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Best Vacation rentals and Airbnb offers in Chesapeake Bay
10 2 reviews
Chesapeake Bay
06/20 – 06/27
$232/nighttotal: $1624 (7 )
Baltimore Vacation Rental - Near Jhu & Art Museum!
3 2
house , Baltimore
This Baltimore vacation rental is located just 2.1 miles from Clifton Park and within a 4.5-mile radius of major attractions like the Baltimore Museum of Art, Johns Hopkins University, and the Walters Art Museum, offering easy access to both the city's cultural highlights and its green spaces. This 3-bedroom house provides ample space for families or groups of friends, accommodating up to 6 guests comfortably in its 1840 square feet of living space. The house features modern amenities like free Wi-Fi, a cable flat-screen TV, a washing machine, and a fully equipped kitchen with an oven and microwave, making it a convenient and comfortable base for exploring Baltimore.
9.7 275 reviews
Chesapeake Bay
09/12 – 09/16
$237/nighttotal: $948 (4 )
Waterfront Solomons Island Art Cottage
1 2
bungalow , Solomons
This waterfront cottage sits on Solomons Island, Maryland, a short walk from Solomons' restaurants and bars. The one-bedroom, one-bathroom house sleeps two, features a full kitchen with dishwasher and microwave, laundry facilities, kayaks for exploring Back Creek and the Patuxent River, and offers stunning sunset views over the Patuxent River.
9.6 51 reviews
Chesapeake Bay
07/20 – 07/27
$172/nighttotal: $1204 (7 )
Private Riverfront Retreat
1 4
apartment , Montross
This Montross residence offers a tranquil riverside setting with a private dock featuring running water and electricity, located a 30-mile drive from Westmoreland State Park and 40 miles from Colonial Beach. This 3-bedroom, 2-bathroom apartment accommodates up to 7 guests and includes a full kitchen, air conditioning, internet, and outdoor amenities like a garden and fire pit, with opportunities for kayaking and crabbing.
8.9 3945 reviews
Chesapeake Bay
07/20 – 07/27
$141/nighttotal: $987 (7 )
Hilton Vacation Club Greensprings Williamsburg
2 4
resort , Williamsburg
Greensprings Vacation Resort is located near the Green Springs National Historic Landmark District in Williamsburg, making it easy to explore the area's rich history. The resort has received very good ratings for user experience, location, and cleanliness. The resort offers spacious, condo-style accommodations with fully equipped kitchens, fireplaces, and laundry facilities. Guests can enjoy amenities like a swimming pool, a Jacuzzi, a fitness center, a tennis court, and a restaurant, as well as access to the Williamsburg National Golf Course.
10 12 reviews
Chesapeake Bay
09/12 – 09/16
$690/nighttotal: $2760 (4 )
Family Retreat At Lansdowne Manor
4 2
farm , Centreville
This Centreville farm stay, a 3,500-square-foot rural rental, is conveniently located within 9-12 miles of attractions like the Hazel Miner Monument, Tuckahoe State Park, Adkins Arboretum, Church Hill Theatre, and Cassinelli Winery and Vineyards. The four-bedroom, three-bathroom house sleeps eight and offers amenities including air conditioning, a full kitchen with dishwasher, internet access, pet-friendliness, and ample parking.
9.6 95 reviews
Chesapeake Bay
08/23 – 08/28
$138/nighttotal: $690 (5 )
Hidden Fells Point Gem / Private Courtyard Patio
1 2
apartment , Baltimore
This smoke-free apartment is located in Fells Point, a historic district in Baltimore, within a mile of Fell's Point Visitor Center and Johns Hopkins Hospital. It has excellent user ratings and is family-friendly, making it a great option for travelers. The apartment has one bedroom and two bathrooms, offering 640 square feet of space and comfortably accommodating up to three guests. It features a modern kitchen, washer/dryer, Smart TV, on-site parking, and internet access, ensuring a comfortable and convenient stay.
10 11 reviews
Chesapeake Bay
06/20 – 06/27
$1790/nighttotal: $12530 (7 )
280 Acre Waterfront Estate With Dock And Pool
5 13
apartment , Madison
Cherry Point Farm, a 280-acre historic sporting estate on the Little Choptank River near Madison, offers over 25,000 feet of shoreline and expansive grounds including a private beach and dock. This luxurious 5-bedroom, 6-bathroom property sleeps 15 guests and features two full kitchens, a boathouse with water sports equipment, a pool, fitness center, and numerous recreational activities such as kayaking, paddleboarding, and lawn games.
8.3 2876 reviews
Chesapeake Bay
10/01 – 10/05
$143/nighttotal: $572 (4 )
The Atrium Resort, Virginia Beach By Vacatia
1 3
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.
