Townhome holiday rentals near Chesapeake Bay

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Top-rated townhouse rentals near Chesapeake Bay

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

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Guest favourite
A comfortable living area features a plush blue sofa with pink accent pillows, complemented by a round mirror. Decorative plants add a touch of greenery. A light wooden coffee table supports a floral arrangement, while two poufs create additional seating in a welcoming space.
Townhouse in North Beach
4.96 out of 5 average rating, 228 reviews

Walk to Beach! King Bed & Free Beach Passes

Welcome to Bay Haven at A Haven Away! Relax in a fully-equipped, plant-filled oasis with a king bed primary suite that our guests love. Its prime location is in walking distance to the beach, restaurants, fresh seafood, and wetlands. We’ll share our beach passes and lots of local recommendations so you can enjoy our little slice of heaven. 12 min walk to the beach, boardwalk, restaurants, and kids play areas in cute North Beach, MD 7 min drive to Herrington Harbor 14 min drive to Tacaro Estate

Guest favourite
A sunlit living area showcases a beige sectional sofa and an accent chair, complemented by a round coffee table. Large windows provide views of the outdoors, while decorative plants and artwork add a touch of style to the inviting space.
Townhouse in Rehoboth Beach
4.98 out of 5 average rating, 106 reviews

Spacious Townhome close to Rehoboth/ Dewey Beaches

Spacious home in the heart of the Rehoboth & Dewey beaches. A short bike ride to downtown Rehoboth, the boardwalk & the beach. 3 full bedrooms each with its own full bathroom as well as a comfortable pullout couch providing sleeping for 10 guests. Fully equipped kitchen, comfortable accommodations, plenty of beach equipment and a screened in porch provides an outdoor dining option. A ground level patio includes outdoor lounge furniture and a sun deck is available off the 3rd fl master bedroom.

Guest favourite
The image showcases a serene waterfront view, featuring calm waters and dock posts spaced along the shoreline. In the background, lush trees and buildings are partially visible, creating a peaceful ambiance typical of a waterfront village.
Townhouse in Hampton
4.75 out of 5 average rating, 623 reviews

Prime Downtown 2BR Near HU & Waterfront

SAFE/WALKABLE GREAT LOCATION📍 Stay here and enjoy ALL the pleasantries of Downtown Hampton's quaint waterfront village. WALKABLE* to the marina, many restaurants, pubs, IMAX theater, museums+ Historic Post Office* Hampton Univ* Mill Point Park* City Hall* Phoebus/Ft Monroe-5 min Hampton Coliseum/Convention Aquaplex-7min Buckroe Beach-8min Boo Williams -11min Langley AFB/Newport News-15min Norfolk/ODU-23min Busch Gardens/Williamsburg-28min Portsmouth-29min Virginia Beach-40min ⭐️⭐️⭐️⭐️⭐️📍

Top Guest favourite
A warm living space features exposed brick walls and wooden beams overhead. A plush sofa is positioned beside a vintage-style lamp, and natural light streams in through large windows. A television is mounted on the wall, providing entertainment.
Townhouse in Baltimore
4.92 out of 5 average rating, 246 reviews

2 levels of Modern Rustic & Artistic Rowhome🦀⛵️-New

This Artistic, Rustic, Bold, Modern, Radical & Avant-Garde remodeled 1900's historic 2 bedroom row home is in one of the quiet lanes in Canton, a historic waterfront neighborhood, steps from the famous O’Donnell Sq with a ton of great food & drink options. Walk and bike score of 98/100. Enjoy a quiet walk to the waterfront or simply relax and watch the sunset off the docks. Walk, run, uber or scooter our neighborhood, Fells Point & Inner Harbor. “NO CHORES”, we’ll take care of everything :).

Guest favourite
A cozy deck is highlighted, featuring comfortable seating around a fire table, surrounded by twinkling outdoor lights. In the background, a charming brick facade of a house and city views are visible, creating an inviting atmosphere for relaxation.
Townhouse in Baltimore
4.96 out of 5 average rating, 198 reviews

Perfect Location by Fed Hill Park 2Bdr/2.5Ba

Our spacious home is waiting for you! You'll love this home's unbeatable & safe location in the heart of Baltimore’s Inner Harbor! Located within walking distance of Federal Hill Park, Convention Center, Orioles & Raven's Stadiums, National Aquarium, Maryland Science Center, M8 Beer, Sagamore Distillery, Fort McHenry, Restaurants/Nightlife/Bars, Farmer’s Market, Shopping, Breweries, Business District, & MARC Train/Metro/Lightrail. Ideal for singles, couples, families, & business travelers.

Top Guest favourite
The living area features a cozy gray sofa, two armchairs, and a circular coffee table. Natural light fills the space through windows adorned with light curtains. A large wall-mounted TV is positioned above a white media console, enhancing the room's modern yet inviting aesthetic.
Townhouse in Cape Charles
4.96 out of 5 average rating, 172 reviews

3 Blocks to Beach, Fenced Backyard, Pet Friendly!

Welcome to Peach Haven, a newly renovated duplex in the Cape Charles historic district. Just 1 block from the park and 3 blocks from the beach, it's the ideal base for your Cape Charles escape. This pet-friendly rental sleeps five guests comfortably with a master bedroom (queen bed) and a second bedroom with a custom-made full-over-full bunkbed. The house has been thoughtfully stocked with everything you'll need for a comfortable stay. Need more space? Ask about renting the other side, too!

