Holiday rentals with beach access in Saint Leonard

4.93 out of 5 average rating, 204 reviews

Cabin in Lusby

Hideaway on the Bay: Waterfront Vintage A Frame

The Hideaway on the Bay is a waterfront A frame where you can disconnect from the things that can wait so you can connect with the people who matter most. A place where kids fall in love with nature, and where old friends make new memories. The house is a 2 bed 1 bath 1974 flat top A Frame that sits on two acres on the outskirts of Lusby, MD—and a low traffic hour(ish) drive from the DMV. Enjoy the indoor fireplace, outdoor fire pit, swinging chairs, kayaks, canoe, fish, and catch crabs --

Tiny home in Saint Inigoes

4.98 out of 5 average rating, 349 reviews

Historic St.Mary's City at the Lazy Bear Cottage

Inquire first on pets, there is a 50 lb. weight limit total, can be split up between 2 small dogs or 1 at 50lbs or less,must be house broken and friendly. Close to Saint Mary's historic city, Pt. Lookout State Park, Sotterley Plantation. Great hiking trails, restored colonial village,a replica of the Maryland Dove. Tour a lighthouse. Great restaurants , or spend a day over in Solomons Island, about 20 miles from us. Peaceful settings for relaxing right on the water,or kayak on the river.

5 out of 5 average rating, 371 reviews

Loft in Lusby

Treetop Loft Retreat w/ Private Beach Access

Come experience our tucked-away loft 5 minutes from beaches, 10 minutes to Solomons, and Calvert Cliffs. Private above-garage apartment with 17 stairs. Our open-concept space, has a bedroom area, bathroom, workspace, & kitchen (convection oven, induction burner, microwave, refrigerator, and Keurig). Enjoy quick Wi-Fi, a 40" Smart TV, a cozy queen bed, and comfy lounge chairs. Bring S'mores fixings to roast over the fire and wrap yourself in a blanket. Choose to stay in or adventure out.

4.99 out of 5 average rating, 212 reviews

Home in Lusby

Cove Point Cottage with Chesapeake Bay views

Welcome to our beach house, just a block from the Cove Point Beach on the Chesapeake Bay. Start your beach day by grabbing the beach wagon from the shed, loading it up with beach chairs, towels, and your cooler. A short stroll takes you to the beach, where you can spend the day searching for shark teeth and shells or swimming in the bay's refreshing waters. After a day in the sun, rinse off in our outdoor shower. Our shady patio provides the perfect spot to relax and enjoy the evening breeze.

4.96 out of 5 average rating, 191 reviews

Cottage in Leonardtown

Beach Front and 'Perfectly Placed'

Escape to our charming Potomac River waterfront cottage, complete with 2 cozy bedrooms, 1 tastefully appointed bathroom, and stunning river views. Enjoy a comfortable living area with large windows, a fully equipped kitchen, and an outdoor picnic table. Perfect for small families or friends seeking a peaceful retreat, our cottage is conveniently located just a short drive from local restaurants and shopping. Come relax, unwind, and make unforgettable memories on the beautiful Potomac River.

4.92 out of 5 average rating, 179 reviews

Home in Saint Leonard

Cozy Cottage on the Chesapeake Bay

Tranquility supreme. Sit on the terrace and gaze at the Chesapeake Bay. Sandy beach -- just 50 steps from front door; quiet residential area; nearby antiquing & fishing; Only 75 min. from DC. Finish your book or just replenish your spirit. Enjoy. Oh, one more thing — looking for the perfect place for a retreat for your small DC team? Strategic planning will be even more creative and enjoyable when you have the Chesapeake Bay as your muse. Note: This property is for non-smokers.

5 out of 5 average rating, 383 reviews

Flat in Lexington Park

Adorable Waterfront Apartment Weekend Getaway

Bright & cheery 1 bedroom waterfront apartment nestled on the banks of the St. Mary's River. Amazing, dreamy views. It's a sweet spot to relax and enjoy a quiet get-away or launch a kayak, take a walk, enjoy great food cuisine. We sit next to St. Mary's College of MD and Historic St. Mary's City. You may see college sailing races, crew teams rowing, or the historic Maryland Dove sailing down the river. It's lovely here fall, winter, spring, summer! SUNSETS!

5 out of 5 average rating, 185 reviews

Home in Lusby

Cove Point Beach Home 1 &1/2 blocks to Beach

"Welcome to our Beach House, located in the unique peaceful private beach community of Cove Point. You'll enjoy the tranquility and the beauty of living less than a 2 min walk to the sandy beach and just a few away from Solomon's Island, MD. Our home was just renovated and is ready for your family to enjoy, offering beach necessities (wagon, chairs, umbrella, & toys) and recreational equipment (bikes & kayaks). This will be your home away from home.

Guest house in Saint Leonard

4.96 out of 5 average rating, 111 reviews

Studio on the Bay.

This studio apartment is in walking or driving distance to three private beaches in our community. There is 1 bedroom with a queen size bed, spacious bathroom and closet. The living room has a pull out full size bed and a kitchenette. Coffee, teas, beach chairs, are provided. Wanna fish??? Ask Joey about Fish Taxi! Fifteen minutes from Solomons Island (home of the Tiki Bar). An hour or so from DC, Annapolis and Waldorf.