10 1 review
Chesapeake Bay
09/12 – 09/16
$190/nighttotal: $760 (4 )
Lovin Life !
1 2
houseboat , Essex
The houseboat rental "Lovin’ Life!" is located in Essex, Maryland, near the National Aquarium in Baltimore, the Baltimore Cruise Terminal, and the Baltimore Inner Harbor Marina, though precise distances aren't provided. This one-bedroom, two-bathroom floating home accommodates two guests and offers a unique waterside experience in Essex, with potential access to nearby attractions and water activities (amenities not specified).
10 16 reviews
Chesapeake Bay
06/20 – 06/27
$833/nighttotal: $5831 (7 )
Stepne Manor
1 13
apartment , Chestertown
Stepne Manor is a renovated 17th-century manor house located in Chestertown, Maryland, within walking distance of Fountain Park and its colonial architecture and shops. The property has received excellent ratings for user experience, location, and cleanliness. The house has five bedrooms and can accommodate up to 15 guests, making it ideal for large families or groups. Stepne Manor offers modern amenities like air conditioning, a fully equipped kitchen, a spa, and a private terrace with a garden, as well as access to nearby water activities like kayaking and jet skiing.
9.4 27 reviews
Chesapeake Bay
10/01 – 10/05
$167/nighttotal: $668 (4 )
Pet-friendly 2br- Near Beach, Bases, & Hospitals
2 3
apartment , Norfolk
This Bayview vacation home in Norfolk is located within 2 miles of Norfolk Beaches, Ocean View Beach, and Sarah Constant Shrine Beach, and 2.1 miles from the Oceanview Fishing Pier. This two-bedroom, one-bathroom rental sleeps six, features a fully equipped kitchen with appliances including a dishwasher, offers a patio, and includes amenities such as Wi-Fi, air conditioning, and on-site parking.
9.9 335 reviews
Chesapeake Bay
09/12 – 09/16
$147/nighttotal: $588 (4 )
"The Little Red Cabin" Aka The Galley
1 2
cabin , Deltaville
This Deltaville cabin is located right on the water in a campground, offering views of the Bay and beach. The cabin has received excellent ratings for location, cleanliness, and overall experience. The cozy cottage features a kitchen, bedroom, bathroom, family room with a fireplace, and a dining area. Guests can enjoy the campground amenities, including a pier, beach, kayaks, and a canoe, and can relax on the large screened-in porch.
Best Chesapeake Bay vacation rentals with a balcony
Chesapeake Bay
06/20 – 06/27
$955/nighttotal: $6685 (7 )
Camp Chesapeake 50% Off 6 Bedroom Private Waterfront Retreat
6 13
apartment , Savageville
This 6-bedroom waterfront vacation rental in Onancock, Virginia, is located 3 hours from Washington D.C. and Richmond, offering 6 acres of private waterfront seclusion with a private sunrise dock. This spacious house accommodates up to 16 guests and features a hot tub, movie room, kids' treehouse, kayaks, and is close to cultural attractions like the Red Queen Gallery and North Street Playhouse.
8.4 5 reviews
Chesapeake Bay
07/20 – 07/27
$234/nighttotal: $1638 (7 )
Artistic Abode Close To Mica & Johns Hopkins
1 4
apartment , Baltimore
This apartment in Madison Park is a great option for travelers visiting Baltimore. It's close to major attractions like the Maryland Institute College of Art, Johns Hopkins University, and Oriole Park at Camden Yards, and has an excellent user rating. The apartment has one bedroom and one bathroom, and can accommodate up to four guests. It features a fully equipped kitchen, a private balcony, and free WiFi. Guests can also enjoy the convenience of a washing machine and parking.
9.8 65 reviews
Chesapeake Bay
08/23 – 08/28
$207/nighttotal: $1035 (5 )
Romantic Waterfront Abode With Patio & Dock!
1 2
house , Deltaville
This waterfront home is located in Deltaville, a charming town on the Chesapeake Bay, approximately 42 miles from Newport News/Williamsburg International Airport, offering a peaceful escape from the hustle and bustle of city life. The house has excellent user, location, and cleanliness ratings, guaranteeing a comfortable and enjoyable stay. This cozy cottage offers 750 square feet of living space with one bedroom and one bathroom, accommodating up to two guests. Enjoy direct waterfront access with a private patio and dock, a fully equipped kitchen, and comfortable amenities like towels and bed linen, plus free Wi-Fi to stay connected.
