Highland Vacation Homes

A suspension bridge over a river with autumn foliage and distant hills.

Change your mind
Book hotels with free cancellation
Treat yourself
Sign in to save 10% or more on thousands of hotels
Sign in
Be picky
Search almost a million properties worldwide

Check prices for these dates

In two weeks

In two months

In three months

In four months

Our top choices for Highland holiday homes

1. Amazing 3-bedroom house with AC in adorable Highland

Highland

HK$3,869 total

includes taxes & fees

31 Aug - 1 Sept

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

Highland

Pinal

HK$5,503 total

includes taxes & fees

8 Sept - 9 Sept

3. The DeVita House Est. 1900

Gardiner

Christopher T.

HK$3,511 total

includes taxes & fees

31 Aug - 1 Sept

Coffee/tea maker, fridge, microwave, oven

4. NEW: Family Pool Retreat in Stone Ridge

Cottekill

Shannon M.

HK$8,006 total

includes taxes & fees

15 Sept - 16 Sept

5. Chic Lakeside Oasis|Near Rhinebeck & Millbrook

Stanfordville

HK$5,434 total

includes taxes & fees

27 Aug - 28 Aug

6. The Studio at the Inn at High Falls

High Falls

Jamie M.

HK$2,137 total

includes taxes & fees

30 Aug - 31 Aug

7. Stunning 5-bedroom house with AC / Heat in charming Poughkeepsie NY

Poughkeepsie

Nicole Y.

HK$4,901 total

includes taxes & fees

14 Sept - 15 Sept

8. Retro Retreat: 1br home w/ WFH desk, livingroom, fire pit and no chores!

Kingston

Brendan B.

HK$1,940 total

includes taxes & fees

22 Sept - 23 Sept

View all properties

Find holiday rentals that suit your style

Apartments

Cabins

Save an average of 15% on thousands of hotels when you're signed in

Top Highland Hotel Reviews

SureStay Plus Hotel by Best Western Highland Poughkeepsie

10/10 Excellent

"Good breakfast. Good coffee. No carpet in rooms is a nice touch."

DoubleTree by Hilton Poughkeepsie Convention Center

8/10 Good

"First-class hotel, except for the breakfast. My spouse and child waited for 40 minutes to be fed until they gave up and left. They observed other patrons not getting any breakfast, either. Probably just as well, as the prices were outrageously high (even if the service had been even remotely competent). The drive-thru window at Dunkin' Donuts provided better service and at much more reasonable prices. I would stay at the Doubletree again, but I would plan to avoid their restaurant at all costs."

Inn at Bellefield / Hyde Park, Residence Inn by Marriott

10/10 Excellent

"Everything was great...fun bar, very nice rooms with kitchen small living room area. But the reason we stayed was the Culinary Institute. The staff told us it was a 5 min walk, Please be advised it is not 5 min more like 10-15 min. The hill from the hotel is step and it's also steep to go up to the Culinary Institute. If your young its fine. But people who don't walk to well should expect to take and Uber maybe 7-10.00$ We took and Uber home because it was dark out after we had our dinner. You can pick up and Uber very easy by the students dorms."

Studio 6 Extended Stay Fishkill Route 9 NY

8/10 Good

"Not fancy, but very clean and it looks like it was updated recently. The location is good, as the many hotels in the area show. This is a budget friendly place, but nicer than most in that category. The staff was great, and Mike at the front desk was especially helpful. I wasn’t thrilled with the $10 fee for staying less than a week, and the $2 housekeeping fee is strange (especially since there wasn’t any during my four night stay… I didn’t need it or miss it but if you go out the way to charge for it… ). Anyway if you want a clean and safe budget stay, it’s a great option."

Find out more about Highland