Search holiday beach houses in Chesapeake Bay from 100+ sites!

2487 available villa offers

7 nights
2
1
  • airbnb
  • booking
  • vrbo
  • expedia
  • sonder
  • priceline
  • tripadvisor
  • tripcom
  • homestay
  • hotelscom
  • orbitz
  • vacasa
Chesapeake Bay villas
Choose the perfect vacation accommodation
Price per night
Accommodation type
Rating

2487 Villa rentals in Chesapeake Bay

Find the Best Seaside Vacation Homes in Chesapeake Bay

Experience relaxing coastal vibes at seaside vacation homes in Chesapeake Bay, located short distances from popular beach-town shorelines.

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.

Find the Best Holiday Houses with Swimming Pool in Chesapeake Bay

Dip in whenever you like, as these vacation homes in Chesapeake Bay come with a swimming pool on-site.

Oasis By The Bay - Waterfront Heated Pool Hot Tub - Chesapeake Bay
10 3 reviews

Oasis By The Bay - Waterfront Heated Pool Hot Tub

house, Highland Beach
This Annapolis waterfront home, located 0.2 miles from Bay Ridge Beach and 4.8 miles from Annapolis Harbor, offers private bay access.
This 5,600-square-foot residence boasts six bedrooms, five bathrooms, sleeps 23 guests, and includes a heated pool, jacuzzi, sauna, spa, and fully equipped kitchen.
Bell House - Chesapeake Bay
9.9 28 reviews

Bell House

house, Montross
This secluded guesthouse, located in Coles Point, Hague, VA, offers creek and river views on 20 acres of protected land near Lower Machodic Creek and the Potomac River.
This accommodation features two bedrooms, a saltwater lap pool, a private dock, 100 feet of beach access, a spa tub, high-speed internet, and parking for up to 5 guests.
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels - Chesapeake Bay
9.6 138 reviews

Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels

cottage, Easton
This charming cottage is located in St. Michaels, just a short walk from the St. Michaels Museum, Chesapeake Bay Maritime Museum, and St. Michaels Winery. It has received excellent ratings from previous guests.
The 1400 square foot home has two bedrooms and three bathrooms, comfortably accommodating up to five guests. Enjoy modern amenities like air conditioning, a swimming pool, a patio, a fireplace, and a fully equipped kitchen.
Coastal Waterfront 1 Bedroom Cottage - Chesapeake Bay
10 224 reviews

Coastal Waterfront 1 Bedroom Cottage

house, Mayo
This waterfront cottage is located just 2 miles from Historic Downtown Annapolis and the United States Naval Academy, offering a quiet retreat on the South River. The property has received excellent ratings for user experience, location, and cleanliness.
The cottage has one bedroom and one bathroom, comfortably sleeping up to three guests. Amenities include a full kitchen, air conditioning, a swimming pool, a garden, a patio, a grill, a fire pit, and laundry facilities.

Frequently Asked Questions about villa rentals in Chesapeake Bay

Popular destinations

Best Chesapeake Bay villas and beach houses with jacuzzi

Bungalow W/ Large Yard: 8 Mi To Cape Charles Beach - Chesapeake Bay
10 3 reviews

Bungalow W/ Large Yard: 8 Mi To Cape Charles Beach

cottage, Cheriton
This Cape Charles cottage, located near Brockenberry Bay and eight miles from the Cape Charles Historic District and beaches, offers easy access to Kiptopeke State Park (12 miles) and Bay Creek Resort & Golf Club (9 miles).
This 400-square-foot vacation home sleeps four with two bedrooms, one bathroom, a full kitchen including a dishwasher, a Jacuzzi, and a private terrace, plus a spacious yard with a fire pit and hammocks.
The Beach Vibe With Hot Tub 8 Min To The Beach - Chesapeake Bay
9.7 54 reviews

The Beach Vibe With Hot Tub 8 Min To The Beach

house, Virginia Beach
This Virginia Beach vacation rental is conveniently located less than a 10-minute walk from the Virginia Beach Convention Center, 0.9 miles from the Virginia Beach Fishing Pier, and within 2 miles of Croatan Beach and the King Neptune Statue.
This 1190-square-foot house features three bedrooms, one bathroom, a fully equipped kitchen with a dishwasher, a private hot tub, free Wi-Fi, on-site parking, and accommodates up to six guests.
Second Floor East Standard Deluxe - Chesapeake Bay
No reviews

Second Floor East Standard Deluxe

house, Charlestown
This Charlestown vacation home, located 30 miles from the Old Dutch House in northeastern Delaware, also offers easy access to the University of Delaware and Dayett Station, both within 21 miles.
The one-bedroom, one-bathroom house sleeps nine guests and boasts a fully equipped kitchen, private parking, a swimming pool, jacuzzi, fitness center, tennis court, and free Wi-Fi; nearby activities include a children's playground and laundry service.
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 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.

