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Waterfront vacation rentals in Parole

Find and book unique waterfront rentals on Airbnb

Quick stats about waterfront rentals in Parole

  • Total vacation rentals

    Explore 10 vacation rentals in Parole

  • Nightly prices starting at

    Parole vacation rentals start at G$56,484 GYD per night before taxes and fees

  • Verified guest reviews

    Over 540 verified reviews to help you choose

  • Family-friendly vacation rentals

    10 properties offer extra space & kid-friendly amenities

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wi-Fi availability

    10 of Parole vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Parole rentals

  • 4.8 Average rating

    Parole stays are highly rated by guests—averaging 4.8 out of 5!

Top-rated waterfront rentals in Parole

Guests agree: these waterfront rentals are highly rated for location, cleanliness, and more.

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Top guest favorite
A spacious living area features large windows that allow natural light to fill the space, showcasing views of the surrounding greenery. Comfortable seating is arranged around a low table, with a television mounted on the wall, and decorative shelves filled with various items.
Cottage in Annapolis

Relaxing Water Views - Mill Creek Cottage

Eclectic three level water view cottage in unique wooded location overlooking beautiful Mill Creek. Minutes from downtown Annapolis and the US Naval Academy; walk to Cantler’s Riverside Inn for crabs, convenient to US 50 and the Bay Bridge and Eastern Shore. Due to the stairs and loft, this accommodation may not be appropriate for toddlers and the mobility challenged Parties are not permitted. Please note that there is no water access on the property, but there is nearby public water access.

4.97 out of 5 average rating, 473 reviews
Top guest favorite
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!

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!

4.98 out of 5 average rating, 185 reviews
Top guest favorite
A wooden dock extends over calm waters, leading to a charming home surrounded by trees. The house, featuring large windows, is illuminated as dusk approaches. Adirondack chairs are placed along the shoreline, inviting relaxation in the natural setting.
Home in Stevensville

Kent Island Waterfront Home with Amazing Sunsets

Relax with the whole family at this peaceful and beautiful home on Thompson Creek! Enjoy the gorgeous sunsets all year-long. Bring your boat, fishing gear or other watercraft and discover Kent Island! Thompson Creek is accessible to the Chesapeake Bay and a short ride to discover Annapolis, The Kent Narrows or St. Michaels. In the mornings, sip coffee on the screened-in porch and bring a book - you may be there for a while! Our home feels remote but is accessible to convenient shopping.

4.99 out of 5 average rating, 152 reviews
Guest favorite
A spacious living area is highlighted by large windows allowing natural light. Modern furniture includes a sectional sofa and accent chairs, complemented by a sleek coffee table. A large television is mounted on the wall, while indoor greenery adds a touch of nature.
Home in Edgewater

Luxury Modern Home on Water+Hotub- Annapolis 25min

Waterside mid-century modern home, perfectly appointed. Join with colleagues, family, and friends. Paddleboard, roast marshmallows, watch fireworks, take a hot tub or team building. Our "Flight Deck" is perfect for meetings and retreats. Breathtaking, peaceful grounds with an abundance of space. Approximately 2800 SF sits on a 3/4 acre property - perfect for lawn games and zip lining. 20x20 furnished deck + dock Mayo Beach and Beverly Triton 1 mile away. Within an hour of the DMV

4.99 out of 5 average rating, 145 reviews
Guest favorite
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!

4.91 out of 5 average rating, 105 reviews
Top guest favorite
Home in Shady Side

Iconic Chesapeake. Unparalleled Luxury.

Autumn at The Cottage at Silver Water is peaceful, cozy, and a little magical. Crisp days invite you to kayak, explore the shoreline, or enjoy the changing colors. Evenings bring golden skies, spectacular sunsets, cool breezes, and fires by the water. Inside, the cottage is warm and inviting, with luxurious bedding, curated art, and thoughtful amenities for a relaxed, memorable stay. Come experience autumn at Silver Water—and see why every guest has given their stay five stars.

5.0 out of 5 average rating, 217 reviews
Top guest favorite
A serene waterfront view is captured, featuring lush green grass leading to a private patio area with a hot tub. In the background, a rainbow arches over the water, framed by a cloudy sky. The cozy apartment stands nearby, enhancing the tranquil setting.
Guest suite in Annapolis

Bay View Studio Apartment

Sweeping views of the Chesapeake Bay Bridge may be enjoyed from your apartment with tall windows facing the bay, private patio, or hot tub! 50 ft of waterfront make this private walk-out garden-level apartment nestled in a small wooded oasis near downtown Annapolis a gem. Walk to the marinas or the Sailing School to catch a water taxi to downtown or book a private sail or fishing tour. Walk to Port Annapolis to get some fresh baked goods at Black Market Bakery.

