Holiday rentals in Winona Lakes

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Top-rated holiday rentals in Winona Lakes

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

Guest favourite

Townhouse in Tannersville

4.94 out of 5 average rating, 47 reviews

A+ Mountaintop Views Ski In/Out HotTub-Tubing-Pool

SKI IN / SKI OUT Upscale complete "Cabin Feel" townhouse on TOP of Camelback Mountain! FOUR SEASON MOUNTAINTOP LOCATION has TONS to do 365!! Crave beautiful views? Feel on top of the world in this amazing IMMACULATE 3 BR CABIN ON TOP OF CAMELBACK POCONOS PA! The ONLY ADIRONDACK FEEL END UNIT that offers wraparound deck bringing indoor living, outdoors w multi patio lighting to set the mood & INCREDIBLE Views! Desire RELAXING ROMANCE, ACTION, ADVENTURE, Ski in/out, Family FUN, GIRLFRIEND RETREAT!

Superhost

Chalet in Jim Thorpe

4.89 out of 5 average rating, 140 reviews

Mountain Modern House. Lake, river, bikes, kayaks

Located in Bear Creek Lake Community with access to amenities such as lake, beach, pools for adults and kids, playground, courts, etc. House has two decks, bar, indoor fireplace, outdoor grill and firepit, game room/home theater with surround system and attached garage for two cars. Rental includes kayaks, bikes, ping pong table, sports equipment and unlimited hot drinks. Excellent location: close to multiple ski resorts, State Parks and steps away from Pocono Whitewater rafting and Paintball.

Guest favourite

Townhouse in Lake Harmony

4.82 out of 5 average rating, 17 reviews

Sleep Beauty, Poconos Vacation 2BR 4Beds Sleep 6+

Note: This property is very nice & very clean renovated Nov 2023. Escape to our newly renovated 4-bed townhome, just 1 min to Jackfrost Golf & Ski Resort, 25 m to Switzerland of America. Your family vacation, a wood-burning fireplace, all new interior/appliances. Sleep in luxury on king memory foam mattress. Enjoy the lake and golf course near Property, clean and private, a relaxing vacation with modern amenities. For an unforgettable Poconos adventure with your loved ones! Very friendly host.

Guest favourite

Home in Tobyhanna Township

4.85 out of 5 average rating, 130 reviews

Hidden Gem Hot Tub Wi- FI, AC, Smart TV, Fire Pit.

Experience the wonders of nature in our cottage home away from home 3 br 2 ba Brand new HotTub high-end fire pit, deck, WiFi internet service, Smart TV, cableTV, kitchen supply and more Located in private gated Community the gold star amenities of Arrowhead Lake in the mountains of Poconos . Offers 3 Large pools, 4 beaches lakes, Boat rental, Fishing, water sports & tennis courts. In addition- ski resort, Spa, casino, restaurant and great shopping all just mins. away. PLEASE SEE OTHER NOTES.

Superhost

Chalet in Pocono Summit

4.91 out of 5 average rating, 113 reviews

Vacation | Lane | Chalet

Welcome to Vacation Lane Chalet; a sophisticated and serene atmosphere where rustic meets modern to create a perfect setting for a quaint and relaxing getaway. The chalet is equipped with top of the line appliance and high end designs and finishes topped off breathing comfort in every corner . Located within a 5 minute drive of all the necessities and super close to the major Pocono attractions such as Kalahari, you’ll have no worries keeping everyone entertained. DESIGH NOT FOR COPY

Superhost

Home in Pocono Summit

4.83 out of 5 average rating, 133 reviews

Poconos Sunset Lakefront !HotTub & amazing sunsets

Beautiful Lakefront Poconos Home w/Hot Tub, 2 Fire Pits & Deck! Hot tub running year round & patio now has patio heaters for those wintery nights ! Classic modern Ranch with ample of sleeping space made available through super comfortable sleeping arrangements. Brand new picnic area ! Welcome to your dream Poconos lakefront vacation home! Our ranch house boasts 4 bedrooms, 2.5 baths, and a private & serene lake access on the shores of one of the most beautiful lakes in the region!

