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Chesapeake Bay vacation rentals
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Best Vacation rentals and Airbnb offers in Chesapeake Bay

Best Chesapeake Bay vacation rentals with a balcony

Cozy Historic Home Near Downtown Ferry - Chesapeake Bay
No reviews

Cozy Historic Home Near Downtown Ferry

house, Portsmouth
This historic house in Portsmouth is located near the downtown ferry, 9.3 miles from Norfolk Botanical Garden and 8.1 miles from Norfolk International Airport.
This 1-bedroom, 2-bathroom house accommodates up to 7 guests and features free WiFi, air conditioning, a balcony, a fully equipped kitchen, and free on-site private parking.
Kent Island Beach House - "Pink" House In Kentmorr - Chesapeake Bay
10 130 reviews

Kent Island Beach House - "Pink" House In Kentmorr

apartment, Stevensville
This Stevensville beach house is located just 9 miles from Matapeake State Park, Paul Reed Smith Guitars, and Love Point State Park, offering easy access to local attractions. The property has excellent ratings for user experience, location, and cleanliness.
This 1800 square foot vacation rental comfortably sleeps 14 guests in its four bedrooms. The house features a fully equipped kitchen, a fireplace, a jetted tub, a private terrace, a garden, a spa, a tennis court, and a playground, perfect for relaxing and entertaining.
Grey's Point Camp Cottage 7 - Chesapeake Bay
9.1 29 reviews

Grey's Point Camp Cottage 7

house, White Stone
Grey's Point Camp Cottage 7 is located in Locklies, a short distance from White Stone and approximately 42 miles from Newport News/Williamsburg International Airport. This cottage has received excellent ratings for its location, cleanliness, and overall experience.
The cottage has one bedroom and one bathroom, perfect for a couple or a small family. It features a fully equipped kitchen, a private patio, a terrace, air conditioning, free Wi-Fi, and easy access to the Chesapeake Bay for boating, fishing, and exploring the area's natural beauty.
Welcome To Our Newly Built House - Chesapeake Bay
9.4 17 reviews

Welcome To Our Newly Built House

apartment, Glen Burnie
This brand new construction is conveniently situated minutes from BWI, Baltimore City, and Washington DC. It is located in the Marley neighborhood of Glen Burnie, offering easy access to water-based activities such as motor boating, fishing, and swimming.
The house has an excellent user rating and can accommodate up to 12 guests with its 4 bedrooms and 3 bathrooms. The house includes a kitchen with a fridge, microwave oven, and dishwasher, as well as air conditioning, a Jacuzzi, a terrace/balcony, a spa, and parking.

Search Family Vacation Rentals in Chesapeake Bay

These family-friendly vacation rentals in Chesapeake Bay offer plenty of room to spread out near local beaches.

Stargazer Tiny Cabin - Chesapeake Bay
9.9 231 reviews

Stargazer Tiny Cabin

cabin, Mathews
This rustic cabin is located in the trees on the back side of a large field, just one mile from two secluded beaches on the bay and a sandy boat launch in Mathews. The cabin has received excellent ratings for user experience, location, and cleanliness.
The cabin offers one bedroom and one bathroom, comfortably accommodating up to five guests. Enjoy off-grid living with solar power, well water, a composting bathroom, and a variety of amenities, activities, and features including a fire pit, outdoor shower, free bicycles, axe throwing, cornhole, kayak rentals, and Wi-Fi.
Cozy Home W/fenced In Yard-dog Friendly With Pet Fee. 2 Block Walk To Downtown! - Chesapeake Bay
9.8 76 reviews

Cozy Home W/fenced In Yard-dog Friendly With Pet Fee. 2 Block Walk To Downtown!

apartment, Havre de Grace
This centrally-located vacation home in Havre de Grace is within walking distance of Susquehanna Museum at the Lock House, Susquehanna River, and Harford Memorial Hospital. It has received excellent user ratings.
The house has 2 bedrooms, 1 bathroom, and a floor area of 1100 square feet. It can accommodate up to 3 guests. It features a private water park, barbecue grills, free WiFi, a sofa bed, a fireplace, a fully functional kitchen, and a smoke-free environment.
Ocean Sands Resort, Oceanfront, Virginia Beach By Vacatia - Chesapeake Bay
8.2 3004 reviews

