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 $244 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 $244 per night (USD)
VRBO
From $628 per night (USD)
Expedia
Lake Front Heated Floors Romantic Hot Tub Firepit Foosball Ski Screen Porch Boat
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
Enjoy the heated floors as you comfortably walk barefoot thru the house. Unique architecture as each bedroom is on a sep ...
From $628 per night (USD)
Expedia
From $243 per night (USD)
VRBO
The Fern Hill Lodge: Cozy and Serene Getaway on 20 Private Acres
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
The Fern Hill Lodge, lovingly renovated by a local master carpenter, is suitable for families, couples or friends lookin ...
From $243 per night (USD)
VRBO
From $241 per night (USD)
Expedia
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 $241 per night (USD)
Expedia
From $376 per night (USD)
VRBO
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 $376 per night (USD)
VRBO
From $3137 per night (USD)
Expedia
Picturesque Cabin in the Woods
Bedrooms:
2
Bathrooms:
3
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 $154 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 $154 per night (USD)
VRBO
From $322 per night (USD)
Expedia
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 $322 per night (USD)
Expedia
From $214 per night (USD)
VRBO
Catskills Woodland Escape: River, Festivals & More
Bedrooms:
1
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 $214 per night (USD)
VRBO
From $783 per night (USD)
Expedia
Lake Home on serene Highland Lake
Bedrooms:
3
Bathrooms:
3
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)
Expedia
From $167 per night (USD)
VRBO
The Delaware Riverfront
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
This 2-bedroom riverfront apartment can comfortably accommodate a family of 4. It is set on over 2 private acres (and at ...
From $167 per night (USD)
VRBO
From $202 per night (USD)
Expedia
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)
Expedia
Click For Pricing
VRBO
An Iconic Upstate Getaway Just 2 Hours from New York City
Bedrooms:
2
Bathrooms:
1
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
From $555 per night (USD)
VRBO
Lakefront - Hot Tub - Beach - Deck - BBQ - Peloton
Bedrooms:
1
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 $555 per night (USD)
VRBO
From $238 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 $238 per night (USD)
VRBO
From $820 per night (USD)
Expedia
Amazing All-Season, Private Lakefront Retreat!
Bedrooms:
2
Bathrooms:
3
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 $820 per night (USD)
Expedia
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 $728 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 $728 per night (USD)
VRBO
From $681 per night (USD)
VRBO
Amazing updated Lakeside/Near Hiking,skiing,water rafting/Gameroom/Dog friendly
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Spacious Yet Cozy Lake Cabin - Newly renovated with upgraded features: - Heated bathroom floors - Brand New High-end App ...
From $681 per night (USD)
VRBO
From $426 per night (USD)
Expedia
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 $426 per night (USD)
Expedia
Click For Pricing
VRBO
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
VRBO
From $796 per night (USD)
Expedia
2 Lake Cabins | Pool+HotTub | Game Room | 23acs
Bedrooms:
3
Bathrooms:
6
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 $796 per night (USD)
Expedia
$Private log cabin nestled at the base of a secluded wooded area \n$
From $397 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 $397 per night (USD)
VRBO
From $302 per night (USD)
Expedia
SwimSpa | Lake | Fish | Kayak | Hike | Firepit
Bedrooms:
1
Bathrooms:
3
Sleeps:
8
The Garden Cottage on 22 Acres with beach and dock access - Save when you book months in advance, enjoy extra discounts ...
From $302 per night (USD)
Expedia
Click For Pricing
VRBO
Dog-friendly Forest Summer Retreat in the Catskills
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Eldred Manor is a cozy country getaway nestled in the heart of the Catskills, just under 2 hours from NYC. Tucked away o ...
Click For Pricing
VRBO
From $216 per night (USD)
Expedia
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 $216 per night (USD)
Expedia
From $492 per night (USD)
VRBO
