Estia Villas - Vacation Rentals in Chesapeake Bay
Villa
10.0
(
77 Reviews
)
3 Bedrooms
3 Bathrooms
6 Guests
1700 ft²
-
Hot Tub -
Parking -
Balcony/Terrace -
Kitchen
US $280
/Night
7 Nights - $1,960
Villa
10.0
(
3 Reviews
)
3 Bedrooms
3 Bathrooms
8 Guests
3229.17 ft²
-
Hot Tub
-
Breakfast -
Parking
-
Balcony/Terrace
US $225
/Night
7 Nights - $1,575
US $3,233
/Night
7 Nights - $22,632
Villa
10.0
(
76 Reviews
)
6 Bedrooms
4 Bathrooms
12 Guests
-
Private Pool -
Parking
-
Pool -
Balcony/Terrace
US $961
/Night
7 Nights - $6,729
Villa
10.0
(
48 Reviews
)
9 Bedrooms
6 Bathrooms
28 Guests
10000 ft²
-
Private Pool
-
Hot Tub
-
Parking
-
Pool
US $1,770
/Night
7 Nights - $12,392
Villa
10.0
(
46 Reviews
)
1 Bedroom
1 Bathroom
2 Guests
375 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $347
/Night
7 Nights - $2,427
Villa
10.0
(
34 Reviews
)
2 Bedrooms
1 Bathroom
4 Guests
-
Private Pool
-
Parking
-
Pool
-
Ocean View
US $448
/Night
7 Nights - $3,134
Villa
10.0
(
24 Reviews
)
6 Bedrooms
6 Bathrooms
12 Guests
5000 ft²
-
Private Pool
-
Parking
-
Pool
-
Balcony/Terrace
US $1,032
/Night
7 Nights - $7,224
See More Chesapeake Bay Vacation Rentals
Luxury Places to Stay in Chesapeake Bay
Over 10000+
Luxury Places to Stay in or Near Chesapeake Bay
House
3 Bedrooms
2 Bathrooms
6 Guests
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
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House
25 Bedrooms
20 Bathrooms
40 Guests
11000.72 ft²
-
Parking
-
Pool
-
View -
Air Conditioner
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House
1 Bedroom
1 Bathroom
50 Guests
17000 ft²
-
Hot Tub
-
Parking
-
Pool
-
Balcony/Terrace
Unlock the Best Price
House
7 Bedrooms
7 Bathrooms
30 Guests
-
Private Pool
-
Parking
-
Pool
-
Kitchen
Unlock the Best Price
New
House
2 Bedrooms
1 Bathroom
-
Air Conditioner
-
Internet -
Child Friendly -
Laundry
Unlock the Best Price
House
3 Bedrooms
2 Bathrooms
1 Guest
-
Air Conditioner
-
Internet
-
Child Friendly
-
Laundry
Unlock the Best Price
New
Apartment
3 Bedrooms
3 Bathrooms
10 Guests
2000 ft²
-
Parking
-
Kitchen
-
Air Conditioner
-
Internet
Unlock the Best Price
House
10.0
(
1 Review
)
4 Bedrooms
3 Bathrooms
7 Guests
2200 ft²
-
Hot Tub
-
Parking
-
Kitchen
-
Air Conditioner
Unlock the Best Price
Find More Chesapeake Bay Villas, Resorts, & Rentals on BedroomVillas
Top-Rated Vacation Rentals with a Pool in Chesapeake Bay
Over 7595+
Top-Rated Vacation Rentals with a Pool in or Near Chesapeake Bay
House
10.0
(
254 Reviews
)
3 Bedrooms
3 Bathrooms
8 Guests
2100 ft²
-
Private Pool
-
Oceanfront -
Hot Tub
-
Parking
US $393
/Night
7 Nights - $2,749
House
10.0
(
214 Reviews
)
3 Bedrooms
2 Bathrooms
12 Guests
-
Private Pool
-
Hot Tub
-
Parking
-
Pool
US $581
/Night
7 Nights - $4,069
House
10.0
(
213 Reviews
)
3 Bedrooms
2 Bathrooms
7 Guests
2200 ft²
-