4.97 out of 5 average rating, 100 reviews
Top guest favorite
The image captures a serene evening scene by the pool with a view of the setting sun over the water. Sunlight filters through trees, creating a warm glow. Poolside lounge chairs are visible, along with a clear pool reflecting the colorful sky.
Guesthouse in Stevensville

Waterfront-View of Bay from your Bed

Enjoy this newly renovated, waterfront private studio apartment with a beautiful view of the Chesapeake Bay. It's a perfect getaway for anyone looking for rest and relaxation amidst a quiet, breath-taking location. Enjoy swimming in the pool, fishing off the point, sitting around an evening gas fire, visiting any of the local sandy beaches, or simply watching stunning sunsets from a private patio. Ample parking, WiFi, TV, boat-ramp access. One pet is welcome.

4.99 out of 5 average rating, 371 reviews
Top guest favorite
Guesthouse in Annapolis

Coastal Waterfront 1 Bedroom Cottage

Enjoy a peaceful waterfront getaway just 2 miles from Historic Downtown Annapolis and the U.S. Naval Academy. Located directly on the South River in a quiet neighborhood, this charming cottage features a full kitchen, 1 bedroom, washer/dryer, and sleeper sofa for up to 4 guests. Relax on the private patio with outdoor seating, grill, and fire pit, or enjoy the beautiful river views. Perfect for exploring Annapolis or simply unwinding by the water.

5.0 out of 5 average rating, 226 reviews
Top guest favorite
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).

4.97 out of 5 average rating, 113 reviews
Top guest favorite
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.

4.98 out of 5 average rating, 168 reviews
Guest favorite
A view of the sunset over Chesapeake Bay is captured from the deck, with warm hues reflecting on the water. The scene includes a grassy area leading to the shoreline and a subtle silhouette of a dock in the background.
Cottage in Deale

Chesapeake Bay Cottage

Cottage Located directly on the Chesapeake Bay. Includes sandy beach, yard, a screened in porch and deck. Two Kayaks to enjoy. Two bedroom plus den. Two full baths. Fully equipped kitchen.Kurig coffee maker and regular available. Master bedroom -queen size mattress. Second bedroom -a full-size mattress (double) third bedroom -a twin day bed with twin pullout. Both twin size mattresses.

4.95 out of 5 average rating, 185 reviews

Popular amenities for Parole waterfront rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Waterfront apartment rentals

Top guest favorite
A serene view showcases the landscaped yard, featuring blooming pink flower clusters in the foreground. A large tree stands in the center with a backdrop of greenery and a peaceful waterway. The two nearby structures are connected by a deck, reflecting the tranquil surroundings.
Apartment in Essex

A place unique on sue creek

4.97 out of 5 average rating, 320 reviews
Top guest favorite
A cozy living area features a brown leather sofa next to a white coffee table. A decorative rug with star patterns lies on the floor. A green potted plant adds a natural touch, complemented by a television on a media unit. Light enters from the window.
Apartment in Chester

Cozy Waterfront Apartment Chester, MD

4.96 out of 5 average rating, 304 reviews
Guest favorite
A serene waterfront scene is captured at sunset, displaying calm water reflecting soft hues of orange and blue. Silhouettes of trees line the shore, while gentle ripples can be seen across the surface, creating a peaceful atmosphere.
Apartment in Deale

Romantic Wtrfnt Flat w Hot Tub@Chesapeake Paradise

4.91 out of 5 average rating, 625 reviews
Top guest favorite
Apartment in Arnold

Celebrate Summer In Your Private Pool & Hot Tub

4.96 out of 5 average rating, 196 reviews
Top guest favorite
An aerial view showcases a large grassy area surrounding a heated pool, with several lounge chairs positioned nearby. A fire pit is set with white adirondack chairs. Two properties are visible, featuring balconies and umbrellas enhancing the outdoor space.
Apartment in Stevensville

Heron Roost

5.0 out of 5 average rating, 96 reviews
Top guest favorite
A spacious dock area displays two Adirondack chairs positioned for enjoying the water views. The wooden platform features a vibrant finish, with boats visible in the distance and trees lining the shoreline under a partly cloudy sky.
Apartment in Pasadena

Relaxing Waterfront Apartment!

4.98 out of 5 average rating, 55 reviews
Superhost
Apartment in Annapolis

Annapolis 4 Steps to Harbor Backs to Gate 1

4.86 out of 5 average rating, 37 reviews
Guest favorite
A serene sunset is viewed over calm waters, reflecting warm orange and gold hues. Silhouettes of trees and a boat dock are visible in the foreground, with a few boats gently resting on the still water.
Apartment in Dundalk

Waterfront Romantic Studio

4.95 out of 5 average rating, 81 reviews

Waterfront house rentals

Guest favorite
A spacious living room features a large sectional sofa, a coffee table, and a TV stand. Natural light enters through multiple windows, illuminating the wood flooring. An open view leads towards the kitchen area, where bar stools are positioned at a counter.
Home in Stevensville

Charming Coastal/Country Home w/3 Acres & Sauna!