Best Chesapeake Bay houses with a kitchen

Riverfront Paradise W/ Hot Tub & Pool In Kinsale! - Chesapeake Bay
9.7 56 reviews

Riverfront Paradise W/ Hot Tub & Pool In Kinsale!

house, Heathsville
This riverfront vacation home in Kinsale, Virginia, offers stunning views and is located approximately 31 miles from the George Washington Birthplace National Monument and Memorial House.
This 3,300-square-foot house features four bedrooms, three bathrooms, a private pool and hot tub, and a fully equipped kitchen, perfect for families or groups seeking a relaxing getaway near Heathsville.
Pet-friendly Smith Island Cottage W/ Golf Cart! - Chesapeake Bay
9.5 2 reviews

Pet-friendly Smith Island Cottage W/ Golf Cart!

house, Smith Island
This Smith Island house rental, perfect for families or groups, offers 1,470 square feet of space with two bedrooms, one bathroom, and sleeps up to seven guests.
The property includes free Wi-Fi, on-site parking, a full kitchen with oven and microwave, a washing machine, and provides linens and towels; bicycle use is also available for exploring Smith Island.
Serenity Manor 1br Private Historic Home First Flr - Chesapeake Bay
10 1 review

Serenity Manor 1br Private Historic Home First Flr

house, Onancock
This historic 19th-century vacation home in Onancock is located 20 miles from the Mid-Atlantic Regional Spaceport and 58 miles from Salisbury-Ocean City Wicomico Regional Airport.
This family-friendly 400 square foot house accommodates up to 7 guests with 1 bedroom, 2 bathrooms, air conditioning, a full kitchen, complimentary Wi-Fi, and on-site parking, featuring an outdoor fireplace.
Pet-friendly Pond Cottage  Nature Escape Near Beaches - Chesapeake Bay
No reviews

Pet-friendly Pond Cottage Nature Escape Near Beaches

cottage, Galestown
This lakeside studio cabin in Dorchester County, Maryland, offers a peaceful retreat approximately 1 hour from Ocean City, MD, and Rehoboth Beach, DE, and 5 minutes from Sharptown Cherry Beach.
This pet-friendly accommodation for up to 4 guests features a full kitchen with a fridge and microwave, air conditioning, a garden, parking, and waterfront access for fishing and wildlife viewing.

Check Out 5-Star Holiday Houses in Chesapeake Bay

These luxury vacation homes in Chesapeake Bay provide expansive layouts and premium service. Experience a refined stay in a high-end private residence.

Restored 1930s Cottage On 1 Acre W/ Fire Pit - Chesapeake Bay
9.5 190 reviews

Restored 1930s Cottage On 1 Acre W/ Fire Pit

house, Gloucester Point

Compare Family Vacation Homes in Chesapeake Bay

Choosing a family vacation home in Chesapeake Bay provides plenty of room to spread out and the perfect space to plan your day with the kids.

Cottage 72 - Chesapeake Bay
9.2 80 reviews

Cottage 72

cottage, Virginia Beach
Walk To Everything Historic Arts District - Chesapeake Bay
9.0 12 reviews

Walk To Everything Historic Arts District

house, Annapolis
Charming Hampton Home W/ Yard: 2 Mi To Beach! - Chesapeake Bay
9.7 127 reviews

Charming Hampton Home W/ Yard: 2 Mi To Beach!

house, Hampton
Private Riverfront Retreat - Chesapeake Bay
10 2 reviews

Private Riverfront Retreat

house, Montross

Guest-Favorite Pet-Friendly Vacation Homes in Chesapeake Bay

These dog-friendly vacation homes in Chesapeake Bay ensure your pet loves the trip as much as you do, featuring great outdoor spaces.

The Little Blue Cottage - Topping : Waterfront! - Chesapeake Bay
9.9 138 reviews

The Little Blue Cottage - Topping : Waterfront!

apartment, White Stone
Heron's Nest 
Back Creek Villa Covered Deck - Chesapeake Bay
9.6 16 reviews

Heron's Nest Back Creek Villa Covered Deck

house, Solomons
Carpenter St. Cottage In The Heart Of St Michaels Village - Large Screened Porch - Chesapeake Bay
9.8 208 reviews

Carpenter St. Cottage In The Heart Of St Michaels Village - Large Screened Porch

cottage, Easton
John Bruff Waterview Cottage - On Harbor And On Park - In Town St. Michaels! - Chesapeake Bay
9.6 133 reviews

John Bruff Waterview Cottage - On Harbor And On Park - In Town St. Michaels!

cottage, Easton

Discover Vacation Homes with Spa in Chesapeake Bay

Unwinding is effortless with an on-site spa. These vacation homes in Chesapeake Bay deliver wellness by the water at its very best.

Kings Creek Plantation By Tripforth - Chesapeake Bay
9.2 857 reviews

Kings Creek Plantation By Tripforth

house, Williamsburg

Best Chesapeake Bay houses with air conditioning

Summer Escape - Dock, Pool, Firepits, & Kayaks - Chesapeake Bay
10 198 reviews

Summer Escape - Dock, Pool, Firepits, & Kayaks

house, Gloucester Courthouse
Pet-friendly Smith Island Cottage W/ Golf Cart! - Chesapeake Bay
10 1 review

Pet-friendly Smith Island Cottage W/ Golf Cart!

cottage, Smith Island
Peek-a-boo Water Views! Port Haywood Home W/ Yard - Chesapeake Bay
No reviews

Peek-a-boo Water Views! Port Haywood Home W/ Yard

house, Mathews
3br Home Near Heritage Park - Chesapeake Bay
8.0 5 reviews

3br Home Near Heritage Park

house, Dundalk
©2026 cozycozy.com