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Featured Highland Beach Cottages

Charming 2-bedroom 1 bath cottage with AC, WiFi in peaceful North Beach, Md.

Charming 2-bedroom 1 bath cottage with AC, WiFi in peaceful North Beach, Md.

2 out of 5
North Beach MD
The price is $277 total per night
$277 total
per night
Nov 30 - Dec 1
At this cottage, guests have access to features like laundry facilities. This smoke-free cottage also has barbecue grills.
Washer
Dryer
Relaxing Waterfront Cottage Near St Michaels, Maryland

Relaxing Waterfront Cottage Near St Michaels, Maryland

Wittman MD
Guests staying at this cottage enjoy an outdoor pool, laundry facilities, and local meal delivery service. Additional amenities include barbecue grills and a garden.
Pool
Kitchen
Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town

Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town

St Michaels MD
Guests staying at this cottage have access to laundry facilities, barbecue grills, and a garden.
Pool
Kitchen
Accessible, Screened-in porch, Sauna, Fire Pit, Dog Friendly

Accessible, Screened-in porch, Sauna, Fire Pit, Dog Friendly

Stevensville MD
Guests staying at this cottage enjoy a sauna, laundry facilities, and barbecue grills. This smoke-free cottage also has a garden.
Kitchen
Washer
Chesapeake Cottages- 2 Quaint Waterfront Retreats

Chesapeake Cottages- 2 Quaint Waterfront Retreats

Pasadena MD
The price is $665 total per night
$665 total
per night
Nov 26 - Nov 27
Guests staying at this cottage have access to laundry facilities, a garden, and barbecue grills.
Kitchen
Washer
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!

John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!

Saint Michaels MD
Guests staying at this cottage have access to laundry facilities, barbecue grills, and a garden.
Pool
Kitchen
The Middle Point Cabin in Saint Michaels

The Middle Point Cabin in Saint Michaels

Neavitt MD
Guests staying at this cottage have access to laundry facilities, barbecue grills, and a garden.
Kitchen
Washer
Charming Waterfront Cottage Retreat near St. Michaels

Charming Waterfront Cottage Retreat near St. Michaels

Bozman MD
At this cottage, guests have access to features like laundry facilities. This smoke-free cottage also has a garden.
Kitchen
Washer
Secluded Cozy Cottage in Historic Downtown

Secluded Cozy Cottage in Historic Downtown

Annapolis MD
The price is $749 total per night
$749 total
per night
Nov 26 - Nov 27
At this cottage, guests have access to a terrace, laundry facilities, and barbecue grills. If you drive, put free offsite parking to good use. This smoke-free cottage also has a garden.
Kitchen
Washer
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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 Beach

    Crowne Plaza Annapolis by IHG

    Crowne Plaza Annapolis by IHG

    173 Jennifer Rd Annapolis MD
    The price is $118 total per night from Nov 30 to Dec 1
    $118 total
    per night
    Nov 30 - Dec 1
    8.6/10 Excellent! (1,008 reviews)
    Historic Inns of Annapolis

    Historic Inns of Annapolis

    58 State Circle Annapolis MD
    The price is $175 total per night from Dec 1 to Dec 2
    $175 total
    per night
    Dec 1 - Dec 2
    8.8/10 Excellent! (1,902 reviews)
    DoubleTree by Hilton Hotel Annapolis

    DoubleTree by Hilton Hotel Annapolis

    210 Holiday Court Annapolis MD
    The price is $68 total per night from Dec 21 to Dec 22
    $68 total
    per night
    Dec 21 - Dec 22
    8.6/10 Excellent! (1,010 reviews)

Cottages

Book a cottage in Highland Beach
Spend your next getaway treating yourself to a quieter, simpler way of life in a private cottage in Highland Beach. 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 Beach better.

Cottage apartments in Highland Beach 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 Beach
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 Beach 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 Beach 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 Beach. 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 Beach Cottages essential information

Accommodation
85 Cottages
Lowest Price
$68
Highest Price
$749
Popular accommodation
Charming 2-bedroom 1 bath cottage with AC, WiFi in peaceful North Beach, Md., Relaxing Waterfront Cottage Near St Michaels, Maryland, Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town, Accessible, Screened-in porch, Sauna, Fire Pit, Dog Friendly, Chesapeake Cottages- 2 Quaint Waterfront Retreats, John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!, The Middle Point Cabin in Saint Michaels, Charming Waterfront Cottage Retreat near St. Michaels, Secluded Cozy Cottage in Historic Downtown