Chesapeake Bay villas

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3618 available villa offers

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3618 Villa rentals in Chesapeake Bay

Premier St. Michaels Cottage - T. Blades House -  Walk To Everything In Town - Chesapeake Bay
9.6Excellent 337 reviews
Chesapeake Bay
2 2
$465/nighttotal: $1860 (4 )

Premier St. Michaels Cottage - T. Blades House - Walk To Everything In Town

cottage - Easton
This family-friendly cottage in St. Michaels is an excellent choice for travelers seeking a charming escape. It's just a short walk from the Chesapeake Bay Maritime Museum and other local attractions, and it has received excellent ratings for its location, cleanliness, and user experience.
The cottage has two bedrooms and can accommodate up to 5 guests. It features a fully equipped kitchen, a cozy fireplace, and a DVD player. Guests can also enjoy the outdoor space, which includes a terrace, a garden, and a swimming pool. The cottage also offers amenities such as air conditioning, Wi-Fi, and parking.
Cottage With A View! - Chesapeake Bay
9.8Excellent 97 reviews
Chesapeake Bay
2 3
$237/nighttotal: $948 (4 )

Cottage With A View!

cottage - Heathsville
This Heathsville cottage is located on Cod Creek with quick access to the Potomac River, providing opportunities for kayaking, paddle boarding, and fishing. It has excellent user, location, and cleanliness ratings.
The cottage has 3 bedrooms, 1 bathroom, and a guest capacity of 8. It features a spacious deck with stunning river views, a fully equipped kitchen, a private dock, and a peaceful neighborhood.
'River's Edge Retreat’ With Kayaks & River Access! - Chesapeake Bay
9.7Excellent 146 reviews
Chesapeake Bay
2 5
$738/nighttotal: $2952 (4 )

'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.
Irvington Country Getaway House - Chesapeake Bay
10Excellent 161 reviews
Chesapeake Bay
2 3
$320/nighttotal: $1280 (4 )

Irvington Country Getaway House

house - Irvington
This Irvington vacation home is located only 0.2 miles from the Steamboat Era Museum, giving you easy access to the many attractions Irvington has to offer. With excellent ratings for its location, cleanliness, and user experience, this home provides a truly comfortable and enjoyable stay. Featuring 3 bedrooms, 2 bathrooms, and sleeping up to 6 guests, this home is designed to accommodate families and groups comfortably. Its amenities include a fully equipped kitchen, a private garden with barbecue grills, a terrace or balcony, and complimentary Wi-Fi.
Blackwater Refuge House On The Farm, Water Access - Chesapeake Bay
10Excellent 146 reviews
Chesapeake Bay
2 1
$144/nighttotal: $576 (4 )

Blackwater Refuge House On The Farm, Water Access

house - Cambridge
House for up to 2 guests with an excellent rating of 100% based on 146 reviews. You will be based in Cambridge.
Services and facilities include a kitchen, a fridge and a coffee place. This house also has air conditioning!
Downtown Oxford | Charming | Pet Friendly | Bikes - Chesapeake Bay
9.2Excellent 50 reviews
Chesapeake Bay
2 4
$757/nighttotal: $3028 (4 )

Downtown Oxford | Charming | Pet Friendly | Bikes

house - Oxford
Vacation house rental for up to 8 people with an excellent rating of 92% based on 50 reviews. This accommodation is based in Oxford.
Facilities and services: a barbecue, a dish washer and a fridge. Take advantage of the Free Parking with this accommodation.
House On Creek With Dock And Private! - Chesapeake Bay
9.6Excellent 83 reviews
Chesapeake Bay
2 1
$184/nighttotal: $736 (4 )

House On Creek With Dock And Private!

house - Urbanna
Vacation house rental for up to 4 people with an excellent rating of 96% based on 83 reviews. You will be based in Urbanna.
Services and facilities include a freeze, a child space and free parking.
Big Cozy Loft Overlooking The Farm And River - Chesapeake Bay
10Excellent 70 reviews
Chesapeake Bay
2 1
$200/nighttotal: $800 (4 )

