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Chesapeake Bay Vacation Rentals

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Price per night
Up to $100
$100 - $199
From $200
Accommodation types
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Rating
Outstanding: 4.5+
Very Good: 4+
Good: 3.5+

Revel in the laidback atmosphere of Chesapeake Bay vacation rentals

Chesapeake Bay, Maryland’s most famous estuary, is actually quite big – approximately 200 miles long. It is home to historical attractions such as Fort McHenry and Chesapeake Bay Maritime Museum, as well as natural attractions such as Blackwater National Wildlife Refuge and Calvert Cliffs.

Chesapeake Bay vacation homes are available in different types and sizes. From luxury townhouses and waterfront cottages to apartments and farmhouses, vacation rentals in Chesapeake Bay are available to suit your every need and desire.

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Best Vacation Home Deals in Chesapeake Bay

House Cape Charles
Dec 23 - Dec 30
-65%
$462
$164 per night
House ∙ 8 guests ∙ 3 bedrooms
House in Cape Charles with Grill
5.0
"Excellent" (14 ratings)
Cape Charles, Northampton County, Virginia, United States
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House Cape Charles
Dec 23 - Dec 30
-63%
$445
$164 per night
House ∙ 11 guests ∙ 3 bedrooms
House in Cape Charles with Grill & Yard
4.9
"Excellent" (16 ratings)
Cape Charles, Northampton County, Virginia, United States
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House Reedville
Jan 13 - Jan 20
-43%
$302
$172 per night
House ∙ 4 guests ∙ 3 bedrooms
House in Reedville with Yard & Grill + Sweeping Views
5.0
"Excellent" (218 ratings)
Reedville, Northumberland County, Virginia, United States
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Find a vacation rental that meets your criteria among the 10,842 welcoming accommodations from 11 partner websites in Chesapeake Bay. HomeToGo instantaneously presents you with the best offers by comparing all of the listed accommodations in Chesapeake Bay from 11 different providers.

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Top-Rated Rentals and Accommodations in Chesapeake Bay

House Annapolis
Dec 23 - Dec 30
-60%
$554
$221 per night
House ∙ 5 guests ∙ 4 bedrooms
Vacation Home in Annapolis with Private Pool
5.0
"Excellent" (108 ratings)
Annapolis, Anne Arundel County, Maryland, United States
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Apartment Northeast Virginia Beach
Jan 20 - Jan 27
-38%
$230
$142 per night
Apartment ∙ 2 guests ∙ 1 bedroom
Apartment in Northeast Virginia Beach with Yard & Grill
5.0
"Excellent" (93 ratings)
Northeast Virginia Beach, Virginia Beach, Virginia, United States
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House Chesapeake Ranch Estates-Drum Point
Feb 10 - Feb 17
-41%
$425
$250 per night
House ∙ 8 guests ∙ 3 bedrooms
Vacation Home in Chesapeake Ranch Estates-Drum Point with Grill + Beautiful View
5.0
"Excellent" (83 ratings)
Chesapeake Ranch Estates-Drum Point, Solomons Island, Maryland, United States
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Recommended Vacation Rentals in Chesapeake Bay

