Calvert Area Rentals
From $95 per night (USD)VRBO
Cozy Cottage by the water - Private courtyard and inground pool
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Private cottage in Southern MD with inground outdoor pool, views of Patuxent River, several nearby Chesapeake Bay beache ...
From $95 per night (USD)VRBO
From $182 per night (USD)VRBO
Sweet Bamboo Beach Cottage
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
If you are looking for a sweet, comfortable and clean home for your stay while visiting our beaches or other Calvert Cou ...
From $182 per night (USD)VRBO
From $455 per night (USD)VRBO
Huge Beach Bungalow w\/Yard, Beach Passes, 2 King Bds near Boardwalk, Restaurants
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
This huge, newly designed home has 4 bedrooms (2 king beds + 2 queen beds). It is a few minutes to the beach, restaurant ...
From $455 per night (USD)VRBO
From $318 per night (USD)VRBO
Waterfront riverhouse on a beautiful farm only 50 minutes from DC
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Great house on the Patuxent river with new kitchen, paint, outdoor deck and 2 full bathrooms. Access to kayaks and pad ...
From $318 per night (USD)VRBO
From $292 per night (USD)VRBO
Our Always Dreaming Cottage - The Bay At Your Back Steps
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to The Aways Dreaming Cottage with two bedrooms which sleeps four (4) – where dreaming is a pastime you will enj ...
From $292 per night (USD)VRBO
From $289 per night (USD)VRBO
Waterfront Log Cabin with Million Dollar View & Luxury Bath! Shark's Teeth!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Comfortable Chesapeake Bay Waterfront Historic Log Cabin in Exclusive Private Community where you can enjoy swimming, te ...
From $289 per night (USD)VRBO
From $399 per night (USD)VRBO
Waterfront, Private Beach, Peaceful Family Getaway
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Experience the Chesapeake from your very own front row seat at Murphy Point on the Chesapeake! Watch dolphins, turtles, ...
From $399 per night (USD)VRBO
From $414 per night (USD)Expedia
Waterfront House with Dock, Kayaks, & Sailboat!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 9
Set sail on an unforgettable vacation with this 4-bedroom, 2-bath California vacation rental as your home-away-from-home ...
From $414 per night (USD)Expedia
From $135 per night (USD)VRBO
Cozy Cedar Cottage & Chesapeake Bay
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Cute, cozy cedar cottage with private community beach. Come enjoy one mile of sandy beach & enjoy beautiful sunrises, ...
From $135 per night (USD)VRBO
From $565 per night (USD)VRBO
Private Beachfront Home with Beautiful Bay View
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Enjoy spectacular 180 degree views of the Chesapeake Bay on this 4 bedroom waterfront home situated on a private treed l ...
From $565 per night (USD)VRBO
From $395 per night (USD)VRBO
Relax in our cottage within walking distance of Herrington on the Bay events.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
The owner has created your own slice of paradise in the Rose Haven community of North Beach. Walk to Herrington Harbour ...
From $395 per night (USD)VRBO
From $250 per night (USD)Expedia
The Normandy Cottage ~ Charming Getaway ~ On The Shores Of The Chesapeake!
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
It was “MAGIC” when I discovered this town years ago. Beautiful sunrises right here on the Chesapeake Bay & glorious “mo ...
From $250 per night (USD)Expedia
From $184 per night (USD)VRBO
Bell Estates-Brand New Bay View, Beautiful Cottage
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Bell Estates is a newly built corner lot across the street from the bay with stunning views of the water from the Master ...
From $184 per night (USD)VRBO
From $277 per night (USD)VRBO
Waterfront Wildlife Retreat on the Patuxent River
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This contemporary waterfront home, located on the Patuxent River, near the entrance to the Solomons Island Harbor, is ...
From $277 per night (USD)VRBO
From $250 per night (USD)VRBO
The Hidaway on the Patuxent River<br>Children allowed and welcomed to stay.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Children are Allowed and Welcomed to stay. I don't know why it says they are not, and I have tried correcting it to no a ...
From $250 per night (USD)VRBO
From $170 per night (USD)VRBO
Chesapeake Bay & Beach Await You~Fido Friendly
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
This cozy and comfy beach house is a short walk to the private community beach. Come beach comb one mile of shoreline. ...
From $170 per night (USD)VRBO
From $210 per night (USD)VRBO
Lovely Waterfront Houes
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
What an opportunity to own waterfront with deep water! Great property with so much potential. Once was an operating mari ...
