Holiday rentals near Bruce Gabrielson's Surf Art Gallery and Museum

We found 368 holiday rentals — enter your dates for availability

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November 2025

December 2025

If you'd like to stay close to Bruce Gabrielson's Surf Art Gallery and Museum, take a look at holiday rentals to find the perfect one for your trip. Whether you’re staying in a holiday home with your children and pets or just with friends, you'll have the best amenities for spending time at your home away from home, which might include parking and a garden. At the end of the day, you'll be sure to find a property to rent for everyone's needs, including accessible or non-smoking choices.

Holiday rentals with weekly discounts - Bruce Gabrielson's Surf Art Gallery and Museum

Showing deals for:6 Feb - 13 Feb

A great spot to soak in the views of the Chesapeake Bay.

Exceptional

(18 reviews)

Modern Waterfront House with amazing views of the Chesapeake Bay and a dock!

North Beach, MD

16% off

for 7 nights, 1 home

AU$892 per night

includes taxes & fees

House and Garage as seen from above (pool on left)

Exceptional

(90 reviews)

Luxurious and Extremely Private Waterfront Estate (SORRY - NO WEDDINGS)

Royal Oak, MD

8% off

for 7 nights, 1 home

AU$3,076 per night

includes taxes & fees

Exceptional

(22 reviews)

Quiet Woodland cottage near St. Leonard's Creek

Lusby, MD

7% off

for 7 nights, 1 cottage

AU$145 per night

includes taxes & fees

Exceptional

(53 reviews)

Stunning views at WATERFRONT St Michaels area historic home, dog friendly

Neavitt, MD

8% off

for 7 nights, 1 home

AU$683 per night

includes taxes & fees

Property grounds: BB court, house, barn, pool and grass volley ball court.

Exceptional

(85 reviews)

Private Waterfront Family Retreat w/ Pier Pool Pickleball Basketball Volleyball

Taylors Island, MD

8% off

for 7 nights, 1 room

AU$930 per night

includes taxes & fees

Exceptional

(5 reviews)

Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.

Benedict, MD

8% off

for 7 nights, 1 cottage

AU$354 per night

includes taxes & fees

Exceptional

(162 reviews)

Harbor Cottage at the Chesapeake Bay - Dog Friendly Beach

St. Leonard, MD

5% off

for 7 nights, 1 cottage

AU$277 per night

includes taxes & fees

View of the main house & guest house from the bay

Exceptional

(7 reviews)

Waterfront retreat, beautiful views!

Cambridge, MD

8% off

for 7 nights, 1 home

AU$1,810 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

for 7 nights, 1 home

AU$2,127 per night

includes taxes & fees

Exceptional

(55 reviews)

Dollhouse in Central Historic St Michaels

St. Michaels, MD

12% off

for 7 nights, 1 home

AU$460 per night

includes taxes & fees

You can't get much closer to the Chesapeake Bay than this 2-bed/1-bath gem that sleeps 6!

Exceptional

(9 reviews)

Unbelievable beach views for 6

North Beach, MD

8% off

for 7 nights, 1 apartment

AU$423 per night

includes taxes & fees

Exceptional

(262 reviews)

Family and Pet-Friendly, Waterfront with Pier

Cambridge, MD

8% off

for 7 nights, 1 cottage

AU$462 per night

includes taxes & fees

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

Exceptional

(74 reviews)

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

Woolford, MD

8% off

for 7 nights, 1 home

AU$1,412 per night

includes taxes & fees

Wonderful

(17 reviews)

Waterfront property with private boat ramp and new dock!

