Photo by Ginie Ying

Town of Highland Holiday Rentals

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Top Holiday Rentals Destinations in Town of Highland

★★★★★ Luxury Waterfront: Hot Tub, Fireplace, Kayaks, XBOX Game Pass, 100mb WiFi!
9.8 out of 10, Exceptional, (279)
"We really enjoyed our stay. The cabin is beautiful, just as the pictures, and location is perfect. Beach is walk distance. Communication with owner, checking in and checking out was smoothly. I would definitely stay again. Things to improve on: the backyard needs maintenance we couldn’t use the canoe because the way to go into the water was obstructed; there should be extra garbage bags, I understand that renters take advantage but at minimum an extra 3-5 bags would do the job."
The price is AU$745
includes taxes & fees
3 Nov - 4 Nov
★★★★★ Luxury Waterfront: Hot Tub, Fireplace, Kayaks, XBOX Game Pass, 100mb WiFi!
Cozy Lake View Cabin on Lake Wallenpaupack with beach area access!!!
9.8 out of 10, Exceptional, (55)
"Took advantage of lake for family relaxation and fun. Beautiful fall getaway"
Cozy Lake View Cabin on Lake Wallenpaupack with beach area access!!!
Tanglwood Resort by VRI Americas
3.5 star property
8.6 out of 10, Excellent, (335)
"Excellent place "
Tanglwood Resort by VRI Americas
Riverfront Cabin nestled between the Poconos/Catskills, Pet/Family Friendly
9.6 out of 10, Exceptional, (196)
"We really liked the house and outdoor space, especially the patio overlooking the river. The biggest drawback, and for me it is a big one, is that bed sheets are not provided. Since we were driving and had room in the car it wasn't a disaster, but hauling 4 beds' worth of sheets fills a duffel bag, and I did not enjoy having to make those beds after a 7 hour drive. I wouldn't mind stripping the beds at the end but for the cost of the accommodations and how little a house full of sheets would...
Riverfront Cabin nestled between the Poconos/Catskills, Pet/Family Friendly
Luxury Lakefront: Hot Tub, Fireplace, Arcade, Kayaks, SPDs,100mb Wi-Fi + more!
10.0 out of 10, Exceptional, (134)
"We enjoyed our stay for September weekend "
The price is AU$926
includes taxes & fees
7 Oct - 8 Oct
Luxury Lakefront: Hot Tub, Fireplace, Arcade, Kayaks, SPDs,100mb Wi-Fi + more!
Trails Head Tiny House
9.0 out of 10, Wonderful, (10)
"Had a great stay at the Tiny House! Surprisingly clean and well appointed with all the basics. Perfect for an escape to the woods while still being able to quickly return to the real world. Proximity to the Neversink trail head is a major plus!"
The price is AU$184
includes taxes & fees
9 Oct - 10 Oct
Trails Head Tiny House
*HUGE 5000SF* Lake Wallenpaupack 250FT Lakefront,Beach Sleeps 12 +Boats included
9.2 out of 10, Wonderful, (89)
"Not enough parking, outdoor has potential but much of the outside area was not mowed. Sewage was overflowing and smelled bad outdoors. Home was very nice and roomy. Hooks for towels in bathrooms would be nice. Trash can liners would have been helpful."
*HUGE 5000SF* Lake Wallenpaupack 250FT Lakefront,Beach Sleeps 12 +Boats included
Amazing Villa! Indoor Hotub 🌟🌟🌟🌟🌟, Heated Pool, Game Room -Sleeps 25+ Ski
9.8 out of 10, Exceptional, (17)
"Pleasant stay and good property. Trash was full and lots of fly and owner called to have pick up but, they didn't take all the trash"
Amazing Villa! Indoor Hotub 🌟🌟🌟🌟🌟, Heated Pool, Game Room -Sleeps 25+ Ski
Lazy River Cottage on the Delaware River
10.0 out of 10, Exceptional, (128)
"Description was accurate. Photos are too except they have new sofas that are blue. Place was spotless. Nice outdoors area. We used the grill and the fire pit ring one day. We drove across the bridge into NY and explored a little over there. It is fun to watch all the people floating by. I am sure in the winter months the river is very quiet. Rafting is a short walk away and looked fun. Thank you for the hospitality! stayed 2 night and drove in"
Lazy River Cottage on the Delaware River
Bear country cabin in the Poconos
10.0 out of 10, Exceptional, (75)
"We very much enjoyed our stay. the owners were pleasant and very helpful. We would love to come back for a future trip. We would also recommend it to our friends. "
Bear country cabin in the Poconos
2 Houses|22+Guests|2 Hot Tubs|Newly Renovated!|Groups & Events Welcome!|Firepit