8.9 3361 reviews
Chesapeake Bay
10/01 – 10/05
$176/nighttotal: $704 (4 )
The Colonies At Williamsburg
2 3
resort , Williamsburg
The Colonies at Williamsburg is conveniently located in Williamsburg, Virginia, just a short drive from historical landmarks like Jamestown and Busch Gardens. The resort has consistently earned excellent ratings for location, cleanliness, and overall guest satisfaction. Each unit provides a comfortable and spacious living area with a kitchen and patio. The resort features a range of amenities including a swimming pool, a fitness center, tennis courts, and a game room, ensuring plenty of activities for everyone.
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.
Chesapeake Bay
08/23 – 08/28
$163/nighttotal: $815 (5 )
Rooftop Pool & Lounge In Downtown Charm Free Indoor Parking
1 2
apartment , Baltimore
This apartment in Downtown Baltimore is located within walking distance to the Inner Harbor, Baltimore Convention Center, and Power Plant, offering convenient access to major attractions. This pet-friendly, family-friendly residence features a rooftop pool with city views, a full kitchen with a dishwasher and microwave, on-site fitness and spa facilities, complimentary indoor and private parking, and a 24-hour front desk.
10 27 reviews
Chesapeake Bay
07/20 – 07/27
$209/nighttotal: $1463 (7 )
Cozy Cedar Cottage-beach Getaway
2 4
apartment , Long Beach
This Long Beach cottage is located an hour south of Washington DC, Annapolis, and Virginia, offering a peaceful escape from the city in a rural setting near Battle Creek Cypress Swamp Sanctuary and Calvert Cliffs State Park. The cottage has earned excellent user ratings for its comfort and amenities. The two-bedroom, one-bathroom cottage spans 1100 square feet and comfortably accommodates up to four guests. The cottage provides a relaxing atmosphere with a private beach, a fire pit, a hammock, and a fully equipped kitchen, plus a variety of outdoor amenities like grills, beach chairs, and a cooler.
10 13 reviews
Chesapeake Bay
06/20 – 06/27
$723/nighttotal: $5061 (7 )
Private 9 Acre Family Retreat On The Chesapeake Bay
5 13
apartment , Madison
This five-bedroom, five-bathroom vacation home in Cambridge, Maryland, offers stunning Chesapeake Bay views and is located 15 miles from Cambridge town, near the Dorchester County Marina and several parks. This spacious rental boasts a large wrap-around deck with a grill and basketball hoop, direct marina access, kayaks, paddleboards, and proximity to attractions like the Richardson Maritime Museum and Great Marsh Park, sleeping up to 13 guests comfortably.
9.4 1692 reviews
Chesapeake Bay
09/12 – 09/16
$196/nighttotal: $784 (4 )
Club Wyndham Governors Green
1 2
resort , Williamsburg
The Club Wyndham Governors Green is located in Williamsburg, Virginia, just three miles from the College of William and Mary and six miles from Camp Peary, offering easy access to the area's historic attractions. This 4-star resort has earned excellent user ratings for its location, cleanliness, and overall experience. The resort provides spacious apartments with full kitchens, separate living and dining areas, and laundry facilities. Guests can enjoy a variety of on-site amenities, including multiple swimming pools, a fitness center, tennis courts, a spa, and a restaurant and bar.
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?
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.
Destinations nearby
Best Chesapeake Bay vacation rentals with parking
9.0 47 reviews
Chesapeake Bay
07/20 – 07/27
$116/nighttotal: $812 (7 )
* Private Suite Full Of Style & Comfort *
1 4
apartment , Lutherville
This apartment is perfect for travelers visiting Lutherville. It is located in the heart of Lutherville Timonium, within a 3-mile radius of Goucher College, Towson Town Center, and Towson University. The apartment has received excellent user ratings and can accommodate up to 4 guests with 1 bedroom and 1 bathroom. The apartment features a fully equipped kitchen, a comfortable living space with a sofa bed, a Smart TV with a DVD player, a washing machine, and access to a garden. It is also pet-friendly and offers parking.
9.0 5803 reviews
Chesapeake Bay
08/23 – 08/28
$134/nighttotal: $670 (5 )
Hilton Vacation Club The Historic Powhatan Williamsburg
1 2
resort , Williamsburg
The Hilton Vacation Club The Historic Powhatan Williamsburg is located just a short drive from Historic Williamsburg and the College of William and Mary, offering easy access to the area's rich history and attractions. This resort consistently receives high ratings for its location, cleanliness, and overall experience. The resort features a restored Manor House setting, providing a unique historical ambiance. Guests can enjoy a range of amenities, including indoor and outdoor pools, tennis courts, a fitness center, and a variety of dining options, making it a perfect choice for families and couples alike.
9.7 13 reviews
Chesapeake Bay
06/20 – 06/27
$811/nighttotal: $5677 (7 )
Rustic Waterfront 5bd Home With 9 Boat Slips!