From $210 per night (USD)VRBO
From $753 per night (USD)Expedia
Indoor pool and spa in contemporary French home secluded in surrounding woods
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Contemporary all-brick French manor nestled within 16-acres of secluded woodlands. Indoor pool/spa with waterfall inside ...
From $753 per night (USD)Expedia
From $167 per night (USD)VRBO
Harbor Cottage at the Chesapeake Bay - Dog Friendly Beach
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Harbor Cottage. Relax on the deck overlooking the fishing and sailboats of Flag Harbor opening onto the Chesapeake Bay. ...
From $167 per night (USD)VRBO
From $160 per night (USD)Expedia
Experience the best of Southern Maryland at the Calvert Cliffs Cottage.
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to the Calvert Cliffs Cottage. Nestled in a quiet country setting our home offers quick access to state parks an ...
From $160 per night (USD)Expedia
From $168 per night (USD)VRBO
Fossil Hunting. Beaches. Hiking nearby. 10 minutes to Solomons Island Boardwalk.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Experience a piece of Southern Maryland history. Bancroft Manor was among the first homes along St Leonard Creek. Every ...
From $168 per night (USD)VRBO
From $950 per night (USD)VRBO
Waterfront Charleston Colonial
- Bedrooms:
- 6
- Bathrooms:
- 4
- Sleeps:
- 10
4 bedroom house. Each room has a private bathroom. 2 half baths located on the main level. Basement level is blocked off ...
From $950 per night (USD)VRBO
From $264 per night (USD)VRBO
'The River's Roost' Home on Patuxent River!
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 10
Situated right on the Patuxent River and offering endless opportunities for fun, this house is the most idyllic place to ...
From $264 per night (USD)VRBO
Click For PricingExpedia
Luxury Cottage w\/ Bay & Boardwalk Views--steps from the water
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 3
Where new Luxury meets Cottage history and charm. Stay in one of the only cottages right on the Boardwalk that features ...
Click For PricingExpedia
From $255 per night (USD)VRBO
North Beach 'Blue Heron Bungalow' w\/ Backyard
- Bedrooms:
- 4
- Bathrooms:
- 2
- Sleeps:
- 7
Live like a local at this North Beach vacation rental! This 2-bedroom, 3.5-bathroom home hosts plenty of space for you a ...
From $255 per night (USD)VRBO
From $250 per night (USD)Expedia
Home located on a farm with a beautiful view of the Patuxent River.
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
This lovely home is nestled on a working farm in Calvert County Maryland overlooking the Patuxent River. Perfectly locat ...
From $250 per night (USD)Expedia
From $314 per night (USD)VRBO
cBay Cottage - On the Chesapeake Bay - Port Republic MD
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
cBay Cottage was built around 1940 as a summer Chesapeake Bay get-away cottage. Folks would pack up the station wagon an ...
From $314 per night (USD)VRBO
From $283 per night (USD)Expedia
Stylish, Panoramic River Views , Waterfront Modern Home 1 Hr to D.C.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 7
A luxurious waterfront retreat with quality stainless appliances, pillowtop and double memory foam bed, cotton rich shee ...
From $283 per night (USD)Expedia
From $277 per night (USD)VRBO
Stylish & Modern Waterfront retreat, Serene and with great views,1Hr to DC
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 7
A luxurious waterfront retreat with quality stainless appliances, pillowtop and double memory foam bed, cotton rich shee ...
From $277 per night (USD)VRBO
From $225 per night (USD)Expedia
Beach House
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
BODHI'S BAY HOUSE - This home is just a few steps from the private community beach, fully stocked with everything you ne ...
From $225 per night (USD)Expedia
From $80 per night (USD)VRBO
Quiet Woodland cottage near St. Leonard's Creek
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Hilltop Cottage has newly installed wifi and cable TV with one loft bedroom with two twin beds. The main floor has one f ...
From $80 per night (USD)VRBO
From $222 per night (USD)Expedia
Guest Quarters at the Inn - 101
- Bedrooms:
- 1
- Bathrooms:
- 0
- Sleeps:
- 4
The Guest Quarters at the Inn is a vacation rental site situated one block from the Chesapeake Bay in the historic and c ...
