Cottages in Chesapeake Bay at the best prices

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Chesapeake Bay cottages
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546 Best cottages in Chesapeake Bay

Best family friendly Chesapeake Bay cottage rentals

Among the 546 accommodations in Chesapeake Bay, here are the 4 best family friendly cottage rentals

Beachfront Hideaway - Pet Friendly, Hot Tub, Ev - Chesapeake Bay
9.4 20 reviews

Beachfront Hideaway - Pet Friendly, Hot Tub, Ev

cottage, Heathsville
This waterfront holiday home in Lottsburg, Virginia, boasts 100+ feet of private beach access (tide dependent) and is situated approximately 320 km from Washington, D.C., and 6.4 km from the Maryland shoreline across the Potomac River.
The 102-square-metre property sleeps five guests in two bedrooms and one bathroom, offering a Jacuzzi, kayaks for exploring the Potomac River and Chesapeake Bay, a fully equipped kitchen with a dishwasher, and blazing-fast broadband internet, plus a ChargePoint Level 2 EV charger.
Peaceful Suite On The Water "Osprey." Sunrise Over The River From Your Porch. - Chesapeake Bay
9.2 10 reviews

Peaceful Suite On The Water "Osprey." Sunrise Over The River From Your Porch.

cottage, Benedict
This Benedict beach house is situated near the Dr Samuel A Mudd House Museum and Drum Point Lighthouse, offering private beach access with over 150 metres of shoreline and a 120-metre pier, and is a 15-minute drive (approx. 24km) from local amenities.
Sleeping six, this self-catering property boasts a queen bed, bunk beds, and a sofa bed, plus a fully equipped kitchen, air conditioning, a terrace, garden, spa, and a gas grill; enjoy birdwatching at Walter's Walk sandbar and explore nearby attractions.
93 M² Cottage ∙ 2 Bedrooms ∙ 4 Guests - Chesapeake Bay
No reviews

93 M² Cottage ∙ 2 Bedrooms ∙ 4 Guests

cottage, Savageville
This Savageville shore cottage, near Onancock and Onley, offers easy access to Chincoteague Island (48km) and Cape Charles (64km), providing diverse beach experiences and proximity to the Onancock Wharf for water activities.
The 92 square metre property sleeps four guests in two bedrooms and one bathroom, boasting a garden, parking, Wi-Fi, air conditioning, a kitchen with fridge and microwave, and is suitable for guests aged 21 and over.
Esva Down By The Sea & Pet Friendly - Chesapeake Bay
9.8 7 reviews

Esva Down By The Sea & Pet Friendly

cottage, Savageville
This seaside holiday home in Onancock, Virginia, is situated a short drive (approx. 48km) from Chincoteague Island and 64km from Cape Charles, offering easy access to the Onancock Wharf and Kegotank Bay.
The 93 square metre property sleeps four guests in two bedrooms and one bathroom, boasting a fully equipped kitchen (fridge, microwave), air conditioning, garden, parking, internet access, and is pet-friendly.

Best Chesapeake Bay cottages with a garden

Historic Beach Side Getaway - Pet Friendly, Wi-fi, Just Steps To The Beach - Chesapeake Bay
8.8 110 reviews

Historic Beach Side Getaway - Pet Friendly, Wi-fi, Just Steps To The Beach

cottage, Norfolk
This family-friendly cottage is located in Norfolk, just a short distance from the beautiful beaches, including Norfolk Beaches, Sarah Constant Shrine Beach, and Oceanview Fishing Pier. It has received excellent user ratings, making it a popular choice for travellers.
The cottage has three bedrooms and two bathrooms, offering ample space for up to ten guests. It features a fully equipped kitchen, a comfortable living area, a patio, a garden, and parking, providing everything you need for a relaxing and enjoyable stay.
Waterfront Cottage In Beautiful Hoopers Island - Chesapeake Bay
10 84 reviews

Waterfront Cottage In Beautiful Hoopers Island

cottage, Chesapeake Ranch Estates
This waterfront cottage is located in Chesapeake Ranch Estates, just 5km from Middle Hooper Island and 8km from Lower Hooper Island, offering a peaceful escape in a picturesque setting. It has received excellent user reviews, making it a popular choice for travellers.
The cottage spans 54 square metres and comfortably accommodates up to 5 guests in its two bedrooms and one bathroom. It includes a fully equipped kitchen, a garden, a terrace, and free Wi-Fi, allowing you to enjoy both indoor and outdoor relaxation, as well as easy access to the surrounding natural beauty.
Serenity Cottage: Central To State Parks, Historic Towns, Md & Va Beaches - Chesapeake Bay
10 19 reviews

