Vacation rentals in Glenarden

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Top-rated vacation rentals in Glenarden

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Guest favorite

A person is seen kayaking on calm waters, with a lighthouse in the background. The kayak is gray with orange and blue accents. The scene captures a peaceful moment on the water, emphasizing the tranquility of the Chesapeake Bay.

Apartment in Annapolis

4.94 out of 5 average rating, 17 reviews

Crow’s Nest Cottage - Down Under: Chesapeake Bay

Crow’s Nest Cottage - Down Under: 3BR/1BA garden-level duplex with fenced Zen garden, natural bamboo, water fountain, gas BBQ grill, brand new gourmet kitchen, sleeps 8. TV in all BR’s, steps to Chesapeake Bay waterfront. Sandy beach, protected swimming lagoon, park, bbq grills & picnic tables. Enjoy coastal Maryland’s beautiful flora & fauna. Nature lovers paradise, lower-level duplex (5 steps down) in waterfront community, access to pier, boat ramp, kayaks. Best vacation rental holiday home

Guest favorite

A spacious bedroom is presented with large windows offering views of a tranquil waterfront. A comfortable bed is paired with a white sofa, creating an inviting area. Natural light streams in, enhancing the warm wood accents throughout the room.

Home in Deale

4.97 out of 5 average rating, 29 reviews

Beautiful Waterfront Escape w/ Gorgeous Views

Escape to this stunning waterfront home on lovely Carr's Creek in Deale, MD. It offers four bedrooms and full bathrooms, two spacious living areas, two sunrooms, and a large fully stocked kitchen. You can birdwatch from the balcony, snuggle by the fireplace, soak in the hot tub, kayak, canoe, or play games and grill outdoors. Nearby, you can take a charter on the Chesapeake, kayak or hike at the Smithsonian Environmental Research Center, and enjoy local seafood restaurants and antique shopping.

Guest favorite

A breathtaking sunrise is captured over calm waters, creating a stunning reflection of vibrant hues of orange, pink, and purple. The private pier is visible on the right, complementing the serene landscape of trees on the distant shore and a tranquil island in the background.

Cottage in Edgewater

4.99 out of 5 average rating, 153 reviews

Waterfront Chesapeake Bay Sunrises w/Private PIER!

Gorgeous sunrises and bay breezes await at this newly remodeled Chesapeake Bay waterfront cottage! Catch crabs or fish from your private pier, relax on the furnished deck, or explore Selby Bay with our complimentary canoe. Enjoy water views from the kitchen, dining, living room, and enclosed porch. Just 15 minutes from Annapolis & the Naval Academy, and 45 from DC—peaceful, clean, full of charm. Ideal for USNA families! Unplug, unwind, and make memories on the water—year-round relaxation & fun!

Top guest favorite

Cottage in North Beach

4.98 out of 5 average rating, 148 reviews

Bell Estates-Brand New Bay View, Beautiful Cottage

Bell Estates is a newly built corner lot across the street from the bay with minimal views of the water from Master bedroom and front yard. Located in the heart of North Beach in the exclusive Holland Point neighborhood, our home provides a cozy get-a-way for a family looking to escape the hustle and bustle of life. Home is 2 minutes away from Herrington Harbor, Ketch 22, North Beach Boardwalk & more. Enjoy local accessibility to fishing from the boardwalk dock or rent a boat to go crabbing.

Superhost

A spacious waterfront house is shown surrounded by lush trees, with multiple balconies and large windows. A sandy area extends toward the water's edge, and smooth stones form a barrier along the shore, reflecting the natural beauty of the Chesapeake Bay.

Home in Shady Side

4.88 out of 5 average rating, 181 reviews

Cattail Landing- Photographer's Waterfront Retreat

Accepting 2025 bookings as of May 1st.... "Cattail Landing" Spring is here, with beautiful sunsets, new foliage on the trees, and our nest of Bald Eagles! Take our kayaks to explore, or go fishing off our landing. In the afternoon enjoy the magnificent sunsets, a drink on the deck, our outdoor hot tub and/or fireplace. A waterfront retreat on 2 acres in a spacious, charming house on the Western Shore of the Chesapeake Bay. Great for a couples getaway, family reunion, or work from home.

Guest favorite

A large tree provides shade over a grassy area, with a view of a calm waterfront. A wooden pier extends into the water, flanked by lush greenery. The scene is serene, evoking a sense of relaxation and natural beauty.