Half Moon Mtn 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 $492 per night (USD)
VRBO
From $290 per night (USD)
Expedia
Corkscrew Cape - Family Friendly Upstate NY Escape
Bedrooms:
2
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 $455 per night (USD)
VRBO
Woodland Manor: Hot Tub | Cozy | 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 $455 per night (USD)
VRBO
From $645 per night (USD)
Expedia
The Cabin at Deep Hollow
Bedrooms:
2
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 $645 per night (USD)
Expedia
Click For Pricing
VRBO
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 ...
Click For Pricing
VRBO
From $366 per night (USD)
Expedia
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 $366 per night (USD)
Expedia
From $167 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 $167 per night (USD)
VRBO
From $410 per night (USD)
VRBO
Stunning Country House in the Barryville Hills overlooking the Delaware River
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
This 3-bedroom country house in Barryville is perfect for your escape. With refined decor and amenities like a yoga room ...
From $410 per night (USD)
VRBO
From $188 per night (USD)
VRBO
Pristine Country Cottage In Eldred, NY
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Escape to our cozy, 5-star rated country retreat—perfect for couples, families, or solo travelers seeking tranquility an ...
From $188 per night (USD)
VRBO
From $445 per night (USD)
Expedia
Centerline Creek• Private River Access• Private Hiking Trails• 11 Acres
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Centerline Creek is a forest retreat nestled on 11 acres, directly across the Delaware River. The property offers direc ...
From $445 per night (USD)
Expedia
From $577 per night (USD)
VRBO
Stonehaven on the Delaware: River Access + Sauna
Bedrooms:
2
Bathrooms:
3
Sleeps:
10
Summary: Stonehaven on the Delaware, just 2 hours from NYC, is a charming 3 bed, 2 bath, 2 powder room home with access ...
From $577 per night (USD)
VRBO
From $591 per night (USD)
Expedia
Roebling House • 1850s Cabin • Hot Tub • Fire Pit
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
The Roebling House is a historic gem in the heart of Barryville, just steps from the Delaware River. This spacious farmh ...
From $591 per night (USD)
Expedia
From $1124 per night (USD)
VRBO
Breathtaking Riverfront Home on the Delaware River
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Welcome to The Riverhouse Getaway. This magnificent property spans four acres of lush woodland and boasts over 1,000 fee ...
From $1124 per night (USD)
VRBO
From $475 per night (USD)
VRBO
Charming 3-bedroom cabin with deck, sauna, fitness room in Eldred
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Relax in this beautiful architect designed cabin in the woods. Enjoy grilling on the deck and the sounds of song birds i ...
From $475 per night (USD)
VRBO
From $683 per night (USD)
VRBO
Woods Edge Private 5 Acres Hot Tub Fire Pit
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Escape to Woods Edge, a serene and inviting retreat for up to 8 guests, nestled deep in the woods with no neighbors in s ...
From $683 per night (USD)
VRBO
From $1355 per night (USD)
VRBO
Lotus Lodge: Pool | Hot Tub | Sauna | Incredible Views
Bedrooms:
6
Bathrooms:
5
Sleeps:
16
Summary: Lotus Lodge is a stunning 5 bed, 4 bath + 2 half bath cabin just 2.5 hours from NYC. Dip in the pool or soak in ...
From $1355 per night (USD)
VRBO
From $1224 per night (USD)
VRBO
Luxury 6BR Catskills Retreat - Lakefront, Saltwater Pool, Home Theatre
Bedrooms:
4
Bathrooms:
6
Sleeps:
14
Escape to your private sanctuary in Eldred, NY, where lake views, lush greenery, and upscale amenities create the ultima ...
From $1224 per night (USD)
VRBO
From $263 per night (USD)
Expedia
A peaceful, quaint cabin in the woods offers a country-side escape for couples, small families, and friends.
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Escape to this serene, rustic-chic cabin tucked in the woods. With two cozy bedrooms, a stylish renovated bath, and thou ...
From $263 per night (USD)
Expedia
Click For Pricing
VRBO
2 Lake Cabins Pool+hottub Game Room 23acs
Bedrooms:
3
Bathrooms:
6
Sleeps:
18
Aparthotel in Highland Lake
Click For Pricing
VRBO

Search Your Destination Now!

Town of Highland Rentals

Rental Rates ($USD weekly)

Guests

Check Rates & Availability:

Results: 45 Rentals