10.0 out of 10, Exceptional, (15)
"We had an unforgettable retreat weekend on the property. It was plenty spacious, clean, and very accommodating. The host was responsive and attentive to all of our needs. Strongly recommend the home for larger groups."
The price is AU$1,730
includes taxes & fees
9 Oct - 10 Oct
2 Houses|22+Guests|2 Hot Tubs|Newly Renovated!|Groups & Events Welcome!|Firepit
Private Indoor Pool - Hot Tub - 2 Fishing Ponds - 33 Acres
9.6 out of 10, Exceptional, (26)
"We enjoyed our stay with a large gathering of friends and their families. The house was spacious and clean. We enjoyed the indoor swimming pool and sauna, as well the outdoor firepit and fishing in the pond. We also enjoyed the proximity to hiking and river rafting (which was kid-friendly). After the kids went to bed, the large dining area/ sun room provided a great space to socialize without having to worry about noise disturbing those who were sleeping. The only downside of the house was that...
Private Indoor Pool - Hot Tub - 2 Fishing Ponds - 33 Acres
Located on Lake Wallenpaupack. Book 2 nights get 1 free. Contact me for details.
10.0 out of 10, Exceptional, (59)
"We have a lot of fun, place is clean, close to lake and duck. We’ll be back:)"
Located on Lake Wallenpaupack. Book 2 nights get 1 free. Contact me for details.
Lucky Lane Cottage
10.0 out of 10, Exceptional, (19)
"Wonderful property that was perfect for my husband and I to get away, unplug and relax. Everything that we needed was provided, and we loved just sitting on the porch and watching the wildlife. Excellent proximity to the Bethel Woods Arts Center - we attended a concert there and went to the Woodstock museum (highly recommend the Behind the Scenes tour!). We would absolutely stay here again when back in the area!"
The price is AU$414
includes taxes & fees
6 Oct - 7 Oct
Lucky Lane Cottage
In the cloud ~your cozy lake house
9.6 out of 10, Exceptional, (76)
"This hous look small out side but it huge. It has everthing u need ,nice view, and conveninct and relax tstay."
The price is AU$489
includes taxes & fees
30 Oct - 31 Oct
In the cloud ~your cozy lake house
Mountaintop Property on 8 acres
8.2 out of 10, Very good, (79)
"Pros: cozy, quiet and secluded property, near Main Street with good options for food and shopping, comfortable bed, Morgan was super responsive. Cons: As a number of other reviewers started (and found to be surprising) the A frame unit is just one of 2 rentals which are connected and share many thin walls — we were shocked to find out we were not alone. We were only told about them once we heard their footsteps and inquired with Morgan. Kitchen needs some love and care, no frills but can...
Mountaintop Property on 8 acres
5 Star Secluded Private Estate -Hot Tub, Pool+Ski >Southwoods Mountain Vacation!
9.6 out of 10, Exceptional, (38)
"The whole family had a great time! We would love to come back!"
5 Star Secluded Private Estate -Hot Tub, Pool+Ski >Southwoods Mountain Vacation!
Wally’s Cottage | Hot Tub|Kayaks|Firepit| GameShed
10.0 out of 10, Exceptional, (26)
"Very easy to find. Host responded promptly to all questions. Property as described. Clean and had everything you'd need. We enjoyed the hot tub! I would recommend to anyone looking for a place. "
The price is AU$551
includes taxes & fees
20 Oct - 21 Oct
Wally’s Cottage | Hot Tub|Kayaks|Firepit| GameShed
Pocono Cabin in Masthope Mountain Community
9.2 out of 10, Wonderful, (24)
"This is a neat little cozy spot near the Delaware Water Gap. My friends and I had a great time enjoying the quiet and the beautiful nature that surrounds the house. There is reliable wifi and decent cell service, and there were plenty of people around so we still felt safe. We were not accustomed to certain practices however, so be prepared. In order to access the lake, you need to have amenity badges, which was not clear to us until after we arrived (we booked understanding that amenity badges...
Pocono Cabin in Masthope Mountain Community
Trails Head Cabin
9.8 out of 10, Exceptional, (68)
"Enjoyed a ride for a bachelor's trip in the Catskill Mountains. The cabin was a perfect overnight stop. "
The price is AU$301
includes taxes & fees
27 Oct - 28 Oct
Trails Head Cabin
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