Condo
10.0(362 Reviews)
2 Bedrooms
6 Guests
Parking
Ocean View
Balcony/Terrace
View
CA $384/Night
7 Nights - CA $2,684
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
CA $226/Night
7 Nights - CA $1,579
Bed & Breakfast
10.0(173 Reviews)
1 Bedroom
Hot Tub
Breakfast- Parking
- Balcony/Terrace
CA $280/Night
7 Nights - CA $1,960
Condo
10.0(285 Reviews)
2 Bedrooms
6 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
CA $368/Night
7 Nights - CA $2,578
Bed & Breakfast
10.0(14 Reviews)
4 Bedrooms
9 Guests
- Breakfast
- Parking
- Balcony/Terrace
- View
CA $312/Night
7 Nights - CA $2,187
Condo
10.0(203 Reviews)
2 Bedrooms
4 Guests
Kitchen- Air Conditioner
Internet
Pet Friendly
CA $406/Night
7 Nights - CA $2,840
House
10.0(199 Reviews)
2 Bedrooms
5 Guests
- Parking
Pool- Ocean View
- Balcony/Terrace
CA $288/Night
7 Nights - CA $2,014
Cottage
10.0(184 Reviews)
2 Bedrooms
6 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
CA $497/Night
7 Nights - CA $3,483
Cabin
10.0(183 Reviews)
2 Bedrooms
5 Guests
Oceanfront- Parking
- Pool
- Ocean View
CA $219/Night
7 Nights - CA $1,535
Luxury Holiday Rentals in Chesapeake Bay
Over 10000+ Luxury Holiday Rentals in or Near Chesapeake Bay
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
25 Bedrooms
50 Guests
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
Unlock the Best Price
House
3 Bedrooms
7 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
Unlock the Best Price
House
10.0(1 Review)
4 Bedrooms
7 Guests
- Hot Tub
- Parking
- Kitchen
- Air Conditioner
Unlock the Best Price
House
10.0(2 Reviews)
3 Bedrooms
8 Guests
- Hot Tub
- Balcony/Terrace
- Kitchen
- Air Conditioner
Unlock the Best Price
Unlock the Best Price
CA $13,409/Night
7 Nights - CA $93,863
CA $12,944/Night
7 Nights - CA $90,606
Top-Rated Holiday Rentals with a Pool in Chesapeake Bay
Over 7584+ The Best Private Villas and Holiday Rentals in Chesapeake Bay with a Pool
Cottage
10.0(278 Reviews)
4 Bedrooms
8 Guests
- Parking
- Pool
- Balcony/Terrace
- View
CA $474/Night
7 Nights - CA $3,319
House
10.0(263 Reviews)
3 Bedrooms
8 Guests
- Private Pool
- Hot Tub
- Parking
- Pool
CA $636/Night
7 Nights - CA $4,449
House
10.0(219 Reviews)
3 Bedrooms
12 Guests
- Private Pool
- Hot Tub
- Parking
- Pool
CA $833/Night
7 Nights - CA $5,829
House
10.0(214 Reviews)
3 Bedrooms
7 Guests
- Private Pool
- Hot Tub
- Parking
- Pool
CA $821/Night
7 Nights - CA $5,745
Condo
10.0(156 Reviews)
3 Bedrooms
6 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
CA $553/Night
7 Nights - CA $3,869
Cottage
10.0(154 Reviews)
2 Bedrooms
4 Guests
- Private Pool
- Parking
- Pool
- Ocean View
CA $712/Night
7 Nights - CA $4,984
House
10.0(151 Reviews)
2 Bedrooms
5 Guests
- Private Pool
- Breakfast
- Parking
- Pool
CA $953/Night
7 Nights - CA $6,672
House
10.0(149 Reviews)
5 Bedrooms
10 Guests
- Private Pool
- Oceanfront
- Parking
- Pool
CA $1,607/Night
7 Nights - CA $11,251
Cottage
10.0(143 Reviews)
2 Bedrooms
5 Guests
- Parking
- Pool
- Balcony/Terrace
- View
CA $645/Night
7 Nights - CA $4,514
Pet-Friendly Holiday Rentals in Chesapeake Bay
Over 9445+ Pet-Friendly Holiday Rentals in or Near Chesapeake Bay
Apartment
10.0(161 Reviews)
1 Bedroom
4 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
CA $419/Night
7 Nights - CA $2,936
CA $836/Night
7 Nights - CA $5,853
Bed & Breakfast
10.0(98 Reviews)
1 Bedroom
- Breakfast
- Parking
- Balcony/Terrace
- Kitchen
CA $524/Night
7 Nights - CA $3,666
House
10.0(145 Reviews)
