Condo
10.0(360 Reviews)
2 Bedrooms
6 Guests
Parking
Ocean View
Balcony/Terrace
View
US $274/Night
7 Nights - US $1,916
Chesapeake Bay Holiday Rentals
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Compare Holiday Rentals, Villas & Resorts in Chesapeake Bay
10.0
House
10.0(17 Reviews)
3 Bedrooms
7 Guests
- Parking
- Balcony/Terrace
- View
Air Conditioner
US $161/Night
7 Nights - US $1,127
Cottage
2 Bedrooms
8 Guests
- Air Conditioner
Internet
Pet Friendly
Child Friendly
US $295/Night
7 Nights - US $2,062
Condo
10.0(284 Reviews)
2 Bedrooms
6 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
US $261/Night
7 Nights - US $1,824
Bed & Breakfast
10.0(11 Reviews)
1 Bedroom
4 Guests
EV Charge Station- Parking
- View
- Air Conditioner
US $187/Night
7 Nights - US $1,312
Condo
10.0(203 Reviews)
2 Bedrooms
4 Guests
Kitchen- Air Conditioner
- Internet
- Pet Friendly
US $224/Night
7 Nights - US $1,568
House
10.0(199 Reviews)
2 Bedrooms
5 Guests
- Parking
Pool- Ocean View
- Balcony/Terrace
US $205/Night
7 Nights - US $1,438
Apartment
10.0(180 Reviews)
2 Bedrooms
4 Guests
- Parking
- Balcony/Terrace
- View
- Kitchen
US $256/Night
7 Nights - US $1,793
House
10.0(176 Reviews)
2 Bedrooms
5 Guests
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
US $417/Night
7 Nights - US $2,917
Luxury Holiday Rentals in Chesapeake Bay
Over 10000+ Luxury Holiday Rentals in or Near Chesapeake Bay
House
3 Bedrooms
6 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
Unlock the Best Price
House
25 Bedrooms
50 Guests
- Parking
- Pool
- View
- Air Conditioner
Unlock the Best Price
House
7 Bedrooms
30 Guests
Private Pool- Parking
- Pool
- Kitchen
Unlock the Best Price
House
1 Bedroom
50 Guests
Hot Tub- Parking
- Pool
- Balcony/Terrace
Unlock the Best Price
House
6 Bedrooms
16 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
Unlock the Best Price
Apartment
4 Bedrooms
10 Guests
- Kitchen
- Air Conditioner
- Internet
- Pet Friendly
Unlock the Best Price
House
8.0(1 Review)
3 Bedrooms
8 Guests
- Kitchen
- Air Conditioner
- Internet
Laundry
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House
8.0(1 Review)
5 Bedrooms
6 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
Unlock the Best Price
House
5 Bedrooms
15 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
Unlock the Best Price
Top-Rated Holiday Rentals with a Pool in Chesapeake Bay
Over 7490+ The Best Private Villas and Holiday Rentals in Chesapeake Bay with a Pool
House
10.0(255 Reviews)
3 Bedrooms
8 Guests
- Private Pool
Oceanfront- Hot Tub
- Parking
US $386/Night
7 Nights - US $2,705
House
10.0(219 Reviews)
3 Bedrooms
12 Guests
- Private Pool
- Hot Tub
- Parking
- Pool
US $537/Night
7 Nights - US $3,758
House
10.0(214 Reviews)
3 Bedrooms
7 Guests
- Private Pool
- Hot Tub
- Parking
- Pool
US $587/Night
7 Nights - US $4,106
Condo
10.0(156 Reviews)
3 Bedrooms
6 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
US $393/Night
7 Nights - US $2,748
Cottage
10.0(153 Reviews)
2 Bedrooms
4 Guests
- Private Pool
- Oceanfront
- Parking
- Pool
US $516/Night
7 Nights - US $3,614
House
10.0(148 Reviews)
5 Bedrooms
10 Guests
- Private Pool
- Oceanfront
- Parking
- Pool
US $1,147/Night
7 Nights - US $8,031
House
10.0(148 Reviews)
2 Bedrooms
5 Guests
- Private Pool
Breakfast- Parking
- Pool
US $716/Night
7 Nights - US $5,015
Cottage
10.0(143 Reviews)
2 Bedrooms
5 Guests
