Compare Vacation Rentals & Airbnb in Chesapeake Bay

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Chesapeake Bay vacation rentals
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9615 Rentals and Airbnb in Chesapeake Bay

Best family friendly Chesapeake Bay vacation rentals

Among the 9615 accommodations in Chesapeake Bay, here are the 4 best family friendly rentals

Relax & Renew In A Waterfront Cottage , Private Pier, Kayaks, Fishing, Wineries. - Chesapeake Bay
10 71 reviews

Relax & Renew In A Waterfront Cottage , Private Pier, Kayaks, Fishing, Wineries.

cottage, Heathsville
This three-bedroom Heathsville waterfront cottage, ideal for families, is centrally located in Lottsburg, offering easy access (within a few kilometres) to marinas, breweries, antique shops, and wineries on the Chesapeake Bay Wine Trail, plus Bush Mill Stream Natural Area Preserve and Sandy Point Beach.
Sleeping up to nine guests, this self-catering holiday home boasts a fully equipped kitchen (fridge, microwave, dishwasher), air conditioning, a garden, tennis court, parking, internet access, and two bathrooms; enjoy water views and proximity to the Kinsale Museum and Northern Neck Farm Museum.
Ocean Sands Resort, Oceanfront, Virginia Beach By Vacatia - Chesapeake Bay
8.2 2981 reviews

Ocean Sands Resort, Oceanfront, Virginia Beach By Vacatia

resort, Virginia Beach
Ocean Sands Resort by VSA Resorts is situated on the oceanfront in Virginia Beach, just half a mile from the amusement park and one mile from the convention centre. The resort consistently receives excellent ratings for its location and cleanliness, as well as very good reviews for its overall experience.
The resort offers a range of self-catering suites with Caribbean-style decor, each with a private balcony or terrace. Guests have access to a variety of on-site amenities, including a swimming pool, hot tub, sauna, fitness centre, tennis court, restaurant, bar, and spa, ensuring a relaxing and enjoyable stay.
Apartment ∙ 3 Bedrooms ∙ 10 Guests - Chesapeake Bay
No reviews

Apartment ∙ 3 Bedrooms ∙ 10 Guests

apartment, Chesapeake Ranch Estates
This Lusby flat is situated in Chesapeake Ranch Estates, offering a peaceful retreat with easy access to local amenities and the Chesapeake Bay beaches, approximately 1.5 kilometres away.
This family-friendly property sleeps up to 10 guests across three bedrooms and two bathrooms, featuring a fully equipped kitchen, air conditioning, a terrace, garden, and parking, with an open-concept living area ideal for gatherings.
The Atrium Resort, Virginia Beach By Vacatia - Chesapeake Bay
8.1 2726 reviews

The Atrium Resort, Virginia Beach By Vacatia

resort, Virginia Beach
The Atrium Resort by VSA Resorts is located directly on the Virginia Beach Boardwalk, just a short walk from the beach and a couple of minutes' drive from attractions like Jungle Golf and the Old Coast Guard Station Museum. The resort has consistently received very good ratings for its location, cleanliness, and overall experience.
The accommodation offers spacious suites with full kitchens and living rooms, ideal for families or groups. Guests can enjoy a range of facilities, including a swimming pool, hot tub, fitness centre, and free Wi-Fi.

Best Chesapeake Bay vacation rentals with a pool

Among the 9615 accommodations in Chesapeake Bay, here are the 4 best rentals with a pool

Waterfront Cambridge Gem W/ Hot Tub, Pool & Dock! - Chesapeake Bay
No reviews

Waterfront Cambridge Gem W/ Hot Tub, Pool & Dock!

house, Madison
This seven-bedroom waterfront property is situated in Woolford, Maryland, approximately 43 kilometres from the Academy of the Arts and 79 kilometres from Salisbury-Ocean City Wicomico Regional Airport.
This luxurious 960-square-metre house, boasting a private dock, swimming pool, jacuzzi, and bar, comfortably accommodates 53 guests and offers free bicycle use for exploring the local area.
The Cottage @ Captain Genes - Secluded Waterfront - Chesapeake Bay
9.9 158 reviews

The Cottage @ Captain Genes - Secluded Waterfront

apartment, Mathews
This luxurious waterfront cottage is located on a private 5-acre property in Mathews County, just 8 kilometres from the centre of Mathews and 6.5 kilometres from a marina. It enjoys excellent guest ratings for its location, cleanliness and overall experience.
The cottage offers 131 square metres of living space, with three bedrooms and a capacity for six guests. Enjoy the private dock and kayak launch, hot tub, swimming pool, and numerous other amenities, including a fully equipped kitchen, a fire pit, and a screened porch.
Jewel Of The Tred Avon - Chesapeake Bay
No reviews

