Holiday rentals in Penn Estates

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Top-rated holiday rentals in Penn Estates

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

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Guest favourite
A game of corn hole is set on the ground, featuring a wooden board with a blue and white design and red bags arranged nearby. In the background, a circle of sturdy wooden chairs is positioned among lush greenery, creating a serene outdoor space.
Home in East Stroudsburg
4.89 out of 5 average rating, 65 reviews

Chalet by the Stream|FirePit|KingBed|PeacefulViews

Retreat to a Charming Streamside Chalet in the Poconos! Awaken to cheerful melodies of a flowing brook and sip your morning coffee on a private deck embraced by tall, whispering trees. Tranquil Streams is a serene 3BR chalet tucked in nature’s beauty. With a king bed, crackling fire pit, and resort-style perks (pools, lake access & more), this hideaway is ideal for couples, families, or friends ready to relax and reconnect. Reserve today and let Tranquil Streams be your joyful doorway to nature.

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.

Guest favourite
A serene outdoor seating area is nestled among trees, featuring comfortable chairs and a wooden coffee table. The view overlooks a calm lake with a fountain, surrounded by rocks and green foliage, reflecting a peaceful natural setting.
Home in East Stroudsburg
4.9 out of 5 average rating, 194 reviews

Lady of the Lake-Poconos Premier Lakefront Retreat

Embodying everything your heart can conjure when dreaming upon the perfect lakefront vacation, this 3500 sq ft Grand Dame of the Poconos, with its stunning lake views in every direction, fresh off a complete remodel, is being offered to the public for the very first time. From hot tubs, hammocks, kayaks & other peaceful places to relax, to game and groovy rooms meant for social shenanigans and fun, this mid-century beauty on the lake will be the talk of friends and family for years to come!

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
A spacious bathroom is equipped with a glass-enclosed shower and a sleek, black concrete soaking tub. Natural light filters through large windows, offering views of the surrounding greenery. Gray tile lines the floors and walls, while modern fixtures add a stylish touch.
Home in East Stroudsburg
4.9 out of 5 average rating, 135 reviews

Modern Poconos Mansion 5BR 3BA | Hot Tub | Sauna +

This is a one of a kind home custom built home, completely remodeled from the ground-up with custom finishes not found in the Poconos! This massive 5 bedroom home is not only stunning inside, but is also filled with amenities such as a outdoor 6 person hot tub, a sauna, a custom made concrete bathroom tub overlooking the forest, and has one of the largest, most breath-taking private deck with endless views of the Poconos forest that you can enjoy with seating for 12 and a propane fire pit!

Top guest favourite
An aerial view captures a modern treehouse nestled among lush trees, with a heated swim spa glowing in blue. A spacious deck features seating arrangements and is framed by surrounding nature, while a colorful sunset illuminates the sky in soft pastels, enhancing the serene environment.
Home in East Stroudsburg
4.95 out of 5 average rating, 99 reviews

!Poconos TREE HOUSE LAKE+Swim SPA+Cinema + Kayak!

Welcome to the Poconos TREEHOUSE + SPA Getaway... Let us take your breath away by capturing beautiful memories during your stay. Surrounded by nature, the lake view sits on an uphill which allows you to enjoy the beautiful sunrise and sunset through our deck access giving it the TREEHOUSE effect... Immerse yourself in our 20 FT HEATED SWIM SPA!!!! Deck can also be used for BBQ days/nights. From our common areas, to outdoors, we also provide indoor entertainment and many more!

Top guest favourite
An outdoor space featuring a large deck with comfortable seating and a fire pit surrounded by chairs. A sauna is visible in a wooden structure, while the newly built home with multiple stories showcases a modern design nestled among trees.
Home in East Stroudsburg
5 out of 5 average rating, 42 reviews

Pocono Bliss 5br | Hot Tub | Sauna | Game Room

Experience Pocono bliss in this new construction, professionally designed, open-concept home. Offering 5 bdrs, 3.5 baths, ideal for family and friends. It boasts spacious bedrooms, a gourmet kitchen, two living areas, an epic game room, large deck, BBQ, hot tub, sauna, fire pit and a putting green. Neighborhood amenities include lake access, pool and more. 12 min- Camelback Mountain 15 min - Delaware Water Gap, Downtown Stroudsburg 20 min - Kalahari Resort, Shawnee Resort

Superhost
A cozy bedroom is presented with a spacious bed adorned with neatly arranged pillows. Flanking the bed, two nightstands each hold lamps that cast a soft light. The backdrop features calming green walls and framed artwork, while a decorative plant adds a touch of nature.
Home in East Stroudsburg
4.91 out of 5 average rating, 135 reviews

✦Peaceful House in the Woods 4BD/3BA w/Game Room✦

Welcome to your home away from home in this newly designed 4-bedroom, 3-bath house in the gated community of Penn Estates, PA. Just 15 minutes from Camelback Mountain Ski Resort, shops, and restaurants. Enjoy nature views, walks to the lake, fun in the game room, and frequent visits from deer and wildlife. Experience the warmth and charm of a home that has created beautiful memories for many, with plenty of space for relaxation and adventure in a peaceful setting.

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 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!

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?

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Avg. price$356 SGD$344 SGD$306 SGD$290 SGD$299 SGD$319 SGD$408 SGD$433 SGD$276 SGD$306 SGD$316 SGD$370 SGD
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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 $92 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!

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