Town of Highland, New York Vacation Rentals. Book Beach Rentals, Lake Houses, Condos, Cabins, Villas, and Homes in Town of Highland, New York on RentalSaver.com!

Town of Highland Rentals

From $268 per night (USD)
VRBO
Retro Countryside Cabin | Cozy Upstate NY Private Retreat!
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
Walkable distance to the quaint town of Eldred! Cute restaurants, unique shops, and many lakes are all very close. Our ...
From $268 per night (USD)
VRBO
From $339 per night (USD)
Expedia
Cozy cottage with beautiful lake views!
Bedrooms:
1
Bathrooms:
3
Sleeps:
8
This cozy cottage is located on Washington Lake with breathtaking views and is just 90 Miles out of NYC. It sleeps 6 co ...
From $339 per night (USD)
Expedia
From $783 per night (USD)
VRBO
Lake Front Heated Floors Romantic Hot Tub Firepit Foosball Ski Screen Porch Boat
Bedrooms:
3
Bathrooms:
4
Sleeps:
12
Enjoy the heated floors as you comfortably walk barefoot thru the house. Unique architecture as each bedroom is on a sep ...
From $783 per night (USD)
VRBO
From $275 per night (USD)
Expedia
The Fern Hill Lodge: Cozy and Serene Getaway on 20 Private Acres
Bedrooms:
2
Bathrooms:
3
Sleeps:
4
The Fern Hill Lodge, lovingly renovated by a local master carpenter, is suitable for families, couples or friends lookin ...
From $275 per night (USD)
Expedia
From $192 per night (USD)
VRBO
Tiny House on Spectacular Riverfront Property - Private Access to Delaware River
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Our private tiny home is on a 1/2 mile of beachfront property along the pristine Upper Delaware River, located on the sc ...
From $192 per night (USD)
VRBO
From $419 per night (USD)
Expedia
The Perfect Catskills Lake House
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Indulge in cabin vibes at this mid-century modern craftsman on a secluded, non-motorized lake. This home has modern ame ...
From $419 per night (USD)
Expedia
From $1582 per night (USD)
VRBO
Iconic private retreat on 52 acres in the Catskills, Sullivan County
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Fall asleep to a natural white noise soundscape of babbling brook, night creatures and whispering trees. An iconic prope ...
From $1582 per night (USD)
VRBO
From $3137 per night (USD)
Expedia
Picturesque Cabin in the Woods
Bedrooms:
2
Bathrooms:
5
Sleeps:
6
Secluded 3 bedroom home nestled in the woods on 3.5 acres of picturesque land. Enjoy the nature while in the comfort of ...
From $3137 per night (USD)
Expedia
From $172 per night (USD)
VRBO
Charming lake community cottage with hot tub PET FRIENDLY
Bedrooms:
1
Bathrooms:
3
Sleeps:
7
Recharge with all the beauty the Catskills have to offer. Welcome to our 100 year old cabin with updates. It is 500 sq ...
From $172 per night (USD)
VRBO
From $232 per night (USD)
Expedia
Modern Catskills Home HOT TUB - Pet Friendly!
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Take in the peace and quiet of the Catskills countryside at this 2-bedroom, 2-bathroom Barryville home. Spend sunny days ...
From $232 per night (USD)
Expedia
From $325 per night (USD)
VRBO
ESCAPE-REFRESH-Large Riverfront Estate-Pristine, Private, Fresh Air-90miles GWB
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Our riverfront home is located on a 1/3 mile of beachfront property along the scenic Upper Delaware River, between the ...
From $325 per night (USD)
VRBO
From $546 per night (USD)
Expedia
Year-Round Retreat Home on Scenic Delaware River 90 miles from NYC, EV CHARGER
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Located on the Delaware River, if you are looking to get away from it all or to commune with nature, 3608 is the place f ...
From $546 per night (USD)
Expedia
From $227 per night (USD)
VRBO
Catskills Woodland Escape: River, Festivals & More
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Escape to nature at our comfortable and spacious upstate home! Relax with a glass of cider and a s'more at our fire pi ...
From $227 per night (USD)
VRBO
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Expedia
Modern Cottage near Delaware River
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
This home is built in the 1920's and was originally a barn. We recently found this beautiful place and made it our home. ...
Click For Pricing
Expedia
From $220 per night (USD)
VRBO
Private Cabin 5 Min to Delaware River, Tusten Trail and Tenmile River Scout Camp
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
In this small quiet cabin surrounded by pine trees, you will find all the amenities of a house. Many hiking trails in th ...
From $220 per night (USD)
VRBO
From $816 per night (USD)
Expedia
Lakefront | 22 acres | HotTub | Game Room
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
Waterfront Cottage on 22 Acres with Hot Tub - Save when you book months in advance, enjoy extra discounts on stays of 3 ...
