Vacation rentals in Parole

4.96 out of 5 average rating, 139 reviews

A modern apartment features a treehouse-style deck that is surrounded by leafy trees. The exterior showcases a combination of dark wood and neutral siding, while large windows allow natural light to enter the space.

Loft in Riva

New Loft w/South River view from treehouse deck!

Enjoy the quiet Sylvan Shores neighborhood and a view of the South River and bridges in this new modern apartment that has a treehouse style deck for relaxing and enjoying the outside. The unit is served by a separate entrance and free street parking. Bring your kayak or stand-up-paddleboard, or try your luck at fishing! The TV is upgraded to a 55". Downtown Annapolis is just 6 miles away and offers cultural attractions, bars and restaurants, historical tours and access to the Naval Academy.

LocationValueNearby

4.91 out of 5 average rating, 152 reviews

An open layout living area features a kitchen equipped with stainless steel appliances and a breakfast bar with high stools. A dining table is visible in the background near large windows. The space is complemented by two leather couches and light hardwood flooring.

Home in Arnold

Rachel's BnB

A well outfitted home away from home! A fully stocked kitchen with everything you need to cook for yourselves and your guests. Close to historic downtown Annapolis, the US Naval Academy, St. John's College and MD Statehouse are less than 10 minutes away There are king and queen beds in the rooms, and the 3rd bed is a comfortable pullout couch in the living room. All linens are Egyptian cotton and the beds have real down duvets. Additional cot beds and linens (up to 4) can be provided ($20 each)

ValueFamilyBiking

5.0 out of 5 average rating, 119 reviews

Modern Annapolis Getaway - 2 Free Parking Spaces

Modern 2 bedroom, 1 bath home located in the heart of historic Annapolis. Completely remodeled with free off-street parking. Located towards the end of a safe, quiet, dead end road, less than 3 miles from downtown Annapolis, the Naval Academy, the Annapolis Mall, St. John’s College, and the Navy-Marine Corps Memorial Stadium. Walk downtown or to the Annapolis Town Center, restaurants, shops, and so much more! -Wi-Fi -2 free parking spaces -Keurig Coffee -TV -Toothbrushes/Paste -Shampoo/Soaps

ValueFamilyParking

4.9 out of 5 average rating, 363 reviews

The entrance of the guest cottage is framed by a charming picket fence, featuring a blue door and a welcoming porch. A small table with two chairs and an umbrella is situated on a wooden deck, surrounded by lush greenery.

Guesthouse in Annapolis

Calico Cottage Guest House, king bed, free parking

Cute-as-a-bugs ear West Annapolis guest cottage just 1.5 miles from the Navy Stadium and less than 2 miles from Academy's Gate 8. Cottage features: high speed WiFi, EZ free parking, washer & dryer, kitchenette, air conditioning, self check-in and laptop friendly workspace. Park 10 feet from front door. Only 1 step to enter. No stairs to negotiate while carrying luggage! 15 min. walk to Weems Creek with scenic, serene waterviews and a few more minutes walk to popular Bean Rush Cafe.

FamilyValueWalkability

4.95 out of 5 average rating, 210 reviews

The image illustrates a charming tiny home nestled among trees, featuring a spacious bluestone patio with outdoor seating and a fire pit. In the background, a gas grill is positioned nearby. Lush green grass surrounds the area, creating a serene and inviting setting.

Guesthouse in Annapolis

Lil’ House - A Serene Tiny Home Experience

Newly renovated, immaculate two room tiny home. A stand-alone gem nestled against a wooded backdrop - well back from the main home - and wrapped in a huge, teak-furnished, blue stone patio with fire pit situated in a sunny opening in the mature tree canopy. Super comfy queen Murphy bed offers easy conversion of the well lit and modern main living space from living room & kitchen by day to main sleeping quarters at night. The adjoining room is a well appointed full bath and dressing area.

ValueLocationGrill

4.92 out of 5 average rating, 100 reviews

A spacious deck offers outdoor seating, including a large dining table and comfortable chairs, overlooking the serene waterfront. Lush trees frame the scene, and the calm water reflects the clear sky, creating a peaceful environment for relaxation.

Home in Riva

Waterfront Annapolis Getaway!

Escape to this serene waterfront house in Annapolis, perfect for couples seeking a peaceful retreat. Nestled on the picturesque South River, this charming home offers stunning waterfront views and tranquil decks where you can unwind and soak in the beauty. Enjoy cozy evenings by the water, dine alfresco on the deck, and explore nearby attractions. With its serene ambiance and beautiful surroundings, this is the ideal spot for a romantic getaway. Book now for an unforgettable escape!

LocationFamilyAccess

5.0 out of 5 average rating, 214 reviews

Home in Shady Side

Iconic Chesapeake. Unparalleled Luxury.

Summer at The Cottage at Silver Water is effortless and indulgent. A sweeping waterfront lawn leads to a private shoreline for swimming, kayaking, and long days in the sun. Evenings bring golden skies, spectacular sunsets, and fires by the water’s edge. Inside, the cottage is beautifully designed with luxurious bedding, curated art, and thoughtful amenities that make every stay relaxed, refined, and unforgettable. See why all our guests only have a 5-Star experience.

