We noticed that you're using an unsupported browser. The Tripadvisor website may not display properly.We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Highland Homes

Destination
Revenue impacts this sort order. Learn more

Bedrooms

Bathrooms

Amenities

Suitability

Property type

Distinctive Features

Distance from

5 mi
20 rentals in Highland.
House in Highland: Secluded Retreat, vacation rental in Highland
House in Highland: Secluded Retreat, vacation rental in Highland
House in Highland: Secluded Retreat, vacation rental in Highland

House in Highland: Secluded Retreat

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Charming home in Hudson Valley, with a seasonal pool, 2 hours from NYC, vacation rental in Highland
Charming home in Hudson Valley, with a seasonal pool, 2 hours from NYC, vacation rental in Highland
Charming home in Hudson Valley, with a seasonal pool, 2 hours from NYC, vacation rental in Highland

Charming home in Hudson Valley, with a seasonal pool, 2 hours from NYC

Rental Home
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
5 miles from New Paltz, close to Vassar, SUNY ideal for weddings and graduations, vacation rental in Highland
5 miles from New Paltz, close to Vassar, SUNY ideal for weddings and graduations, vacation rental in Highland
5 miles from New Paltz, close to Vassar, SUNY ideal for weddings and graduations, vacation rental in Highland

5 miles from New Paltz, close to Vassar, SUNY ideal for weddings and graduations

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Beautiful Home - 4BR/2.5BA - Hot tub and Patio - Minutes from New Paltz, vacation rental in Highland
Beautiful Home - 4BR/2.5BA - Hot tub and Patio - Minutes from New Paltz, vacation rental in Highland
Beautiful Home - 4BR/2.5BA - Hot tub and Patio - Minutes from New Paltz, vacation rental in Highland

Beautiful Home - 4BR/2.5BA - Hot tub and Patio - Minutes from New Paltz

Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Charming Vacation House w/ Pool & HotTub, vacation rental in Highland
Charming Vacation House w/ Pool & HotTub, vacation rental in Highland
Charming Vacation House w/ Pool & HotTub, vacation rental in Highland

Charming Vacation House w/ Pool & HotTub

Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
6 Acre Private Hudson Valley Estate, vacation rental in Highland
6 Acre Private Hudson Valley Estate, vacation rental in Highland
6 Acre Private Hudson Valley Estate, vacation rental in Highland

6 Acre Private Hudson Valley Estate

Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Private mountain forest escape, vacation rental in Highland
Private mountain forest escape, vacation rental in Highland
Private mountain forest escape, vacation rental in Highland

Private mountain forest escape

Rental Home
5 bedrooms
3 bathrooms
Sleeps 11
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Classic Hudson Riverfront Home & Pool with Spectacular View, vacation rental in Highland
Classic Hudson Riverfront Home & Pool with Spectacular View, vacation rental in Highland
Classic Hudson Riverfront Home & Pool with Spectacular View, vacation rental in Highland

Classic Hudson Riverfront Home & Pool with Spectacular View

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Vintage Farmhouse in the heart of Hudson Valley, vacation rental in Highland
Vintage Farmhouse in the heart of Hudson Valley, vacation rental in Highland
Vintage Farmhouse in the heart of Hudson Valley, vacation rental in Highland

Vintage Farmhouse in the heart of Hudson Valley

Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
14 bdrm 1790 Hudson Valley Estate w/bridal studio: wedding/corporate/group, vacation rental in Highland
14 bdrm 1790 Hudson Valley Estate w/bridal studio: wedding/corporate/group, vacation rental in Highland
14 bdrm 1790 Hudson Valley Estate w/bridal studio: wedding/corporate/group, vacation rental in Highland

14 bdrm 1790 Hudson Valley Estate w/bridal studio: wedding/corporate/group

Rental Home
14 bedrooms
10 bathrooms
Sleeps 37
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Elixir Spring House Apartment 1, vacation rental in Highland
Elixir Spring House Apartment 1, vacation rental in Highland
Elixir Spring House Apartment 1, vacation rental in Highland

Elixir Spring House Apartment 1

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Lovely Highland Home w/ Pool & Hot Tub!, vacation rental in Highland
Lovely Highland Home w/ Pool & Hot Tub!, vacation rental in Highland
Lovely Highland Home w/ Pool & Hot Tub!, vacation rental in Highland

Lovely Highland Home w/ Pool & Hot Tub!

Rental Home
4 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Black Walnut Tree Farm: Farmhouse on 50 Acres, vacation rental in Highland
Black Walnut Tree Farm: Farmhouse on 50 Acres, vacation rental in Highland
Black Walnut Tree Farm: Farmhouse on 50 Acres, vacation rental in Highland

Black Walnut Tree Farm: Farmhouse on 50 Acres

Rental Home
5 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
The Juniper House near Poughkeepsie & New Paltz, vacation rental in Highland
The Juniper House near Poughkeepsie & New Paltz, vacation rental in Highland
The Juniper House near Poughkeepsie & New Paltz, vacation rental in Highland

The Juniper House near Poughkeepsie & New Paltz

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Spacious country getaway for family celebrations, vacation rental in Highland
Spacious country getaway for family celebrations, vacation rental in Highland
Spacious country getaway for family celebrations, vacation rental in Highland

Spacious country getaway for family celebrations

Rental Home
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Our home is perfect for relaxing and having lots of fun, with near by activity’s, vacation rental in Highland
Our home is perfect for relaxing and having lots of fun, with near by activity’s, vacation rental in Highland
Our home is perfect for relaxing and having lots of fun, with near by activity’s, vacation rental in Highland

Our home is perfect for relaxing and having lots of fun, with near by activity’s

Rental Home
4 bedrooms
2 bathrooms
Sleeps 12
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Large Private Apt w King bed near New Paltz, vacation rental in Highland
Large Private Apt w King bed near New Paltz, vacation rental in Highland
Large Private Apt w King bed near New Paltz, vacation rental in Highland

Large Private Apt w King bed near New Paltz

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Splendid Isolation: Private Luxury. Breathtaking Modern Villa On Hudson Bluffs., vacation rental in Highland
Splendid Isolation: Private Luxury. Breathtaking Modern Villa On Hudson Bluffs., vacation rental in Highland
Splendid Isolation: Private Luxury. Breathtaking Modern Villa On Hudson Bluffs., vacation rental in Highland

Splendid Isolation: Private Luxury. Breathtaking Modern Villa On Hudson Bluffs.

Rental Home
4 bedrooms
6 bathrooms
Sleeps 8
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
The Scenic Mansion With Breathtaking View, vacation rental in Highland
The Scenic Mansion With Breathtaking View, vacation rental in Highland
The Scenic Mansion With Breathtaking View, vacation rental in Highland

The Scenic Mansion With Breathtaking View

Rental Home
4 bedrooms
6 bathrooms
Sleeps 10
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Charming Country Apt by New Paltz, mtn’s, wineries, vacation rental in Highland
Charming Country Apt by New Paltz, mtn’s, wineries, vacation rental in Highland
Charming Country Apt by New Paltz, mtn’s, wineries, vacation rental in Highland

Charming Country Apt by New Paltz, mtn’s, wineries

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 5
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Showing results 1-20 of 20
Frequently Asked Questions about Highland