Ocean Sands Resort, Oceanfront, Virginia Beach By Vacatia

resort, Virginia Beach
Ocean Sands Resort by VSA Resorts is located directly on the oceanfront in Virginia Beach, just a half-mile from the amusement park and one mile from the convention center. The resort has received very good user ratings, with an excellent location rating and very good cleanliness rating.
The resort offers a variety of accommodations, including suites with fully equipped kitchens. Guests can enjoy a seasonal restaurant, a gym, tanning facilities, a hot tub, sauna, massage services, a tennis court, and free parking.
Cottage 72 - Chesapeake Bay
9.2 80 reviews

Cottage 72

cottage, Virginia Beach
This family-friendly cottage is located in Virginia Beach, just a short walk from First Landing State Park, Atlantic University, and Edgar Cayce's Association for Research and Enlightenment. It has excellent user, location, and cleanliness ratings, making it a popular choice for travelers. This 1,500 square foot vacation rental is perfect for families, with three bedrooms and a sofa bed. Guests can enjoy the on-site spa, pool, barbecue grill, and garden, as well as the fully equipped kitchen and free Wi-Fi.

Frequently Asked Questions about vacation rentals in Chesapeake Bay

  • Which neighborhood in Baie de Chesapeake should you consider for a vacation rental?

    If you're looking for a charming and historic area, consider staying in Annapolis. It's the state capital of Maryland and has a lot to offer, including great restaurants, shops, and attractions. You can also find some beautiful waterfront vacation rentals in Annapolis.
  • What are the best Airbnb and vacation rentals in Chesapeake Bay?

    Gem In The Heart Of The Fan #1, Lovely Large Room By River In "Kingsmill On The James" and Beautiful 1-bdrm Carytown - Fan - Vmfa are the most popular Airbnb and vacation rentals in Chesapeake Bay among travelers.

  • What are the top family-friendly attractions in Baie de Chesapeake?

    The Maryland Science Center in Baltimore is a great place for kids of all ages. They have interactive exhibits, a planetarium, and an IMAX theater. Also, the National Aquarium in Baltimore is a must-see, with a variety of marine life, including sharks, dolphins, and sea turtles.
  • What are the most popular Airbnbs in Chesapeake Bay?

  • When is the best time to book a vacation rental in Baie de Chesapeake?

    The best time to book a vacation rental in Chesapeake Bay is in the spring or fall. The weather is mild and the crowds are smaller. If you're looking for a beach vacation, you might want to book in the summer, but be prepared for higher prices and more crowds.
  • What are the best vacation rentals with a pool in Chesapeake Bay?

  • What events or festivals should visitors check out in and around Baie de Chesapeake?

    The Annapolis Maritime Museum hosts the annual Annapolis Boat Show in October. It's a great place to see all kinds of boats and talk to experts about boating. Also, the Chesapeake Bay Wine Festival in Stevensville is a great event to enjoy the local wines.
  • What are the best rentals for families and kids in Chesapeake Bay?

  • What are the best budget-friendly activities in Baie de Chesapeake?

    You can enjoy a beautiful walk or bike ride along the Bay Trail, which runs for miles along the shores of the Chesapeake Bay. You can also visit one of the many state parks in the area, like Sandy Point State Park, which offers hiking, fishing, and camping.
  • What are the best rentals or Airbnbs with a jacuzzi in Chesapeake Bay?

  • What are the best restaurants with local dishes in Baie de Chesapeake?

    Try the Chesapeake Inn in Stevensville for their famous crab cakes. They're made with fresh, local crab meat and are a true taste of the Chesapeake Bay. You can also check out the Blackwall Hitch in Annapolis, which has a great selection of seafood and other Chesapeake Bay dishes.
  • What are the best walking or cycling routes in Baie de Chesapeake?

