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?

Among the Airbnbs in Chesapeake Bay, Dune Cottage Sea Suite - 2 Mins To Beach - Laundry , Gem In The Heart Of The Fan #1 and Beautiful 1-bdrm Carytown - Fan - Vmfa are the most popular ones.

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?

Refreshed - Pet-friendly 4 Br Townhouse Walking Distance To The Beach And Boardwalk (408a) , Williamsburg 3 Bd Lo Condo - Near Colonial Williamsburg and Cozy - Dog-friendly Duplex At The North End Short Walk To The Beach 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?

The best rentals for families and kids in Chesapeake Bay are Lovely Large Room By River In "Kingsmill On The James" , Refreshed - Pet-friendly 4 Br Townhouse Walking Distance To The Beach And Boardwalk (408a) and Gorgeous 1-bdrm In The Fan Near Carytown & Vmfa .

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?

The best vacation rentals or Airbnb with a jacuzzi in Chesapeake Bay are Lovely Large Room By River In "Kingsmill On The James" , Williamsburg 3 Bd Lo Condo - Near Colonial Williamsburg and House In The Middle Of Everything Vcu/fan/o Hill .

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.

Chesapeake Bay Vacation rentals & Airbnb

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.

8.9 4226 reviews

Club Wyndham Kingsgate

resort, Williamsburg

Club Wyndham Kingsgate is located in Williamsburg, just a short walk from the historic area, offering a tranquil escape amidst the colonial charm. This 3-star hotel receives very good user ratings for its comfortable accommodations and amenities.
The resort features a colonial-style design, creating a unique atmosphere. Guests can enjoy a variety of amenities, including a swimming pool, jacuzzi, fitness center, restaurant, bar, and tennis court.

10 71 reviews

2 Full Bed|smk|newport News Pa

apartment, Newport News

This one-bedroom, one-bathroom condo in North Newport News is located less than 2 miles from Fort Eustis and a short drive from Busch Gardens Europe and Water Country USA.
This 150 sq ft apartment accommodates up to 4 guests and offers air conditioning, cable TV with free movies, free high-speed internet, and on-site coin-operated laundry facilities, with some units featuring kitchenettes.

9.6 52 reviews

King Bed Smoking

apartment, Newport News

This Newport News studio apartment is located less than three miles from Fort Eustis and minutes from Busch Gardens Europe and Newport News/Williamsburg International Airport.
This 150 square foot studio features one bathroom, can accommodate two guests, and offers amenities such as air conditioning, parking, cable TV with free movies, and free high-speed internet, with some units including kitchenettes and whirlpool bathtubs.

9.8 45 reviews

Country Get Away Studio Apartment

studio, Chesapeake City

This Chesapeake City apartment rental is conveniently located within 6 miles of the historic district, town hall, and docks, offering easy access to Chesapeake Inn Marina and Elkton Golf and Batting Center.
The one-bedroom, one-bathroom unit sleeps two guests and features a kitchenette with a refrigerator and microwave, a private patio, free WiFi, a smart TV, and amenities such as a coffee/tea maker and hairdryer.

10 10 reviews

Our Haven Cabin

cabin, Secretary

This East New Market vacation home is located 21 miles from the Academy of the Arts and 30 miles from Salisbury Zoo.
This 900-square-foot, one-bedroom house accommodates up to three guests and features a kitchenette, air conditioning, free Wi-Fi, and private parking, with water sports and fishing available nearby.

10 53 reviews

King Bed|smk|newport News Pa

apartment, Newport News

This apartment is located in North Newport News, under 2 miles from Fort Eustis and a short drive from popular attractions like Busch Gardens Europe and Water Country USA.
This 150-square-foot studio offers accommodation for 2 guests with 1 bathroom, cable TV, complimentary high-speed internet, and optional kitchenettes, and is conveniently located near Christopher Newport University and Hampton University.

9.9 47 reviews

Island Voices In The Wine Near Chincoteague & Nasa

apartment, Saxis

This recently renovated, two-story apartment in Saxis offers a unique waterfront experience in a historic Waterman's Fishing Village, situated on three sides by water and a wildlife refuge, with Chincoteague and Assateague Islands, and NASA Wallops Flight Facility a short drive away.
This accommodation, ideal for up to four guests, features two bedrooms and one bathroom, air conditioning, internet, a full kitchen with a fridge, freezer, and microwave, a garden, and parking, with immediate access to beach activities, a fishing pier, boat ramp, and nearby dining and cultural attractions.

9.2 2024 reviews

Patriots Inn

resort, Williamsburg

Patriots Inn is located in Williamsburg, just a short drive from the College of William & Mary and Colonial Williamsburg. The resort boasts excellent user, location, and cleanliness ratings, making it a top choice for travelers. The hotel offers comfortable rooms with private bathrooms and amenities like air conditioning, a TV, and free Wi-Fi. Guests can enjoy a swimming pool, a Jacuzzi, a fitness center, and a garden for relaxation and recreation.