Home in Deale

4.98 out of 5 average rating, 106 reviews

8 Acre Waterfront Oasis! Pets are Free! 140ft Pier

3 Bedroom, 2 Bath Waterfront Paradise. This rustic rambler on Broadwater Creek in Churchton, MD, is a family vacation dream. A compound spanning 8 acres with over 700 feet of Waterfront will allow you to fish, crab, paddleboard, kayak, and enjoy the waterfront dream. Located near the small quaint waterman town of Deale, MD, you may never want to leave this relaxing area with direct access to the Chesapeake Bay. Brand new 140ft pier with views straight out to the bay, crabbing, and fishing!

Guest favorite

A screened-in porch features a comfortable swing with orange and navy striped cushions. Sheer white curtains frame large windows that provide views of the surrounding area and distant beach. A small green plant adds a touch of nature to the space.

Cottage in Chesapeake Beach

4.93 out of 5 average rating, 87 reviews

Cozy Getaway - Breezy Point Beach

If you're planning a family trip, this 2 bedroom, 1 bathroom beach cottage will not dissapoint. Enjoy a cup of coffee or tea watching the sunrise from the screened-in porch. Listen to the waves while reading a book on the porch swing. Breezy Point Beach is located just steps away from a fun filled day of beach activities. For fishing and crabbing enthusiasts, there is a 200-foot pier for your pleasure. Jet Ski| Waterpark | Golfcourse mins away. Wheelchair Friendly| Free Parking| Free Wifi

Guest favorite

Home in Deale

4.88 out of 5 average rating, 100 reviews

Chesapeake Paradise Lite 4-5 Br 3 Ba Vacation Home

Fabulous 4-5 bedroom 3-bath house with spectacular views on a lush, waterfront point! Shady waterfront lawns & sunny pier, breezy open spaces, sparkling views, & wildlife. Hidden but close to services. Couples & groups love our wonderful, nature-filled spot, a fun, relaxing, serene retreat on the WEST shore of the Chesapeake (close proximity to D.C., Annapolis, Baltimore)! Crabbing, kayaks, fire pit on two country-like acres. See “NEW Amazing” for whole 6-7 bed 4 ba listing of same house.

Guest favorite

A new wood pier extends over still waters towards a green, tree-lined shore. The pier is flanked by posts, leading to a rocky bank, with a clear view of a nearby cottage among the trees. Sunshine reflects gently off the water.

Cottage in Pasadena

4.97 out of 5 average rating, 172 reviews

Ft. Smallwood Overlook. Waterfront with Kayaks!

Delightful cottage at the confluence of Rock Creek, Patapsco River (Baltimore Inner Harbor) and the Chesapeake Bay. Adjoins Ft. Smallwood Park with its private coves and beaches. Secluded setting features water on 3 sides with beautiful relaxing views. Teeming with wildlife: ducks, geese, egrets, osprey, eagles, deer, foxes and other. Convenient to Annapolis, BWI Airport, Baltimore & Washington, D.C. Walk to the park. Cast a line, catch what you may! Total renovation 2018-2019.

Guest favorite

A wooden dock extends over calm waters, featuring four Adirondack chairs arranged facing the serene view. A light casts a soft glow on the water's edge, and the distant shoreline is lined with trees and structures, hinting at nearby activity.

Cottage in Pasadena

4.88 out of 5 average rating, 124 reviews

Chesapeake Cottages- 2 Quaint Waterfront Retreats

Our tastefully appointed cottages sit on almost an acre of waterfront property. Peaceful and tranquil, yet close to shops and restaurants, this property is perfect for serene getaways and family gatherings. With 2 separate cottages on one property, everyone will enjoy a unique and private space to relax. From peaceful mornings to magical sunsets on the 60-foot pier, this setting will quickly become a family favorite. This area is great for fishing, kayaking and paddle boarding!

Guest favorite

A bright bedroom features a spacious bed dressed in neutral linens. Large windows provide natural light and views of an outdoor area with snow. A wooden dresser and desk complement the room's simple furnishings, while dark curtains frame the windows.

Home in Arlington

4.85 out of 5 average rating, 111 reviews

Next to Virginia Hospital Center

Welcome to your future home away from home! This stunning 5-bedroom single-family corner house is the epitome of comfort and convenience. -A step a way from VHC hospital. - Metro bus stop at the end of the block - 5 car parking lot - has access to house without stairs, and walk in shower for those experiencing difficulty with movement or stepping over tub. -sleeps 10 guests comfortably (3 queen beds, 4 twin beds) -1.4 miles from Ballston metro stop

Guest favorite

Home in Annapolis

4.99 out of 5 average rating, 70 reviews

Captain’s Retreat! Newly Renovated - Beach House!