    The Bay Trail is a great option for walking or cycling. It runs for over 300 miles along the shores of the Chesapeake Bay, offering beautiful views and a chance to experience the natural beauty of the area. You can also find some great walking and cycling routes in the state parks, like Sandy Point State Park.
  • Are there pet-friendly attractions in Baie de Chesapeake?

    Many of the state parks in the area are pet-friendly, like Sandy Point State Park. You can also find many pet-friendly restaurants and shops in the area. Just be sure to check with individual businesses to see if they allow pets.
  • What are the benefits of choosing a vacation rental in Baie de Chesapeake?

    Vacation rentals offer more space and privacy than a hotel, and you can often find rentals that are pet-friendly. You can also find rentals in a variety of locations, from waterfront properties to those in the heart of town.

Popular destinations

Best Chesapeake Bay vacation rentals with parking

Bayberry - Awesome Solo Stove Fire Pit - Chesapeake Bay
9.8 80 reviews

Bayberry - Awesome Solo Stove Fire Pit

apartment, Kilmarnock
This charming cottage is located in Reedville, Virginia, just a short drive from the Northern Neck Wine Trail and the George Washington Birthplace National Monument. It offers a peaceful and private setting on a quiet street ending at the Chesapeake Bay, and has consistently received excellent ratings for location, cleanliness, and user experience.
The 3-bedroom, 1-bathroom cottage comfortably accommodates up to 6 guests. It includes a well-equipped kitchen, modern bathrooms, and a sunporch with a daybed and table, a deck, and a patio with a fire pit and Adirondack chairs. The cottage is perfect for families or groups looking to enjoy outdoor activities like boating, fishing, hiking, and exploring local wineries and historical sites.
Worlds Best Sunsets On Upper Chesapeake Bay -Crystal Beach Manor, Earleville,md - Chesapeake Bay
10 67 reviews

Worlds Best Sunsets On Upper Chesapeake Bay -Crystal Beach Manor, Earleville,md

apartment, Cecilton
This studio apartment is located in Earleville, a short drive from Cecilton and close to Mount Harmon Plantation, Concord Point Lighthouse, Elk Neck State Park, and Betterton Beach. It has received excellent user ratings, making it a popular choice for travelers.
The apartment has one bedroom and one bathroom, comfortably accommodating up to three guests. It features amenities like parking, Wi-Fi, an outdoor shower, central air, beach chairs, towels, sheets, a cooler, and free bags of ice, along with access to nearby hiking trails and a boat ramp.
Welcome To Our Newly Built House - Chesapeake Bay
8.7 23 reviews

Welcome To Our Newly Built House

house, Glen Burnie
This Glen Burnie house is conveniently located within a 12-mile radius of popular Baltimore attractions like the University of Maryland – Baltimore, Pier Six Concert Pavilion, Inner Harbor, and Historic Ships in Baltimore. This 4-bedroom, 3-bathroom house offers a comfortable stay for up to 19 guests with modern amenities including a fully equipped kitchen, free Wi-Fi, and private parking.
Choptank Coastal Cottage - Chesapeake Bay
9.9 64 reviews

Choptank Coastal Cottage

apartment, Cambridge
This recently renovated historic district apartment in Cambridge offers a prime location within walking distance of downtown dining, two blocks from the Choptank River and lighthouse, and near the Harriet Tubman mural. This residence accommodates up to six guests and features a gourmet kitchen with a double oven, two luxurious bathrooms with heated floors and a soaker tub, and a spa-like upstairs shower.

Check Out Vacation Rentals with a Pool in Chesapeake Bay

A vacation rental with a pool in Chesapeake Bay is the ideal way to complement your daily coastal adventures.