Guest favourite
A spacious bedroom features a king size bed dressed in white linens and accented with colored pillows. Two bedside lamps illuminate the room, complemented by a ceiling fan. A comfortable bench sits at the foot of the bed, with a vibrant throw blanket draped across.
Townhouse in Hampton
4.98 out of 5 average rating, 103 reviews

*Beautiful Water Views* King Bed*Fast WIFI

Do you desire Peace, Quiet & Tranquility? This townhome is the PERFECT getaway! It's RIGHT on the water and features the following: *Newer Furnishings! *Blazing Fast Panoramic WIFI & Dedicated Workspace *Bedroom 1: KING size bed overlooking the water. Not a bad way to wake up?!? *Gourmet Kit w/Granite Countertops, Stainless Steel Appliances, complete w/a Convection Oven & Coffee Maker & Creamers * Smart TVs w/Adjustable Wall Mounts for your view preference, in Each Bedroom & Living Room.

Guest favourite
A spacious living area features a combination of comfortable seating, including a patterned armchair and a gray sofa. Natural light brightens the space, which includes a dining table in the background. A staircase with wooden steps leads to the upper level.
Townhouse in Annapolis
4.9 out of 5 average rating, 166 reviews

Beautiful Townhome Downtown Annapolis

Located in the Historic District of Annapolis, you're in walking distance of State Circle, Church Circle, Naval Stadium, Naval Academy, and surrounded by all things Annapolis! Enjoy amazing shops, entertainment venues, and great restaurants for food and happy hour! In between exploring Annapolis, comfortably relax with a good movie on the smart tv or with your wifi-enabled devices. Bring family and/or friends to enjoy the comfort of our beautiful home in an absolutely wonderful City!

Top Guest favourite
The living area features large sliding doors that open to a porch with stunning bay views during sunset. A neutral-colored couch and a cozy chair create a welcoming space. A wooden dining table complements the serene atmosphere, illuminated by the warm glow from the setting sun.
Townhouse in Ocean City
4.97 out of 5 average rating, 496 reviews

Edgewater Escape - Luxury Bayfront Loft with Porch

You've never seen waterfront like this. Welcome to Edgewater Escape, a luxury bayfront loft apartment that hangs entirely over the bay on 7th street in downtown Ocean City. Sit on the bay front porch or hang out inside and watch boats, dolphin, birds, and sometimes even seals swim by within feet of the porch. The loft has a roomy king sized bed and the downstairs couch pulls out into a comfy queen bed. Recently renovated, it comes fully equipped for your big trip or quiet staycation :)

Top Guest favourite
A bright living room is showcased with hardwood flooring and a large area rug. A sectional sofa is displayed with decorative pillows. A coffee table sits at the center, and artwork adorns the walls, adding a modern touch. The dining area is partially visible in the background.
Townhouse in Baltimore
4.93 out of 5 average rating, 228 reviews

Charming Little Italy Townhouse + Free Parking

⭐ LOCATION, LOCATION, LOCATION! ⭐ Stay in the heart of Downtown Baltimore in our Little Italy townhouse—just a 10-min walk to the National Aquarium, 20-min to the Convention Center, and steps from the Inner Harbor. This 3BR/2BA home features cozy living & dining areas, a modern kitchen, workspace, outdoor sitting area, and FREE private parking (a rare find downtown!). Walk to Pier 6 Pavilion, Starbucks, shops, museums, restaurants & bars—the perfect base to explore Downtown Baltimore!

Top Guest favourite
A custom-built open kitchen features navy blue cabinets and a marble backsplash. Stainless steel appliances, including a refrigerator and microwave, are showcased. A wooden island with three stools offers additional seating, while pendant lighting adds warmth. A door leads to the private backyard, enhancing accessibility.
Townhouse in Alexandria
4.92 out of 5 average rating, 252 reviews

Cozy 1BR Basement | Private Entry & 2 free Parking

Wake up to the charming sound of birds from the wooded park just behind this cozy retreat. Enjoy the electric recliner and 65” smart TV by the fireplace. Custom-built open kitchen (no oven), comfortable queen bedroom, private full bath, laundry, and fenced backyard for relaxing privacy. Perfect for couples or business travelers—minutes to Kingstowne, Ft. Belvoir, National Harbor, Old Town Alexandria & Washington DC, with easy metro access and two assigned parking spaces.

Guest favourite
A comfortable living area showcases a modern sectional sofa with decorative pillows, complemented by a fur throw. A sleek coffee table sits atop a patterned rug, with light entering through sliding glass doors that open to a private outdoor space.
Townhouse in Rehoboth Beach
4.91 out of 5 average rating, 262 reviews

Beach Modern Living Townhome

Step into a beautifully comfortable, designer townhome, and relax in style just blocks from the restaurants & beach on Rehoboth Avenue. From the space to all the furnishing, everything about this 1100sq foot, 3 completely remodeled stories is brand new. New Gourmet Kitchen, Great Room combination, 3 gorgeous bedrooms, 2 full baths, 1 half bath, and patio with outdoor shower. Every detail is of the highest quality to evoke a relaxed upscale modern beach vibe.

Popular amenities for townhouse rentals near Chesapeake Bay

Quick stats about townhouse rentals near Chesapeake Bay

  • Total holiday rentals

    Explore 240 holiday rentals in Chesapeake Bay

  • Nightly prices starting at

    Chesapeake Bay holiday rentals start at $51 NZD per night before taxes and fees

  • Verified guest reviews

    Over 10,200 verified reviews to help you choose

  • Family-friendly holiday rentals

    170 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 80 rentals that welcome pets

  • Holiday rentals with a pool

    20 properties feature pools

  • Rentals with dedicated workspaces

    130 properties have a dedicated workspace

  • Wi-Fi availability

    240 of Chesapeake Bay holiday rentals include Wi-Fi 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!

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