
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.

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

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.

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 ⭐️⭐️⭐️⭐️⭐️📍

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 :).

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!

*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.

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!

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 :)

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!

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.

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
Family-Friendly townhouses

Bring your Pet! Arlington Cozy & Clean Home!

Terraced Townhouse Getaway in Georgetown

Renovated Basement Studio 300ft to Metro!

Family-Friendly Retreat at Quiet Delaware Beach

Back Creek Villa Covered Deck

STUDIO SUITE IN THE TREE TOPS:ADAMS MORGAN,WOODLEY

Walkable 2 Orioles & Ravens Stadium

2 BR Waterfront Townhouse in North OC
Townhouse rentals with a washing machine and dryer
Superb, Designed, Historic House in Georgetown

Cheerful 2-bedroom row house with rooftop deck

1802 Historic Townhome

Alexandria Old Town Charm

Unique 2bd townhouse quietly located in the city.

Luxuriously Restored Loft in Historic Old Town Alexandria

Romantic Hot Tub Getaway, Walk to Fells Point

Fed Hill ☆ Parking ☆ Deck ☆ Walk Score 95 ☆ Harbor
Townhouses with a patio

Beautiful Townhome in Shaw/Bloomingdale

Discover Charm City from a Cozy Retreat.

CapHill Oasis Townhouse-Free Parking-EasternMarket

Positive vibes on Market St

Cozy Oasis-Spacious 4 Bedroom Condo!

Historic 3 Bedroom Downtown Annapolis Townhome

Charming Townhome with Outdoor Deck

Quarry Landing • River Views in Historic Town
Other townhome holiday rentals

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

Tiki Shack

Perfect place for your family

Luxurious & Cozy ~ 5* Location ~ Scenic Canal View

Cozy One Bedroom Apartment!

Cozy Cottage in Columbia

The Brick House Retreat w/ *HOT TUB*

Fiddler On The Creek-Kayaks, Canoe & Shared Pier
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!
Destinations to explore
- Rentals with outdoor seating Chesapeake Bay
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- Townhouse rentals United States
- Virginia Beach Oceanfront
- Busch Gardens Williamsburg
- Chincoteague Island
- Water Country USA
- Buckroe Beach
- First Landing State Park
- Jamestown Settlement
- Cape Charles Beachfront
- Outlook Beach
- Norfolk Botanical Garden
- Ocean Breeze Waterpark
- Chrysler Museum of Art
- Virginia Zoological Park
- Colonial Williamsburg's Merchants Square
- Nauticus
- Town Point Park
- First Landing Beach
- Virginia Living History Museum
- Old Dominion University
- Hampton University
- Chrysler Hall
- Neptune's Park
- USS Wisconsin (BB-64)
- Children's Museum of Virginia




