
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.

THE STANLEY 1 BLOCK TO BEACH/BOARDS & DINE/IMBIBE
ONE BLOCK FROM THE BEACH/BOARD, ONE BLOCK FROM DINE AND IMBIBE. 1 SPOT OFF STREET IN-TOWN PARKING!! This loft-style townhome has been completely restored with full modern kitchen, two ensuite bathrooms, comfortable living space, office loft and private outdoor deck. Modern, clean and beautiful featuring exposed high ceilings, shiplap and sea grass through out. We provide everything you need for your beach getaway. Luxe linens, beach chairs and towels, bath and cleaning products. Just come enjoy!

Beach Passes, King Bed - hosted by A Haven Away
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

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.

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!

Alexandria Old Town Charm
Location. Location. Location. Immerse yourself in all that historic Old Town Alexandria Virginia has to offer. This beautifully furnished town home is wonderfully located on a quiet, picturesque, tree lined street. Take a short walk through the city's storied neighborhoods to its great restaurants, music venues and historic sites. Take the free Old Town Trolley to the King Street Metro and then on to Washington DC or a short Uber ride to National Harbor and it bustling convention centers.

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 :)

Waterfront GEM - HUGE HOME for FAM/WORK/FUN!
Watch boats cruise along the harbor from your waterfront balcony overlooking Broadway Pier, Sagamore Pendry, and Historic Thames Street! Our unbeatable location in the heart of Fell's Point is nearby all of the areas top attractions! Step out the front door to be immersed in cobblestone charm with dozens of restaurants, bars, shops, and boutiques, within steps. Award-winning architecture, local art, and special touches have delighted our guests for years: we hope your group is next!

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!

Luxe Two Bed/Bath Townhome Near Metro Pet Friendly
Welcome to Maison du Voyageur Noir, a luxurious, culturally rich sanctuary designed for curious, open-minded travelers who want to experience Washington, DC at its most vibrant. Entertain in a chef-caliber kitchen, unwind on the serene private deck, and enjoy hotel-level details throughout. Featuring secure parking, plush queen beds, blazing-fast Wi-Fi, smart TV, washer/dryer, and Nest climate control. A 10-minute walk to Metro. Pets welcome. We look forward to hosting you.

Elegant Townhome in Arlington Kid-Friendly
Elegant 3-story townhome in Ballston, ideal for exploring DC's top landmarks like the White House, National Mall, and Smithsonian Museums. This beautifully renovated retreat features queen beds, a private backyard, and modern amenities including a fully equipped kitchen. Perfect for families and pets, the home is steps from local bars, restaurants, parks, and the library. Enjoy easy access to public transportation, making your D.C. adventure both convenient and memorable.

Terraced Townhouse Getaway in Georgetown
This three story townhouse offers the perfect getaway within the city. An uplifting space ideally located on a quaint block of Burleith; just a short walk to Georgetown Campus and at a convergence of parks and lush pathways. A spacious and sunlit home suited for families, groups of friends, and Georgetown graduate students. Plenty of restaurants, cafes and a variety of super markets to reach by foot. All main historical and national attractions within a 4 mile radius.

STUDIO SUITE IN THE TREE TOPS:ADAMS MORGAN,WOODLEY
Private living/sleeping space in home overlooking Rock Creek Park. Studio bedroom has a cathedral ceiling, sleeping loft and living eating space. Private bathroom. AC /heating unit. Separate study/ bedroom looks onto park. Access to spectacular roof deck, kitchen and family home with all amenities including laundry and parking: All in the heart of Adams Morgan/Kalorama Excellent for a single person and/or a couple: the loft stairs are steep LGBTQ friendly
Popular amenities for townhouse rentals near Chesapeake Bay
Family-Friendly townhouses

On Beach 3BD+Loft: Sauna|HotTub|Billard|FencedDeck

Bring your Pet! Arlington Cozy & Clean Home!

Historic Home Next to Capitol, Walk to Everything

2BR Capitol Hill Light Filled Home Family Friendly

Walkable 2 Orioles & Ravens Stadium

Comfy Home in Charming Hampden

Beach Livin' by the Chesapeake Bay - VA Beach

Charming Duplex in the heart of Leonardtown
Townhouse rentals with a washing machine and dryer

Oceanfront Getaway Private Beach & Stunning View

Beautiful Townhome in Shaw/Bloomingdale

Fells Point - Close to Attractions

Garden Retreat on Carroll Creek + Free Parking!

Beautiful Downtown Annapolis Home!

Parkfront Hot Tub Haven for Families & Pets

Historic 3 Bedroom Downtown Annapolis Townhome

Newly Renovated Beautiful 3 bedroom home!
Townhouses with a patio

CapHill Oasis Townhouse-Free Parking-EasternMarket

Cheerful 2-bedroom row house with rooftop deck

Cozy Oasis-Spacious 4 Bedroom Condo!

Positive vibes on Market St

Back Creek Villa Covered Deck

Cozy 1BR Basement | Private Entry & 2 free Parking

Charming Townhome with Outdoor Deck

Historic Mill Workers Cottage
Other townhome holiday rentals

Charming Historic Townhouse Steps From USNA

Coastal Crush | Steps to the Sand + Rooftop Lounge

Perfect place for your family

Charming Downtown Annapolis Retreat

Spacious Townhome Near DC | Garage & Workspace

Gorgeous Rowhouse in Historic Neighborhood

Gorgeous home on Chincoteague-Misty Mare Townhouse

Spacious Luxury Townhome available close to DC
Quick stats about townhouse rentals near Chesapeake Bay

Total holiday rentals
Explore 250 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 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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- Townhouse rentals United States
- Busch Gardens Williamsburg
- Virginia Beach Oceanfront
- Chincoteague Island
- Buckroe Beach
- Water Country USA
- Cape Charles Beachfront
- First Landing State Park
- Jamestown Settlement
- Norfolk Botanical Garden
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