Airbnb your place

Condo rentals near Chesapeake Bay

Find and book unique condos on Airbnb

Top-rated condo rentals near Chesapeake Bay

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

1 of 1 pages1 / 1
Guest favourite
A cozy living area is furnished with a gray sectional sofa and a vibrant pink accent chair. A glass coffee table is centered on a decorative rug, while large windows allow natural light to fill the room. Artwork adorns the walls, adding a touch of style.
Condo in Arlington

Newly Renovated & Modern 1BR Condo - Unit 2

Completely renovated, stylishly furnished condo unit in Arlington, VA just one stoplight from Washington DC, the Pentagon, Clarendon, Crystal City and National Airport. Spacious unit with free cable TV, secure Internet/Wi-Fi, FREE RESERVED PARKING space in private lot, in-unit Washer/Dryer, Full Kitchen. Steps away from public transit buses that route to multiple Orange/Blue/Silver line Metro train. Comfortably accommodates the traveling professional, those on vacation and is kid friendly.

4.86 out of 5 average rating, 294 reviews
Top guest favourite
A dining area is showcased with a grey table set for six, surrounded by vibrant yellow chairs and a metal wire-frame chair. A modern light fixture hangs above, and a decorative wreath adorns the wall, complemented by abstract artwork on either side.
Condo in Rehoboth Beach

Renovated Condo Near Outlets, 3.5 Miles to Beach

Enjoy your stay in this recently renovated and beautifully furnished two-bedroom, two-bathroom 3rd-floor condo conveniently located 3.5 miles from the Rehoboth Beach boardwalk, and 4.5 miles from Lewes Beach. The proximity to the beaches, stores, and restaurants make this condo a great spot to spend a fun-filled vacation at the beach. Our condo amenities include a community pool*( seasonal), free parking, free WiFi, smart TV, washer, and dryer. We supply all the sheets & towels for your stay.

4.98 out of 5 average rating, 220 reviews
Top guest favourite
A serene waterfront scene is captured at sunset, with vibrant colors reflected in the calm water. A charming building with large windows is illuminated, surrounded by lush trees, and boats are docked along the waterfront, creating a peaceful atmosphere.
Condo in Ocean Pines

Water view at Ocean Pines Yacht Club Condo

Steps to 2 pools, 2 marinas, tiki bar and OP Yacht Club. Live music Thursday-Sunday evenings from 6-10pm, (in season). Beach day? Ocean City 15 min drive or walk to the marina and hop on a boat with friends and head across the bay into OC. Assateague Island is a 20 min drive. Crabbing? Fishing? Walk to one of the many Ocean Pines canals or ponds. Golfing? The links are just across the Parkway. Wedding party? Be footsteps away from make lasting memories. Free beach parking on 49th included

4.97 out of 5 average rating, 224 reviews
Guest favourite
A serene landscape captures a sunset over the James River, with vibrant hues of orange and pink reflecting on the water. Silhouettes of trees frame the view, and a gently sloping green lawn leads toward the riverbank, enhancing the tranquil atmosphere.
Condo in Williamsburg

Luxury Riverfront Condo w/ sunrise & sunset views

Luxury One Bedroom Condo with stunning views of sunrises and sunsets overlooking the James River. Perfect for a romantic getaway or a small family adventure, you can sit on the private balcony and enjoy the serene views of the river and the marina, or venture out for kayaking, jet ski, pontoon boat, Busch Gardens, historic Colonial Williamsburg, wineries, award winning golf courses and restaurants, spa and so much more. Come and experience an unforgettable vacation while making many memories.

4.93 out of 5 average rating, 152 reviews
Top guest favourite
A spacious living area features a sectional sofa adorned with red accent pillows. A wooden coffee table sits in front, contrasted by a patterned area rug. Natural light streams through large windows, highlighting a piece of wall art depicting a serene landscape.
Condo in Lewes

Beach Sunrise: Walk to Downtown & Lewes Beach

Skip the traffic and parking stress — stay where everything is steps away. Experience the best of Lewes (pronounced loo-iss) from this perfectly located, walkable condo. Step outside and you’re minutes from the beach, downtown dining, scenic parks, and bike trails. With ultra-fast 2-Gig Wi-Fi, KING bed, free bikes, coffee bar, easy parking, and thoughtful amenities, this is the ideal home base for couples or small families seeking comfort, convenience, and an authentic local stay.