Big Cozy Loft Overlooking The Farm And River

gîte - Fairmount
Gîte listing for up to 2 people with an excellent rating of 100% based on 70 reviews. You will be based in Fairmount.
Facilities and services: a freeze, an iron and a barbecue. Take advantage of the Free Parking with this accommodation.
Heart Of Irvington W/fireplace Walk To Tides Inn &  Restaurants - Dog Friendly! - Chesapeake Bay
9.7Excellent 443 reviews
Chesapeake Bay
2 2
$256/nighttotal: $1024 (4 )

Heart Of Irvington W/fireplace Walk To Tides Inn & Restaurants - Dog Friendly!

house - Irvington
This Irvington vacation home enjoys a prime location near the Steamboat Era Museum, Historic Christ Church, and Compass Entertainment Complex. Its excellent user, location, and cleanliness ratings ensure a comfortable and enjoyable stay.
With a floor area of 1,300 square feet, the house accommodates four guests in two bedrooms and two bathrooms. Amenities include a fully equipped kitchen, a fireplace, a patio, a garden, a spa tub, a tennis court, and free WiFi.
Huge Sandbox! Play Beach Volleyball By The Marina & Kentmorr Beach Bar And Grill - Chesapeake Bay
9.9Excellent 192 reviews
Chesapeake Bay
2 4
$1119/nighttotal: $4476 (4 )

Huge Sandbox! Play Beach Volleyball By The Marina & Kentmorr Beach Bar And Grill

house - Stevensville
House rental listing for up to 14 people with an excellent rating of 99% based on 192 reviews. You will be based in Stevensville.
Facilities and services: a jacuzzi, a barbecue and a child space. This house in Stevensville also has air conditioning!
Quiet Cottage On Wooded Property - Chesapeake Bay
9.4Excellent 25 reviews
Chesapeake Bay
2 1
$136/nighttotal: $544 (4 )

Quiet Cottage On Wooded Property

bungalow - Long Beach
Accommodation for up to 2 people with an excellent rating of 94% based on 25 reviews. Your accommodation will be based in Long Beach.
Services and facilities: a freeze, a fridge and a washing machine. This accommodation also has air conditioning!
Cozy Modern Chesapeake Bay Home - Chesapeake Bay
9.7Excellent 346 reviews
Chesapeake Bay
2 2
$252/nighttotal: $1008 (4 )

Cozy Modern Chesapeake Bay Home

bungalow - Deale
Bungalow for up to 4 people with an excellent rating of 97% based on 346 reviews. You will be based in Deale.
Facilities and services: a fridge, a coffee place and a kitchen. This accommodation in Deale also has a Jacuzzi to relax in!

Other accommodation types in Chesapeake Bay

Best Chesapeake Bay villas and beach houses with a pool

Among the 3618 accommodations in Chesapeake Bay, here are the 8 best villas and beach houses with a pool

Private Beach And Beautiful Views - Chesapeake Bay
9.6Excellent 213 reviews
Chesapeake Bay
2 3
$443/nighttotal: $1772 (4 )

Private Beach And Beautiful Views

house - Deltaville
House rental with an excellent rating of 96% based on 213 reviews. You will stay in Deltaville.
Services and facilities: a terrace, a dish washer and free parking. This is a family-friendly house!
Contemporary Waterfront 4br Home Close To Downtown Annapolis - Stunning Water Views W\/private Dock\/pier\/ Private Pool And Kayaks. - Chesapeake Bay
10Excellent 11 reviews
Chesapeake Bay
2 4
$1754/nighttotal: $7016 (4 )

Contemporary Waterfront 4br Home Close To Downtown Annapolis - Stunning Water Views W\/private Dock\/pier\/ Private Pool And Kayaks.