- Parking
- Pool
- Balcony/Terrace
- View
US $460/Night
7 Nights - US $3,222
House
10.0(126 Reviews)
4 Bedrooms
8 Guests
- Private Pool
- Hot Tub
- Parking
- Pool
US $601/Night
7 Nights - US $4,205
Pet-Friendly Holiday Rentals in Chesapeake Bay
Over 9324+ Pet-Friendly Holiday Rentals in or Near Chesapeake Bay
Cottage
10.0(122 Reviews)
1 Bedroom
5 Guests
- Oceanfront
- Hot Tub
- Breakfast
- Parking
US $319/Night
7 Nights - US $2,234
US $597/Night
7 Nights - US $4,178
Bed & Breakfast
10.0(97 Reviews)
1 Bedroom
- Breakfast
- Parking
- Balcony/Terrace
- Kitchen
US $374/Night
7 Nights - US $2,617
House
10.0(96 Reviews)
2 Bedrooms
6 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $491/Night
7 Nights - US $3,434
House
10.0(6 Reviews)
3 Bedrooms
8 Guests
- Oceanfront
- Hot Tub
- Parking
Spa
US $288/Night
7 Nights - US $2,017
House
10.0(94 Reviews)
2 Bedrooms
4 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
US $380/Night
7 Nights - US $2,659
House
10.0(93 Reviews)
2 Bedrooms
4 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $309/Night
7 Nights - US $2,163
House
10.0(84 Reviews)
2 Bedrooms
6 Guests
- Kitchen
- Air Conditioner
- Internet
- Pet Friendly
US $282/Night
7 Nights - US $1,977
House
10.0(77 Reviews)
2 Bedrooms
6 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $736/Night
7 Nights - US $5,155
Large Holiday Rentals and Private Villas in Chesapeake Bay
Over 4351+ Large Holiday Rentals and Private Villas in or Near Chesapeake Bay
House
10.0(23 Reviews)
1 Bedroom
10 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $711/Night
7 Nights - US $4,978
House
10.0(5 Reviews)
4 Bedrooms
11 Guests
- Parking
- Balcony/Terrace
- View
- Air Conditioner
US $219/Night
7 Nights - US $1,534
US $3,233/Night
7 Nights - US $22,632
US $344/Night
7 Nights - US $2,409
House
10.0(4 Reviews)
6 Bedrooms
22 Guests
- EV Charge Station
- Parking
- Balcony/Terrace
- View
US $989/Night
7 Nights - US $6,922
House
10.0(4 Reviews)
1 Bedroom
16 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $841/Night
7 Nights - US $5,886
US $484/Night
7 Nights - US $3,386
House
10.0(2 Reviews)
2 Bedrooms
10 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $654/Night
7 Nights - US $4,581
House
10.0(2 Reviews)
2 Bedrooms
11 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $455/Night
7 Nights - US $3,184
Wheelchair Accessible Holiday Homes in Chesapeake Bay
Over 7375+ Wheelchair Accessible Holiday Homes in or Near Chesapeake Bay
Condo
10.0(96 Reviews)
2 Bedrooms
6 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $423/Night
7 Nights - US $2,959
House
10.0(4 Reviews)
1 Bedroom
2 Guests
- Hot Tub
- Balcony/Terrace
- View
- Kitchen
US $185/Night
7 Nights - US $1,292
US $538/Night
7 Nights - US $3,765
Condo
10.0(70 Reviews)
2 Bedrooms
5 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
US $283/Night
7 Nights - US $1,982
Villa
10.0(3 Reviews)
3 Bedrooms
8 Guests
- Hot Tub
- Breakfast
- Parking
- Balcony/Terrace
US $225/Night
7 Nights - US $1,575
Condo
10.0(54 Reviews)
2 Bedrooms
6 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $541/Night
7 Nights - US $3,785
Condo
10.0(44 Reviews)
2 Bedrooms
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $267/Night
7 Nights - US $1,871
Condo
10.0(37 Reviews)
2 Bedrooms
6 Guests
- Parking
- Pool
- Ocean View
- Balcony/Terrace
US $758/Night
7 Nights - US $5,306
Condo