Kingsmill Resort - Chesapeake Bay
8.7 1302 reviews

Kingsmill Resort

resort, Williamsburg
Kingsmill Resort is located in Williamsburg, Virginia, just a short drive from Busch Gardens, Water Country, and the Colonial Williamsburg Historic Area. The resort has received very good ratings for user experience, location, and cleanliness.
The resort offers a variety of rooms and suites, some with full kitchens and living areas. Guests can enjoy a range of amenities, including two 18-hole golf courses, a spa, a fitness center, an indoor pool, and tennis courts.
Hilton Virginia Beach Oceanfront - Chesapeake Bay
8.3 3650 reviews

Hilton Virginia Beach Oceanfront

resort, Virginia Beach
The Hilton Virginia Beach Oceanfront is located directly on the Virginia Beach Oceanfront, just steps away from the boardwalk, the Shoppes at 31, and the Virginia Aquarium and Marine Science Center. The resort has received very good user ratings, with an excellent location rating and very good cleanliness rating.
The hotel offers a variety of amenities and activities including a rooftop infinity pool, a fitness center, and a spa. Guests can enjoy on-site dining at the Catch 31 restaurant and the Sky Bar, as well as room service and valet parking.
Pool Access! Cozy Couple's Getaway In Kilmarnock - Chesapeake Bay
No reviews

Pool Access! Cozy Couple's Getaway In Kilmarnock

apartment, Kilmarnock
This studio apartment in Kilmarnock is located 4 miles from Main Street and offers Chesapeake Bay views, with Williamsburg 61 miles away.
This 500 square foot studio features a kitchenette with a microwave and mini refrigerator, air conditioning, a shared outdoor pool, and parking, accommodating up to 2 guests.
Oceanfront Condo With Indoor Pool - Chesapeake Bay
9.4 139 reviews

Oceanfront Condo With Indoor Pool

apartment, Virginia Beach
This oceanfront Virginia Beach condo, directly on the boardwalk, offers unparalleled ocean views and easy access to the beach, shops, and restaurants.
The 2-bedroom, 2-bathroom unit sleeps six, features a fully equipped kitchen, in-unit laundry, high-speed Wi-Fi, assigned parking (6'4" height max), and access to a year-round indoor pool and fitness center.

Find the Best Seaside Vacation Rentals in Chesapeake Bay

Relax near the shore in these coastal Chesapeake Bay vacation rentals, combining comfortable amenities with beautiful seaside scenery just moments away.

Egrets Point On The Creek - Chesapeake Bay
10 117 reviews

Egrets Point On The Creek

apartment, Onancock
Unique Tangier Cottage W/ Chesapeake Bay Views! - Chesapeake Bay
10 2 reviews

Unique Tangier Cottage W/ Chesapeake Bay Views!

house, Tangier
Idle Hour 3 Br 1 1/2 B W/ Golf Cart Rental - Chesapeake Bay
10 86 reviews

Idle Hour 3 Br 1 1/2 B W/ Golf Cart Rental

apartment, Smith Island
Tiny House At St. George Island - Chesapeake Bay
8.4 5 reviews

Tiny House At St. George Island

cottage, Piney Point

Compare Luxury Vacation Rentals in Chesapeake Bay

Refined interiors and prime locations make these luxury waterfront vacation rentals in Chesapeake Bay the ideal choice for your stay.

Ocean Key Resort - Chesapeake Bay
9.0 11 reviews

Ocean Key Resort

resort, Virginia Beach

Discover Vacation Rentals with Saunas in Chesapeake Bay

Maximize your wellness with vacation rentals in Chesapeake Bay featuring on-site saunas and steam rooms.

Waterfront | Swim Spa + Sauna + Beach + Game Room - Chesapeake Bay
10 21 reviews

Waterfront | Swim Spa + Sauna + Beach + Game Room

apartment
Oasis By The Bay - Waterfront Heated Pool Hot Tub! - Chesapeake Bay
8.8 6 reviews

Oasis By The Bay - Waterfront Heated Pool Hot Tub!

apartment, Highland Beach
Long Beach Wellness Retreat Hot Tub/sauna/plunge - Chesapeake Bay
10 6 reviews

Long Beach Wellness Retreat Hot Tub/sauna/plunge

apartment, Charlestown
Bayhamas ️️ Beachfront Home 3 Bedrooms-private-white Stone- Sauna-dock - Chesapeake Bay
8.8 20 reviews

Bayhamas ️️ Beachfront Home 3 Bedrooms-private-white Stone- Sauna-dock

apartment, White Stone
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