9.9 248 reviews

Serenity Suite On Chesapeake Bay

apartment, Calvert Beach

This apartment is located on the scenic Calvert Cliffs, just a short walk from a private community bay shoreline, offering easy access to the waterfront and the nearby town of Solomon's Island. It has received excellent ratings for user experience, location, and cleanliness, making it a great choice for travelers. The basement suite features a spacious open floor plan with a living area, dining area, kitchen, and sleeping area, comfortably accommodating up to 3 guests. Enjoy stunning bay views from the backyard, relax in the spacious outdoor area with Adirondack chairs and a Weber grill, and explore the shoreline for fossils and wildlife viewing.

8.5 5153 reviews

Delta Hotels By Marriott™ Virginia Beach Waterfront Suites

resort, Virginia Beach

The Delta Hotels by Marriott Virginia Beach Waterfront sits right on the Chesapeake Bay, just a short distance from Seashore State Park and the Virginia Marine Science Museum. This resort has received very good ratings for its location, cleanliness, and overall experience.
The hotel offers spacious rooms with separate living and sleeping areas, perfect for families or groups. Guests can enjoy a variety of amenities, including a private beach, an outdoor pool, a fitness center, a restaurant, a bar, and more.

10 6 reviews

Rooftop Chesapeake Bay Views! Waterfront Retreat

apartment, Mathews

This studio apartment on Virginia's Middle Peninsula offers direct Chesapeake Bay access and waterfront views, ideal for a tranquil coastal retreat.
This pet-friendly accommodation for two features a kitchen with a fridge, microwave, and dishwasher, air conditioning, a swimming pool, garden, parking, and a rooftop deck for sunset views.

Best Chesapeake Bay vacation rentals with a balcony

10 2 reviews

Lavish Luxe 2bd-1ba Apartment In Federal Hill

apartment, Baltimore

This recently renovated 1900-era apartment is located in Baltimore's Federal Hill district, offering proximity to the Inner Harbor (1.3 miles), Baltimore Convention Center (1.1 miles), and the Sports Legends Museum at Camden Yards (1.2 miles).
This 1450 square foot residence features 2 bedrooms, 1 bathroom, and accommodates up to 11 guests, with amenities including air conditioning, a dishwasher, a terrace with city views, and free Wifi.

9.5 2 reviews

Family-friendly Main St Gloucester Apt W/ Balcony!

apartment, Gloucester Courthouse

This Gloucester Courthouse apartment rental is conveniently located near major attractions, including Busch Gardens, Water Country USA, Colonial Williamsburg, and Cary-Zable Stadiums, all within a 24-27 mile radius.
This 900-square-foot, two-bedroom, one-bathroom unit sleeps up to 13 guests and boasts amenities such as a private balcony, fully equipped kitchen, in-unit laundry, free Wi-Fi, and a spa, plus parking.

9.7 130 reviews

Waterfront 3br/3ba Getaway: Beach, Dock, Firepit!

apartment, Heathsville

This Heathsville vacation rental is located just a short drive from the Heathsville Farmers' Market and Rice's Hotel / Hughlett's Tavern, giving you easy access to local attractions and a taste of the area's history. The property has received excellent ratings for location, cleanliness, and overall user experience.
This 3-bedroom, 3-bathroom house comfortably accommodates up to 10 guests in its 2000 square feet of living space. Enjoy amenities such as a private fenced yard, a terrace, a spa, and a fully equipped kitchen, perfect for families and groups looking for a relaxing getaway.

9.4 30 reviews

Perfect Beach Getaway For 5! Steps To The Sand!

apartment, Hampton

This Hampton vacation rental is conveniently located just 0.3 miles from Buckroe Beach and Park, offering easy access to the sandy shores and the nearby Buckroe Beach and Park. The two-bedroom home comfortably accommodates up to five guests, features a fully equipped kitchen, washer/dryer, and a private terrace for outdoor dining.

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.

No reviews

Woodsy + Secluded! Amish Country Retreat In Hartly

cabin, Hartly

This apartment in Hartly, Kent County, is located near local Amish markets and within 17 miles of Blackbird State Forest and Bombay Hook National Wildlife Refuge.
This 320 sq ft studio dwelling accommodates two guests and features a kitchenette with a fridge and microwave, air conditioning, parking, and a front porch, with the option for dog-friendly stays for an additional fee.

9.8 120 reviews

Lovely 2 Bedroom Condo In 4diamond Historic Resort

apartment, Williamsburg

This smoke-free condo is located in Kingsmill, just a short drive from Busch Gardens Williamsburg, Kingsmill Beach, and Redoubt Park, making it a convenient base for exploring Williamsburg's attractions. The condo has received excellent ratings for its location, cleanliness, and overall experience.
The two-bedroom condo comfortably sleeps six guests and features a fully equipped kitchen, private balcony, and access to resort amenities like a swimming pool and playground. Guests can enjoy the convenience of on-site parking and a smoke-free environment.

9.8 23 reviews

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

apartment, Millington

This Millington apartment rental boasts a riverside location, conveniently situated within six miles of Crumpton Park and Tilmon's Island Winery, and under nine miles from Pinkney Park and Chase Island.
The one-bedroom, one-bathroom unit sleeps two guests and includes free WiFi, a Smart TV, in-unit appliances (refrigerator, microwave, coffee/tea maker, hairdryer), on-site parking, and a playground.