Jewel Of The Tred Avon

house, Oxford
This large Oxford residence, Jewel of the Tred Avon, is situated 20.9 kilometres from the Academy Of The Arts.
This expansive property offers accommodation for 19 guests across 632 square metres, featuring air conditioning, a private swimming pool, a garden, a fitness centre, and parking, with complimentary high-speed Wi-Fi available throughout.
Holiday Inn Express Annapolis East-kent Island By Ihg - Chesapeake Bay
9.2 1250 reviews

Holiday Inn Express Annapolis East-kent Island By Ihg

resort, Kent Narrows
The Holiday Inn Express Annapolis East-Kent Island is situated in Grasonville, just 20 miles from Annapolis Harbor and 30 miles from Baltimore-Washington International Airport, offering easy access to both bustling city life and the tranquil beauty of Kent Narrows. The hotel has received very good user ratings for cleanliness and an excellent rating for its location.
The hotel features 25 square metre rooms with one bedroom and one bathroom, each with a range of modern amenities. Guests can enjoy a variety of activities, including swimming in the seasonal outdoor pool, relaxing in the garden, and dining at the on-site restaurant and bar, as well as taking advantage of the fitness centre and tennis court.

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 great location for a vacation rental, I'd recommend Ocean City. It's a lively seaside town with plenty of shops, restaurants, and attractions. You'll find a wide range of rental options, from cosy beach houses to spacious apartments, to suit your group size and budget.
  • 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?

    For family fun, you can't beat the National Aquarium in Baltimore. It's home to a wide variety of marine life, including sharks, dolphins, and sea turtles. Another great option is the Maryland Science Center, which has interactive exhibits and a planetarium. And for a day of outdoor adventure, head to Assateague Island National Seashore, where you can spot wild horses roaming the beach.
  • What are the most popular Airbnbs in Chesapeake Bay?

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

    To get the best deals and avoid the crowds, it's best to book your vacation rental in the shoulder seasons, like spring or autumn. The weather is still pleasant, but the prices are lower and the crowds are smaller. If you're looking for a summer getaway, book your rental well in advance, as they tend to sell out quickly.
  • 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?

    There are lots of great events to check out in the area, but one of my favourites is the Annapolis Maritime Museum's OysterFest in October. It's a celebration of all things oyster, with live music, food stalls, and oyster shucking competitions. You can also check out the annual Maryland Seafood Festival, which takes place in October in Crisfield. It's a huge festival with a focus on fresh seafood and local culture.
  • What are the best rentals for families and kids in Chesapeake Bay?

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

    For a budget-friendly day out, head to the Chesapeake Bay Maritime Museum in St. Michaels. It's a great place to learn about the history of the Bay and see historic boats. You can also explore the many parks and nature trails in the area, which are free to access. For a unique experience, take a free ferry ride to Tilghman Island, which is known for its beautiful scenery and charming shops.
  • 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?

    For a taste of local cuisine, you should try the Chesapeake Inn in Stevensville. They're famous for their crab cakes, which are made with fresh, local crab meat. Another great option is The Chart House in Annapolis, which has stunning views of the Bay and a menu featuring fresh seafood dishes. You'll also find plenty of casual seafood restaurants along the waterfront, where you can enjoy a delicious meal with a view.
  • What are the best walking or cycling routes in Baie de Chesapeake?

    For a scenic walk or bike ride, check out the Bay Trail, which stretches for over 300 kilometres along the shores of the Chesapeake Bay. There are several sections of the trail, so you can choose a route that suits your fitness level and interests. Another great option is the Annapolis Loop Trail, which takes you through the historic streets of Annapolis and along the waterfront. You can also find plenty of shorter trails in local parks and nature reserves.
  • Are there pet-friendly attractions in Baie de Chesapeake?

    Yes, there are plenty of pet-friendly attractions in the area. Many of the beaches allow dogs, and there are also several dog parks where your furry friend can run and play. You can also find pet-friendly restaurants and cafes, where you can enjoy a meal with your dog. For a fun day out, check out the Chesapeake Bay Maritime Museum, which welcomes well-behaved dogs on a leash.
  • What are the benefits of choosing a vacation rental in Baie de Chesapeake?

    Vacation rentals offer a great deal of flexibility and privacy, as you have your own space to relax and unwind. They're also often more spacious and affordable than hotels, especially if you're travelling with a large group or family. Many rentals also have kitchens, which allow you to prepare your own meals and save money on dining out.
  • What are the top sports attractions and facilities in Baie de Chesapeake?

    The Chesapeake Bay area is a great place for sports enthusiasts. You can enjoy water sports like sailing, kayaking, and fishing. There are also several golf courses in the area, including the renowned Bayside Resort Golf Club. For a unique sporting experience, check out the US Naval Academy in Annapolis, which offers tours of its athletic facilities and events.

