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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

Walk To Parks & Marina! Waterfront Cambridge Condo - Chesapeake Bay
No reviews

Walk To Parks & Marina! Waterfront Cambridge Condo

house, Cambridge
This waterfront condo in Cambridge offers a prime location with walking access to local parks and the marina, situated 16 miles from the Academy of the Arts and 22 miles from Federalsburg Marina.
This 800-square-foot apartment accommodates up to 11 guests and features air conditioning, a private patio, high-speed Wi-Fi, a full kitchen with an oven and microwave, and an outdoor dining area.
Waterfront Home With Boat Dock & Study - Chesapeake Bay
10 1 review

Waterfront Home With Boat Dock & Study

house, Irvington
Waterfront Home With Boat Dock & Study is located in Weems, just a short drive from Irvington, a charming town on the Northern Neck of Virginia. The home offers stunning views and direct access to the water, perfect for fishing, kayaking, or simply relaxing by the water's edge.
The 2,000 square foot house is perfect for families or groups of up to 6 people. Enjoy the convenience of a fully equipped kitchen, a private garden and terrace, a fireplace, and free Wi-Fi.
'River's Edge Retreat’ With Kayaks & River Access! - Chesapeake Bay
9.6 118 reviews

'River's Edge Retreat’ With Kayaks & River Access!

house, Heathsville
This waterfront vacation home in Heathsville is within 6 miles (10 kilometers) of Northern Neck Farm Museum, Reedville Fishermen's Museum, and Buzzard's Point Marina. It has excellent user, location, and cleanliness ratings.
The 3800-square-foot home has 5 bedrooms and can accommodate up to 12 guests. It features an arcade/game room, an outdoor garden, charcoal grills, a fully equipped kitchen, a DVD player, and a fireplace.
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.

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.

Updated North Beach Cottage: Pet Friendly! - Chesapeake Bay
9.6 77 reviews

Updated North Beach Cottage: Pet Friendly!

house, North Beach
This pet-friendly cottage is located in Deale, a short drive from North Beach, offering easy access to both the vibrant city of Annapolis and the quieter charm of North Beach. Guests consistently rate the property excellent for its cleanliness, location, and overall experience.
The 3-bedroom, 2-bathroom home comfortably accommodates up to 8 guests with 1440 square feet of living space. Amenities include a fully equipped kitchen, air conditioning, a private patio, a swimming pool, a garden, and a spa, making it a perfect choice for families and groups seeking a relaxing getaway.
Sojourn's Harborage | Pet-friendly - Chesapeake Bay
8.0 2 reviews

Sojourn's Harborage | Pet-friendly

apartment, Norfolk
This East Ocean View rental is less than half a mile from Norfolk Beaches and within easy driving distance of Community Beach and Ocean View Beach.
The 800-square-foot apartment features one bedroom, one bathroom, sleeps two, includes a fully equipped kitchen, in-unit laundry, a private balcony, free parking, and complimentary Wi-Fi.
Modern 2nd-story Studio Apartment - Chesapeake Bay
10 193 reviews

Modern 2nd-story Studio Apartment

apartment, Accomac
This 1-bedroom vacation home is located in a residential neighborhood in Accomac, within a short driving distance from popular destinations such as the Eastern Shore Railway Museum, Hang Glide Virginia, and North Street Playhouse, making it ideal for travelers seeking proximity to attractions. The house has received excellent feedback on user reviews, location, and cleanliness.
The vacation home can accommodate up to six guests and provides a private garden with outdoor dining space and a patio, a modern kitchen, a Smart TV, a washer, and a dryer. Free WiFi and parking on the property are also offered, ensuring a seamless and comfortable stay during your trip to Accomac.
Holiday Inn Club Vacations Williamsburg Resort - Chesapeake Bay
9.0 1071 reviews

Holiday Inn Club Vacations Williamsburg Resort

resort, Williamsburg
The Holiday Inn Club Vacations Williamsburg Resort, An Ihg Hotel, is conveniently located near the Cedar Valley Shopping Center and Williamsburg Marketcenter, about 6 miles from Camp Peary and within 12 miles of Water Country USA and Busch Gardens amusement park. Guests have rated the resort highly, particularly for its excellent location, very good cleanliness, and very good overall experience.
The resort offers spacious one-bedroom villas with fully equipped kitchens, fireplaces, balconies, and modern amenities like cable TV, DVD players, and free Wi-Fi. Guests can enjoy the outdoor pool, gym, concierge service, BBQ facilities, and a relaxing atmosphere.

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

Cozy Haven In Hampton Roads Near Beaches, Military Bases & Historic Sites - Chesapeake Bay
9.8 15 reviews

Cozy Haven In Hampton Roads Near Beaches, Military Bases & Historic Sites

house, Hampton
This Hampton vacation rental is conveniently located near the Virginia Living Museum (11 miles) and Newport News/Williamsburg International Airport (12 miles).
The 110-square-foot home features two bedrooms, one bathroom, and accommodates up to 11 guests, offering free Wi-Fi, parking, and a fully equipped kitchen.
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.
Affordable Luxuryhome Near Stadiums. - Chesapeake Bay
9.5 505 reviews

Affordable Luxuryhome Near Stadiums.