9.7 308 reviews

Red, White & Waterview Studio Apt With Pool

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.

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?
Among the Airbnbs in Chesapeake Bay, Dune Cottage Sea Suite - 2 Mins To Beach - Laundry, Gem In The Heart Of The Fan #1 and Beautiful 1-bdrm Carytown - Fan - Vmfa are the most popular ones.
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?
Refreshed - Pet-friendly 4 Br Townhouse Walking Distance To The Beach And Boardwalk (408a), Williamsburg 3 Bd Lo Condo - Near Colonial Williamsburg and Cozy - Dog-friendly Duplex At The North End Short Walk To The Beach 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?
The best rentals for families and kids in Chesapeake Bay are Lovely Large Room By River In "Kingsmill On The James", Refreshed - Pet-friendly 4 Br Townhouse Walking Distance To The Beach And Boardwalk (408a) and Gorgeous 1-bdrm In The Fan Near Carytown & Vmfa.
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?
The best vacation rentals or Airbnb with a jacuzzi in Chesapeake Bay are Lovely Large Room By River In "Kingsmill On The James", Williamsburg 3 Bd Lo Condo - Near Colonial Williamsburg and House In The Middle Of Everything Vcu/fan/o Hill.
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

10 7 reviews

Private Tiny Home Near Havre De Grace Attractions

cabin, Aberdeen

This secluded tiny home offers a unique cabin experience on 5 private acres, located minutes from Havre de Grace, a town known for its historical sites and waterfront activities.
This minimalist retreat accommodates up to 4 guests with a queen bed, futon, and twin sleeping loft, featuring a fully equipped kitchen, air conditioning, garden, parking, and an enclosed outdoor bathroom with a hot water shower.

8.7 7 reviews

Cozy Unit In Milford, Delaware -Close To De Turf

house, Milford

This Milford, Delaware house rental is conveniently located 21 miles from Dover International Speedway and 25 miles from Rehoboth Beach, offering easy access to area attractions.
The one-bedroom unit, sleeping up to seven guests, features a fully equipped kitchenette, air conditioning, free Wi-Fi, and a private garden; Killens Pond State Park is 10 miles away.

9.0 11 reviews

Ocean Key Resort

resort, Virginia Beach

The Ocean Key Resort, a 3-star hotel in Virginia Beach, is located in a district near the ocean, with some rooms offering direct ocean views.
This family-friendly resort provides amenities such as air conditioning, a swimming pool, a fitness center, a restaurant, a bar, and parking, with select rooms featuring balconies or terraces and in-room entertainment.

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 located in Grasonville, just a short drive from the charming town of Kent Narrows and its waterfront restaurants, as well as the historical attractions of Annapolis Harbor. This hotel has received very good user ratings, excellent location ratings, and very good cleanliness ratings.
The hotel has 270 square foot rooms with one bedroom and one bathroom. Guests can enjoy amenities such as a swimming pool, tennis court, fitness center, restaurant, bar, and free parking.

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.

No reviews

Upscale Gated Retreat W/ Plush Bed & Garden Views Minutes From Jamestown

resort, Williamsburg

The Upscale Gated Retreat W/ Plush Bed & Garden Views Minutes From Jamestown is located in Williamsburg, a short drive from Busch Gardens, Colonial Williamsburg, and Newport News/Williamsburg Airport, with easy access to Water Country USA and Historic Jamestowne.
This 485 sq. ft. resort offers 2 bedrooms, accommodating up to 4 guests, with amenities including air conditioning, a swimming pool, garden, fitness center, kitchenette, and complimentary daily cleaning.

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.

10 1 review

Rooftop Chesapeake Bay Views! Waterfront Retreat

apartment, Mathews

This studio apartment in Westville offers direct Mobjack Bay access from the community dock, located 13 miles from Williams Wharf Landing and Gwynn's Island Museum, and 28 miles from Yorktown.
This pet-friendly accommodation spans 650 square feet, features a private balcony and rooftop deck, a community outdoor pool and kayaks, and accommodates up to 2 guests with amenities including a gas grill and flat-screen TV.

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.

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.

10 92 reviews

Heron Roost

apartment, Stevensville

10 4 reviews

Golden Anchor Retreat Lux Living!

house, Mayo

9.7 81 reviews

Cozy Sunrise Waterfront Cottage & Dock

apartment, Piney Point

9.0 326 reviews

Oceanfront & Out Of Office

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.

9.2 4 reviews

Private Duplex Near Bwi Easy Access To I95

apartment, Linthicum

Discover Vacation Rentals with Saunas in Chesapeake Bay

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

10 4 reviews

Come Enjoy This True Escape From Reality!

apartment, Cape Charles

9.0 3 reviews

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

house, Stevensville

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Beautiful Condo In Golf Community Featuring Access To Club Amenities!

apartment, Cape Charles

9.8 77 reviews

Luxury North End | Pool | Beach | Sleeps 10

apartment, Virginia Beach

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