Popular destinations

Best Chesapeake Bay vacation rentals with a balcony

Beautiful Private Double Bed Guest Room /Full Bath - Chesapeake Bay
9.6 187 reviews

Beautiful Private Double Bed Guest Room /Full Bath

apartment, Williamsburg
This apartment is situated in Kingsmill, just 0.3 kilometres from the Kingsmill Plantation Golf Course and 2.6 kilometres from Busch Gardens Williamsburg, offering a convenient location close to popular attractions. The property has received excellent ratings for location, cleanliness, and overall user experience.
The apartment has two bedrooms, providing ample space for families or groups of friends, and covers 117 square metres. It offers a range of amenities, including a swimming pool, jacuzzi, terrace, and garden, as well as a fully equipped kitchen, internet access, and parking.
Family-friendly Home In Baltimore With Wifi, Ac, Pool Table, Washer & Dryer - Chesapeake Bay
9.0 9 reviews

Family-friendly Home In Baltimore With Wifi, Ac, Pool Table, Washer & Dryer

apartment, Baltimore
This Berea property is conveniently located 2.4km from Johns Hopkins Hospital and 1.8km from the Maryland Institute College of Art, offering easy access to both medical facilities and cultural attractions.
This two-bedroom, two-bathroom house sleeps four guests and features a fully equipped kitchen, free Wi-Fi, on-site parking, and a family-friendly playground nearby, making it ideal for families visiting Baltimore.
Refreshed 2025 | Beach House By Boardwalk (410a) - Chesapeake Bay
9.4 188 reviews

Refreshed 2025 | Beach House By Boardwalk (410a)

house, Virginia Beach
This charming house is located in Northeast Virginia Beach, just a short walk from the beach, boardwalk and Pacific Avenue. The property has received excellent ratings for location, cleanliness and user experience.
The house has two bedrooms and is 121 square metres in size. Guests can enjoy a range of amenities including a swimming pool, spa, fitness centre, restaurant and concierge service.
❤️Charming Coastal/country Home W/3 Acres & Sauna!❤️ - Chesapeake Bay
9.0 3 reviews

❤️Charming Coastal/country Home W/3 Acres & Sauna!❤️

house, Stevensville
This detached house in Stevensville is located 2.7 kilometres from Matapeake Beach and 27 kilometres from Annapolis Harbour.
This spacious 232 square metre property offers four bedrooms, three bathrooms, a garden, sauna, and private parking, accommodating up to 27 guests.

Best Chesapeake Bay vacation rentals with parking

Peace Point - Waterfront, Secluded, Home W/hot Tub - Chesapeake Bay
10 135 reviews

Peace Point - Waterfront, Secluded, Home W/hot Tub

apartment, Piney Point
This secluded apartment is situated on a private wooded creek off the Chesapeake Bay in Piney Point, approximately 0.5 kilometres from the water's edge, offering complete peace and quiet. The apartment boasts excellent user, location and cleanliness ratings.
The apartment has three bedrooms and two bathrooms, comfortably accommodating up to six guests. Enjoy the large deck with a propane grill, unwind in the hammock, or play corn hole, and relax in the hot tub with waterfront views, all while taking in the breathtaking scenery.
Retro Relaxo - Chesapeake Bay
10 30 reviews

Retro Relaxo

apartment, Onancock
This waterfront apartment in Onancock, Virginia offers easy access to local shops and restaurants, its precise location within the town centre unspecified.
The two-bedroom, one-bathroom flat sleeps four guests, boasting a full kitchen, laundry facilities, private dock, fire pit, and an enclosed breezeway; a deck is under construction.
Lakefront Lusby Home W/ Fire Pit: 3 Mi To Beach! - Chesapeake Bay
10 1 review

Lakefront Lusby Home W/ Fire Pit: 3 Mi To Beach!

house, Chesapeake Ranch Estates
This Lusby lakefront property in Chesapeake Ranch Estates is located 4.8km from the beach and 8.8km from the Calvert Marine Museum, offering easy access to local attractions.
This two-bedroom, two-bathroom house boasts 204 square metres of floor space, sleeps 19 guests, includes a fully equipped kitchen, bar, garden, parking, and air conditioning, perfect for a relaxing Chesapeake Bay getaway.
Citystay - Chesapeake Bay
9.0 4 reviews

Citystay

house, Baltimore
CityStay, a detached house in Baltimore, is located between 2.1 and 2.7 kilometres from Fell's Point, the Power Plant, and the Historic Ships.
This non-smoking dwelling offers air conditioning, complimentary WiFi, a fully equipped kitchen, and private balcony, accommodating up to eleven guests across two bedrooms and four bathrooms.