From $816 per night (USD)
Expedia
From $783 per night (USD)
VRBO
Lake Home on serene Highland Lake
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
A quiet, safe, family/kids paradise. Newly remodeled with new construction of 2nd and 3rd floors. 3100 sq foot home. T ...
From $783 per night (USD)
VRBO
From $202 per night (USD)
Expedia
The Delaware Riverfront
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
This 2-bedroom riverfront apartment can comfortably accommodate a family of 4. It is set on over 2 private acres (and at ...
From $202 per night (USD)
Expedia
From $202 per night (USD)
VRBO
Welcome to a space that embodies the true original spirit of Airbnb.
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
This is one of 2 spaces on the property available, but there is no connectivity between the apartments. It is very priva ...
From $202 per night (USD)
VRBO
From $960 per night (USD)
VRBO
Renovated Lake Home with a Spectacular View
Bedrooms:
2
Bathrooms:
6
Sleeps:
10
Highland Lake is a very peaceful and safe private lake with spectacular sunset views, great fishing, lots of birds and w ...
From $960 per night (USD)
VRBO
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VRBO
An Iconic Upstate Getaway Just 2 Hours from New York City
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Schoolhouse 82 is a historic Sullivan County dwelling nestled on a hillside in the Catskills of Upstate New York. The pr ...
Click For Pricing
VRBO
$House w\/ Hot Tub on 10 Acres near Delaware River$
From $367 per night (USD)
Expedia
House w\/ Hot Tub on 10 Acres near Delaware River
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
***You should drive a 4WD during the winter if there is a snow storm during your stay.*** Enjoy our house in the woods, ...
From $367 per night (USD)
Expedia
From $697 per night (USD)
VRBO
Lakefront - Hot Tub - Beach - Deck - BBQ - Peloton
Bedrooms:
3
Bathrooms:
5
Sleeps:
15
Our family home sits on Swinging Bridge Reservoir. The outdoor space is amazing including a massive deck with outdoor ki ...
From $697 per night (USD)
VRBO
From $247 per night (USD)
VRBO
Cozy Catskills Farmhouse in Barryville near the Delaware River
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
This is a simply furnished colonial farmhouse in the heart of Barryville, NY along the Delaware River. There are 4 equa ...
From $247 per night (USD)
VRBO
From $463 per night (USD)
VRBO
Amazing All-Season Private Lakefront Retreat!
Bedrooms:
2
Bathrooms:
5
Sleeps:
8
Under a 2-hour drive from New York City with skiing at Big Bear close by, not far from Milford, PA, and Bethel Woods Ar ...
From $463 per night (USD)
VRBO
From $3173 per night (USD)
VRBO
16 Bedroom 20 Bathroom Mansion with Indoor Pool
Bedrooms:
16
Bathrooms:
16
Sleeps:
42
****We have discounted pricing based on longer stay. Unfortunately homeaway does not allow for discount pricing based on ...
From $3173 per night (USD)
VRBO
From $693 per night (USD)
VRBO
Stunningly Private Lake Front - Pickleball Court
Bedrooms:
2
Bathrooms:
4
Sleeps:
6
Less than two hours from NYC!!! Available to enjoy every season!!! Our home will become a part of your families precious ...
From $693 per night (USD)
VRBO
From $230 per night (USD)
VRBO
Private Loft Style Home Perched on Cliff overlooking the Delaware River
Bedrooms:
3
Bathrooms:
2
Sleeps:
6
Perched on a mountain ledge in the Pennsylvania Poconos, A Loft House on The Delaware, overlooks the Delaware River and ...
From $230 per night (USD)
VRBO
From $417 per night (USD)
VRBO
Cozy Lakefront Cabin upstate NY Dog friendly
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Welcome to our cozy lakefront cottage on Washington Lake in Yulan, NY. Peaceful retreat from the hustle and stresses o ...
From $417 per night (USD)
VRBO
$Modern Mohican Lake Abode w\/ Fire Pit & Views$
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Expedia
Modern Mohican Lake Abode w\/ Fire Pit & Views
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Enjoy blissful days 'on lake time' at this newly built 2-bedroom, 1-bath apartment. While days are best spent soaking in ...
Click For Pricing
Expedia
From $348 per night (USD)
VRBO
5 Acre Nature Escape · Rockpine Cabin
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Tucked away from the road, Rockpine Cabin awaits you—a secluded nature retreat where modern comforts meet upstate charm. ...
