Townhome vacation 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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Top guest favorite
The exterior of a historic townhome is showcased, featuring red brick walls and black shutters. Lush greenery and colorful flowers enhance the garden area. A flag may be seen hanging from the building, set against a clear blue sky.
Townhouse in Annapolis
4.95 out of 5 average rating, 212 reviews

Historic 3 Bedroom Downtown Annapolis Townhome

Be close to everything when you stay at this centrally-located, historic townhome! Located steps from the Naval Academy, Downtown Restaurants, Bars, Shopping, and Festivals. Enjoy and relax on your large private, fenced-in patio or in your modern living room. While the restaurant scene is mouth-watering in Annapolis, you can also stay "home" and cook in your gourmet kitchen. Explore all that Annapolis has to offer from the comfort of your home away from home! No on-site parking but lots of off.

Top guest favorite
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, 198 reviews

Walk to Beach and Park! Outdoor shower&Fenced Yard

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 four 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. Ask about our optional golf cart rental during your stay!

Top guest favorite
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, 249 reviews

Beachside Oasis + Beach Passes | A Haven Away

Welcome to Bay Haven, one of five A Haven Away getaways! This plant-filled oasis is in a quiet North Beach neighborhood, steps from the wetlands park and 12 minutes on foot to the beach. We share our community beach passes and loads of local tips. The house is stocked with everything you need for a relaxed stay. 12 min walk to the beach, boardwalk, restaurants, and kids play areas in North Beach, MD 7 min drive to Herrington Harbor 14 min drive to Tacaro Estate Find us on Insta ahavenaway.

Guest favorite
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, 113 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.

Top guest favorite
A charming residential street is depicted, featuring a row of two-story townhouses with varying exterior colors. Each unit is complemented by front steps leading to a door adorned with a seasonal wreath. Lush greenery and trees line the sidewalk, providing a peaceful setting.
Townhouse in Old Town
4.96 out of 5 average rating, 338 reviews

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.

Top guest favorite
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, 538 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 favorite
A waterfront balcony is furnished with a black metal table surrounded by six matching chairs. Potted plants add a touch of greenery, and a view of the harbor and nearby buildings is visible, enhancing the outdoor space.
Townhouse in Fells Point
4.98 out of 5 average rating, 274 reviews

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!

Top guest favorite
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 Inner Harbor
4.94 out of 5 average rating, 264 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!

Guest favorite
A bright and airy dining area features a large wooden table surrounded by six modern green chairs. Decorative wall art made of woven materials enhances the space, while a view of greenery is visible through the adjacent doors leading to the patio.
Townhouse in Georgetown
4.97 out of 5 average rating, 357 reviews

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.

Top guest favorite
The exterior of a two-story duplex is featured, showcasing a light brown facade with white trim. A peach-colored front door is visible, adorned with a decorative lantern. Several windows are framed by black shutters, and greenery lines the pathway leading to the entrance.
Townhouse in Leonardtown
4.99 out of 5 average rating, 125 reviews

Charming Duplex in the heart of Leonardtown

This bright, stylish duplex is the perfect base to explore St Mary’s county. Nestled in downtown Leonardtown , this contemporary living space has everything to make you feel at home – WiFi, Netflix, washer and dryer, queen size beds in 2 of the 3 bedrooms, two twin beds in the 3rd. Kitchen is well equipped with just about everything you might need including basic spices, sugar and cooking oil. Spend your evenings relaxing on the back deck under the soft lighting.

Top guest favorite
A duplex with a shingled exterior is displayed, featuring a rooftop deck accessible by an exterior spiral staircase. A fenced yard is visible, along with a gravel surface below. Large glass doors lead to the lower level, enhancing connection to the outdoors.
Townhouse in Dewey Beach
4.91 out of 5 average rating, 139 reviews

McKinley Duplex

Enjoy the Ocean and Bay Views from the roof top deck of this Pet Friendly duplex located in the ocean block in the heart of Dewey Beach! Just steps to the beach with a large enclosed porch, open living area, 6 bedrooms and 3.5 baths (2 King, 1 Queens, 6 Twins and a sofa bed), ample parking and much more. Walk to all the restaurants and nightlife - take the Jolly Trolley into Rehoboth to enjoy the beach, boardwalk and some of the finest dining in the area!

Guest favorite
A spacious living area features a large sectional sofa and two armchairs, complemented by a coffee table and area rug. Natural light floods through sliding glass doors that lead to a private deck, with water views visible from the room. Decorative wall art adds a calming touch.
Townhouse in Ocean City
4.91 out of 5 average rating, 295 reviews

Bayfront Townhouse: Fishing, Sunsets & Family Fun!

Escape to this stunning, updated bayfront townhouse in midtown Ocean City! Featuring 3 bedrooms with 3 ensuite bathrooms, enjoy breathtaking sunsets from your private deck. This entertainer's dream offers a spacious open layout with a gourmet kitchen and waterfall countertops. Benefit from two assigned parking spots, fish directly off the back deck pier, a local favorite fishing spots, you'll love the waterfront access and relaxing atmosphere.

Popular amenities for townhouse rentals near Chesapeake Bay

Quick stats about townhouse rentals near Chesapeake Bay

  • Total vacation rentals

    Explore 240 vacation rentals in Chesapeake Bay

  • Nightly prices starting at

    Chesapeake Bay vacation rentals start at G$6,274 GYD per night before taxes and fees

  • Verified guest reviews

    Over 10,550 verified reviews to help you choose

  • Family-friendly vacation rentals

    170 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 80 rentals that welcome pets

  • Vacation rentals with a pool

    20 properties feature pools

  • Rentals with dedicated workspaces

    130 properties have a dedicated workspace

  • Wi-Fi availability

    230 of Chesapeake Bay vacation 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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