Beautiful newly renovated 3500 square foot 4 bedroom 2.5 bath home located in Arundel on the Bay. Steps to the Beach and a large community playground. With three large decks, enjoy nature, sitting with a glass of wine or coffee in the morning. Gourmet Kitchen opens to a deck with plenty of seating to enjoy outdoor entertaining. Perfect for large groups or multiple families. Custom solid wood bunk beds - Twin XL's over Kings!

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What guests are saying

Wits-end rustic beach cottage

5 out of 5 average rating, 4 reviews14 months ago

My family and I had a wonderful stay at Siobhan’s house. The house was bigger than expected with lots of room for our family of 5 plus two dogs. The doggie door was very convenient and the yard was a great additional hang out spot. Siobhan was very friendly and responsive. Highly recommended and will stay again!

Home in Chesapeake Beach

What guests are saying

Rare Find 5 Star, No Cleaning fee, Salt Water Pool

5 out of 5 average rating, 37 reviews8 months ago

Katie’s place was a wonderful place for a weekend reunion with friends. The house was clean, comfortable and pretty - exactly as advertised and as shown in the pictures. The beds were comfortable and the kitchen well-stocked. The outdoor garden and pool were lovely and had lots of comfortable seating areas. The house was an easy drive to Annapolis for restaurants and shopping but had a great movie watching set up that would be great for a rainy day. Nearby nice grocery store.

Cottage in Arnold

What guests are saying

Patterson Park Apt; Walk to Hopkins, Bars, Cafes

4.97 out of 5 average rating, 31 reviews2 days ago

Jenny’s place was exactly what we needed for our long weekend trip. I loved that it was spacious, clean and had excellent natural light. We spent lots of time walking through the park across the street and appreciated how quiet the street/block was at night. 10/10 would recommend!

Apartment in Canton

What guests are saying

Charming Home, Firepit & Fenced Yard in Annapolis!

5 out of 5 average rating, 26 reviews1 day ago

Tammy’s place was worth every penny! We felt right at home from the very start. Everything was very clean and the enclosed patio was an amazing space to watch the sunrise and relax with a glass of wine. It was great to bring our two dogs along and not worry about wandering off because the entire backyard was fenced in. We would definitely stay there again !

Home in Annapolis

What guests are saying

Lux Family Xcape with HotTub, Fireplace, Deck, BBQ

4.95 out of 5 average rating, 85 reviews3 weeks ago

Perfect Stay in a Beautiful Home! Our stay in Silver Spring, MD, was absolutely amazing! The house was stunning—beautifully decorated, spacious, and stocked with everything we needed and more. From the well-equipped kitchen to the cozy and comfortable bedrooms, every detail was thoughtfully designed to make our stay enjoyable. The location was also perfect, with easy access to D.C. and surrounding areas. The host was responsive and accommodating, making the entire experience seamless. We couldn’t have asked for a better place to stay and would definitely book again✨

Home in Silver Spring

What guests are saying

Fabulous Private Potomac Waterfront Retreat

4.94 out of 5 average rating, 85 reviews5 months ago

This is a lovely and spacious home in a beautiful setting along the Potomac River. We enjoyed sitting on the back deck with our morning coffee or in the evening, watching the sun set or the deer along the river. Those views were also available in the spacious living room facing the deck. The kitchen was well appointed, which we always appreciate when cooking meals in and the beds and linens were nice and comfortable. There were games available in the closet and my adult kids enjoyed setting up and playing badminton on the back lawn. Sylvia was a wonderful host that communicated clearly and was very helpful. We will look forward to coming back some time in the future.

Home in Bryans Road

What guests are saying

Cozy Cottage By The Beach-Pet Friendly

5 out of 5 average rating, 16 reviews3 days ago

This place is nice and cozy. Looks like the photos and makes you feel at home. The place is stocked with everything you need. From Chargers to first aid kits. I am glad that I picked this place. Lori is super friendly and reliable in f you have questions. Only about 1 hr from DC. I will come back again.

Home in North Beach

What guests are saying

Riverview Retreat on Warehouse Creek

4.83 out of 5 average rating, 18 reviews4 months ago

Hosts were very accommodating and actually contacted us the day before check out informing us we could stay longer because the house was not being rented after we left. This is the perfect place for a getaway in the Spring or Summer when you can get out on the water in the backyard.

Guesthouse in Edgewater

What guests are saying

The Waterside Nest

5 out of 5 average rating, 4 reviews2 weeks ago

Our family enjoyed our first visit to Maryland and staying here made the visit a relaxing one. We enjoyed the views, the local wildlife, and the amenities within to make it feel like home. Tanya was always easy to reach and had a binder full of local recommendations and best use of items throughout the home. We would recommend any family to stay and will consider it for future trips!

Home in Essex

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