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

Westgate Historic Williamsburg Resort - Chesapeake Bay
8.7 1788 reviews

Westgate Historic Williamsburg Resort

resort, Williamsburg
The Westgate Historic Williamsburg Resort is conveniently located in Williamsburg, Virginia, just a short distance from Busch Gardens and the historic district. The resort has consistently received very good ratings for its location, cleanliness, and overall experience.
The resort offers a range of accommodation options, from comfortable rooms to spacious suites, all with modern amenities. Guests can enjoy a variety of facilities, including a swimming pool, fitness centre, tennis court, and a restaurant and bar.
Ocean Sands Resort, Oceanfront, Virginia Beach By Vacatia - Chesapeake Bay
8.2 3008 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.
Kings Creek Plantation By Tripforth - Chesapeake Bay
9.2 833 reviews

Kings Creek Plantation By Tripforth

house, Williamsburg
King's Creek Resort By Endless Resorts is conveniently located just outside Williamsburg's historic district, offering easy access to both theme parks and the historic landmarks of Colonial Williamsburg, which is just 7.2 miles away. The resort has received excellent ratings for its location, cleanliness and overall user experience.
The resort offers a range of accommodation options, including rooms and suites. Guests can enjoy amenities such as a swimming pool, fitness centre, restaurant and spa, as well as activities like mini-golf and a playground for families.
* Private Suite Full Of Style & Comfort * - Chesapeake Bay
9.0 48 reviews

* Private Suite Full Of Style & Comfort *

apartment, Lutherville
This one-bedroom apartment is situated in Lutherville Timonium, just 5km from Goucher College, Loch Raven Reservoir, and Towson Town Center, offering easy access to a range of attractions and amenities. It has received excellent user ratings, indicating a high level of satisfaction from previous guests.
The apartment comfortably accommodates up to four guests and features a fully equipped kitchen, a washing machine, a terrace, a garden, and parking. Enjoy a relaxing stay with access to a range of amenities, including a Smart TV, DVD player, and air conditioning.

Best Chesapeake Bay vacation rentals with a pool

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

Ocean Key Resort - Chesapeake Bay
9.0 11 reviews

Ocean Key Resort

resort, Virginia Beach
Ocean Key Resort, a 3-star hotel in Virginia Beach, is located in a district offering ocean views and potential for integrated balconies or terraces, suggesting proximity to the coast. This family-friendly accommodation provides rooms with separate living areas, in-room entertainment, air conditioning and laundry service in select rooms, alongside a swimming pool, restaurant, bar, fitness centre, room service, and parking.
Holiday Inn Express Annapolis East-kent Island By Ihg - Chesapeake Bay
9.2 1256 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.
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, approximately 42 miles from Newport News/Williamsburg International Airport. The cottage has received excellent ratings for its location, cleanliness, and overall user experience.
This self-catering property has a separate bedroom and a private patio, perfect for enjoying the fresh air. The cottage also offers a terrace, air conditioning, free Wi-Fi, and a fully equipped kitchen with a microwave and fridge.
Chesapeake Bay Beach House With Pool And Hot Tub - Chesapeake Bay
10 95 reviews

Chesapeake Bay Beach House With Pool And Hot Tub

apartment, Mayo
This three-bedroom house in Mayo is a two-minute walk from Beverly Beach, a playground, and a 340-acre nature park in a quiet Chesapeake Bay beach community.
The property boasts a large kitchen, family room with gas fireplace, private pool (open mid-May to mid-October), hot tub, and Trex deck, comfortably accommodating four guests and offering key code access.

