Compare Highland Cottage Rentals

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Featured Cottages in Highland

At this cottage, guests have access to features like laundry facilities. This smoke-free cottage also has a garden.

Streamside Cottage Half Mile to Town of Woodstock

$303 nightly

$339 total

Nov 4 - Nov 5

Total with taxes and fees

Guests staying at this cottage have access to barbecue grills and a garden.

Cozy Cottage Near Hiking, Infrared Sauna & Fireplace | Dream House in the Gunks

$264 nightly

$268 total

Oct 20 - Oct 21

Total with taxes and fees

Guests staying at this cottage enjoy a sauna, laundry facilities, and a garden. This smoke-free cottage also has barbecue grills.

Wappinger Cottage - Scandinavian retreat on a creek

Guests staying at this cottage enjoy free WiFi in public areas, laundry facilities, and a garden. This smoke-free cottage also has barbecue grills.

At this cottage, guests have access to a garden.

Charming Cottage in the Heart of the Shawangunks

At this cottage, guests have access to features like laundry facilities. This smoke-free cottage also has barbecue grills.

Kitchen

Washer

Historic 1800s Cornwall-on-hudson Cottage!

This cottage features free WiFi in public areas and barbecue grills. There's free offsite parking if you drive.

Lily Cottage - a cozy accomodation moments from the beautiful Ashokan reservoir

At this cottage, guests have access to features like laundry facilities. This smoke-free cottage also has a garden.

At this cottage, guests have access to features like an arcade/game room.

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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Hotel Options in Highland

SureStay Plus Hotel by Best Western Highland Poughkeepsie

3423 US Highway 9W Highland NY

$80 nightly

$90 total

Nov 1 - Nov 2

Total with taxes and fees

8/10 Very Good! (1,001 reviews)

Hyatt Place Poughkeepsie / Hudson Valley

2165 South Road Poughkeepsie NY

$94 nightly

$109 total

Nov 9 - Nov 10

Total with taxes and fees

9/10 Wonderful! (1,112 reviews)

Beekman Arms and Delamater Inn

6387 MILL ST Rhinebeck NY

$169 nightly

$191 total

Nov 9 - Nov 10

Total with taxes and fees

Cottages

Book a cottage in Highland
Spend your next getaway treating yourself to a quieter, simpler way of life in a private cottage in Highland. Cozy and charming, cottage rentals are the ideal spot when you want the comforts of home paired with a one-of-a-kind experience. They’re perfect for a single traveler looking for peace and quiet, or small groups who want to get to know Highland better.

Cottage apartments in Highland range from rustic to luxurious, with just about everything in between. Orbitz gives you the best deals on all of them.

Find the best cottages in Highland
City cottages are great if you want a cozy, comfy place to stay without being far from the all the cool spots you want to check out. A cottage makes a great home base for a day filled with adventure in Highland and the surrounding area. Not willing to give up all the comforts of a fine hotel? A luxury cottage turns up the charm while offering perks like room service, cable television, sunken spa tubs and housekeeping.

Stay in a Highland cottage and swap busy days for peaceful evenings. Use the kitchenette or full kitchen to come up with a meal or reheat leftovers from your afternoon in Highland. You may even be able to use a pool and laundry facilities. Whether you’re in the mood for quiet relaxation or a night on the town, a cottage puts you right where you want to be.

Highland Cottages essential information

Accommodation	110 Cottages
Lowest Price	$90
Highest Price	$339
Popular accommodation	Mountain View escape, Streamside Cottage Half Mile to Town of Woodstock, Cozy Cottage Near Hiking, Infrared Sauna & Fireplace \| Dream House in the Gunks, Wappinger Cottage - Scandinavian retreat on a creek, Reset and Relax in Luxury Cottage, Charming Cottage in the Heart of the Shawangunks, Historic 1800s Cornwall-on-hudson Cottage!, Lily Cottage - a cozy accomodation moments from the beautiful Ashokan reservoir, Magnificent View on Whaley Lake