Holiday rentals near Bay Ridge Beach

We found 686 holiday rentals — enter your dates for availability

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November 2025

December 2025

If you'd like to stay close to Bay Ridge Beach, scroll through and discover private holiday rentals to find the perfect home base for your trip. Whether you're staying in a holiday rental with your children or with friends, you'll find the amenities that you need and want, such as parking and air conditioning. You'll be sure to find a property to rent for everyone's needs, including places that are non-smoking or accessible.

Holiday rentals with weekly discounts - Bay Ridge Beach

Showing deals for:6 Feb - 13 Feb

Exceptional

(30 reviews)

NEW LISTING! Waterfront cottage, hot tub, fire pit, gated community, pier, kayak

Annapolis, MD

11% off

for 7 nights, 1 cottage

AU$635 per night

includes taxes & fees

Exceptional

(44 reviews)

Chesapeake Houseboat Getaway on Kent Island, Maryland

Stevensville, MD

12% off

for 7 nights, 1 houseboat

AU$464 per night

includes taxes & fees

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

Exceptional

(16 reviews)

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

Stevensville, MD

5% off

for 7 nights, 1 home

AU$657 per night

includes taxes & fees

Exceptional

(26 reviews)

New! Stylish downtown home w/awesome outdoor area!

Stevensville, MD

8% off

for 7 nights, 1 home

AU$442 per night

includes taxes & fees

Quiet, tree-filled neighborhood. The apartment is above the garage.

Exceptional

(18 reviews)

Annapolis Tree House Apartment- luxury shower, separate space

Annapolis, MD

7% off

for 7 nights, 1 apartment

AU$370 per night

includes taxes & fees

Exceptional

(55 reviews)

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

Stevensville, MD

8% off

for 7 nights, 1 cottage

AU$715 per night

includes taxes & fees

Exceptional

(13 reviews)

Waterfront Architectural Masterpiece with private dockage available.

Annapolis, MD

12% off

for 7 nights, 1 home

AU$2,102 per night

includes taxes & fees

The exterior of Annapolis Charm with a great water view!

Exceptional

(24 reviews)

Annapolis Charm - Waterfront Private Fishing Dock Pier Near Beach - Navy Academy

Annapolis, MD

8% off

for 7 nights, 1 home

AU$808 per night

includes taxes & fees

Exceptional

(12 reviews)

Charming Home located minutes from the Naval Academy and Downtown Annapolis

Annapolis, MD

8% off

for 7 nights, 1 home

AU$923 per night

includes taxes & fees

Exceptional

(8 reviews)

NEW Charming Historic Home <.75mile to Navy Stadium, 1mile to USNA and Downtown

Annapolis, MD

12% off

for 7 nights, 1 home

AU$578 per night

includes taxes & fees

Exceptional

(8 reviews)

Chessie Cottage-Chesapeake Bay Great views from easy single floor living!

Stevensville, MD

8% off

for 7 nights, 1 cottage

AU$996 per night

includes taxes & fees

Lavish, spacious, well-appointed 3-bed, 3.5 bath home just minutes from downtown Annapolis

Exceptional

(7 reviews)

Mins to Annap; Luxury Townhome

Arnold, MD

7% off

for 7 nights, 1 home

AU$634 per night

includes taxes & fees

Exceptional

(31 reviews)

25-50% Off~Private Beach~Hot Tub~Fire Table~

Stevensville, MD

8% off

for 7 nights, 1 home

AU$707 per night

includes taxes & fees

Exceptional

(221 reviews)

Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA

Edgewater, MD

8% off

for 7 nights, 1 cottage

AU$610 per night

includes taxes & fees

Exceptional

(7 reviews)

Spacious 6-bedroom country house on the water in beautiful Shady Side with WiFi

Shady Side, MD

7% off

for 7 nights, 1 home

AU$1,123 per night

includes taxes & fees

Exceptional

(202 reviews)

Island Life! Kent Island Waterfront with Pool-Bring your boat!

Stevensville, MD

12% off

for 7 nights, 1 room

AU$713 per night

includes taxes & fees

Exceptional

(37 reviews)

3 acre waterfront estate - heated pool, hot tub, yard, pier, game and pub room!

Crownsville, MD

8% off

for 7 nights, 1 home

AU$5,093 per night

includes taxes & fees

3 covered balconies, a ground floor patio, and ceramic and propane grills.

Exceptional

(56 reviews)

Charming Annapolis WaterVIEW Home

Annapolis, MD

8% off

for 7 nights, 1 home

AU$893 per night

includes taxes & fees

FAMILY ROOM W/FIREPLACE & FLAT SCREEN TV

Exceptional

(35 reviews)

Excellent Location, Super Clean, Super Spacious, Near Bay & Downtown Annapolis

Annapolis, MD

11% off

for 7 nights, 1 home

AU$1,367 per night

includes taxes & fees

Exceptional

(22 reviews)

Chesapeake Bay Getaway | New Waterfront With Private Pier | Near Annapolis /USNA

Edgewater, MD

8% off

for 7 nights, 1 home

AU$848 per night

includes taxes & fees

Find spaces that suit your style

House

Condo/Apartment

Find the best place to stay - Bay Ridge Beach

Lakefront home with private dock, deck, hot tub, firepit, Ping-Pong, large yard

Sleeps 16 · 6 bedrooms · 4+ bathrooms

Premier Host

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

Sleeps 6 · 3 bedrooms · 2 bathrooms

Premier Host

Multi-unit Waterfront Home with Private Pool and Pier Mins to Downtown Annapolis

Sleeps 14 · 6 bedrooms · 4 bathrooms

The expansive backyard and deck is a beautiful view when walking up from the private pier at the home's riverfront.

Premier Host

Stay Mins from Annapolis in Luxury Waterfront Home on Deep Water w Private Pier & Gourmet Kitchen

Sleeps 12 · 4 bedrooms · 4 bathrooms

Top rated rentals - Bay Ridge Beach

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

Premier Host

Fantastic house - clean, warm & perfectly located to get around Annapolis

Property was fully equipped with everything we needed - like a ‘home away from home’. John was extremely helpful and informative during our planning and everything was as we expected. Thanks a lot!

Simon M.

Stayed Dec 2017

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Holiday rentals near Bay Ridge Beach

Holiday rentals with weekly discounts - Bay Ridge Beach

Image gallery for NEW LISTING! Waterfront cottage, hot tub, fire pit, gated community, pier, kayak

NEW LISTING! Waterfront cottage, hot tub, fire pit, gated community, pier, kayak

Find spaces that suit your style

Find the best place to stay - Bay Ridge Beach

Lakefront home with private dock, deck, hot tub, firepit, Ping-Pong, large yard

Top rated rentals - Bay Ridge Beach

SPECTACULAR!!!

Peace of mind

More quality time

All the privacy of home

More for less

Holiday Rental options near Bay Ridge Beach

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