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

The Tides Inn - Chesapeake Bay
8.9 391 reviews

The Tides Inn

resort, Irvington
The Tides Inn is located in West Irvington, a short distance from the charming downtown area and within easy reach of the scenic Chesapeake Bay. The resort has received very good user ratings, with excellent reviews for its location and cleanliness.
The hotel offers a range of amenities and activities, including a swimming pool, fitness centre, tennis court, restaurant, and bar. Guests can also enjoy the peaceful garden setting or explore the area on complimentary bikes.
Sojourn's Chic Bungalow < 10 Min. Stroll To Beach - Chesapeake Bay
9.2 19 reviews

Sojourn's Chic Bungalow < 10 Min. Stroll To Beach

apartment, Norfolk
This Norfolk apartment, situated in the East Ocean View district, is less than 0.8km from Norfolk Beaches and within 4.8km of Little Creek Beach and Ocean View Beach.
This 74 square metre self-catering flat offers two bedrooms, one bathroom, sleeps four, and includes a private balcony, free Wi-Fi, on-site parking, and a fully equipped kitchen.
Rodo Beach Cottage - Dog Friendly Private Beach Wi - Chesapeake Bay
9.9 70 reviews

Rodo Beach Cottage - Dog Friendly Private Beach Wi

apartment, Piney Point
This charming cottage is located in Piney Point, Maryland, just a short distance from the Chesapeake Bay. It benefits from excellent user, location and cleanliness ratings.
The cottage has three bedrooms, accommodating up to eight guests, and offers a range of amenities, including private beach access, a fishing pier, kayaks and stand-up paddle boards, a Tesla charger, and contactless check-in.
Charming Annapolis Water View Home - Chesapeake Bay
9.7 270 reviews

Charming Annapolis Water View Home

apartment, Highland Beach
This charming Annapolis home is located on Chestnut Avenue, just 45 metres from the Chesapeake Bay, offering stunning water views and easy access to the beautiful Thomas Point and Quiet Waters parks. The property has consistently received excellent ratings for location, cleanliness, and overall user experience.
This spacious four-bedroom house, spanning 279 square metres, comfortably accommodates up to 14 guests. The property offers a range of amenities, including a fully equipped kitchen, a Jacuzzi, a terrace, a garden, a spa, and parking, as well as access to a community beach, fishing piers, and crabbing facilities.

Best Chesapeake Bay vacation rentals with parking

Club Wyndham Kingsgate - Chesapeake Bay
8.9 4305 reviews

Club Wyndham Kingsgate

resort, Williamsburg
Club Wyndham Kingsgate is located in Williamsburg, less than a kilometre from the historic area, making it a great base for exploring the town's rich history. This 3-star hotel has consistently received very good user ratings, suggesting a comfortable and enjoyable stay.
The hotel offers a range of amenities and activities, including a swimming pool, jacuzzi, and tennis court, making it suitable for families and those seeking relaxation. Guests can also enjoy a restaurant, bar, and fitness centre, ensuring a convenient and enjoyable stay.
Patriots Inn - Chesapeake Bay
9.2 2019 reviews

Patriots Inn

resort, Williamsburg
Patriots Inn is located in Williamsburg, just a short drive from both the College of William & Mary and Colonial Williamsburg, making it an ideal base for exploring this historic city. The resort has consistently received excellent reviews from guests for its location, cleanliness, and overall experience.
Each room offers comfortable accommodation with air conditioning, a flat-screen TV, and a private bathroom. The resort also features a swimming pool, Jacuzzi, fitness centre, and free parking, ensuring a relaxing and enjoyable stay for guests.
Gorgeous Studio Apt. In Historic Chapel W/ Parking - Chesapeake Bay
9.9 416 reviews

Gorgeous Studio Apt. In Historic Chapel W/ Parking

church, Baltimore
This Baltimore studio apartment, situated in a renovated church building, offers convenient street-level access via smart lock and is within easy reach of Baltimore's major attractions, though precise distances aren't specified.
The self-catering unit features a fully equipped kitchenette, a 55" smart TV, luxurious down feather bedding, and a stunning stone tile rain shower; sleeping two guests, it may also offer access to a chapel space (subject to availability), and includes a free bike for exploring the city.
The Atrium Resort, Virginia Beach By Vacatia - Chesapeake Bay
8.1 2793 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.
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