!

Top guest favourite
An outdoor area features a spacious deck with a hot tub at its center, surrounded by wooden fencing. Dining furniture is arranged on the deck, and decorative string lights hang overhead, enhancing the inviting atmosphere of the space.
Cabin in East Stroudsburg
5 out of 5 average rating, 126 reviews

Hot Tub, GameRoom, Fire Pit, Mins to Skiing, Pets

Escape to the Poconos at the Whispering Willow Lodge. Relax with family or friends at our beautifully appointed 4 bedroom + loft with plenty of space for everyone. Enjoy the outdoors on our spacious deck, have a soak in the hot tub or cozy up by the fireplace. Centrally located in Penn Estates Private, gated community which offers swimming pools, lakes, beach, tennis, volleyball & more. Minutes to skiing, water parks, shopping, rafting, hiking, and wineries.

Top guest favourite
An outdoor space features a wood barrel sauna set among autumn foliage. Black, Adirondack-style chairs surround a circular firepit with flickering flames, creating a cozy gathering area. The sauna is minimally designed with a wooden exterior and a single door.
Home in East Stroudsburg
4.92 out of 5 average rating, 196 reviews

Sauna | Movie Theater | Hot Tub | Dogs OK |Firepit

Discover the tranquility of the Pocono Mountains at our 3-bedroom, 2-bathroom home, where the perfect blend of nature and luxury awaits. This spacious retreat is perfect for families and friends, accommodating up to 8 people, ensuring a comfortable and unforgettable stay. We also welcome up to 2 furry pets. With a range of fantastic amenities, you'll have everything you need to make your Pocono getaway truly exceptional!

Superhost
A cozy dining area features a wooden table with a checkered tablecloth and two chairs. Decorative items, including a flower arrangement and wall art, enhance the warm ambiance. Large windows allow natural light to brighten the space, creating a welcoming atmosphere.
Farm stay in Saylorsburg
4.94 out of 5 average rating, 244 reviews

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!

Top guest favourite
A collage of the lakefront villa highlights includes a bright kitchen with modern appliances, a fire pit surrounded by seating, a hot tub set in a wooded area, adults and children kayaking on the tranquil lake, a game room showcasing a ping pong table, and private lake access with a spacious deck.
Home in East Stroudsburg
4.97 out of 5 average rating, 188 reviews

Dog Friendly🐶 Lakefront🎣 Hot Tub🔥 Newly Renovated🤩

Pet-friendly 3,000 sq ft lakefront home with 1,000 sq ft of patio space, private lake access, kayaks, fishing, hammocks, BBQ grill, a 6-person hot tub & more! 6 bedrooms, 3 full bathrooms across 2 levels that features a game room, laundry area, living and dining rooms, a full well equipped kitchen, and central A/C & heat. Ample parking, free access to community amenities, and no additional pet fees!

Popular amenities for Penn Estates holiday rentals

When is the best time to visit Penn Estates?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. price$355 SGD$344 SGD$306 SGD$290 SGD$299 SGD$319 SGD$408 SGD$433 SGD$276 SGD$306 SGD$316 SGD$370 SGD
Avg. temp-1°C0°C5°C11°C17°C22°C24°C23°C19°C13°C7°C2°C

Frequently Asked Questions

  • Are there pet-friendly vacation rentals in Penn Estates?

    Four-legged friends are welcome in Penn Estates. Choose from more than 150 vacation rentals for guests traveling with pets.

  • Are there vacation rentals with a dedicated workspace in Penn Estates?

    Yes! Work meets play with ease at over 130 vacation rentals in Penn Estates featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Are there Penn Estates vacation rentals on Airbnb with pools?

    Yes! Dive into the perfect getaway at one of over 160 vacation homes with pools in Penn Estates, available on Airbnb. Make a splash and soak up the sun in style!

  • How much does it cost to stay in cabin rentals in Penn Estates?

    Experience the best of Penn Estates with our cabin rentals, starting at about $120 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Do cabin rentals in Penn Estates have a bbq area?

    Absolutely! We offer over 10 cabin rentals with a bbq area in Penn Estates. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Penn Estates have air conditioning?

    Absolutely! We offer over 180 house rentals with air conditioning in Penn Estates. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Penn Estates have a gym?

    Absolutely! We offer over 30 house rentals with a gym in Penn Estates. Enjoy a tailored experience with all the comforts you desire.

  • Are there family-friendly cabin rentals in Penn Estates?

    Penn Estates has more than 10 family-friendly cabin rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

  • Do house rentals in Penn Estates have wifi?

    Absolutely! We offer over 190 house rentals with wifi in Penn Estates. Enjoy a tailored experience with all the comforts you desire.

  • What are the most popular amenities for Cabin Rentals in Penn Estates?

    Enhance your stay in our Cabin Rentals with the most popular amenities: over 10 homes with wifi, over 10 homes with air conditioning, over 10 homes with a bbq area, and more. Indulge in the ultimate retreat, tailored to your preferences.

Quick stats about holiday rentals in Penn Estates

  • Total holiday rentals

    Explore 220 holiday rentals in Penn Estates

  • Nightly prices starting at

    Penn Estates holiday rentals start at $91 SGD per night before taxes and fees

  • Verified guest reviews

    Over 12,990 verified reviews to help you choose

  • Family-friendly holiday rentals

    210 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 150 rentals that welcome pets

  • Holiday rentals with a pool

    160 properties feature pools

  • Rentals with dedicated workspaces

    130 properties have a dedicated workspace

  • Wifi availability

    220 of Penn Estates holiday rentals include wifi access

  • Popular amenities for guests

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

  • 4.8 Average rating

    Penn Estates stays are highly rated by guests – averaging 4.8 out of 5!

Destinations to explore