1 Bedroom
2 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
CA $346/Night
7 Nights - CA $2,422
House
10.0(6 Reviews)
3 Bedrooms
8 Guests
- Hot Tub
- Parking
- Balcony/Terrace
- View
CA $423/Night
7 Nights - CA $2,964
Cottage
10.0(125 Reviews)
1 Bedroom
5 Guests
- Hot Tub
- Breakfast
- Parking
- Ocean View
CA $419/Night
7 Nights - CA $2,929
House
10.0(103 Reviews)
2 Bedrooms
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
CA $618/Night
7 Nights - CA $4,330
House
10.0(96 Reviews)
2 Bedrooms
6 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
CA $698/Night
7 Nights - CA $4,885
House
10.0(95 Reviews)
2 Bedrooms
4 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
CA $537/Night
7 Nights - CA $3,757
Large Holiday Rentals and Private Villas in Chesapeake Bay
Over 4472+ Large Holiday Rentals and Private Villas in or Near Chesapeake Bay
Cabin
10.0(92 Reviews)
2 Bedrooms
10 Guests
- Parking
- Pool
- Balcony/Terrace
- Kitchen
CA $824/Night
7 Nights - CA $5,769
House
10.0(7 Reviews)
4 Bedrooms
11 Guests
- Balcony/Terrace
- View
- Air Conditioner
- Internet
CA $307/Night
7 Nights - CA $2,149
CA $4,529/Night
7 Nights - CA $31,705
Apartment
10.0(33 Reviews)
1 Bedroom
100 Guests
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
CA $436/Night
7 Nights - CA $3,053
House
10.0(4 Reviews)
6 Bedrooms
22 Guests
EV Charge Station- Parking
- Balcony/Terrace
- View
CA $1,385/Night
7 Nights - CA $9,697
House
10.0(23 Reviews)
1 Bedroom
10 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
CA $996/Night
7 Nights - CA $6,974
CA $476/Night
7 Nights - CA $3,334
House
10.0(4 Reviews)
1 Bedroom
16 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
CA $1,178/Night
7 Nights - CA $8,246
House
10.0(3 Reviews)
2 Bedrooms
10 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
CA $917/Night
7 Nights - CA $6,417
Wheelchair Accessible Holiday Homes in Chesapeake Bay
Over 7376+ Wheelchair Accessible Holiday Homes in or Near Chesapeake Bay
Condo
10.0(96 Reviews)
2 Bedrooms
6 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
CA $592/Night
7 Nights - CA $4,145
House
10.0(4 Reviews)
1 Bedroom
2 Guests
- Hot Tub
- Balcony/Terrace
- View
- Kitchen
CA $258/Night
7 Nights - CA $1,810
CA $754/Night
7 Nights - CA $5,274
Condo
10.0(74 Reviews)
2 Bedrooms
5 Guests
- Parking
- Pool
- Ocean View
- Balcony/Terrace
CA $410/Night
7 Nights - CA $2,868
Apartment
10.0(3 Reviews)
1 Bedroom
4 Guests
Private Beach- Oceanfront
- Hot Tub
- Parking
CA $252/Night
7 Nights - CA $1,765
Condo
10.0(54 Reviews)
2 Bedrooms
6 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
CA $760/Night
7 Nights - CA $5,321
Condo
10.0(45 Reviews)
2 Bedrooms
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
CA $395/Night
7 Nights - CA $2,767
Condo
10.0(37 Reviews)
2 Bedrooms
6 Guests
- Parking
- Pool
- Ocean View
- Balcony/Terrace
CA $1,062/Night
7 Nights - CA $7,433
Condo
10.0(33 Reviews)
2 Bedrooms
7 Guests
- Parking
- Pool
- Balcony/Terrace
- Kitchen
CA $668/Night
7 Nights - CA $4,678
Chesapeake Bay Private Villas and Holiday Homes Under $200
Over 10487+ Chesapeake Bay Private Villas and Holiday Homes Under $200
CA $231/Night
7 Nights - CA $1,619
Bed & Breakfast
10.0(11 Reviews)
1 Bedroom
4 Guests
- EV Charge Station
- Parking
- View
- Air Conditioner
CA $263/Night
7 Nights - CA $1,838
Bed & Breakfast
10.0(74 Reviews)
1 Bedroom
- Hot Tub
- Breakfast
- Parking
- Pool
CA $277/Night
7 Nights - CA $1,939
Apartment
10.0(130 Reviews)
1 Bedroom