Private Pool
-
Hot Tub
-
Parking
-
Pool
US $599
/Night
7 Nights - $4,192
House
10.0
(
199 Reviews
)
2 Bedrooms
1 Bathroom
5 Guests
1250 ft²
-
Oceanfront
-
Parking
-
Pool
-
Ocean View
US $206
/Night
7 Nights - $1,443
Apartment
10.0
(
163 Reviews
)
1 Bedroom
1 Bathroom
4 Guests
450 ft²
-
Parking
-
Pool
-
Kitchen
-
Air Conditioner
US $76
/Night
7 Nights - $529
Cottage
10.0
(
153 Reviews
)
2 Bedrooms
2 Bathrooms
4 Guests
1200 ft²
-
Private Pool
-
Oceanfront
-
Parking
-
Pool
US $867
/Night
7 Nights - $6,070
New
Condo
10.0
(
151 Reviews
)
3 Bedrooms
2 Bathrooms
6 Guests
1329 ft²
-
Parking
-
Pool
-
Ocean View
-
Balcony/Terrace
US $520
/Night
7 Nights - $3,639
House
10.0
(
146 Reviews
)
2 Bedrooms
2 Bathrooms
5 Guests
1100 ft²
-
Private Pool
-
Breakfast
-
Parking
-
Pool
US $651
/Night
7 Nights - $4,557
Pet-Friendly Vacation Rentals in Chesapeake Bay
Over 9233+
Pet-Friendly Vacation Rentals in or Near Chesapeake Bay
Cottage
10.0
(
381 Reviews
)
3 Bedrooms
2 Bathrooms
8 Guests
1500 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $261
/Night
7 Nights - $1,825
Apartment
8.9
(
44 Reviews
)
3 Bedrooms
2 Bathrooms
8 Guests
914.93 ft²
-
Parking
-
Balcony/Terrace
-
Air Conditioner
-
Internet
US $161
/Night
7 Nights - $1,127
House
4 Bedrooms
3 Bathrooms
10 Guests
-
Parking
-
Pool
-
Spa -
Ocean View
US $676
/Night
7 Nights - $4,733
House
10.0
(
209 Reviews
)
5 Bedrooms
3 Bathrooms
23 Guests
3690 ft²
-
Hot Tub
-
Parking
-
Ocean View
-
Balcony/Terrace
US $678
/Night
7 Nights - $4,744
![Award Winning Ocean Front Architectural Gem [Home Share per VA Beach Zoning] in Virginia Beach](https://imgservice.estiavillas.com/640x287/award-winning-oce-us-virginia-beach-ha-321391482-0.jpg)
House
10.0
(
201 Reviews
)
4 Bedrooms
3 Bathrooms
12 Guests
3100 ft²
-
Oceanfront
-
Hot Tub
-
Parking
-
Ocean View
US $1,319
/Night
7 Nights - $9,233
Cottage
10.0
(
142 Reviews
)
2 Bedrooms
1 Bathroom
5 Guests
1000 ft²
-
Parking
-
Pool
-
Ocean View
-
Balcony/Terrace
US $457
/Night
7 Nights - $3,200
House
10.0
(
42 Reviews
)
5 Bedrooms
3 Bathrooms
10 Guests
3100 ft²
-
Private Pool
-
Oceanfront
-
Breakfast
-
Parking
US $942
/Night
7 Nights - $6,595
Cottage
9.8
(
249 Reviews
)
2 Bedrooms
1 Bathroom
6 Guests
-
Parking
-
Ocean View
-
Balcony/Terrace
-
View
US $549
/Night
7 Nights - $3,844
See More Pet-Friendly Vacation Rentals in Chesapeake Bay on PetFriendly.io
Large Vacation Homes & Villas in Chesapeake Bay
Over 4321+
Large Vacation Homes & Villas in or Near Chesapeake Bay
House
10.0
(
88 Reviews
)
5 Bedrooms
4 Bathrooms
8 Guests
5000 ft²
-
Private Pool
-
Hot Tub
-
Parking
-
Pool
US $1,168
/Night
7 Nights - $8,177
Apartment
5.8
(
17 Reviews
)
6 Bedrooms
6 Bathrooms
20 Guests
898.79 ft²
-
Parking
-
Air Conditioner
-
Internet
-
Child Friendly
US $126
/Night
7 Nights - $882
Villa
1 Bedroom
1 Bathroom
