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Apartment rentals near Chesapeake Bay

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Top-rated apartment rentals near Chesapeake Bay

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Top Guest favourite
A serene sunset over the Patuxent River, with warm hues reflecting on the water. Boats are anchored near a private pier, and a bridge spans the horizon. Fencing and grassy areas frame the scene, adding to the tranquil coastal atmosphere.
Apartment in California
4.93 out of 5 average rating, 242 reviews

Our Little Piece of Heaven

Our cozy studio apartment sets on the Patuxent River. With the perfect views of Myrtle Beach, Point Patient and Thomas Johnson Bridge. Relax watching the boats and birds or take a walk along the water for a lovely neighborhood to stroll for 2.5 miles. Your favorite moments may be when you wake to see the sun rise and again to see the orange sky set. Just over the bridge from the popular Solomon's Island which is full of fabulous restaurants, boat rentals, charter fishing and summer concerts.

Top Guest favourite
A modern living area features a light-colored sofa adorned with a teal throw blanket. A round wooden table accompanied by metal chairs is positioned nearby. A decorative mirror and an abstract painting are displayed on the wall, while a stone fireplace adds a subtle touch of warmth.
Apartment in Stevensville
4.98 out of 5 average rating, 303 reviews

Boutique by the Bay

Completely renovated and exquisitely decorated, this one bedroom apartment has a private entrance from the main house and features a modern farmhouse vibe. Fully equipped kitchen with new glass top stove, large walk-in shower and queen sleeper sofa make this perfect for a couple or family. Located 9 miles south of the Bay Bridge, off of Route 8 on Kent Point Road ,this location is convenient for weddings at the Chesapeake Bay Beach Club or Swan Cove. Access to large in-ground pool included.

Top Guest favourite
The historic building features a distinctive red brick façade, complemented by large windows and decorative trim. Lush green trees provide shade in front, while parked vehicles line the street, enhancing the inviting urban atmosphere.
Apartment in Baltimore
4.98 out of 5 average rating, 518 reviews

Butchershill- Clean, Fireplace, King Bed, Parking!

My name is John S Marsiglia. Always clean, very comfortable new King Mattress, Warm & Cozy Fireplace, Self checkin , Historic 2207 E Baltimore St. Search online. 900 Sq Ft. 12 ft ceilings,Fully equipped kitchen/kitchenette,Coffee,Tea,Cream,Brita filtered water pitcher,50" 4K smart TV, streaming only, Free Netflix, Prime,top speed WiFi, surround sound, comfortable clean furniture, antiques, oriental rugs, workspace w/desk, modern beautiful bathroom, dual shower heads&seats, private full size W&D

Superhost
The exterior of a two-story beach house is shown, featuring white siding and dark shutters. A welcoming front porch is visible, adorned with a small American flag. A pathway leads through green grass to the entrance, surrounded by landscaped shrubs.
Apartment in North Beach
4.89 out of 5 average rating, 102 reviews

Spacious Beach House Top Floors - Walk Everywhere!

This booking is for the entire SECOND story & loft of a DUPLEX-style beach house. Entrance, access, & all indoor spaces of the unit are private, however there are often other guests and families on the first floor. There is also a STAIRCASE to the 2nd floor unit and a STAIRCASE to the loft. Please ensure this home suits your needs. The space has an open floor design with 14' cathedral ceilings for a spacious modern feel with beach-house charm. Walk 2 blocks to the beach, boardwalk, and more!

Top Guest favourite
The exterior of a blue, two-story cottage is showcased among lush green trees. Spacious decks are visible on both levels, and a gravel driveway leads up to the entrance. The surrounding yard features manicured grass and a border of decorative stones.
Apartment in North
4.98 out of 5 average rating, 254 reviews

Little Cove Cottage, Couples Retreat/Mathews

Little Cove Cottage: a charming studio in Mathews County with private entrance. Mathews is a rural town with several beautiful beaches close by and many areas to access the water. This apartment offers a small water view of the North River, with a pier and boat ramp just 400 yards away. Bring your Kayaks or use ours. . We are just minutes away from the Mobjack and Chesapeake Bays. Mathews is home to great restaurants with fresh seafood. We also have a wonderful farmer's market. Come enjoy!

Top Guest favourite
The exterior of a two-story wooden structure is presented, featuring a staircase leading to a covered balcony. The building is surrounded by trees displaying fall foliage, creating a serene outdoor atmosphere. A gravel area is noted at the base, with a vibrant red and white camper positioned nearby.
Apartment in Greenwood
4.97 out of 5 average rating, 669 reviews

Beach Highway Hobby Farm

We are a hobby farm with pygmy goats and free-range hens located along Beach Highway near Greenwood, Delaware, in the heart of the Mennonite Community (not to be confused with the Amish). We are centrally located in southern Delaware with many attractions within easy driving distance: Rehoboth Beach (35 minutes) Delaware State Fairgrounds (10 minutes) Dover Downs/Firefly (30 minutes) Ocean City, MD (50 minutes) Cape May/Lewes Ferry Terminal (30 minutes) DE Turf Sports Complex (20 minutes)