10.0(32 Reviews)
2 Bedrooms
7 Guests
- Parking
- Pool
- Balcony/Terrace
- Kitchen
US $581/Night
7 Nights - US $4,066
Chesapeake Bay Private Villas and Holiday Homes Under $200
Over 10489+ Chesapeake Bay Private Villas and Holiday Homes Under $200
US $165/Night
7 Nights - US $1,156
House
10.0(11 Reviews)
1 Bedroom
2 Guests
- Parking
- Balcony/Terrace
- Air Conditioner
- Internet
US $110/Night
7 Nights - US $773
Bed & Breakfast
10.0(172 Reviews)
1 Bedroom
- Hot Tub
- Breakfast
- Parking
- Balcony/Terrace
US $200/Night
7 Nights - US $1,399
Apartment
10.0(128 Reviews)
1 Bedroom
2 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $176/Night
7 Nights - US $1,233
Apartment
10.0(8 Reviews)
1 Bedroom
2 Guests
- Parking
- Air Conditioner
- Internet
- Child Friendly
US $175/Night
7 Nights - US $1,226
US $135/Night
7 Nights - US $947
House
10.0(77 Reviews)
1 Bedroom
4 Guests
- Parking
- Pool
- Balcony/Terrace
- Kitchen
US $151/Night
7 Nights - US $1,058
Apartment
10.0(71 Reviews)
1 Bedroom
3 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $167/Night
7 Nights - US $1,172
New
Apartment
10.0(39 Reviews)
1 Bedroom
2 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $150/Night
7 Nights - US $1,051
Instantly Bookable Holiday Homes in Chesapeake Bay
Over 16945+ Instantly Bookable Holiday Homes in or Near Chesapeake Bay
Cottage
10.0(125 Reviews)
2 Bedrooms
4 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $363/Night
7 Nights - US $2,543
House
9.4(31 Reviews)
4 Bedrooms
8 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
US $537/Night
7 Nights - US $3,761
House
10.0(100 Reviews)
2 Bedrooms
4 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $467/Night
7 Nights - US $3,272
Cottage
10.0(93 Reviews)
1 Bedroom
4 Guests
- Parking
- Balcony/Terrace
- View
- Kitchen
US $310/Night
7 Nights - US $2,170
Apartment
10.0(87 Reviews)
2 Bedrooms
4 Guests
- Private Pool
- Parking
- Pool
- Ocean View
US $394/Night
7 Nights - US $2,757
Cottage
10.0(77 Reviews)
1 Bedroom
4 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $293/Night
7 Nights - US $2,049
House
10.0(75 Reviews)
2 Bedrooms
8 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $614/Night
7 Nights - US $4,296
Apartment
10.0(73 Reviews)
1 Bedroom
4 Guests
- Hot Tub
- Parking
- Ocean View
- Balcony/Terrace
US $388/Night
7 Nights - US $2,713
House
10.0(69 Reviews)
2 Bedrooms
4 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $247/Night
7 Nights - US $1,731
Book a Last Minute Place to Stay in Chesapeake Bay
About Casai's Private Villas and Holiday Rentals in Chesapeake Bay
Discover more than 29146 vacation rentals available in Chesapeake Bay. These rentals, ranging from vacation rentals to Casai Homes and other short-term private accommodations, offer top-notch amenities with unbeatable value, ensuring both comfort and luxury. Enjoy more space and value when you stay at a Casai property in Chesapeake Bay.
Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Chesapeake Bay, you can effortlessly compare various deals with just a click. Whether you're looking for a Casai with exceptional swimming pools, hot tubs, pet-friendly options, or large master suite bedrooms equipped with large screen televisions, you'll find a variety of options near Chesapeake Bay. On average, places to stay near Chesapeake Bay offer 718.83 ft², with nightly prices averaging US $365.