2 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
CA $274/Night
7 Nights - CA $1,918
House
10.0(11 Reviews)
1 Bedroom
2 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
CA $155/Night
7 Nights - CA $1,083
CA $190/Night
7 Nights - CA $1,327
House
10.0(77 Reviews)
1 Bedroom
4 Guests
- Parking
- Pool
- Balcony/Terrace
- Kitchen
CA $213/Night
7 Nights - CA $1,491
Apartment
10.0(72 Reviews)
1 Bedroom
3 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
CA $259/Night
7 Nights - CA $1,814
Cottage
10.0(66 Reviews)
2 Bedrooms
6 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
CA $268/Night
7 Nights - CA $1,876
Instantly Bookable Holiday Homes in Chesapeake Bay
Over 17265+ Instantly Bookable Holiday Homes in or Near Chesapeake Bay
Apartment
10.0(130 Reviews)
2 Bedrooms
2 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
CA $357/Night
7 Nights - CA $2,501
CA $705/Night
7 Nights - CA $4,934
Cottage
10.0(126 Reviews)
2 Bedrooms
4 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
CA $473/Night
7 Nights - CA $3,309
House
10.0(100 Reviews)
2 Bedrooms
4 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
CA $711/Night
7 Nights - CA $4,980
Cottage
10.0(94 Reviews)
1 Bedroom
4 Guests
- Parking
- Balcony/Terrace
- View
- Kitchen
CA $537/Night
7 Nights - CA $3,763
House
10.0(93 Reviews)
2 Bedrooms
4 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
CA $458/Night
7 Nights - CA $3,209
House
10.0(86 Reviews)
2 Bedrooms
6 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
CA $672/Night
7 Nights - CA $4,707
House
10.0(86 Reviews)
2 Bedrooms
6 Guests
- Kitchen
- Air Conditioner
- Internet
- Pet Friendly
CA $372/Night
7 Nights - CA $2,600
House
10.0(81 Reviews)
2 Bedrooms
5 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
CA $322/Night
7 Nights - CA $2,254
Book a Last Minute Place to Stay in Chesapeake Bay
About Casai's Private Villas and Holiday Rentals in Chesapeake Bay
Discover more than 29585 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 730.18 ft², with nightly prices averaging CA $507.
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 29585 Chesapeake Bay, US Holiday Rentals
- Prices for a holiday home in Chesapeake Bay start at CA $31
- 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 ❃King Bed ❃Fully Fenced Yard❃ ~ Twisted Stairs ~
- Most expensive holiday rental in Chesapeake Bay is 25 Bedrooms - Retreat Center Waterfront Renovated
Recently Booked Holiday Rentals in Chesapeake Bay
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
- Autumn in Virginia where the air is delightful!
- 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.
- Family and Pet-Friendly, Waterfront with Pier
- Riverfront House, Dock, Hot Tub, Salt Pool, near beach, Free WiFi
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.ca holiday rentals are available in Chesapeake Bay?
As of 2026, Casai boasts over 29585 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 | 1792 |
| Northeast Virginia Beach Vacation Rentals in Chesapeake Bay, US | 980 |
| Northeast Vacation Rentals in Chesapeake Bay, US | 655 |
| Capitol Hill Vacation Rentals in Chesapeake Bay, US | 601 |
| Downtown Washington D.C. Vacation Rentals in Chesapeake Bay, US | 561 |
| Downtown Baltimore Vacation Rentals in Chesapeake Bay, US | 509 |
| Dupont Circle Vacation Rentals in Chesapeake Bay, US | 211 |
| 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 | 125 |
| 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 |