Serenity Cottage: Central To State Parks, Historic Towns, Md & Va Beaches

cottage, Pocomoke City
Serenity Cottage, a two-bedroom self-catering property near Pocomoke City, Maryland, offers easy access (within a few kilometres) to Pocomoke River State Park and the Delmarva Discovery Museum.
This octagonal house sleeps five, features a fully equipped kitchen with vintage touches, a unique second-floor cupola room, and allows pets; nearby activities include kayaking, canoeing, hiking, and exploring historical towns on the Eastern Shore.
Relaxing, Peaceful House In Calvert County, Md Close To Beach Towns And Dc. - Chesapeake Bay
10 52 reviews

Relaxing, Peaceful House In Calvert County, Md Close To Beach Towns And Dc.

cottage, Dunkirk
This charming cottage is situated just a short distance from Fridays Creek Winery and the Patuxent River, offering a peaceful escape in the heart of Dunkirk, Maryland. It has received excellent reviews from previous guests, making it a popular choice for travellers seeking a relaxing getaway.
The cottage spans 84 square metres and comfortably accommodates up to four guests in its two bedrooms and one bathroom. Guests can enjoy a range of amenities, including a private outdoor pool, barbecue grills, and a spacious garden, as well as the convenience of a fully equipped kitchen, free Wi-Fi and a private patio.

Frequently Asked Questions about cottages in Chesapeake Bay

  • What would be a good 2-days itinerary for visiting Baie de Chesapeake?

    For a two-day trip, you could spend the first day exploring Annapolis, the state capital of Maryland. Visit the historic Naval Academy and the charming downtown area. On the second day, head to the Eastern Shore, perhaps visiting St. Michaels, a beautiful town with a maritime museum. You can also enjoy a scenic boat tour on the bay.
  • What are the best cottage rentals in Chesapeake Bay?

    Among the cottage rentals in Chesapeake Bay, Historic Cottage On Ware River Estate, Enchanted Holiday Cottage and Cottage On A Private Island In The York River are the most popular ones.

  • What part of Baie de Chesapeake is ideal for renting a cottage?

    The Eastern Shore is a popular choice for renting cottages. The towns of St. Michaels, Easton, and Oxford are particularly charming and offer a range of options, from quaint waterfront cottages to larger family homes. You'll find plenty of beautiful scenery and a peaceful atmosphere.
  • What are the best cottage rentals with a pool in Chesapeake Bay?

  • When is the best time to rent a cottage in Baie de Chesapeake?

    The best time to visit Chesapeake Bay is during the spring and autumn. The weather is pleasant, and you can enjoy a variety of activities, including boating, fishing, and hiking. Summer can be hot and humid, but it's a great time for swimming and enjoying the beach.
  • What are the best cottage rentals with a jacuzzi in Chesapeake Bay?

  • What are the can't-miss sights in Baie de Chesapeake?

    Some can't-miss sights include the Chesapeake Bay Bridge, the US Naval Academy in Annapolis, the Chesapeake Bay Maritime Museum in St. Michaels, and Assateague Island National Seashore. You can also enjoy the charming towns of Annapolis, St. Michaels, and Easton, each with its own unique character.
  • What are the best cottage rentals for families and kids in Chesapeake Bay?

  • Why consider renting a cottage in Baie de Chesapeake for your stay?

    Renting a cottage offers a more intimate and relaxing experience compared to staying in a hotel. You can enjoy privacy, a home-like atmosphere, and often stunning views of the bay. Many cottages also come with amenities like private docks and outdoor spaces, perfect for enjoying the beautiful surroundings.
  • What are the best pet friendly cottage rentals in Chesapeake Bay?

  • Can you easily explore Baie de Chesapeake on foot or by bike?

    While some areas are walkable, it's best to have a car to explore the Chesapeake Bay region. The towns are spread out, and you'll want the flexibility to visit different attractions and enjoy the scenic drives along the bay.
  • What are the best cottage rentals with parking in Chesapeake Bay?

  • What are the best restaurants in Baie de Chesapeake with nature views?

    The Chart Room in St. Michaels offers stunning views of the harbour from its waterfront location. The restaurant serves fresh seafood and has a lively atmosphere. The Inn at Perry Cabin in St. Michaels also has a beautiful restaurant with outdoor seating overlooking the bay.
  • What family-friendly activities are available in Baie de Chesapeake?