4.9 out of 5 average rating, 267 reviews

Cabin in Lusby

Peaceful Waterfront Retreat on The Bay

Escape to a serene waterside cabin with a private dock on quiet St. Leonard Creek, just an hour from Washington, DC. This rustic studio offers a cozy retreat for solo travelers, couples, or small families looking for peace and relaxation. Whether you're here to unwind, work remotely, or explore the outdoors, you'll find plenty to enjoy—including two kayaks, two canoes, and stunning waterfront views.

4.96 out of 5 average rating, 643 reviews

Tiny home in Solomons

“Cabana by the Bay”-tiny home on a pier!

This tiny home is a newly renovated cabana sitting on a pier. Fall asleep to the sound of waves crashing under you! Enjoy shared use of our private beach. Bikes are available April-October and are stored directly across the street. Go crabbing or fishing off the pier and walk to one of the many nearby restaurants. Check out the summer concert series at the Calvert Marine Museum.

4.96 out of 5 average rating, 187 reviews

Guest house in Lusby

Cozy Lakeside Studio Retreat.

Cozy basement studio that provides a perfect get away. From beach combing, kayaking, fishing, swimming in the Bay, dock, fire pit, and corn hole, there’s lots to do. Or simply just relax and enjoy the serene surroundings. Photography package available, message host for details 2 GUESTS ONLY; please check with host regarding children

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Popular amenities for rentals with beach access in Saint Leonard

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Wifi

Pool

Free parking on premises

Air conditioning

Apartment rentals with beach access

4.88 out of 5 average rating, 104 reviews

Flat in Annapolis

King George Downtown Annapolis Getaway

5 out of 5 average rating, 48 reviews

Flat in Stevensville

Heron Roost

4.9 out of 5 average rating, 130 reviews

Flat in Cambridge

Little Slice of Cambridge. 2 bedroom, pet friendly

4.97 out of 5 average rating, 568 reviews

Flat in Lexington Park

Historic St. Mary's City, MD

4.92 out of 5 average rating, 53 reviews

Flat in Colonial Beach

Sail Away To - Beachfront Views & Private Balcony

4.96 out of 5 average rating, 131 reviews

Flat in North Beach

Bayside Oasis of Southern Maryland

4.97 out of 5 average rating, 29 reviews

Flat in Annapolis

Bayside Retreat

4.88 out of 5 average rating, 82 reviews

Flat in North Beach

Spacious Beach House Top Floors - Walk Everywhere!

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House rentals with beach access

4.97 out of 5 average rating, 162 reviews

Home in Hague

Osprey's roost: Spring and summer 2025

DavidRating, 5 stars5 days ago

Very roomy for a family vacation. Great location and covered porch was great for taking in views of river and enjoying summer breeze. Host was responsive and provided detailed instructions.

4.98 out of 5 average rating, 106 reviews

Home in Montross

Waterfront Retreat| Kayak+Beaches+Pool | Gameroom

DavidRating, 5 stars2 weeks ago

What a find! We were attending a wedding on the Potomac and found this gem of a place basically right next door. A perfectly appointed home in a peaceful, tranquil, beautiful setting. Connie was great! Responsive to our need to find the iron, not exactly an emergency, Connie responded immediately with it's location. Loved it!

4.92 out of 5 average rating, 208 reviews

Home in Montross

The Glebe

KristinaRating, 5 stars2 weeks ago

We had such a wonderful stay! The house was beautiful, peaceful, and had everything we needed for a relaxing getaway. The layout was perfect for spending quality time together while still giving everyone space to unwind. Private beach access made it even more special—we made great memories, met some lovely neighbors, and even had a chance to paddle board and spot a stingray! Huge shout-out to Leigh, our amazing host—so thoughtful, responsive, and kind. We’re so grateful for the experience and would absolutely stay here again. Highly recommend!

5 out of 5 average rating, 142 reviews

Home in North Beach

Waterfront, Dog-friendly, Hot Tub, Peleton

StephanieRating, 5 stars6 days ago

This was our second time staying at Kimberly’s home, and it was just as magical as we remembered. The views of the water are absolutely stunning—whether you’re enjoying your morning coffee or winding down in the evening, it’s hard to look away. The location is perfect: peaceful but just a short walk to shops and restaurants. We also really appreciated the Peloton and treadmill—such a bonus for staying active during our trip. Everything was spotless and thoughtfully prepared. Honestly, we didn’t want to leave. Already looking forward to our next visit!

4.95 out of 5 average rating, 272 reviews

Home in Grasonville

River Front, Private Single Family Home

HeatherRating, 5 stars2 days ago

the stay was wonderful. A very relaxing and peaceful place. Easy to locate and get into. reasurants and grocery stores are near by

5 out of 5 average rating, 170 reviews

Home in Shady Side

Luxe Modern Chesapeake Waterfront Oasis - 5 Star

MelindaRating, 5 stars4 days ago

The venue, property and service made great memories. Our host went above and beyond to help and especially with a special request that only an exceptional person would do. We had a wonderful stay and look forward to another visit.

4.9 out of 5 average rating, 134 reviews

Home in Scotland

Spacious Gorgeous Waterfront Home with Sunset View

KathrynRating, 5 stars3 days ago

My family of 10 had a great stay here! There was plenty of space to spread out and the location is perfect and serene. We were able to fish out on the dock and caught a few spot! One of the friendly neighbors even stopped by to offer some raspberries from their bush and extra firewood. We did run into an issue after check in with one of the bathrooms, but Karina was quick to respond and sent someone out to handle it as quickly as possible. Thank you for the wonderful stay!