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $3,233
/Night
7 Nights - $22,632
House
10.0
(
74 Reviews
)
4 Bedrooms
3 Bathrooms
10 Guests
-
Private Pool
-
Oceanfront
-
Parking
-
Pool
US $749
/Night
7 Nights - $5,245
House
9.8
(
136 Reviews
)
4 Bedrooms
2 Bathrooms
15 Guests
2440 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $669
/Night
7 Nights - $4,686
House
9.8
(
117 Reviews
)
4 Bedrooms
3 Bathrooms
12 Guests
2200 ft²
-
Oceanfront
-
Parking
-
Ocean View
-
Balcony/Terrace
US $406
/Night
7 Nights - $2,840
House
9.8
(
98 Reviews
)
4 Bedrooms
2 Bathrooms
12 Guests
2100 ft²
-
Parking
-
Ocean View
-
Balcony/Terrace
-
View
US $660
/Night
7 Nights - $4,619
House
9.8
(
52 Reviews
)
3 Bedrooms
2 Bathrooms
12 Guests
-
Private Pool
-
Hot Tub
-
Parking
-
Pool
US $776
/Night
7 Nights - $5,433
See More Family Vacation Rentals in Chesapeake Bay on FVR
Wheelchair Accessible Vacation Homes in Chesapeake Bay
Over 7356+
Wheelchair Accessible Vacation Homes in or Near Chesapeake Bay
Condo
9.8
(
205 Reviews
)
2 Bedrooms
2 Bathrooms
6 Guests
1055 ft²
-
Oceanfront
-
Parking
-
Pool
-
Ocean View
US $409
/Night
7 Nights - $2,864
Apartment
2 Bedrooms
2 Bathrooms
5 Guests
1076.39 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $285
/Night
7 Nights - $1,995
Bed & Breakfast
10.0
(
44 Reviews
)
1 Bedroom
1 Bathroom
-
Breakfast
-
Parking
-
Pool
-
Spa
US $538
/Night
7 Nights - $3,765
House
9.6
(
27 Reviews
)
5 Bedrooms
3 Bathrooms
15 Guests
45284 ft²
-
Private Pool
-
Oceanfront
-
Parking
-
Pool
US $782
/Night
7 Nights - $5,475
Condo
10.0
(
94 Reviews
)
2 Bedrooms
2 Bathrooms
6 Guests
1100 ft²
-
Parking
-
Ocean View
-
Balcony/Terrace
-
View
US $423
/Night
7 Nights - $2,959
Condo
10.0
(
52 Reviews
)
3 Bedrooms
2 Bathrooms
8 Guests
1800 ft²
-
Parking
-
Pool
-
Ocean View
-
Balcony/Terrace
US $505
/Night
7 Nights - $3,532
House
9.8
(
58 Reviews
)
7 Bedrooms
6 Bathrooms
21 Guests
5000 ft²
-
Private Pool
-
Oceanfront
-
Hot Tub
-
Parking
US $3,177
/Night
7 Nights - $22,240
Condo
8.2
(
24 Reviews
)
2 Bedrooms
2 Bathrooms
5 Guests
2831 ft²
-
Oceanfront
-
Parking
-
Pool
-
Ocean View
US $259
/Night
7 Nights - $1,816
Chesapeake Bay Vacation Rentals and Airbnb Places to Stay Under $200
Over 10243+
Chesapeake Bay Vacation Rentals and Airbnb Places to Stay Under $200
Apartment
10.0
(
63 Reviews
)
1 Bedroom
1 Bathroom
5 Guests
600 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $192
/Night
7 Nights - $1,345
Apartment
5.0
(
1 Review
)
1 Bedroom
1 Bathroom
3 Guests
6458.35 ft²
-
Parking
-
Air Conditioner
-
Internet
US $137
/Night
7 Nights - $959
Cottage
10.0
(
1 Review
)
1 Bedroom
1 Bathroom
-
Oceanfront
-
Parking
-
Ocean View
-
View
US $194
/Night
7 Nights - $1,358
House
8.6
(
15 Reviews
)
1 Bedroom
1 Bathroom
5 Guests
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $117