From $222 per night (USD)Expedia
From $205 per night (USD)VRBO
Guest Quarters at the Inn - 103
- Bedrooms:
- 1
- Bathrooms:
- 0
- Sleeps:
- 2
The Guest Quarters at the Inn is a vacation rental site situated one block from the Chesapeake Bay in the historic and c ...
From $205 per night (USD)VRBO
From $221 per night (USD)Expedia
Guest Quarters at the Inn - 102
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
The Guest Quarters at the Inn is a vacation rental site situated one block from the Chesapeake Bay in the historic and c ...
From $221 per night (USD)Expedia
From $259 per night (USD)VRBO
Guest quarters at the inn - 205
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
The Guest Quarters at the Inn is a vacation rental site situated one block from the -Bay in the historic and charming to ...
From $259 per night (USD)VRBO
From $257 per night (USD)Expedia
Guest quarters at the inn - 204
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
The Guest Quarters at the Inn is a vacation rental site situated one block from the Chesapeake Bay in the historic and c ...
From $257 per night (USD)Expedia
From $350 per night (USD)VRBO
Fall at the beach! Check our weekly discount! Near Herrington Harbour South.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Walk to Herrington Harbour South, Rose Haven's 2 acre waterfront park or the market, hair salon, bar and restaurant. Th ...
From $350 per night (USD)VRBO
From $290 per night (USD)VRBO
Beach wonderland
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 8
Perfect getaway from the hustle and bustle of the city but close enough to drive and enjoy. Places like Annapolis, Solo ...
From $290 per night (USD)VRBO
From $393 per night (USD)VRBO
Plant-Filled Oasis Near Beach Town with Passes & Tips
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to A Haven Away! Relax in a plant-filled oasis which offers the perfect setting to unplug, relax, and connect wi ...
From $393 per night (USD)VRBO
From $150 per night (USD)VRBO
Lovely 3 bedroom 2 bath cottage Sleeps 6 just a few blocks from the water
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Looking for a clean neat quaint home to stay while visiting the North Beach, Chesapeake Beach area? Well honey you have ...
From $150 per night (USD)VRBO
From $400 per night (USD)VRBO
Breathtaking Views, 450 pier, kayaks, fossils, priv beach, 45 min to D.C.
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
See video of the house: https://youtu.be/hDuRBLZR03c Step into a world of enchantment at our Magical Bayfront Home, nes ...
From $400 per night (USD)VRBO
From $115 per night (USD)VRBO
Nearby! Fossil Hunting - Solomons Boardwalk - Paddleboard\/Boat Rentals - Museum
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
The Manor resides on 3 secluded acres. Close to everything Southern Maryland has to offer, yet feels a million miles awa ...
From $115 per night (USD)VRBO
From $225 per night (USD)VRBO
Spacious house, great deck & grill, close to boardwalk, shops, and restaurants.
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 9
Modern three-bedroom, two full bath home with half-bath and new furnishings. Quiet neighborhood easily accessible to Sa ...
From $225 per night (USD)VRBO
From $325 per night (USD)Expedia
Harbor Breezes at Herrington Harbor
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 7
If you are looking for a comfortable and clean home for your stay while visiting Herrington Harbor, our beaches or other ...
From $325 per night (USD)Expedia
From $205 per night (USD)VRBO
Blue Heron on Little Kingston Creek
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Recently renovated 2 br,1 bath waterfront (downstairs) apartment, with full kitchen and bath, loaded with amenities from ...
From $205 per night (USD)VRBO
From $145 per night (USD)Expedia
Studio on the Bay.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
A studio apartment sits on a hill. You will have to walk up stairs from the parking oad and a grassy hill (can be consid ...
From $145 per night (USD)Expedia
From $258 per night (USD)VRBO
Club Carp North Beach
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Renovated throughout with three bedrooms and two full baths. This kid-friendly home has a large fenced yard with a swing ...
From $258 per night (USD)VRBO
From $150 per night (USD)Expedia
Bay view from Calvert Cliffs, Solomons Island & State Park nearby
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
You will love this peaceful escape just steps from the beautiful Chesapeake Bay and Calvert Cliffs. Beaches, fossil hun ...
From $150 per night (USD)Expedia
From $375 per night (USD)VRBO
Stunning Views from Waterfront Log Cabin With Fireplace On The Chesapeake Bay
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Relax with a beautiful water view this Winter and Spring. A rustic and cozy log cabin, in the woods, with a fire place ...