house - Annapolis
This waterfront vacation home in the Hillsmere neighborhood of Annapolis offers stunning views of the South River and private access to a dock and pier. Just a short distance from downtown Annapolis, it has an excellent user rating.
The home features four bedrooms, including a massive master suite with a private balcony and yoga space, and five bathrooms. It boasts a modern and stylish interior with Brazilian hardwood floors, designer kitchen and baths, and artwork throughout. Guests can enjoy a large contemporary pool, private garden with seating areas, and access to kayaks and bikes.
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels - Chesapeake Bay
9.5Excellent 193 reviews
Chesapeake Bay
2 2
$432/nighttotal: $1728 (4 )

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

cottage - Easton
This cottage in St. Michaels offers a unique location within easy walking distance of major tourist attractions such as St. Michaels Museum, Chesapeake Bay Maritime Museum, and St. Michaels Winery. With excellent user ratings, this cottage provides a cozy and comfortable stay for up to 5 guests in its 1400 square feet of floor area with 2 bedrooms and 3 bathrooms.
The cottage features a fully equipped kitchen, multiple bathrooms, a private patio with a TV, and access to a garden with barbecue grills. Other amenities include air conditioning, a swimming pool, a terrace or balcony, and parking, making it an ideal choice for travelers seeking a convenient and well-equipped accommodation in Easton.
Carpenter St. Cottage In The Heart Of St Michaels Village - Large Screened Porch - Chesapeake Bay
9.9Excellent 301 reviews
Chesapeake Bay
2 2
$516/nighttotal: $2064 (4 )

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

cottage - Easton
This cottage in St. Michaels is close to many attractions such as the Chesapeake Bay Maritime Museum and the St. Michaels Museum. It has received excellent user ratings.
It has 2 bedrooms and 2 bathrooms, a floor area of 1400 square feet, and a guest capacity of 5. It has a swimming pool, a spa, a garden, a terrace or balcony, parking, air conditioning, internet, a kitchen with a fridge, microwave oven, and dishwasher, and it allows pets.
Waterfront Estate.  **Walk To St. Michaels!** - Chesapeake Bay
9.9Excellent 25 reviews
Chesapeake Bay
2 6
$1888/nighttotal: $7552 (4 )

Waterfront Estate. **Walk To St. Michaels!**

house - Easton
House for up to 12 guests with an excellent rating of 99% based on 25 reviews. You will be in Easton.
Services and facilities: a barbecue, a kitchen and a garden. Pets are welcome in this house.
Annapolis Cozy Beachfront/waterfront W/chesapeake Bay Bridge View - Chesapeake Bay
10Excellent 16 reviews
Chesapeake Bay
2 3
$842/nighttotal: $3368 (4 )

Annapolis Cozy Beachfront/waterfront W/chesapeake Bay Bridge View

house - Highland Beach
House with an excellent rating of 100% based on 16 reviews. This accommodation is located in Highland Beach.
Services and facilities: a swimming pool, a tennis court and a terrace. Pets are welcome in this house.
Annapolis Area Private, 3 Bedroom Pool, Jacuzzi & Sauna & Casino-like Game Room - Chesapeake Bay
10Excellent 1 review
Chesapeake Bay
2 3
$1071/nighttotal: $4284 (4 )

Annapolis Area Private, 3 Bedroom Pool, Jacuzzi & Sauna & Casino-like Game Room

house - Riva
Vacation rental for up to 6 people with an excellent rating of 100% based on 1 reviews. This accommodation is located in Riva.
Facilities and services: a fridge, a swimming pool and a dish washer. Take advantage of the Free Parking with this accommodation in Riva!
Quailsar Farm | An Esvr Property - Chesapeake Bay
10Excellent 1 review
Chesapeake Bay
2 5
$1232/nighttotal: $4928 (4 )

Quailsar Farm | An Esvr Property

farm - Easton
Farm rental from $656 for 10 people with an excellent rating of 100% based on 1 reviews. You will be located in Easton.
Services and facilities include free parking, a washing machine and a fridge. Take advantage of the pool in this accommodation.