1 13
apartment , California
This California waterfront home, boasting six private deep-water piers perfect for boating and fishing, offers kayak access and is conveniently located near crabbing opportunities. Sleeping 14 guests comfortably in five bedrooms with nine beds, this three-bathroom rental features a rustic, boho-style interior with air conditioning, a full kitchen, parking, and internet access.
9.5 490 reviews
Chesapeake Bay
10/01 – 10/05
$161/nighttotal: $644 (4 )
Affordable Furnished Luxurytownhouse Near Stadiums In Baltimore Pig Town.
2 3
apartment , 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.
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.
8.8 4920 reviews
Chesapeake Bay
09/12 – 09/16
$182/nighttotal: $728 (4 )
The Schooner Inn
1 2
hotel , Virginia Beach
The Schooner Inn, a two-star Virginia Beach hotel, boasts a beachfront location near the Virginia Beach Boardwalk, offering easy access to shops and restaurants. This 1-bedroom, 1-bathroom lodging features kitchenettes, private balconies with ocean views, a swimming pool, and limited on-site parking; water sports are readily available nearby.
9.7 290 reviews
Chesapeake Bay
09/12 – 09/16
$143/nighttotal: $572 (4 )
First Floor Studio Apartment In Historic Chestertown
1 2
studio , Kingstown
This one-bedroom apartment is located in Chestertown, Maryland, just a short drive from Washington College and Rolphs Wharf Marina. The apartment has received excellent ratings for its location, cleanliness, and overall experience. This comfortable rental can accommodate up to three guests and features a private pool, fitness center, spa tub, and barbecue grills. Enjoy modern amenities like a Smart TV, sofa bed, refrigerator, washer and dryer, and free Wi-Fi.
8.9 28 reviews
Chesapeake Bay
07/20 – 07/27
$269/nighttotal: $1883 (7 )
Grey's Point Camp Cottage 7
1 4
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.
8.7 54 reviews
Chesapeake Bay
07/20 – 07/27
$315/nighttotal: $2205 (7 )
King's Creek Resort By Endless Resorts
2 4
resort , Williamsburg
King's Creek Resort by Endless Resorts is conveniently located in Williamsburg, just a short drive from Busch Gardens & Water Country and Colonial Williamsburg. The resort has earned excellent ratings for its location and very good ratings for cleanliness and overall experience. The resort offers a variety of comfortable accommodations, including spacious suites and villas with full kitchens. Guests can enjoy a range of amenities, such as a swimming pool, fitness center, restaurant, spa, and playground, along with activities like mini-golf, hiking, and cycling.
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.
9.8 19 reviews
Chesapeake Bay
07/20 – 07/27
$242/nighttotal: $1694 (7 )
Pet-friendly Smith Island Cottage W/ Golf Cart!
2 4
cottage , Smith Island
9.9 249 reviews
Chesapeake Bay
07/20 – 07/27
$142/nighttotal: $994 (7 )
Hedgerow, Deer Haven In The Nnk- Dock & Boat Ramp
1 4
apartment , Lancaster
9.2 79 reviews
Chesapeake Bay
09/12 – 09/16
$271/nighttotal: $1084 (4 )
Beach Side Hideaway - Pet Friendly, Wifi, Smart Tv, Central Heat/ac, Parking
1 2
apartment , Norfolk
9.8 390 reviews
Chesapeake Bay
08/23 – 08/28
$153/nighttotal: $765 (5 )
The Moore Cottage
1 2
apartment , White Stone
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.
10 155 reviews
Chesapeake Bay
07/20 – 07/27
$265/nighttotal: $1855 (7 )
Irvington Country Getaway House
3 4
apartment , Irvington
Discover Vacation Rentals with Saunas in Chesapeake Bay
Maximize your wellness with vacation rentals in Chesapeake Bay featuring on-site saunas and steam rooms.
8.0 15 reviews
Chesapeake Bay
07/20 – 07/27
$599/nighttotal: $4193 (7 )
Oceansands Oceanfront Free Bike & Chair Use Aquarium Admission
1 4
apartment , Virginia Beach
10 3 reviews
Chesapeake Bay
09/12 – 09/16
$1416/nighttotal: $5664 (4 )
Oasis By The Bay - Waterfront Heated Pool Hot Tub
6 2
house , Highland Beach
10 3 reviews
Chesapeake Bay
09/12 – 09/16
$706/nighttotal: $2824 (4 )
Come Enjoy This True Escape From Reality!
3 2
apartment , Cape Charles
9.0 17 reviews
Chesapeake Bay
09/12 – 09/16
$666/nighttotal: $2664 (4 )
Bayhamas ️️ Beachfront Home 3 Bedrooms-private-white Stone- Sauna-dock