From $375 per night (USD)VRBO
From $310 per night (USD)Expedia
Vintage Waterfront A Frame- Hideaway On The Bay
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
The Hideaway on the Bay is a waterfront A frame where you can disconnect from the things that can wait so you can connec ...
From $310 per night (USD)Expedia
Click For PricingVRBO
Charming Villa
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Find your Zen at "Morning Promise" . A completely renovated waterfront villa on the Chesapeake Bay. Morning Promise fa ...
Click For PricingVRBO
From $555 per night (USD)Expedia
Large RENOVATED 6 bedroom 5 bath private home with LOTS of space!
- Bedrooms:
- 7
- Bathrooms:
- 6
- Sleeps:
- 15
The Mackall House is a spacious fully-remodeled six bedroom home with two primary suites, five full baths, and two half ...
From $555 per night (USD)Expedia
From $189 per night (USD)VRBO
Adorable Beach Cottage w\/ Hot Tub & Tropical Bar!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
With calm bayside waters, plenty of fishing opportunities, and a variety of family-friendly attractions, Chesapeake Beac ...
From $189 per night (USD)VRBO
From $338 per night (USD)Expedia
Newly Renovated Secluded Luxury waterfront cottage with private deep water pier!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Ivy Cove is located in the The Soundings neighborhood; a family community designed exclusively for boating enthusiasts. ...
From $338 per night (USD)Expedia
From $185 per night (USD)VRBO
Welcome to Hickory House on the Chesapeake Bay!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 2
Welcome to Hickory House on the Bay! Charming 2 bedroom, 1 bath cottage overlooking the Chesapeake Bay within walking di ...
From $185 per night (USD)VRBO
From $207 per night (USD)Expedia
The Blue Crab Beach House - Free beach passes
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to The Blue Crab just a few blocks from the Chesapeake Bay. You will enjoy staying at our newly renovated luxury ...
From $207 per night (USD)Expedia
From $563 per night (USD)VRBO
Waterfront house with private beach and pier
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Our property is a private estate with access to St Lenord Creek which is peaceful, uncrowded anchorages with beautiful s ...
From $563 per night (USD)VRBO
From $265 per night (USD)Expedia
Waterfront North Beach Home ~ 2 Mi to Beach!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Highlighted by its coastal charm and scenic location, this well-appointed North Beach home is well-suited for small grou ...
From $265 per night (USD)Expedia
Click For PricingVRBO
Waterfront Home On The Chesapeake Bay
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Cozy waterfront home. Watch the sunrise on the Chesapeake Bay. 2 bedroom/1 bathroom in the center of town within walking ...
Click For PricingVRBO
From $220 per night (USD)Expedia
BeachWalk Cottage - Charm by the Chesapeake Bay
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Lovely place to build a memorable experience. It is where you want it to be! Calvert Co. Is surrounded on East side by ...
From $220 per night (USD)Expedia
From $318 per night (USD)VRBO
Come Stay on the Bay! Beautifully Renovated Oasis
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Relax with the family at this peaceful beach house oasis fit for everyone to enjoy! Whether you're a couple(s) looking f ...
From $318 per night (USD)VRBO
From $163 per night (USD)VRBO
Fossil hunting - Museum - Solomons Boardwalk - Paddleboard\/Boat Rentals nearby!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Spacious 1 bd, 1 ba private cottage on 3 acres. Beaches, marina's, fishing, boating nearby! Experience a piece of South ...
From $163 per night (USD)VRBO
From $300 per night (USD)VRBO
Bright and airy waterfront getaway
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Mermaids Foley has received some upgrades including a full kitchen with full size stove and refrigerator so you can come ...
From $300 per night (USD)VRBO
From $350 per night (USD)VRBO
Welcome to the Boathouse on Mill Creek!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Fully renovated waterfront cottage with private dock on Mill Creek in Lusby MD. Located less than 45 miles from the cap ...
From $350 per night (USD)VRBO
From $650 per night (USD)VRBO
Magnificent Water Front Property
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 12
Totally protected water with private pier, gentle walk to the pier from the ground level. High ceiling heights, the incr ...
From $650 per night (USD)VRBO
From $291 per night (USD)Expedia
Delightful Pet Friendly Family Home In Great Location! by RedAwning
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 9
Enjoy time relaxing with family and friends (even the furry ones!) in this wonderful single family home. The prime loc ...
