
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.

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

Walkable 2 Orioles & Ravens Stadium
Experience the best of Baltimore from our Federal Hill location! You"ll be steps away from some of the city's top restaurants, bars, West Covington Park, M&T Bank Stadium, Camden Yard, and more! Take a stroll through the charming streets to the nearby Federal Hill Park for stunning views of the Inner Harbor. Enjoy easy access to major highways and public transportation, making it easy to explore all the city has to offer. You'll find something for everyone within walking distance of our space.

Moose’s Happy Place
Built in 2019 with open spaces and happy places on historic Eastport Peninsula. A fresh take on coastal contemporary with front & back porches just steps from the Severn River & Spa Creek. Easy to enjoy the salty vibe with short walks to water access areas as well as Eastport's best local pubs and restaurants; or head over the Eastport bridge to downtown Annapolis and the Naval Academy - also accessible by water-taxi, rental boats & paddle-boards... A great NEW place in a great OLD place!!!

2 Bed Bath Otakon and Citi Open Metro Pet Friendly
Welcome to Maison du Voyageur Noir. We are delighted to host you during a vibrant late summer stretch in Washington, DC, with Citi Open tennis, Otakon, DC250 experiences, Smithsonian exhibitions, National Mall activities, and Southeast DC traditions bringing extra energy to the city. Culture-forward and group-friendly: Well-suited for families, couples, and friends who want a comfortable home after days filled with museums, tennis, design installations, dining, and neighborhood exploration.

*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.

Beach house on lake!
2 miles from the beach in a complex called Mallard Lakes in Fenwick Island, DE.Close to great views, restaurants, beach, and family activities.Bird watching outside screened-in porch, fishing, crabbing, two outdoor pools/hot tub (open Memorial Day-Labor Day), tennis, volleyball and basketball courts, tot lot, horseshoe pit, shuffleboard, grilling area and a shopping center across the street.Free water aerobics, outside shower, fireplace, umbrella and chairs for beach, comfortable sofa bed.

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.

Comfortable Studio Apartment
A cute studio apartment in the basement of a newly renovated home. Guests have a private entrance with their own private bathroom. You also have use of a full-size washer and dryer. Other amenities include an honor bar stocked with beer and wine, an arcade style game with over 200 popular titles including Ms. Pac Man, and coffee/tea. Please note that we live upstairs, but the space is private. It is separated by a stairwell and a locking door. It is comparable to a hotel room, but nicer.

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 :)

TOWNSAND 1 block to ocean 1 block to dine/imbibe
Where the city meets the sea. One block to the beach and boards, one block to the best restaurants in Rehoboth. Townsand loft is the perfect location for your stay in Rehoboth. Park the car in the dedicated off street spot in front of Townsand and walk to everything. This light filled home features a designer renovation with exposed rafters, upscale full kitchen, custom bathroom and vaulted ceilings. The sleeping loft makes for a cozy slumber after a day of sun and a night on the town.

Annapolis Downtown Pleasant St Townhome 3 bedrooms
Immerse yourself in the best that the downtown Historic District of Annapolis has to offer while staying in this completely renovated, midcentury modern getaway. 10 min walk to Main St. 15 min walk from Naval Academy. 300 Mbps high-speed Nest wireless internet. Parking available, as well as another parking garage nearby 600 ft. Cozy up with a great show or movie on the smart TV or on your WiFi-enabled device. Unwind and relax in any of three finely appointed, luxurious bedrooms.

Bright & Charming 2bd In The Heart Of Fells
Built in 1920, this charming 2 bedroom townhouse has a brand new, stunning renovation with a location that cannot be beat. Just slightly removed but only steps from the bustle of the historic downtown area of Fells Point, it’s a great spot to unwind after a day/night on the town. This space, featuring brand new appliances, a brand new queen Casper mattress in one bedroom & a full bed in the second, also has an extra loft space & small patio/garden area to relax & enjoy.
Popular amenities for townhouse rentals near Chesapeake Bay
Family-Friendly townhouses

Townhome Steps to Capitol Bldg Backyard & Parking

Modern Beach Vibe - Rehoboth Beach

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

Weekends in White Marsh

Seaside Getaway: Bethany Beach Charm

Perfect place for your family

Back Creek Villa Covered Deck

The Peach at the Beach ~ nice pool!
Townhouse rentals with a washing machine and dryer

Perfect Location by Fed Hill Park 2Bdr/2.5Ba

Beautiful Townhome in Shaw/Bloomingdale

DC Escape- Cozy and Stylish Stay + Private Hot Tub

Historic 3 Bedroom Downtown Annapolis Townhome

Newly Renovated Beautiful 3 bedroom home!

Charming Little Italy Townhouse + Free Parking

Entire Upper Fells Point 3 Bedroom Beauty!

Romantic Hot Tub Getaway, Walk to Fells Point
Townhouses with a patio

Discover Charm City from a Cozy Retreat.

Garden Retreat on Carroll Creek + Free Parking!

Terraced Townhouse Getaway in Georgetown

Cozy 1BR Basement | Private Entry & 1 free Parking

2BR/2BA Apartment with Patio Next to Zoo & Metro

Modern & Cozy Townhouse in Rosslyn - Free Parking

Quarry Landing • River Views in Historic Town

Cheerful 2 bedroom townhouse with fireplace
Other townhome holiday rentals

Cozy Private Suite w/Yard —10 min to BWI/F. Meade

Charming Rowhome in Downtown Annapolis

Modern 4-Story Townhome Retreat Minutes From DC

Spacious Townhome Near DC | Garage & Workspace

Sitting on the Dock of the Bay | 8 min to Buckroe

Walk to Dock USNA - Renovated 2BR Downtown

2 Bedroom with Historic Charm In Fells Point

Modern Retreat | 4BD 3.5BA | 15 min to IAD Airport
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 $52 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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- Townhouse rentals United States
- Virginia Beach Oceanfront
- Busch Gardens Williamsburg
- Chincoteague Island
- Buckroe Beach
- Cape Charles Beachfront
- Water Country USA
- First Landing State Park
- Jamestown Settlement
- Norfolk Botanical Garden
- Outlook Beach
- Ocean Breeze Waterpark
- Old Dominion University
- Chrysler Museum of Art
- First Landing Beach
- Colonial Williamsburg's Merchants Square
- Neptune's Park
- Nauticus
- The Mariners' Museum
- Virginia Zoological Park
- Town Point Park
- Virginia Living History Museum
- Hampton University
- Cape Henry Light House
- USS Wisconsin (BB-64)