/Night
7 Nights - $822
Apartment
9.8
(
119 Reviews
)
1 Bedroom
1 Bathroom
5 Guests
750 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $183
/Night
7 Nights - $1,283
Apartment
9.0
(
7 Reviews
)
1 Bedroom
1 Bathroom
1 Guest
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
-
Internet
US $130
/Night
7 Nights - $911
Cottage
8.4
(
47 Reviews
)
2 Bedrooms
1 Bathroom
5 Guests
940 ft²
-
Parking
-
Ocean View
-
Balcony/Terrace
-
View
US $192
/Night
7 Nights - $1,341
Apartment
9.8
(
70 Reviews
)
1 Bedroom
1 Bathroom
3 Guests
300 ft²
-
Parking
-
Pool
-
Ocean View
-
Balcony/Terrace
US $167
/Night
7 Nights - $1,169
See More Chesapeake Bay Vacation Rental Deals
Instantly Bookable Vacation Homes in Chesapeake Bay
Over 16862+
Instantly Bookable Vacation Homes in or Near Chesapeake Bay
Apartment
10.0
(
293 Reviews
)
1 Bedroom
1 Bathroom
4 Guests
725 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $311
/Night
7 Nights - $2,178
Apartment
2 Bedrooms
2 Bathrooms
4 Guests
-
Air Conditioner
-
Internet
-
Child Friendly
-
Laundry
US $411
/Night
7 Nights - $2,879
House
10.0
(
231 Reviews
)
3 Bedrooms
2 Bathrooms
8 Guests
1295 ft²
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
-
Internet
US $533
/Night
7 Nights - $3,734
House
10.0
(
215 Reviews
)
3 Bedrooms
2 Bathrooms
8 Guests
2335 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $817
/Night
7 Nights - $5,718
House
10.0
(
161 Reviews
)
3 Bedrooms
2 Bathrooms
6 Guests
1740 ft²
-
Oceanfront
-
Parking
-
Ocean View
-
Balcony/Terrace
US $276
/Night
7 Nights - $1,931
House
10.0
(
127 Reviews
)
4 Bedrooms
3 Bathrooms
8 Guests
3250 ft²
-
Oceanfront
-
Parking
-
Ocean View
-
Balcony/Terrace
US $716
/Night
7 Nights - $5,013
House
10.0
(
102 Reviews
)
3 Bedrooms
2 Bathrooms
6 Guests
1800 ft²
-
Parking
-
Ocean View
-
Balcony/Terrace
-
View
US $495
/Night
7 Nights - $3,463
Cottage
10.0
(
76 Reviews
)
1 Bedroom
1 Bathroom
4 Guests
260 ft²
-
Parking
-
Ocean View
-
Balcony/Terrace
-
View
US $297
/Night
7 Nights - $2,078
About Chesapeake Bay Vacation Rentals
With more than 316 Chesapeake Bay vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Estiavillas and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at a rental property in Chesapeake Bay.
Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Estiavillas Chesapeake Bay, you have the flexibility of comparing different options of various deals with a single click. Looking for a rental by owner with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner, and other popular Airbnb-style properties in Chesapeake Bay. Places to stay near Chesapeake Bay are 1052.67 ft² on average, with prices averaging US $476 a night.
Estiavillas makes it easy and safe to find and compare vacation rentals in Chesapeake Bay with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.