From $291 per night (USD)Expedia
From $99 per night (USD)VRBO
Coastal Pet-Friendly Cottage <½ Mi to Beaches
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Escape to Chesapeake Beach and relax effortlessly thanks to this 2-bed, 1-bath cottage! Sporting a spacious fenced-in ba ...
From $99 per night (USD)VRBO
From $304 per night (USD)VRBO
Beach Home Away from Home Near Beaches & Popular Hangouts
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 4
Looking for a weekend getaway or somewhere to stay during business travel? Consider Serenity Beach House. This fully fur ...
From $304 per night (USD)VRBO
From $933 per night (USD)VRBO
Bayfront Home with Amazing Rooftop Deck!
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 15
Large, comfortable home is made for family and friend gatherings, lodging for wedding or graduation guests and work offs ...
From $933 per night (USD)VRBO
Click For PricingExpedia
Historic, Elegant, Luxurious.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Susannah’s Watch is a historic family estate that has been converted into a unique Bed & Breakfast and wedding venue on ...
Click For PricingExpedia
From $337 per night (USD)VRBO
Cozy Getaway - Breezy Point Beach & Marina
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
If you're planning a family trip, this 2 bedroom, 1 bathroom beach cottage will not dissapoint. Enjoy a cup of coffee or ...
From $337 per night (USD)VRBO
From $295 per night (USD)Expedia
Cottage Located on the Patuxent River!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Elegant Cottage located on the Patuxent River and only eight minutes from Running Hare Vineyard & Wedding Facility. Pro ...
From $295 per night (USD)Expedia
From $1620 per night (USD)VRBO
Resort Style Country Living on the Patuxent River
- Bedrooms:
- 7
- Bathrooms:
- 7
- Sleeps:
- 14
This 6 bedroom/6.5 Bath, manor house has been completely renovated from its original 1782 historic state. It offers mode ...
From $1620 per night (USD)VRBO
From $411 per night (USD)Expedia
Tranquil Port Republic Home w\/ Water Views!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 7
Nestled right on the Chesapeake Bay, this 3-bedroom, 3-bath home offers an idyllic retreat for your next Maryland stay. ...
From $411 per night (USD)Expedia
From $248 per night (USD)VRBO
Mid-Century Modern and Marvelous on the Bay
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Come enjoy living in mid-century modern style, with sweeping views of the Chesapeake Bay, all within a short drive from ...
From $248 per night (USD)VRBO
From $553 per night (USD)Expedia
Stunning River Front Home - Private Dock - 90 minutes from Washington DC
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 12
Come enjoy the beauty and bounty of Southern Maryland including the Chesapeake Bay, beaches, rivers, golf courses, winer ...
From $553 per night (USD)Expedia
From $165 per night (USD)VRBO
Relax & Unwind in a Historic 102-year-old farmhouse fully restored!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Relax & Unwind at the Historic Lyle Simmons House in a Peaceful & quiet setting. Whether visiting family or friends, at ...
From $165 per night (USD)VRBO
From $149 per night (USD)Expedia
Three Blocks to the Boardwalk!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Park right in front of this beautiful cottage enclosed with a white picket fence. Everything is in walking distance fr ...
From $149 per night (USD)Expedia
From $140 per night (USD)VRBO
Relaxing and peaceful guest house close to beach towns and DC. Lotsa amenities.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
A relaxing and peaceful guest house perfect for visiting family / attending events in the area, sight-seeing, nature lov ...
From $140 per night (USD)VRBO
From $352 per night (USD)Expedia
Cozy Cottage with access to and partially obstructed views of the bay.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
Take it easy at this unique and tranquil getaway; with morning visits from deer in the yard, bald eagles and jet fighter ...
From $352 per night (USD)Expedia
From $417 per night (USD)VRBO
Lakeside Cabin with Arcade
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to The Lake House - our freshly updated 3 bedroom, 3 bath cabin on Lake Vista with views of the Patuxent River/C ...
From $417 per night (USD)VRBO
From $339 per night (USD)Expedia
Block to Beach! Fossil Hunting, Hot Tub, Coffee Bar, Screened Deck, 1hr to DC
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Relax at this renovated cottage with views of the Chesapeake Bay! Features large screened in deck, hot tub, around corne ...
From $339 per night (USD)Expedia
From $320 per night (USD)VRBO
Lake-house with a magnificent view
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Minutes of walk away from the beach. Hot tub with the lake view. Surrounded by wonderful trails, restaurants and beaches ...