4.98 out of 5 average rating, 368 reviews
Top guest favourite
Condo in Lewes

Modern & Cozy Retreat | Pool | Close to Beaches

Enjoy a relaxing Lewes getaway nestled just off Coastal Highway, with easy access to beaches, dining, and local attractions. Less than 5 miles to Lewes Beach and less than 7 miles to Rehoboth and Dewey Beach, making it easy to enjoy the ocean, boardwalk, and everything the area has to offer. Just minutes from Nassau Valley Vineyards, Georgetown-Lewes Trail, Cape Henlopen State Park, historic downtown Lewes, great restaurants, breweries, and tax-free shopping at Tanger Outlets.

4.95 out of 5 average rating, 322 reviews
Guest favourite
A bright studio space features a queen bed with cozy linens and decorative pillows. A sofa provides additional seating, while a desk and chair are positioned near a window. Light wood flooring and neutral walls create an open and welcoming atmosphere.
Condo in Lake Ridge

The Bird's Nest in Historic Occoquan (Mins to DC)

Spacious condo in the heart of walkable historic Town of Occoquan. Second floor loft with full kitchen, bath, a comfortable queen bed, work station, w/d in unit & one free parking spot. The Town of Occoquan offers unique experiences (kayaking, fishing, birdwatching and shopping) all within walking distance. Excellent dining choices from award winning restaurants to casual eateries. Mins to I-95, 123, VRE. D.C. (35min); Quantico (25min); Potomac Mills (10min). Tysons (25min).

4.91 out of 5 average rating, 866 reviews
Top guest favourite
Condo in Ocean View

Bethany Bay. Sleeps 4. AC, Pool, Ground Floor

Unit 6302 at Bethany Bay is a 2 BR, 2 Bath, ground floor unit with panoramic views of the waterways and Indian River Bay. Sleeps 4. Free parking. Fully equipped kitchen, AC, fireplace, community outdoor pool, jogging/hiking path, 9 hole golf course. NON-SMOKING UNIT. Enjoy dinner and drinks on the enclosed rear porch and take in the view. 5 miles to Bethany Beach, 12 miles to Ocean City, 17 miles to Rehoboth Beach. I will allow one dog and the pet fee is $50 per night.

4.98 out of 5 average rating, 130 reviews
Top guest favourite
A bright living area features a comfortable sofa and a patterned armchair, arranged around a wooden coffee table. A rug adds warmth to the hardwood floor, while ample natural light enters through multiple windows. The kitchen, adjacent to the living space, is equipped with modern appliances.
Condo in Annapolis

Funky Uptown Apt meets Downtown - Hist District

Location location location where Uptown meets Downtown in the Historic District. 1/2 block to Dinner Under The ✨ , First Sunday Arts. Tsu, 49 West, Level in the front yard Ramshead, Stan and Joes and Reynold's Tavern in the back. EVERYTHING Annapolis (USNA, Stadium, Statehouse, Ego Alley, Main St, Eastport) is walking distance from this unique 2nd floor unit w elevated deck for morning coffee as Jazz wafts in, full kitchen, w/d, clawfoot shower/tub, MBR with Queen.

4.96 out of 5 average rating, 126 reviews
Guest favourite
A bright living area features stylish seating arrangements with two blue sofas and a central ottoman. A wall-mounted television is positioned beneath decorative shelving. An open kitchen space is visible, showcasing modern bar stools and a dining area bathed in natural light from a nearby window.
Condo in Annapolis

Renovated Apt In Historic Dist w/2 Parking Spots

Renovated upstairs unit two bedroom with TWO parking spots in the Historic District. Everything is high end and used exclusively as a short term rental. Private entrance, cute small custom kitchen, ceiling fans, mini split AC/ heat in every room for year round comfort. Hardwood floors, quality linens , lucid mattresses, Keurig coffee bar, toiletries. Walk to town in 10 min or less or take the free trolley to Main St, USNA, Churches, AYC. No children under 12.