From $348 per night (USD)
VRBO
$Amazing Lake View \/ Close to Hiking, white water rafting \/ Gameroom\/Dog friendly$
From $637 per night (USD)
VRBO
Amazing Lake View \/ Close to Hiking, white water rafting \/ Gameroom\/Dog friendly
Bedrooms:
4
Bathrooms:
4
Sleeps:
10
Spacious Yet Cozy Lake Cabin - Newly renovated with upgraded features: - Heated bathroom floors - Brand New High-end App ...
From $637 per night (USD)
VRBO
From $431 per night (USD)
VRBO
New Custom A-Frame in Swinging Bridge Lake Community
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Be one of the first to stay at this newly constructed custom A-frame home situated on 4 private wooded acres, right next ...
From $431 per night (USD)
VRBO
From $4659 per night (USD)
Expedia
The Compound by Malon Villas
Bedrooms:
16
Bathrooms:
13
Sleeps:
16
Summary: Have you ever wished you could have you're very own boutique hotel experience for just you, your family and fri ...
From $4659 per night (USD)
Expedia
$Lakefront Lodge w\/ Pvt Dock, Sauna, GameRm, Pickle\/Basketball Court, Firepit$
From $1309 per night (USD)
VRBO
Lakefront Lodge w\/ Pvt Dock, Sauna, GameRm, Pickle\/Basketball Court, Firepit
Bedrooms:
5
Bathrooms:
4
Sleeps:
18
With a short walk to our private dock, you'll be swimming, fishing, and boating in no time. Our game room is fully equip ...
From $1309 per night (USD)
VRBO
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Expedia
Lakefront home on five acres
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Enjoy lakefront living. Swim, fish, kayak and canoe, enjoy a book under the shade of our dockside gazebo. Relax in the ...
Click For Pricing
Expedia
From $1147 per night (USD)
VRBO
2 Lake Cabins | Pool+HotTub | Game Room | 23acs
Bedrooms:
4
Bathrooms:
8
Sleeps:
16
Lake + Garden Cottage (2 homes .3 miles from each other. 30 second drive, 5 min. walk) on 23 Acres with HotTub+Pool - Sa ...
From $1147 per night (USD)
VRBO
$Private log cabin nestled at the base of a secluded wooded area \n$
From $426 per night (USD)
VRBO
Private log cabin nestled at the base of a secluded wooded area \n
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Just 2 hours from NYC, Yulan Woodlands is a private oasis surrounded by trees and nature. 4 bedrooms & 2 bathrooms comf ...
From $426 per night (USD)
VRBO
From $674 per night (USD)
VRBO
Enchanting River - Waterfront A Frame Cabin
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Enchanting River is a magical 2BR 1Bath A-Frame home secluded on 4 acres of serine forest nestled beside beaver brook ru ...
From $674 per night (USD)
VRBO
From $565 per night (USD)
Expedia
SwimSpa | Lake | Fish | Kayak | Hike | Firepit
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
The Garden Cottage on 22 Acres with beach and dock access - Save when you book months in advance, enjoy extra discounts ...
From $565 per night (USD)
Expedia
From $436 per night (USD)
VRBO
Dog-friendly Summer Retreat in the Catskills
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Eldred Manor is a cozy country retreat nestled in the heart of the Catskills, located less than 2 hours from NYC. Set do ...
From $436 per night (USD)
VRBO
$Seasonal Retreat- 60 day minimum-Sticks and Stones \Cottage on the Brook\$
From $173 per night (USD)
Expedia
Seasonal Retreat- 60 day minimum-Sticks and Stones \"Cottage on the Brook\"
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Sticks and Stones is one of those exciting properties that exudes a personal style that is both engaging and welcoming, ...
From $173 per night (USD)
Expedia
From $315 per night (USD)
VRBO
Highland Hideaway: Designer Renovated Cottage in the Catskills
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
A designer renovated 1920s cottage in Sullivan County Catskills on a windy road near the Delaware River. Come hideaway 2 ...
From $315 per night (USD)
VRBO
From $487 per night (USD)
Expedia
*Escape The City* | Lakefront home with hot tub and sunset views
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
Welcome to the 'The Highland Lake Hideaway', your serene lakeside escape in the heart of the Catskills! This inviting 3b ...
From $487 per night (USD)
Expedia
From $266 per night (USD)
VRBO
Cozy 2 Bdrm In Heart Of Barryville! Raft, Hike On Scenic Byway Rte 97
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
This rustic air-conditioned 2-Bedroom country apartment is located on the Route 97 Scenic Byway. It overlooks the Scenic ...
From $266 per night (USD)
VRBO
From $649 per night (USD)
VRBO
Little River: Waterfront Sauna & Chic Log Cabin
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Summary: Escape to Little River, a stunning log cabin sitting along a mountain stream in the southern Catskills, just 2 ...