Top Rental Accommodation Types in Chesapeake Bay
| Type | Count |
|---|---|
| Villas | 284 |
| Holiday Apartments | 19 |
| Vacation Homes | 12 |
| Hotels | 1 |
Use these Quick Filters to Find a Vacation Rental in Chesapeake Bay
★ Pro Tip: Estiavillas makes it easy to compare the best listings on Estiavillas homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Estiavillas homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Chesapeake Bay.
Weather in Chesapeake Bay
View the weather forecast for Chesapeake Bay before booking your Chesapeake Bay Vacation Rentals to confirm your best time to go.
December - February
High 60°F Low 26°F
March - May
High 77°F Low 40°F
June - August
High 91°F Low 64°F
September - November
High 84°F Low 38°F
Top Attractions Around Chesapeake Bay, US
Estiavillas offers a large selection of top attractions around Chesapeake Bay. Research things to do on your vacation before you visit Chesapeake Bay.
White House
Busch Gardens Williamsburg
National Mall
Virginia Beach Boardwalk
Washington Monument
National Aquarium in Baltimore
Colonial Williamsburg
Walter E. Washington Convention Center
George Washington University
Arlington National Cemetery
Smithsonian National Air and Space Museum
Naval Station Norfolk
Lincoln Memorial
Baltimore Cruise Terminal
University of Maryland-College Park
Johns Hopkins University
Capital One Arena
United States Capitol
Baltimore Convention Center
National Museum of Natural History
Other Places to Stay Near Chesapeake Bay, US
Maryland
15,597 Properties
Northern Chesapeake Bay
9,116 Properties
Washington
3,229 Properties
District of Columbia
3,020 Properties
Norfolk - Virginia Beach
2,773 Properties
Northwest
1,820 Properties
Virginia Beach
1,795 Properties
Anne Arundel County
1,287 Properties
Baltimore
1,275 Properties
James City County
1,045 Properties
Williamsburg
1,045 Properties
Accomack County
1,011 Properties
Complexes around Chesapeake Bay, US
Wyndham Patriots Lockoff Williamsburg
165 Properties
Phoenixpark Washington
22 Properties
Alexandria
44 Properties
Virginia Beach Oceanfrnt
94 Properties
Wyndham National Harbor
66 Properties
Inn
18 Properties
Ballston
42 Properties
Enjoy Beauty The Chesapeake Bay
40 Properties
Bethesda
33 Properties
Georgetown
28 Properties
Dupont Circle Nr U Street Metro Glen Mkt
12 Properties
Crystal City Arlington Va
7 Properties
Capitol Hill
13 Properties
Pentagon City
12 Properties
Prince George St Annapolis
6 Properties
Chesapeake Bay Vacation Rental Frequently Asked Questions
What are the top vacation rentals in Chesapeake Bay?
There are a lot of options in Chesapeake Bay. If you plan on staying in the Chesapeake Bay area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Chesapeake Bay:
- Historic Carriage House at the Church Point Manor
- Breathtaking Waterfront Estate
- Stunning 9-Bedroom Villa on the Chesapeake Bay: Pool, Hot Tub, Boat Dock & Sauna
- Washington Family Property, Upper Carriage House in Old Town on 107 S Lee Street
- Luxury home with 9 Bedrooms, 8.5 Baths – 2 minutes walking to metro station.
- Secluded Waterfront Retreat 2 bed 1 1/2 baths private guest house w Pool & Beach
- Blake House Historic Estate with Private Inn
- Luxury Townhome 1 BLOCK from Beach, on Boardwalk
- Beautiful Bayside Villa on Chesapeake
- Massive Mid-Century Marvel: 5 Bedrooms and Parking
How many vacation rentals have private pools in Chesapeake Bay?
There are 1317 vacation rentals with private pools near Chesapeake Bay. Top-rated homes that have access to a swimming pool include:
Which vacation homes in Chesapeake Bay are best for families?
If you are looking for a family-friendly vacation home in Chesapeake Bay, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Chesapeake Bay:
How many vacation rentals are available in Chesapeake Bay?
Currently, the total number of properties listed in 2026 is over 316 in the Chesapeake Bay area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Chesapeake Bay.
