Holiday rentals near Customs House

We found 392 holiday rentals — enter your dates for availability

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August 2025

September 2025

Take a look at holiday rentals within easy reach of Customs House that are perfect for your trip. Whether you're travelling with family, friends or just your furry companion, holiday homes have the best amenities for hanging out with the people that matter most, which might include parking and a washer and dryer. Whatever you're looking for, you'll be able to choose a property to rent that has what everyone needs, including accessible or non-smoking choices.

Holiday rentals with weekly discounts - Customs House

Showing deals for:14 Nov - 21 Nov

Exceptional

(49 reviews)

The Middle Point Cabin in Saint Michaels

Neavitt, MD

8% off

AU$523 per night

includes taxes & fees

Baja Deck with umbrella- sit in pool on plastic adirondack chairs and read!

Exceptional

(134 reviews)

Modern St Michaels estate -Pier, Pool, Gas fire pit, Bikes, Kayaks

Easton, MD

8% off

AU$1,886 per night

includes taxes & fees

Charming Downtown Studio — Walk to Waterfront, Dining, and Shops

Exceptional

(22 reviews)

Historic Downtown St. Michaels Studio | Walk to Waterfront, Dining & Shops

St. Michaels, MD

12% off

AU$439 per night

includes taxes & fees

Backyard view from the deck. Fire pit on the right side of the photo

Exceptional

(130 reviews)

Waterfront Family Retreat with gorgeous views and a large Deepwater Dock. 5' MLW

Cambridge, MD

8% off

AU$720 per night

includes taxes & fees

Exceptional

(15 reviews)

CH Waterfront Home w/ Dock, Pool, Sandy Beach, Kayaks, 5BR/3.5BA Sleeps up to 16

Cambridge, MD

8% off

AU$1,902 per night

includes taxes & fees

Exceptional

(6 reviews)

Crabby Casa; Waterfront with pool and dock on the Choptank River in Cambridge MD

Cambridge, MD

8% off

AU$887 per night

includes taxes & fees

Our home blends into towering pines, lawns & hundreds of feet of waterfront

Exceptional

(73 reviews)

Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock

Woolford, MD

8% off

AU$1,424 per night

includes taxes & fees

Exceptional

(6 reviews)

Fish, kayak, bike, and more at this private serene 24-acre waterfront estate.

Cambridge, MD

8% off

AU$667 per night

includes taxes & fees

Magnificent property for crabbing, fishing, volleyball and badmitten

Exceptional

(77 reviews)

Year Round Waterfront Estate / Family Reunions / Retreats - Sleeps 28

Cambridge, MD

9% off

AU$1,950 per night

includes taxes & fees

Exceptional

(122 reviews)

Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels

St. Michaels, MD

8% off

AU$535 per night

includes taxes & fees

Thomas Harrison House looking from St. Michaels Town Harbor

Exceptional

(129 reviews)

Large -IN TOWN- Historic House on Harbor in St Michaels - Walk to Everything!

St. Michaels, MD

8% off

AU$1,175 per night

includes taxes & fees

Exceptional

(12 reviews)

Alpaca Farm on Chesapeake Bay - 86 Private Acres, Heated Pool, Beach, 600' Pier

Cambridge, MD

8% off

AU$2,399 per night

includes taxes & fees

Exceptional

(11 reviews)

Spacious 2 bedroom duplex located conveniently near Route 50 East and West.

Grasonville, MD

17% off

AU$408 per night

includes taxes & fees

Exceptional

(50 reviews)

Stunning Waterfront Eastern Shore Home,Pool & Hot Tub,15 Acres,15%off 7day stay

Cambridge, MD

8% off

AU$1,420 per night

includes taxes & fees

Find spaces that suit your style

House

Condo/Apartment

Find the best place to stay - Customs House

An Afternoon Nap in the Hammock is a Must.

Sleeps 6 · 3 bedrooms · 2+ bathrooms

Woodland Retreat on Kent Island: 5 beds, 5 miles from Bay Bridge, on 5 acres.

Sleeps 10 · 4 bedrooms · 3 bathrooms

20 x 40 Salt Water Pool - Open June- October (not heated)

Waterfront Cottage, Private Hot Tub, Fire Pit, Pool - perfect Romantic Getaway

Sleeps 4 · 2 bedrooms · 2 bathrooms

Top rated rentals - Customs House

Premier Host

SPECTACULAR!!!

CONGRATULATIONS! You have found the best house on Kent Island and all of VRBO.We just finished an incredible stay here and were blown away from the moment we pulled up the driveway. The house is spotless, beautifully decorated, and fully stocked with everything you could possibly need. The amenities truly went above and beyond. The outdoor spaces are immaculate and luxurious, with a wraparound porch on both levels and a breathtaking pool. Our family especially enjoyed the daily deer sightings on the property.As for the host, John was extremely hospitable. His attention to detail is unmatched. He was accessible, accommodating, and made sure everything was perfect for our stay.We will forever cherish the family memories we made here. If you're lucky enough to see this place available, book it!

Charlene U.

Stayed June 2025

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Enjoy full kitchens, laundry, pools, gardens and more
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