4.93 out of 5 average rating, 366 reviews
Top guest favorite
Home in Deale

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

4.98 out of 5 average rating, 155 reviews
Top guest favorite
An inviting front yard is presented, featuring a pathway of round stones leading to the entrance of a two-story guesthouse. Lush greenery is framed by ornamental plants and mulched beds, creating a serene outdoor setting surrounded by trees.
Home in Annapolis

Quiet Waterfront

4.98 out of 5 average rating, 191 reviews
Guest favorite
A spacious bed is adorned with decorative orange pillows and flanked by elegant bedside lamps. Framed artwork featuring floral designs hangs above the headboard, complementing the soft color palette of the room.
Home in Fells Point

Luxury Fells Home w/Hot Tub, Poker Room, & Parking

4.95 out of 5 average rating, 122 reviews
Top guest favorite
A comfortable living area is framed by large windows showcasing a vibrant sunset over the water. Soft furnishings include two chairs with decorative pillows and a coffee table. Plants are positioned thoughtfully, enhancing the serene atmosphere.
Home in North Beach

Waterfront, Dog-friendly, Hot Tub, Gas Fireplaces

5.0 out of 5 average rating, 189 reviews
Top guest favorite
The exterior of a two-story house is framed by mature trees, complemented by a wide concrete driveway. A welcoming front porch with multiple steps leads to the entrance, and landscaped areas surround the home, enhancing its natural setting.
Home in Cape St. Claire

Serene Riverfront Home

4.97 out of 5 average rating, 124 reviews
Guest favorite
A tranquil view of the Chesapeake Bay is captured, showcasing a grassy expanse leading to the water. Two stone boundary walls are visible, framing the lush landscape. A solitary beach umbrella and chair rest on the shore, inviting relaxation by the calm water.
Home in Cape St. Claire

Country House on the Bay

4.9 out of 5 average rating, 230 reviews
Top guest favorite
The cottage features a welcoming exterior with a combination of siding and a shingled roof. A well-maintained lawn surrounds the home, and landscaping includes a variety of shrubs. Large windows are visible on the front, providing ample natural light.
Home in Deale

Hannah’s Hideaway

4.99 out of 5 average rating, 161 reviews

Waterfront condo rentals

Top guest favorite
Condo in Annapolis

Captains Quarters | Waterfront & Pool

4.98 out of 5 average rating, 124 reviews
Superhost
A modern living area features a sleek flat-screen television mounted above a stone fireplace. On either side, wooden shelving units are filled with decorative items and books. The ambient light from the fireplace creates a cozy atmosphere, complemented by neutral wall colors.
Condo in Inner Harbor

Historic Federal hills urban lifestyle

4.86 out of 5 average rating, 291 reviews
Superhost
A light-filled living area features a comfortable sectional sofa with pillows and a cozy throw. A round coffee table sits in the center, surrounded by a woven basket and a wooden armchair. The kitchen area is visible in the background, equipped with dark cabinetry and stainless-steel appliances.
Condo in Annapolis

Amazing Views from Spa Creek 2BD Condo with Pool

4.75 out of 5 average rating, 85 reviews
Guest favorite
An aerial view captures the condo building with a red roof, framed by a sandy beach and the Chesapeake Bay. A wooden pier extends into the water, where gentle waves create rippling patterns. The surrounding area includes a path lined with trees and beachgoers enjoying the day.
Condo in North Beach

Bayfront Boardwalk Condo w/ Sunrise Views

4.93 out of 5 average rating, 57 reviews
Guest favorite
Condo in Annapolis

Waterfront Eastport Condo w Pool & Parking

4.85 out of 5 average rating, 13 reviewsThe bedroom features a queen-sized bed with light bedding and decorative pillows. Two windows with brown shades allow natural light. A desk and chair are positioned nearby, with a mounted television above. Warm wood flooring adds to the room's comfort and style.
Condo in Georgetown

Historical Georgetown Modern Penthouse 12 min DCA

4.66 out of 5 average rating, 138 reviews
Guest favorite
Condo in Inner Harbor

Luxury Harborplace Condo Near Orioles, Ravens, M&T

4.8 out of 5 average rating, 20 reviewsA modern, multi-story resort building is prominently displayed under a clear blue sky. Light-colored brick and stone create a contemporary façade, while balconies and large windows emphasize the welcoming design. The entrance features a sheltered area, enhancing accessibility for guests.
Condo in National Harbor

Luxury @ Wyndham National Harbor

4.91 out of 5 average rating, 38 reviews

Destinations to explore