4.94 out of 5 average rating, 451 reviews
Top guest favourite
A living area features a gray couch adorned with decorative pillows against a light wall. A recliner is positioned nearby, and a wall-mounted Smart TV is visible. A dresser with a plant sits below the TV. Natural light streams in through nearby windows.
Condo in Annapolis

1st Floor Condo in Annapolis

This newly renovated, 1st floor studio is perfectly located just across Spa Creek from historic Annapolis in Eastport. Within easy walking distance of restaurants (3 min), Main Street/City Dock (10 min) & USNA's Gate 1 entrance (14 min), our studio includes a full kitchen, high-speed wifi, free onsite parking lot, a secure building entrance, dock (limited access) and a rooftop patio (with a seasonal pool) that offers beautiful views of downtown Annapolis.

4.96 out of 5 average rating, 172 reviews
Top guest favourite
A spacious living area features two large sofas, one being a queen sleeper bed. A wooden coffee table sits on a neutral area rug. A dresser and smart TV are positioned along the wall, with a dining area visible through an open layout.
Condo in Rehoboth Beach

The Loft 2B/2BA minutes to Rehoboth & Lewes Beach

Escape to a stylish coastal 2 bedroom 2 bath condo designed for relaxing beach vacations, family trips, and weekend getaways. Conveniently located just minutes from Rehoboth Beach and Lewes, The Loft offers the perfect combination of comfort, convenience, and coastal charm. Whether you're planning a family beach trip, a couples retreat, shopping weekend, or exploring Delaware’s beautiful coastline, you'll have everything you need for a memorable stay.

5.0 out of 5 average rating, 122 reviews

Popular amenities for condo rentals near Chesapeake Bay

KitchenWifiPoolFree parking on premisesAir conditioning

Weekly condo rentals

Top guest favourite
The spacious master bedroom features a large bed with decorative pillows and a coordinating gold bedspread. A patterned rug lies beneath, while a stylish lamp and a plant add warmth. An elegant mirror and chair provide additional functionality, and soft lighting enhances the serene ambiance.
Condo in Alexandria

Cozy Old Town Apartment

4.98 out of 5 average rating, 143 reviews
Top guest favourite
A spacious bedroom is presented, featuring a four-poster bed with a light-colored bedding set. Flanking the bed are two bedside tables, each with a lamp. Natural light filters through the window, illuminating the soft, neutral tones of the room.
Condo in Rehoboth Beach

Coastal Modern Condo • Balcony, 2 Baths, East Rt 1

4.99 out of 5 average rating, 118 reviews
Top guest favourite
Condo in Annapolis

Annapolis Waterfront Condo - Unit #: A-203

4.97 out of 5 average rating, 345 reviews
Guest favourite
An oversized balcony features comfortable seating with deep blue cushions. A glass-top table sits between the chairs. Below, the water view showcases boat traffic, while string lights add a gentle ambiance. The surrounding area includes other residential units and docks.
Condo in Ocean City

Bayside Retreat in the Heart of Ocean City!

4.88 out of 5 average rating, 277 reviews
Top guest favourite
A bright guestroom is furnished with two double beds, each featuring a light-colored quilt. Nightstands with lamps are positioned beside the beds. A large window offers views of greenery, with soft curtains complementing the decor.
Condo in Williamsburg

Comfy 1BR w pond view Kingsmill

4.96 out of 5 average rating, 161 reviews
Guest favourite
A modern living area features a spiral staircase leading to the upper floor. Natural light filters through skylights and large windows. A mix of furnishings, including a green accent chair, a brown couch, and a glass coffee table, adds to the stylish ambiance.
Condo in Richmond

Sixteen West - Modern Apartment in Richmond

4.91 out of 5 average rating, 335 reviews
Guest favourite
The living area features a light grey sofa, two teal armchairs, and a wooden coffee table. A woven basket holds a soft throw. In the background, a kitchenette is visible, along with cabinets and appliances, illuminated by natural light from skylights.
Condo in Williamsburg