Best family friendly Chesapeake Bay villas and beach houses

Among the 3618 accommodations in Chesapeake Bay, here are the 8 best family friendly villas and beach houses

4 King Bedrooms 2 Baths Free Sunsets-kent Island Across The Water From Annapolis - Chesapeake Bay
9.9Excellent 78 reviews
Chesapeake Bay
2 4
$1119/nighttotal: $4476 (4 )

4 King Bedrooms 2 Baths Free Sunsets-kent Island Across The Water From Annapolis

house - Stevensville
Book this vacation rental for up to 9 guests with an excellent rating of 99% based on 78 reviews. This accommodation is based in Stevensville.
Services and facilities: a cleaning service, a swimming pool and a child space. Pets are welcome in this house.
Kent Island Waterfront | Game Room | Pool | Private Dock | Pet Friendly - Chesapeake Bay
9.5Excellent 22 reviews
Chesapeake Bay
2 4
$1128/nighttotal: $4512 (4 )

Kent Island Waterfront | Game Room | Pool | Private Dock | Pet Friendly

house - Grasonville
This Grasonville vacation home offers a unique location within 9 miles of major attractions like the Chesapeake Bay Environmental Center and Queenstown Premium Outlets. With excellent user, location, and cleanliness ratings, this smoke-free home provides a comfortable and convenient stay for travelers.
The spacious 3490 square foot home features 4 bedrooms and 3 bathrooms, accommodating up to 8 guests. Guests can enjoy amenities such as a fully equipped kitchen, free WiFi, an arcade/game room, a fitness center, a garden, and a terrace/balcony.
Spring Is Firepit And Kayak Season! - Chesapeake Bay
10Excellent 82 reviews
Chesapeake Bay
2 3
$540/nighttotal: $2160 (4 )

Spring Is Firepit And Kayak Season!

house - Irvington
House listing for 8 guests with an excellent rating of 100% based on 82 reviews. You will be based in Irvington.
Services and facilities: a kitchen, a barbecue and a child space. This house in Irvington also has air conditioning!
Cozy Cottage By The Beach - Waterview<br>minutes From Downtown Annapolis - Chesapeake Bay
10Excellent 160 reviews
Chesapeake Bay
2 2
$380/nighttotal: $1520 (4 )

Cozy Cottage By The Beach - Waterview<br>minutes From Downtown Annapolis

house - Highland Beach
House rental with an excellent rating of 100% based on 160 reviews. You will be in Highland Beach.
Services and facilities: an iron, a terrace and a barbecue. Take advantage of the Spa in this house in Highland Beach.
Secluded, Waterfront Home: Huge Game Room, Private Dock, Pedal Boat, & 4 Kayaks! - Chesapeake Bay
9.9Excellent 197 reviews
Chesapeake Bay
2 3
$536/nighttotal: $2144 (4 )

Secluded, Waterfront Home: Huge Game Room, Private Dock, Pedal Boat, & 4 Kayaks!

house - Kilmarnock
This waterfront vacation home in Reedville is 0.5 miles from the Reedville Fishermen's Museum and within 6 miles of Smith Point Marina and Buzzard's Point Marina. It has excellent user, location, and cleanliness ratings.
The house has 3 bedrooms, 2 bathrooms, and a floor area of 3200 square feet. It can accommodate up to 8 guests. It features a fully equipped kitchen, two bathrooms, a washing machine, free WiFi, a dining area, and a smoke-free environment. It also has an arcade/game room, a garden with barbecue grills, a tennis court, and parking.
Waterfront 3br/3ba Getaway: Beach, Dock, Firepit! Amazing Sweeping Views! - Chesapeake Bay
9.8Excellent 113 reviews
Chesapeake Bay
2 3
$600/nighttotal: $2400 (4 )

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

house - Heathsville
Vacation house to rent for 10 guests with an excellent rating of 98% based on 113 reviews. You will stay in Heathsville.
Services and facilities include a child space, a barbecue and a fridge. This house also has a Spa!
Beachfront Urbanna Home W/ Gas Grill & Deck! - Chesapeake Bay
9.9Excellent 84 reviews
Chesapeake Bay
2 1
$957/nighttotal: $3828 (4 )