With Casai, finding and comparing holiday rentals in Chesapeake Bay is easy and secure, often at a 30-40% discount compared to hotel prices. Simply search for your destination and secure your reservation today.
Other Places to Stay in Chesapeake Bay, US
There are 29146 Chesapeake Bay, US Holiday Rentals
- Prices for a holiday home in Chesapeake Bay start at US $30
- Top rated vacation home in Chesapeake Bay is Cottage on a Private Island in the York River
- Most popular short term in Chesapeake Bay is Washington Plaza Hotel
- Cheapest place to stay in Chesapeake Bay is Private suite, beautiful old house, quiet location
- Most expensive holiday rental in Chesapeake Bay is Spacious Family Stay, Large Dining, 3 Cozy Bedrooms, Home Near Buckroe Beach
Frequently Asked Questions About Chesapeake Bay?
What are the top holiday rentals in Chesapeake Bay?
With numerous options available in Chesapeake Bay, planning to stay in the area? Consider booking a few nights at one of these properties, rated as the Top Holiday Rentals in Chesapeake Bay:
- Cottage on a Private Island in the York River
- Cozy, Dog-friendly Duplex At The North End Short Walk To The Beach!
- Water Front Retreat - Sunrise and Sunset Water Views - Lots of Amenities
- Fantastic home in the heart of the VB Resort Area Walk to Beach, Boardwalk.
- Private Apt. in Historic Home: Walk to Monuments, Museums & Convention Center.
- Historic Cottage on Ware River Estate
- Breezy, Quaint, and Dog- Friendly North End duplex.
- Riverfront House, Dock, Hot Tub, Salt Pool, near beach, Free WiFi
- PERFECT LOCATION in the heart of history
- Island Life! Kent Island Waterfront with Pool-Bring your boat!
How many holiday rentals have private pools in Chesapeake Bay?
Discover a selection of holiday rentals with private pools near Chesapeake Bay with Casai. Experience the epitome of luxury and relaxation in our top-rated villas and holiday homes, where you can enjoy exclusive access to refreshing swimming pools.
Which holiday homes in Chesapeake Bay are best for families?
If you're searching for a family-friendly holiday home in Chesapeake Bay, consider one of the following properties. Each comes highly recommended, with excellent reviews for families or groups staying in Chesapeake Bay:
How many Casai.nz holiday rentals are available in Chesapeake Bay?
As of 2026, Casai boasts over 29146 properties listed in the Chesapeake Bay area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Chesapeake Bay.
Nearby Neighborhood (16)
| Neighborhood | Property Count |
|---|---|
| Northwest Vacation Rentals in Chesapeake Bay, US | 1769 |
| Northeast Virginia Beach Vacation Rentals in Chesapeake Bay, US | 969 |
| Northeast Vacation Rentals in Chesapeake Bay, US | 631 |
| Capitol Hill Vacation Rentals in Chesapeake Bay, US | 597 |
| Downtown Washington D.C. Vacation Rentals in Chesapeake Bay, US | 548 |
| Downtown Baltimore Vacation Rentals in Chesapeake Bay, US | 505 |
| Dupont Circle Vacation Rentals in Chesapeake Bay, US | 210 |
| Crystal City Vacation Rentals in Chesapeake Bay, US | 183 |
| Downtown Vacation Rentals in Chesapeake Bay, US | 135 |
| Rosslyn Vacation Rentals in Chesapeake Bay, US | 127 |
| Old Town Alexandria Vacation Rentals in Chesapeake Bay, US | 122 |
| Georgetown Vacation Rentals in Chesapeake Bay, US | 68 |
| Fells Point Vacation Rentals in Chesapeake Bay, US | 59 |
| Foggy Bottom Vacation Rentals in Chesapeake Bay, US | 53 |
| Pentagon City Vacation Rentals in Chesapeake Bay, US | 31 |
| Chic's Beach Vacation Rentals in Chesapeake Bay, US | 31 |