LocationFamilyLayout

4.94 out of 5 average rating, 145 reviews

Guest suite in Annapolis

Annapolis Garden Suite

Welcome to our oasis, tucked away on a forested residential street. ~7 minutes from the Annapolis Towne Centre, ~15m from the coast, and ~30m from Baltimore and DC. Tl;dr: This is a ground-level guest suite. Inside, you’ll find 3 beds, 2 bedrooms, 1 desk, 1 kitchen with a dishwasher, oven, Nespresso/pour over, 2 TVs, a laundry room, fast wifi, a pool, patio and a forest view. We live on the top floor (separated by stairs and a locked door; separate entrances).

LocationValueHiking

4.97 out of 5 average rating, 110 reviews

A spacious great room features large windows that offer sweeping views of the water. Comfortable seating arrangements with soft furnishings are complemented by a working fireplace. A staircase is visible in the background, leading to additional living spaces.

Home in Shady Side

Waterfront Sanctuary only 50 Min. From DC/Balt.

New full home renovation with gourmet kitchen, wide open floor plan, multiple guests rooms, and a bunk room that accommodates 12. An inviting space that welcomes any couple or a large extended family. This home sits with only three other homes on a private peninsula and has water access on both sides. It is conveniently located less than an hour from DC and Baltimore on the west coast of the Bay (no need to cross the Bay Bridge).

FamilyLocationWalkability

4.95 out of 5 average rating, 214 reviews

Guest suite in Arnold

Captains Quarters Oasis Near Annapolis, Sleeps 4

This updated suite is designed for comfort & convenience. Enjoy a king bed and a (queen bed) LoveSac sofa perfect for 2-4 guests. The suite includes a private en-suite bathroom, high-speed internet, a fully furnished kitchen, and a coffee bar to make you feel right at home. Located just 4 miles from Annapolis, you're close to all the best spots. Whether you’re here to relax or explore, this suite has everything you need!

FamilyValueHot tub

4.99 out of 5 average rating, 165 reviews

A spiral staircase leads to a lofted sleeping area in a well-lit living space. Warm wood tones are present in the furniture and flooring. A small kitchen area is visible, along with a dining table set for four. Lighting fixtures enhance the modern feel.

Guesthouse in Annapolis

Garden View, 1 Bedroom and a Loft.

Relax and unwind at this peaceful and charming retreat, nestled in a quiet neighborhood. Located just minutes from Route 50, I-95, and Downtown Annapolis, Garden View is ideally situated for exploring Naval Academy sports, the Renaissance Festival, Boat Shows, and golf at The Preserve. If you prefer staying in, the fully equipped kitchen and free Wi-Fi make it easy to work or cook from the comfort of your space.

LocationValueSolo travel

4.98 out of 5 average rating, 164 reviews

Cottage in Annapolis

Weems Creek Cottage, Annapolis Waterfront

(August, 2025) Jim is the best host we’ve ever had. Super responsive, reached out to let us know the place was ready and we could check in early. The house is perfect size for 2 adults and a kid. Beautiful view and really comfortable. We loved the screened in porch. We walked to breakfast at the smoothie place and had a great walk down to the naval academy. We would definitely stay here again.

ValueLocationGetting around

Popular amenities for Parole vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great vacation rentals in Parole

4.98 out of 5 average rating, 181 reviews

Two adirondack chairs in blue and teal are positioned on a wooden pier, facing the sunset over calm waters. A small white table sits between them, holding two coffee mugs. The vibrant orange and pink hues of the sky reflect on the water's surface.

Home in Edgewater

Waterfront Chesapeake Bay Sunrises & Fishing Dock!

FamilyLocationLong stay

5.0 out of 5 average rating, 22 reviews

A spacious dining area is showcased with a large wooden table surrounded by black chairs. Natural light streams through multiple windows adorned with white blinds, illuminating the room. A cozy living area is visible in the background, featuring a light-colored sofa and decorative plants.

Home in Riva

Riverside | 15 mins to USNA

FamilyLocationNearby

4.98 out of 5 average rating, 85 reviews

A charming cottage exterior is presented in a pastel pink hue, featuring a welcoming front porch with a railing and several potted plants. Large windows allow natural light to filter into the interior, while trees provide partial shade, enhancing the warm, inviting ambiance.

Cottage in Riva

The Coral Cottage

FamilyLocationLong stay

4.98 out of 5 average rating, 42 reviews

An aerial view showcases the stunning Heron House nestled on a waterfront point, surrounded by lush greenery and water. A spacious deck with outdoor seating and dining is visible, along with nearby boats docked along the shoreline under a twilight sky.

Home in Crownsville

Welcome to Heron House! Annapolis Waterfront Oasis

FamilyLocationOutdoor spaces

5.0 out of 5 average rating, 7 reviews

The Corner House-Annapolis

ValueLocationAmenities

A modern two-story home is showcased with a well-maintained lawn and landscaped flower beds. The façade features a mixture of siding and brick, complemented by large windows and a welcoming front porch with double doors.

4.96 out of 5 average rating, 45 reviews

The General's House-Spacious Home w/Pool & Hot Tub

FamilyLocationComfort

A spacious bedroom features a cozy bed with neutral-toned bedding and decorative pillows. Natural light fills the room through large windows, revealing views of the garden outside. A bedside table and a lamp complement the inviting space, with soft carpeting underfoot.

4.96 out of 5 average rating, 81 reviews

CJ's Cottage

LocationFamilyNearby