2 Bedroom Stylish Kingsmill condo

4.95 out of 5 average rating, 154 reviews
Top guest favourite
The open-plan space features a sleek kitchen with dark cabinetry and a breakfast bar, alongside a cozy seating area with a gray sofa. A decorative rug adds warmth to the tiled floor, while light flows in from multiple sources, highlighting the clean lines and neutral palette.
Condo in Logan Circle

Bright, large zen studio on historic Logan Circle

4.89 out of 5 average rating, 533 reviews

Pet-friendly condo rentals

Guest favourite
An open living area features a sectional sofa, stylish chairs, and a glass coffee table atop a textured rug. The kitchen bar is surrounded by high stools, with modern appliances and white cabinetry visible in the background. Soft, ambient lighting adds to the space's welcoming feel.
Condo in Dupont Circle

Sojourn in DuPont Circle: Modern Meets Historic

4.89 out of 5 average rating, 105 reviews
Top guest favourite
A modern living room features a spacious gray sofa paired with two armchairs, set against a light wall. Art pieces are hung above the sofa, and natural light enters through a large window. A dining area with a round table and four chairs is visible in the background.
Condo in Capitol Hill

Hill East BnB - Modern Style and Comfort 3BR/3BA

4.98 out of 5 average rating, 349 reviews
Superhost
A cozy living area is highlighted by a large 65" TV on a white media console, flanked by tall speakers. A soft sofa is paired with a round dining table set for two, complemented by a potted plant and framed artwork on the wall.
Condo in Northwest Washington

New, Sunny, 2BR - Parking, Patio, Firepit

4.9 out of 5 average rating, 279 reviews
Guest favourite
Condo in Centreville

Peaceful patio condo

4.9 out of 5 average rating, 143 reviews
Top guest favourite
The living room showcases a warm wooden floor and is furnished with a black leather sofa and loveseat, providing ample seating. A coffee table sits on a patterned rug, complemented by a small table with a decorative plant. Two doors lead to private spaces.
Condo in Logan Circle

Entire 2 Bedroom/ 2 Bathroom unit (Heart of SHAW)

4.97 out of 5 average rating, 211 reviews
Top guest favourite
A tranquil lakeside scene captures two individuals on paddleboards gliding across calm water. Sandy shores are lined with chairs, offering a peaceful spot to relax. In the background, a spacious building features a wraparound deck, providing views of the serene landscape.
Condo in Williamsburg

Walk to beach lovely 2/2 in "Kingsmill on James"

4.97 out of 5 average rating, 119 reviews
Top guest favourite
A cozy bedroom features a king-size bed with crisp white linens and decorative pillows. A large window offers a view of a green space beyond, with a sitting area including a chair and small table. A 50" TV and coffee station are positioned on a wooden dresser.
Condo in Williamsburg

Kingsmill 1bed/1ba on Golf Course 9th Fairway

4.95 out of 5 average rating, 221 reviews
Superhost
A two-story condo building is set against a twilight sky, with blooming trees framing the entrance. Pathways lined with greenery lead to the front, showcasing a well-maintained exterior and inviting balcony spaces on the upper floor.
Condo in Annandale

Remodeled 1BR/1BA Condo: close to DC with pool!

4.83 out of 5 average rating, 169 reviews

Condo rentals with a pool

Top guest favourite
A comfortable living area features a dark sofa adorned with patterned throw pillows. A coffee table sits atop a patterned area rug, while natural light enters through multiple windows adorned with wooden blinds. A TV is positioned on an entertainment unit across from the seating area.
Condo in Lewes

Beautiful condo in Villages of Five Points, Lewes

4.95 out of 5 average rating, 159 reviews
Top guest favourite
A spacious living area is presented, featuring a comfortable green sofa and a matching armchair. A large television is positioned on a low cabinet. Natural light streams through sliding glass doors, leading to a screened-in porch, enhancing the atmosphere with a view of greenery.
Condo in Rehoboth Beach

2BR Coastal Escape with Pool Near Rehoboth Beach

4.95 out of 5 average rating, 119 reviews
Superhost
A round blue dining table is set for four, featuring neutral plates and glasses. Surrounding chairs have a classic black design. A large piece of abstract art adorns the wall, while the kitchen area is visible in the background, showcasing light cabinetry and appliances.
Condo in Rehoboth Beach

Clean and Comfy, Close to Beach and Shopping

4.93 out of 5 average rating, 456 reviews
Guest favourite
A modern kitchen and dining area are showcased, featuring a granite countertop with three black stools, and a dining table with dark chairs. Striped wallpaper adds a bold touch, complemented by a wall art piece and decorative accents, creating a cohesive aesthetic.
Condo in Rehoboth Beach

Modern Beach Glam in the heart of outlets.