house, Baltimore
This Baltimore vacation rental is located in Pigtown, a lively neighborhood just a short walk from the Charm'tastic Mile shopping district, Oriole Park at Camden Yards, and M&T Bank Stadium. The house consistently receives excellent ratings for location, cleanliness, and overall user experience.
This 2-bedroom home comfortably sleeps 5 guests and features a fully equipped kitchen, two bathrooms, a washer and dryer, and a smart TV. Enjoy outdoor grilling, a private garden, and easy access to public transportation.
The Atrium Resort, Virginia Beach By Vacatia - Chesapeake Bay
8.0 2797 reviews

The Atrium Resort, Virginia Beach By Vacatia

resort, Virginia Beach
The Atrium Resort by VSA Resorts is located just a 2-minute walk from the Virginia Beach Boardwalk, placing you right in the middle of the action with easy access to the beach, restaurants, and entertainment. The resort consistently receives very good ratings for its location, cleanliness, and overall user experience.
The resort offers spacious suites with fully equipped kitchens and living rooms, perfect for families or groups. Guests can enjoy amenities such as an indoor pool, hot tub, fitness center, and free Wi-Fi, ensuring a comfortable and enjoyable stay.

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.

Elegant Family Cottage In Gated Area  Close To Busch Gardens & More - Chesapeake Bay
10 1 review

Elegant Family Cottage In Gated Area Close To Busch Gardens & More

resort, Williamsburg
This resort in Williamsburg offers the "Elegant Family Cottage In Gated Area Close To Busch Gardens & More," providing a prime location minutes from Busch Gardens and Colonial Williamsburg, with easy access to Water Country USA and Historic Jamestowne, and is near Newport News/Williamsburg Airport.
This family-friendly accommodation features 500 sq. ft. cottages with 2 bedrooms and 2 bathrooms to accommodate up to 6 guests, offering amenities like a kitchenette, air conditioning, a swimming pool, fitness center, garden, tennis, miniature golf, saunas, daily cleaning, and free parking.
Kings Creek Plantation By Tripforth - Chesapeake Bay
9.2 834 reviews

Kings Creek Plantation By Tripforth

house, Williamsburg
King's Creek Resort by Endless Resorts is located in Williamsburg, just a short drive from popular attractions like Busch Gardens, Water Country USA, and Colonial Williamsburg. The resort has earned excellent ratings for its location, cleanliness, and overall guest experience.
The resort offers a variety of accommodations, including rooms, suites, and villas. Guests can enjoy a range of amenities, including an outdoor pool, a fitness center, a restaurant, a spa, a tennis court, and a playground.
Virginia Beach Oceanfront Studio, Boardwalk, Beach, Pool - Chesapeake Bay
9.8 65 reviews

Virginia Beach Oceanfront Studio, Boardwalk, Beach, Pool

studio, Virginia Beach
This Virginia Beach apartment is located just steps from Resort Beach and the Virginia Beach Boardwalk, putting you right in the heart of the action. With an excellent user rating, you can be sure you'll have a comfortable and enjoyable stay.
The apartment offers a 300 square foot space with a fully equipped kitchen, in-unit laundry, and a private patio. Enjoy amenities like an outdoor pool, free Wi-Fi, and parking, making your beach getaway even more relaxing.
Walk To Dtwn! Waterfront 3br Cambridge Townhome - Chesapeake Bay
No reviews

Walk To Dtwn! Waterfront 3br Cambridge Townhome

house, Cambridge
This Cambridge townhome is located less than 5280 feet from the downtown waterfront area.
The 1800 square foot residence offers 3 bedrooms, 4 bathrooms, air conditioning, a fully equipped kitchen, a swimming pool, and parking for up to 11 guests, with check-out at 10:00 AM.

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.

Bayside Bliss At Cape Charles - New Home In Bay Creek W Pool & More! - Chesapeake Bay
No reviews

Bayside Bliss At Cape Charles - New Home In Bay Creek W Pool & More!

house, Cheriton
The Glick - Short Stays On Market - Chesapeake Bay
10 2 reviews

The Glick - Short Stays On Market

apartment, Onancock
Cambridge Apt In Walkable Neighborhood - Chesapeake Bay
8.0 4 reviews

Cambridge Apt In Walkable Neighborhood

apartment, Cambridge
Oceanfront Condo With Indoor Pool - Chesapeake Bay
9.4 142 reviews

Oceanfront Condo With Indoor Pool

apartment, Virginia Beach

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.

Guest Suite For Up To 2 In A Victorian On The Chester River - Chesapeake Bay
9.8 27 reviews

Guest Suite For Up To 2 In A Victorian On The Chester River

apartment, Millington

Discover Vacation Rentals with Saunas in Chesapeake Bay

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

St. Michaels Estate Offers Waterfront Pool, Pier, Dock And 15 Acs Pet Friendly - Chesapeake Bay
9.8 43 reviews

St. Michaels Estate Offers Waterfront Pool, Pier, Dock And 15 Acs Pet Friendly

apartment, Tilghman Island
Bayhamas Beachfront 3 Bedroom-home-sauna-dock - Chesapeake Bay
9.7 92 reviews

Bayhamas Beachfront 3 Bedroom-home-sauna-dock

apartment, White Stone
On Beach 5bd+7ba: Sauna|hottub|billards|fenceddeck - Chesapeake Bay
No reviews

On Beach 5bd+7ba: Sauna|hottub|billards|fenceddeck

apartment, Norfolk
Mai Villa-hampton - Where Good Times Happen! - Chesapeake Bay
9.8 50 reviews

Mai Villa-hampton - Where Good Times Happen!

apartment, Hampton
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