From $649 per night (USD)
VRBO
From $306 per night (USD)
VRBO
Sweet Old Farmhouse in a Tranquil Setting
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Comfortable 2-bed/1-bath home with a partial view of Highland Lake in NY. Enjoy nature at its best with swimming, canoei ...
From $306 per night (USD)
VRBO
From $528 per night (USD)
Expedia
Waterfront 1900s · Hot Tub · Eldred Homestead
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
The Eldred Homestead is a charming, spacious cabin set on over 5 acres with a large pond. Originally built in 1900, it h ...
From $528 per night (USD)
Expedia
From $307 per night (USD)
VRBO
Modern Barndominium in Eldred, NY
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
This brand new 3,200 sq ft building on 2 acres is set back over 300' from the road, with no neighboring structures in vi ...
From $307 per night (USD)
VRBO
$Farmhouse w\/ Game Room and Massive Yard near the Delaware River.$
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Expedia
Farmhouse w\/ Game Room and Massive Yard near the Delaware River.
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Welcome to Willow Creek, a cozy Catskills farmhouse nestled in the banks of the scenic Delaware River. With a large priv ...
Click For Pricing
Expedia
From $476 per night (USD)
VRBO
Half Moon Mountain House - Modern Chalet in Barryville
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Summary: Welcome to Half Moon Mountain House, a beautiful, newly built 4-bedroom, 3-bathroom chalet-style home in the se ...
From $476 per night (USD)
VRBO
From $290 per night (USD)
Expedia
Corkscrew Cape - Family Friendly Upstate NY Escape
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Welcome to your serene escape upstate New York in the town of Barryville. A haven of charm and comfort nestled in the he ...
From $290 per night (USD)
Expedia
From $414 per night (USD)
VRBO
Woodland Manor: Serene, Stylish + Family Friendly
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Summary: Welcome to Woodland Manor, a serene & stylish Catskills escape just 2 hrs from NYC! Set on 5 acres, this 3-bed, ...
From $414 per night (USD)
VRBO
From $506 per night (USD)
Expedia
The Cabin at Deep Hollow
Bedrooms:
3
Bathrooms:
5
Sleeps:
16
The Cabin on Deep Hollow Road is an ideal, cozy escape into nature and comfort only 2 hours away from NYC and 1 hour awa ...
From $506 per night (USD)
Expedia
From $1427 per night (USD)
VRBO
Indoor Pool,11 Yrs Hosting, 7 bdrm, Hot Tub, Designer Home
Bedrooms:
6
Bathrooms:
7
Sleeps:
18
11 year SuperHost (6 year Premier Host)! Indoor, heated pool slides open in the summer to become an outdoor pool. Swim 3 ...
From $1427 per night (USD)
VRBO
From $188 per night (USD)
Expedia
Welcoming cottage with WiFi in charming Barryville
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Escape to this peaceful cottage in picturesque Barryville. This charming retreat features 2 cozy bedrooms, one with a qu ...
From $188 per night (USD)
Expedia
From $560 per night (USD)
VRBO
Secluded modern cabin with hot tub
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Romantic & Family-Friendly Modern Cabin in a Secluded Forest This cozy, modern cabin offers a peaceful retreat for both ...
From $560 per night (USD)
VRBO
From $285 per night (USD)
Expedia
Serendipity on Highland Lake
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
A great place to get out of town and have a meet-up! Surrounded by pristine mountains, hiking trails and plenty of lakes ...
From $285 per night (USD)
Expedia
$Waterfront Studio w\/ Loft & Dock Near Narrowsburg!$
From $158 per night (USD)
VRBO
Waterfront Studio w\/ Loft & Dock Near Narrowsburg!
Bedrooms:
2
Bathrooms:
4
Sleeps:
3
Canoeing & Kayaking On-Site | Quiet Surroundings | Furnished Outdoor Area | 10 Mi to Skiing Savor quality time and enjo ...
From $158 per night (USD)
VRBO
From $263 per night (USD)
Expedia
Charming 2-bedroom cottage in delightful Eldred with WiFi
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Unwind in Eldred at this lovely cottage. This charming retreat features 2 queen bedrooms, a cozy living room with a sofa ...
From $263 per night (USD)
Expedia
From $249 per night (USD)
VRBO
Designer renovated 2-Bedroom 1920s cottage in Sullivan County Catskills
Bedrooms:
2
Bathrooms:
3
Sleeps:
4
Discover 2 Bedroom cottage on a windy road near the Delaware River and Bethel Arts Center. Come hideaway 2 hours from NY ...
From $249 per night (USD)
VRBO

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Town of Highland Rentals

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Results: 61 Rentals