From $320 per night (USD)VRBO
From $248 per night (USD)Expedia
Updated North Beach Cottage: Pet Friendly!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Step into this charming coastal cottage and let North Beach welcome you to a relaxing getaway! The 3-bedroom, 2-bathroom ...
From $248 per night (USD)Expedia
From $130 per night (USD)VRBO
Secluded very private minutes from beaches, marina, water park 1.5 bed apartment
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Vacation like setting ampul car parking very close to navy base and Calvert nuclear power station modern upgraded kitche ...
From $130 per night (USD)VRBO
From $175 per night (USD)Expedia
Hideaway By The Bay - Sunroom, bay view, propane fire pit, 6ft tall wood fence
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 7
Welcome to Hideaway By The Bay! Make yourself at home, get nice and cozy and kick back by the Bay! As the host and hom ...
From $175 per night (USD)Expedia
From $249 per night (USD)VRBO
SoMD Cottage 1.5 acres of gorgeous coastal living!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to our Southern MD beach house. This 3 bedroom and 2 bath home is situated on nearly 1.5 acres of property where ...
From $249 per night (USD)VRBO
From $550 per night (USD)Expedia
Bayfront Home w\/Hot Tub
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 5
Comfortable home with a million dollar view of the Chesapeake Bay. Pet friendly, outdoor hot tub, solo stove, and gourme ...
From $550 per night (USD)Expedia
From $352 per night (USD)VRBO
Shewell’s Rambler in the Chesapeake Ranch Estates
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 13
This stylish place to stay is perfect for group trips. Bring your family on vacation, stay with business partners on a b ...
From $352 per night (USD)VRBO
From $169 per night (USD)Expedia
Private First Floor of Duplex Walking Distance to Everything!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 8
The home is a upstairs/downstairs duplex with two separate and private units that have been lovingly renovated and resto ...
From $169 per night (USD)Expedia
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Shewell's Townhouse in Prince Frederick
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 8
Make this your home away from home while visiting Southern Maryland for business, family events, or retreat. This home i ...
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From $212 per night (USD)Expedia
North Beach Cottage - Walk to Chesapeake Bay
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Experience life like a local with a stay at this 3-bedroom, 2-bathroom vacation rental cottage in North Beach. This 100- ...
From $212 per night (USD)Expedia
From $352 per night (USD)VRBO
Shewell’s Light House at Long Beach
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 16
This is a big house with a lot of windows, glass doors, and skylights that let an abundance of light in. Combine that, w ...
From $352 per night (USD)VRBO
From $155 per night (USD)Expedia
Charming Cottage by the Bay - 1 block from private Calvert beach
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
“La Casita de Dragonfly" (The Dragonfly Cottage) Relax in this calm, stylish space on the Chesapeake Bay, one block from ...
From $155 per night (USD)Expedia
From $395 per night (USD)VRBO
NEW: Life on the River! Luxury estate with jacuzzi and private pier!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to the Blue Pearl - a luxurious river front estate with a private pier to catch crabs, fish, kayak, soak in the ...
From $395 per night (USD)VRBO
From $479 per night (USD)VRBO
Coastal Oasis On The Chesapeake, King Bd sleeps12
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 12
Welcome to Coastal Oasis On The Chesapeake (PARTYFREE zone) where you come to: RELAX, DECOMPRESS and RE-CHARGE! You'll e ...
From $479 per night (USD)VRBO
From $231 per night (USD)VRBO
Spacious 4 Bdr Home Chesapeake Beach
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 9
4 bedroom home with 3 full baths that can comfortably sleep 9 in Chesapeake Beach, MD. Less than a mile from the bay. Th ...
From $231 per night (USD)VRBO
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Waterfront
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Beautiful split-level house with a large open kitchen, gas range, and plenty of space to relax and enjoy the waterfront ...
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From $480 per night (USD)VRBO
Riverside House w\/ Kayaks, Piano & Fireplace
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 9
Fall in love with The Seafarer. This 5-bed, 2.5-bath colonial home has beautiful views from every room! The vacation ren ...
From $480 per night (USD)VRBO
From $350 per night (USD)Expedia
3 Bedrooms Relaxing Rustic House on Saint Thomas CreeK
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to our peaceful getaway on Saint Thomas Creek and the Patuxent River. A place to be, feel & experience relaxatio ...
From $350 per night (USD)Expedia