Guest favourite

Home in Bushkill

4.98 out of 5 average rating, 132 reviews

Sweet Home Poconos (NOT Lake Front But Awesome)

Beautiful home with plenty outdoor living area, access to pools, sport courts, lake, our own ski slopes and so much more! Within minutes of our gates there is horseback riding, zip lines, tree adventure programs, go-kart racing, Delaware River National Park, walking trails, Shawnee Ski Area. If you want to go for a drive you’ll get to Camelback, Kalahari Water Park, The Commons Outlet Mall which features over 100 designer stores. Most important, we welcome guests of all walks of life

Superhost

Chalet in Albrightsville

4.85 out of 5 average rating, 123 reviews

*Hot Tub, 4bdr, loft - close to attractions

Brand New Kitchen!!! Great Location! SKI slopes OPEN -Blue Mountains, Camelback, Big Boulder and Jack Frost Property located 10-25 min driving distance to Skirmish, horseback riding, white water rafting, hiking, Waterfalls, Pocono Raceway, Big Boulder, Lake Harmony water sports, Split Rock Resort, shooting range, butterfly sanctuary and other outdoor adventures. Our place is great for couples' retreat, family reunions and group getaways. 10 min walk to Community Beach and Pool.

Superhost

Cabin in Tobyhanna Township

4.86 out of 5 average rating, 14 reviews

New! Loft in Arrowhead on the Stream

Take it easy at this unique and newly remodeled tranquil getaway. *Deck with bar and outdoor TV *Temporary Membership fees included for Arrowhead! *Fire Pit, gas BBQ With a babbling brook running through the back yard you can get into the mountains and still be near the water. Community also hosts a ton of amenities. *Sand Beaches *Pools *Playgrounds *Loft bed designed for minors To avoid late reservation fee we must have registration information 3 full days prior to check-in.

Guest favourite

Home in East Stroudsburg

4.94 out of 5 average rating, 62 reviews

GameRoom-Skiing-KingBed FirePit-Shared Heated Pool

Escape to The Penn House at Saw Creek Estates, your perfect getaway just 90 minutes from NYC! This spacious 4-bedroom, 2-bath home with a fun-filled game room offers everything you need to relax and unwind. Enjoy pools, lakes, tennis, basketball, a ski lift, and a fitness center. Explore Bushkill Falls, Shawnee Ski Resort, ziplining, and more—all within 15 minutes. Camelback Ski & Water Park is just 35 minutes away. Don’t wait—book your unforgettable stay now!

Guest favourite

Home in Greentown

4.95 out of 5 average rating, 242 reviews

Brand new one bedroom paradise

Gorgeous Brand new Cottage! Close to many ski resorts! Montage, Jack Frost, Elk Mountain Big Bear, and Camelback. 25-35 minutes out. Away from the hustle and bustle!Perfect getaway! All you need is your clothes and food! Fully sanitized& filled with all essentials. GLAZE under the stars around the fire pit. This beautiful house is minutes away from grocery stores, shops and other facilities. 25 minutes away from Woodloch Pines and 20 minutes from SkyTop!

Guest favourite

Home in Hopatcong

4.93 out of 5 average rating, 134 reviews

Lakefront Hopatcong w/dock kayaks fishing near NYC

3800 sqt 4b 2.5b, stunning lakefront house on the largest lake in NJ. Breathtaking lake views from every room. Sunrise coffee at bedroom balcony. Grill in the sunset at the spacious patio, fishing off the private dock. two spacious living rm for multi family, well equipped kitchen, large washer dryer, 3 kayak, fishing rods, grill, everything you need for your group to have a comfortable lake retreat and make some beautiful memories. 1 hr to NYC.