Top Guest favourite
A bright yellow building features large blue shutters and a welcoming entrance. A sign is placed outside, and vibrant flowers border the steps. In the background, another structure is visible, along with flags proudly displayed.
Apartment in Saint Michaels
4.97 out of 5 average rating, 140 reviews

Blue Crab Lodge

Welcome to your charming and cozy short-term rental above the heart of St. Michaels' vibrant community! Nestled right above the delightful aroma of freshly brewed coffee, this unique and inviting space offers the perfect blend of comfort and convenience. Stepping outside, you'll find yourself in the heart of St. Michaels' quaint streets. The rental's prime location provides easy access to the town's boutique shops, waterfront promenades, and a diverse array of restaurants.

Guest favourite
A spacious living area is highlighted by large angled windows, allowing natural light to fill the space. A comfortable sectional sofa is complemented by a coffee table, while a kitchenette is visible in the background. An attached image shows a private outdoor deck with seating.
Apartment in Washington
4.98 out of 5 average rating, 291 reviews

Luxury escape in DC now with a private Deck!

History and luxury meet in your rental which is a meticulously renovated luxury floor which includes top of the line amenities, private rooftop deck with Pergola, dual sided gas fireplace, luxurious and spacious bathroom including washer dryer, solar powered black-out blinds and leading gourmet coffee machine! We are close to Capital Hill, Brookland, Ivy City, Union Market, & H street corridor and a 10 minute Uber ride from Union Station. Free parking is provided onsite!

Top Guest favourite
A red umbrella provides shade over a square table with a glass top, accompanied by two cushioned chairs. Lush green grass surrounds the seating area, framed by tall trees and distant views of the water, creating a serene outdoor space.
Apartment in Port Republic
4.96 out of 5 average rating, 243 reviews

Serenity Suite on Chesapeake Bay

Come enjoy our waterfront home on the scenic Calvert Cliffs. Take in beautiful Bay views in Adirondack chairs with stunning vistas. Photograph wildlife. Comfortable ½ mile walk to private community bay shoreline. Have breakfast in the yard while enjoying the sunrise. Stroll the community shoreline and explore fossil hunting, hike at nearby trails. No pets are allowed because I have a severe allergic reaction to pet hair and dander. Thanks for your understanding.

Top Guest favourite
A blue decorative anchor rests on a white surface, featuring a rustic rope detail. The soft lighting highlights the anchor's design, creating a nautical theme. A blurred background suggests a bright and airy space, complementing the apartment's beach-inspired decor.
Apartment in Milton
4.97 out of 5 average rating, 205 reviews

Beachin' Inn Milton

Welcome to Beachin' Inn Milton! This cozy apartment located in the quaint, historical town of Milton, DE is the perfect getaway. Our apartment is light and airy with a beach theme. Enjoy the entire apartment to yourself with a keyless private entrance, full bath, washer/dryer, free Wifi and stocked assorted coffee pods. There is no stove/oven, however, we offer a microwave, toaster oven, Air Fryer and induction burner.There is private parking right out front

Guest favourite
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
4.91 out of 5 average rating, 623 reviews

Romantic Wtrfnt Flat w Hot Tub@Chesapeake Paradise

Gift yourself this private, secluded second floor Flat & Solarium Bedroom. Best hideaway to rest, bond, restore, create, or work. A breezy, country-like setting provides space to escape the city hustle! Nearby scenic drives & groceries, or venture to Annapolis or other local walks. Fully relax with pier, kayaks, hot tub, swings, fire pit, starry nights, sun-drenched loungers, cozy up with books/movies & luxuriate in the deep soaking tub or European shower.

Top Guest favourite
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
4.96 out of 5 average rating, 285 reviews

Cozy Waterfront Apartment Chester, MD

*Oven is currently broken, replacement coming June 4th* Hello travelers!! Looking for a cozy & comfortable place to stay on Kent Island? Come enjoy our clean & beautifully renovated apartment above our family home, overlooking Cox Creek. This apt. Is built above our garage. Private entrance on the side of our house (20 steep steps up). 1 bedroom, queen bed. WiFi included. Private porch to enjoy water view!

Popular amenities for apartment rentals near Chesapeake Bay

Quick stats about apartment rentals near Chesapeake Bay

  • Total holiday rentals

    Explore 940 holiday rentals in Chesapeake Bay

  • Nightly prices starting at

    Chesapeake Bay holiday rentals start at $42 AUD per night before taxes and fees

  • Verified guest reviews

    Over 39,400 verified reviews to help you choose

  • Family-friendly holiday rentals

    410 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 410 rentals that welcome pets

  • Holiday rentals with a pool

    60 properties feature pools

  • Rentals with dedicated workspaces

    550 properties have a dedicated workspace

  • Wi-Fi availability

    940 of Chesapeake Bay holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Chesapeake Bay rentals

  • 4.7 Average rating

    Chesapeake Bay stays receive an average rating of 4.7 out of 5 from guests

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