    There are plenty of family-friendly activities in the Chesapeake Bay area. You can visit the Chesapeake Bay Maritime Museum in St. Michaels, explore the Assateague Island National Seashore, or go crabbing or fishing. Many towns also have parks, playgrounds, and beaches for kids to enjoy.

Popular destinations

Best Chesapeake Bay cottage rentals with jacuzzi

Among the 546 accommodations in Chesapeake Bay, here are the 2 best cottage rentals with a jacuzzi

Charming 3-bedroom Villa With Wifi, And  Jaccuzzi , Just Minutes From Yorktown - Chesapeake Bay
8.4 5 reviews

Charming 3-bedroom Villa With Wifi, And Jaccuzzi , Just Minutes From Yorktown

cottage, Gloucester Point
This Gloucester Point holiday home is situated near Yorktown, a short drive (approximately 8km) from the Yorktown Victory Center and Gloucester Museum of History, offering easy access to the York River.
Sleeping up to 10 guests, the property features three queen beds, one double bed, and a bunk bed, alongside a spacious living area, two bathrooms (one with an outdoor shower, an indoor shower is coming soon), and Wi-Fi; a marina and boat ramp are directly opposite.
Smith Beach Cottage W/ Private Sunset - Chesapeake Bay
9.8 7 reviews

Smith Beach Cottage W/ Private Sunset

cottage, Eastville
This two-bedroom holiday home in Eastville offers private beach access for sunset viewing and is situated approximately 5.6 kilometres from Chesapeake Bay and 7.2 kilometres from Cape Charles Beach.
This Eastville holiday home accommodates up to four guests, featuring a king and a queen bedroom, a private hot tub, air conditioning, and Wi-Fi, with a check-out time of 12:00 PM.

Best pet friendly Chesapeake Bay cottage rentals

Among the 546 accommodations in Chesapeake Bay, here are the 4 best pet friendly cottage rentals

Golden Days River Cottage - Family & Pet Friendly, River View, Water Access - Chesapeake Bay
10 6 reviews

Golden Days River Cottage - Family & Pet Friendly, River View, Water Access

cottage, Lancaster
This holiday cottage in Morattico, Lancaster, offers a peaceful river getaway with direct access to a shared river porch for fishing on the Rappahannock River, located across the street, and is a short walk to a shared beach and pier on Lancaster Creek for kayaking and swimming, with proximity to the Morattico Waterfront Museum.
Spanning 81 square meters, this accommodation sleeps up to eight guests across three bedrooms and a separate studio building with twin bunks and a queen bed, featuring a well-stocked kitchen, air conditioning, a fenced garden, an outdoor shower, and Wi-Fi.
Waterfront Urbanna Home W/ Private Dock - Chesapeake Bay
10 12 reviews

Waterfront Urbanna Home W/ Private Dock

cottage, Urbanna
This six-bedroom waterfront holiday home, near Urbanna, is situated 2.6 km from the Urbanna Historic District and 7.2 km from the Middlesex County Museum.
The 165 square metre property boasts a private pool, patio with gas grills, fully equipped kitchen with dishwasher, and in-unit laundry facilities; accommodating up to six guests.
2 Bedroom Cottage At Coles Point Marina - Chesapeake Bay
No reviews

2 Bedroom Cottage At Coles Point Marina

cottage, Montross
This Montross cottage is situated in Hague, a 5-minute walk from Coles Point Marina and a 14-minute drive from The Hague Winery, with Sandy Point Beach 39 kilometres and Cedar Island 77 kilometres away.
This 2-bedroom, 2-bathroom holiday home accommodates up to six guests, offering air conditioning, internet, and a dryer, with nearby access to Kinsale Museum, Westmoreland County Museum, Saint Mary's Fairground, and Michael P. O'Brien Athletics and Recreation Center.
Hosta Cottage | Creekfront Nature Escape W/ Kayaks, Fire Pit + Resort Access, Pet Friendly - Chesapeake Bay
9.6 5 reviews

Hosta Cottage | Creekfront Nature Escape W/ Kayaks, Fire Pit + Resort Access, Pet Friendly

cottage, Sanford
This waterfront self-catering property near Sanford, Eastern Shore of Virginia, is situated within 19 kilometres of the Virginia Welcome Centre at New Church, Bloxom Winery, and the US 13 North Welcome Centre, and 20 kilometres from the Wallops Flight Facility.
The one-bedroom, one-bathroom cottage sleeps two guests and boasts a fully equipped kitchen, private balcony, swimming pool, garden, parking, and Wi-Fi; limited housekeeping is available.
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