Vacation rentals near Academy of the Arts

We found 390 vacation rentals — enter your dates for availability

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August 2025

September 2025

Discover a selection of vacation rentals near Academy of the Arts that can be your home away from home. Whether you're traveling with family, friends, or just your furry companion, vacation homes have the amenities you expect for your stay, which might include a garden and pool. What you'll find is a rental to meet everyone's needs, including options that are accessible or non-smoking.

Vacation rentals with weekly discounts - Academy of the Arts

Showing deals for:Nov 14 - Nov 21

Welcome to the Beachcomber on Kent Island, uniquely situated between a marina and a beach.

Exceptional

(12 reviews)

One-level waterfront home with beach and stunning views all the way to the Bay Bridge

Stevensville, MD

5% off

includes taxes & fees

Exceptional

(7 reviews)

Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)

Cambridge, MD

5% off

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

10% off

includes taxes & fees

Exceptional

(47 reviews)

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

Bozman, MD

6% off

includes taxes & fees

Very good

(5 reviews)

Travelers Rest Spacious 5BR Pool riverfront Pier charming Easton Saint Michaels

Easton, MD

19% off

includes taxes & fees

Exceptional

(15 reviews)

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

Cambridge, MD

10% off

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

10% off

includes taxes & fees

Exceptional

(6 reviews)

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

Cambridge, MD

10% off

includes taxes & fees

Exceptional

(6 reviews)

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

Cambridge, MD

10% off

includes taxes & fees

Exceptional

(12 reviews)

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

Cambridge, MD

10% off

includes taxes & fees

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

Exceptional

(72 reviews)

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

Woolford, MD

10% off

includes taxes & fees

Exceptional

(11 reviews)

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

Grasonville, MD

20% off

includes taxes & fees

Exceptional

(48 reviews)

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

Cambridge, MD

10% off

includes taxes & fees

Find spaces that suit your style

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Find the best place to stay - Academy of the Arts

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 - Academy of the Arts

"Overlook on Dun's Cove" -- luxury, year-round waterfront vacation rental

Premier Host

Perfectly Peaceful

This property provided the perfect, peaceful weekend escape for my husband and I. Dun’s Cove proved to be the best location to stay in the area with all the attractions and amenities nearby yet, we were always welcomed back by the tranquility of this property nestled along the shore. The views from within the home enhanced the feeling of being outdoors at all times and the added bonus of a wood burning fireplace truly made our time special. Whether you are in the area and need a place to stay or as a destination home, we would highly recommend renting this property.

Sheri W.

Stayed Dec 2021

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, yards and more
More for less
More space, more privacy, more amenities — more value