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Featured Highland Cottages

Charming Cottage in the Heart of the Shawangunks

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.
Junebug Cottage: peace, love and privacy a short walk to Woodstock village green

Junebug Cottage: peace, love and privacy a short walk to Woodstock village green

Guests staying at this cottage have access to a garden and barbecue grills.
Be in Nature at this Gorgeous Riverfront Cabin

Be in Nature at this Gorgeous Riverfront Cabin

This cottage features free WiFi in public areas and a garden. This smoke-free cottage also has barbecue grills.
Pet-friendly Cottage at Historic Millbrook Farm Estate

Pet-friendly Cottage at Historic Millbrook Farm Estate

At this cottage, guests have access to laundry facilities, local meal delivery service, and a garden. This smoke-free cottage also has barbecue grills.
Streamside Cottage Half Mile to Town of Woodstock

Streamside Cottage Half Mile to Town of Woodstock

Guests staying at this cottage have access to barbecue grills and a garden.
Relaxing Catskill Mountain Cottage.

Relaxing Catskill Mountain Cottage.

Guests staying at this cottage have access to a garden and barbecue grills.
ADORABLE CREEK COTTAGE Charming Original Details, Fireplace, Near Town, WiFi

ADORABLE CREEK COTTAGE Charming Original Details, Fireplace, Near Town, WiFi

Guests staying at this cottage have access to laundry facilities, barbecue grills, and a garden.
Woodstock Cottage with hot tub. Close to town yet very private.

Woodstock Cottage with hot tub. Close to town yet very private.

At this cottage, guests have access to ski-in/ski-out access, a water park, and a hot tub. Other amenities at this ski cottage include laundry facilities, a garden, and barbecue grills.
Scenic Hudson Valley Getaway • Farms & Vineyards

Scenic Hudson Valley Getaway • Farms & Vineyards

At this cottage, guests have access to features like laundry facilities.
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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

    SureStay Plus Hotel by Best Western Highland Poughkeepsie

    3423 US Highway 9W, I-87 Exit 18 to I-9W, Highland, NY
    $71 nightly
    The price is $80 total per night from Nov 2 to Nov 3
    $80 total
    Nov 2 - Nov 3
    Total with taxes and fees
    7.6/10 Good! (890 reviews)
    Best Western Plus Kingston Hotel And Conference Center

    Best Western Plus Kingston Hotel And Conference Center

    503 Washington Ave, Kingston, NY
    $122 nightly
    The price is $137 total per night from Oct 13 to Oct 14
    $137 total
    Oct 13 - Oct 14
    Total with taxes and fees
    7.6/10 Good! (1,020 reviews)
    Wildflower Farms, Auberge Collection

    Wildflower Farms, Auberge Collection

    2702 Main St, Gardiner, NY
    $1,338 nightly
    The price is $1,498 total per night from Oct 27 to Oct 28
    $1,498 total
    Oct 27 - Oct 28
    Total with taxes and fees
    9.4/10 Exceptional! (53 reviews)

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
122 Cottages
Lowest Price
$80
Highest Price
$1,498
Popular accommodation
Charming Cottage in the Heart of the Shawangunks, Junebug Cottage: peace, love and privacy a short walk to Woodstock village green, Be in Nature at this Gorgeous Riverfront Cabin, Pet-friendly Cottage at Historic Millbrook Farm Estate, Streamside Cottage Half Mile to Town of Woodstock, Relaxing Catskill Mountain Cottage. , ADORABLE CREEK COTTAGE Charming Original Details, Fireplace, Near Town, WiFi, Woodstock Cottage with hot tub. Close to town yet very private., Scenic Hudson Valley Getaway • Farms & Vineyards

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