Beachfront Urbanna Home W/ Gas Grill & Deck!

house - Urbanna
House for up to 12 people with an excellent rating of 99% based on 84 reviews. You will be based in Urbanna.
Services and facilities: a barbecue, a spa and a foosball. Take advantage of the air conditioning in this house in Urbanna.
Lancaster Gem - Cozy Cottage - Chesapeake Bay
9.7Excellent 84 reviews
Chesapeake Bay
2 2
$194/nighttotal: $776 (4 )

Lancaster Gem - Cozy Cottage

cottage - Lancaster
Cottage listing for 4 people with an excellent rating of 97% based on 84 reviews. Your accommodation will be located in Lancaster.
Facilities and services: a kitchen, a fridge and a terrace. Pets are allowed in this accommodation.

Frequently asked questions about villa rentals in Chesapeake Bay

Destinations nearby

Best pet friendly Chesapeake Bay villas and beach houses

Among the 3618 accommodations in Chesapeake Bay, here are the 4 best pet friendly villas and beach houses

Spacious Waterfront Home On The Chesapeake Bay - Chesapeake Bay
10Excellent 70 reviews
Chesapeake Bay
2 3
$473/nighttotal: $1892 (4 )

Spacious Waterfront Home On The Chesapeake Bay

house - Heathsville
This waterfront vacation home in Heathsville is surrounded by stunning views and is within 12 miles of major tourist attractions, including Smith Point Marina and Northern Neck Farm Museum. It has excellent user, location, and cleanliness ratings.
The house has 3 bedrooms, a 2600-square-foot floor area, and can accommodate up to 6 guests. It features a fully equipped kitchen, a fitness center, a private garden with barbecue grills, a fireplace, a DVD player, and a patio. It also has air conditioning, internet, parking, and allows pets.
Cottage On Cabin Creek - Chesapeake Bay
10Excellent 138 reviews
Chesapeake Bay
2 1
$318/nighttotal: $1272 (4 )

Cottage On Cabin Creek

cottage - Secretary
Secluded on the waterfront in Secretary, this waterfront cottage offers private piers for fishing and boating. It's close to local attractions and restaurants, yet provides a relaxing setting for 1-2 guests.
With excellent user, location, and cleanliness ratings, this 1-bedroom, 1-bathroom cottage features a kitchen with a fridge and microwave, air conditioning, a terrace or balcony, a garden, parking, and a charcoal grill and fire pit for outdoor cooking. It also offers internet access and welcomes pets.
'Cora's Cottage' Near Chesapeake Bay Access! - Chesapeake Bay
10Excellent 2 reviews
Chesapeake Bay
2 3
$272/nighttotal: $1088 (4 )

'Cora's Cottage' Near Chesapeake Bay Access!

cottage - Harborton
This charming cottage in Harborton is a perfect getaway for families and pet owners. It is located by the sea, within easy reach of popular attractions like The Blue Crow Antique Mall and Hang Glide Virginia. The cottage has received excellent ratings for its location, cleanliness, and user experience.
With 3 bedrooms, 2 bathrooms, and a spacious 1350 square feet of floor area, this cottage can accommodate up to 6 guests comfortably. It features a fully equipped kitchen, air conditioning, a garden, and parking, providing all the amenities you need for a relaxing and enjoyable stay.
1943 Beach House Walk To Town & Beach & Boardwalk. - Chesapeake Bay
9.9Excellent 27 reviews
Chesapeake Bay
2 2
$237/nighttotal: $948 (4 )

1943 Beach House Walk To Town & Beach & Boardwalk.

cabin - North Beach
This North Beach cabin is ideally situated in the heart of the town, within walking distance of restaurants and the waterfront. It has received excellent ratings for its location, cleanliness, and user experience.
The cabin has 2 bedrooms and 1 bathroom, with a guest capacity of 4. It features a fully equipped kitchen, air conditioning, a private backyard with a screened porch, and on-site parking. Guests can enjoy the outdoor seating areas, barbecue facilities, and proximity to the beach.