Cambridge, MD

8% off

for 7 nights, 1 cottage

AU$428 per night

includes taxes & fees

Exceptional

(24 reviews)

Eastern Shore Waterside Cottage Near St. Michaels

Neavitt, MD

8% off

for 7 nights, 1 cottage

AU$521 per night

includes taxes & fees

Exceptional

(14 reviews)

"Point of View" Waterfront cottage with panoramic views on Tilghman Island

Tilghman, MD

9% off

for 7 nights, 1 cottage

AU$557 per night

includes taxes & fees

Our 400 foot pier, great for fishing crabbing watching Osprey's or hanging out

Exceptional

(19 reviews)

Bright and airy waterfront getaway

Benedict, MD

8% off

for 7 nights, 1 home

AU$467 per night

includes taxes & fees

Exceptional

(191 reviews)

Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch

St. Michaels, MD

8% off

for 7 nights, 1 cottage

AU$644 per night

includes taxes & fees

Exceptional

(12 reviews)

Grace Cottage, Saint Michaels Walk to everything!

St. Michaels, MD

8% off

for 7 nights, 1 home

AU$647 per night

includes taxes & fees

Exceptional

(50 reviews)

Secluded Waterfront Property on 3 acres with swimming pool and dock.

Bozman, MD

5% off

for 7 nights, 1 home

AU$1,345 per night

Premier Host

Cozy Cottage with access to and partially obstructed views of the bay.

Sleeps 10 · 3 bedrooms · 2 bathrooms

for 3 nights, 1 cottage

AU$488 per night

includes taxes & fees

Peace of mind
Our Book with Confidence Guarantee gives you 24/7 support
More quality time
From booking to staying, the whole process is simple and enjoyable
All the privacy of home
Enjoy full kitchens, laundry, pools, gardens and more
More for less
More space, more privacy, more amenities — more value

Holiday rentals with weekly discounts - Bruce Gabrielson's Surf Art Gallery and Museum

Modern Waterfront House with amazing views of the Chesapeake Bay and a dock!

Cottage Located on the Patuxent River!

Luxurious and Extremely Private Waterfront Estate (SORRY - NO WEDDINGS)

Private Waterfront Home w/ Pier and 2+ Acres!

Quiet Woodland cottage near St. Leonard's Creek

Stunning views at WATERFRONT St Michaels area historic home, dog friendly

The Middle Point Cabin in Saint Michaels

Private Waterfront Family Retreat w/ Pier Pool Pickleball Basketball Volleyball

Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.

Harbor Cottage at the Chesapeake Bay - Dog Friendly Beach

Waterfront retreat, beautiful views!

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

Dollhouse in Central Historic St Michaels

Dee's Lounge, Your Relaxation Oasis

Unbelievable beach views for 6

Family and Pet-Friendly, Waterfront with Pier

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

Waterfront property with private boat ramp and new dock!

Eastern Shore Waterside Cottage Near St. Michaels

"Point of View" Waterfront cottage with panoramic views on Tilghman Island

Bright and airy waterfront getaway

Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch

Grace Cottage, Saint Michaels Walk to everything!

Secluded Waterfront Property on 3 acres with swimming pool and dock.

Find spaces that suit your style

Find the best place to stay - Bruce Gabrielson's Surf Art Gallery and Museum

Modern Waterfront House with amazing views of the Chesapeake Bay and a dock!

Private Chesapeake Bay Beach community…love to feel the sand between your toes?

The Blue Crab Beach House - Free beach passes

The Cozy Crab- Your Charming Haven in Lovely North Beach!

Sweet Bamboo Beach Cottage

Cozy Cottage with access to and partially obstructed views of the bay.

Peace of mind

More quality time

All the privacy of home

More for less

Holiday Rental options near Bruce Gabrielson's Surf Art Gallery and Museum

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Holiday rentals near Bruce Gabrielson's Surf Art Gallery and Museum

Holiday rentals with weekly discounts - Bruce Gabrielson's Surf Art Gallery and Museum

Image gallery for Modern Waterfront House with amazing views of the Chesapeake Bay and a dock!

Modern Waterfront House with amazing views of the Chesapeake Bay and a dock!

Find spaces that suit your style

Find the best place to stay - Bruce Gabrielson's Surf Art Gallery and Museum

Modern Waterfront House with amazing views of the Chesapeake Bay and a dock!

Peace of mind

More quality time

All the privacy of home

More for less

Holiday Rental options near Bruce Gabrielson's Surf Art Gallery and Museum

More Holiday Rentals ideas

People also search for