4.89 out of 5 average rating, 292 reviews
Guest favourite
A circular glass table with four woven chairs is positioned on the patio, overlooking a tranquil lake surrounded by greenery. Sunlight filters through the trees, casting soft reflections on the water's surface.
Condo in Rehoboth Beach

Right on Silver Lake walk to the beach and town!

4.91 out of 5 average rating, 179 reviews
Top guest favourite
A living area is presented with a gray sofa and wooden coffee table, featuring decorative items. A flat-screen television rests on a wooden console, while a clock and window with sheer curtains provide a bright atmosphere. A doorway leads to an adjacent bedroom.
Condo in Lewes

Beach Escape Condo w/ Pool - Lewes Beach 3.5 Miles

4.97 out of 5 average rating, 131 reviews
Top guest favourite
Condo in Rehoboth Beach

Cozy Creekwood Condo - Relaxing Getaway - W/ Pool

4.98 out of 5 average rating, 307 reviews
Top guest favourite
Condo in Virginia Beach

Oceanfront Studio: Boardwalk, Beach, & Pool Views

4.97 out of 5 average rating, 153 reviews

Private condo rentals

Guest favourite
The living area features a light-colored sofa positioned across from a modern coffee table. A bar area with two stools is visible in the background, leading to a kitchen with white cabinetry. Natural light illuminates the space, creating a bright and open atmosphere.
Condo in Virginia Beach

Beach Bungalow on the Boardwalk

4.86 out of 5 average rating, 180 reviews
Top guest favourite
Condo in Lewes

A bit of Paradise

4.87 out of 5 average rating, 341 reviews
Guest favourite
A spacious living area features a light-colored sectional sofa paired with vibrant accent pillows. A wooden coffee table sits in front, complementing the warm wooden flooring. The adjacent kitchen showcases turquoise cabinetry and modern bar stools, with large windows allowing natural light to fill the space.
Condo in Sterling

The Loft at Lakeside

4.93 out of 5 average rating, 183 reviews
Guest favourite
A riverboat glides along the waterway, illuminated by warm lights. Boats are docked along the marina, and twinkling lights line the shore. A vibrant sunset casts hues of purple and orange across the sky, reflecting on the water's surface.
Condo in Cambridge

Station House West: Upscale Condo in Cambridge, MD

4.92 out of 5 average rating, 37 reviews
Top guest favourite
An outdoor covered deck offers seating with a sectional sofa and a coffee table. High chairs are positioned at a bar-style table, with views of greenery and the bay in the distance. The area is brightened by natural light and features a welcoming atmosphere.
Condo in Betterton

Beach Haven Hideaway ~ stunning water views!

5.0 out of 5 average rating, 48 reviews
Top guest favourite
Condo in Solomons

The Solomons Sunrise Suite

5.0 out of 5 average rating, 76 reviews
Guest favourite
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, 54 reviews
Top guest favourite
Condo in Potomac

Private 2-Bedroom Suite on Gated Potomac Estate

4.98 out of 5 average rating, 51 reviews

Quick stats about condo rentals near Chesapeake Bay

  • Total vacation rentals

    Explore 140 vacation rentals in Chesapeake Bay

  • Nightly prices starting at

    Chesapeake Bay vacation rentals start at $14 CAD per night before taxes and fees

  • Verified guest reviews

    Over 5,840 verified reviews to help you choose

  • Family-friendly vacation rentals

    100 properties offer extra space and kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 40 rentals that welcome pets

  • Vacation rentals with a pool

    40 properties feature pools

  • Rentals with dedicated workspaces

    80 properties have a dedicated workspace

  • Wifi availability

    130 of Chesapeake Bay vacation rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Chesapeake Bay rentals

  • 4.8 Average rating

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

Destinations to explore