Find your perfect vacation rental in Chesapeake Bay: from $90 per night

House Gwynn
Oct 21 - Oct 28
$150 per night
House ∙ 6 guests ∙ 2 bedrooms
Vacation Home in Gwynn with Free Parking + Expansive Views
5.0
"Excellent" (244 ratings)
Gwynn, Piankatank, Virginia, United States
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House Foster
Jun 1 - Jun 8
$305 per night
House ∙ 6 guests ∙ 4 bedrooms
Vacation Home in Foster with Yard & Grill + Water View
5.0
"Excellent" (107 ratings)
Foster, Westville, Virginia, United States
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House Heathsville
Sep 2 - Sep 9
$379 per night
House ∙ 10 guests ∙ 5 bedrooms
Vacation Home in Heathsville with Yard, Pool & Grill
4.9
"Excellent" (74 ratings)
Heathsville, Northumberland County, Virginia, United States
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House Northampton County
Sep 19 - Sep 26
$152 per night
House ∙ 6 guests ∙ 2 bedrooms
House in Northampton County with Yard, Pool & Grill
5.0
"Excellent" (26 ratings)
Northampton County, Virginia, United States
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House Havre de Grace
Jul 15 - Jul 22
$98 per night
House ∙ 3 guests ∙ 2 bedrooms
House in Havre De Grace with Electric Fireplace
4.9
"Excellent" (33 ratings)
Havre de Grace, Harford County, Maryland, United States
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House Stevensville
Apr 5 - Apr 12
$353 per night
House ∙ 4 guests ∙ 3 bedrooms
House in Stevensville with Yard, Pool & Grill
5.0
"Excellent" (204 ratings)
Stevensville, Kent Island, Maryland, United States
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House Buckroe Beach
Nov 25 - Dec 2
$219 per night
House ∙ 8 guests ∙ 3 bedrooms
Wonderful House in Buckroe Beach with Grill + Unobstructed View + Next to Beach
4.9
"Excellent" (104 ratings)
Buckroe Beach, Hampton, Virginia, United States
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House Cape Charles
Jan 20 - Jan 27
$236 per night
House ∙ 8 guests ∙ 4 bedrooms
Nice Vacation Home in Cape Charles with Grill & Yard
4.7
"Outstanding" (135 ratings)
Cape Charles, Northampton County, Virginia, United States
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House Northwest
Feb 3 - Feb 10
-56%
$328
$151 per night
House ∙ 8 guests ∙ 3 bedrooms
Vacation Home in Northwest + Close to Beach
4.9
"Excellent" (82 ratings)
Northwest, Virginia Beach, Virginia, United States
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Budget-friendly Vacation Rentals in Chesapeake Bay

Cabin Port Republic
Feb 10 - Feb 17
-67%
$449
$149 per night
Cabin ∙ 5 guests ∙ 2 bedrooms
Cabin in Port Republic with Grill, Yard & Pool + Waterfront View
5.0
"Excellent" (176 ratings)
Port Republic, Solomons Island, Maryland, United States
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House Buckroe Beach
Sep 16 - Sep 23
$262 per night
House ∙ 8 guests ∙ 3 bedrooms
House in Buckroe Beach with Grill & Yard + Clear View + Next to Beach
4.9
"Excellent" (178 ratings)
Buckroe Beach, Hampton, Virginia, United States
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House Lamberts Point
Sep 19 - Sep 26
$330 per night
House ∙ 12 guests ∙ 6 bedrooms
Beautiful Vacation Home in Lamberts Point with Yard & Grill
4.5
"Outstanding" (11 ratings)
Lamberts Point, Norfolk, Virginia, United States
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Vacation rentals with Wi-Fi

Stay connected while traveling and book a Chesapeake Bay accommodation with high-speed internet.

Condo Internet Northeast Virginia Beach
Nov 26 - Dec 3
-34%
$325
$215 per night
Condo ∙ 6 guests ∙ 2 bedrooms
Lovely Condo in Northeast Virginia Beach with Indoor Pool + Ocean Views + Close to Beach
4.9
"Excellent" (70 ratings)
Northeast Virginia Beach, Virginia Beach, Virginia, United States
Internet
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House Internet Sherwood
Feb 10 - Feb 17
-21%
$290
$230 per night
House ∙ 4 guests ∙ 2 bedrooms
Vacation Home in Sherwood with Wood-Burning Fireplace + Glorious Views
5.0
"Excellent" (127 ratings)
Sherwood, Bay Hundred, Maryland, United States
Internet
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House Internet Port Haywood
Apr 30 - May 7
$243 per night
House ∙ 6 guests ∙ 3 bedrooms
House in Port Haywood with Pool, Yard & Grill
4.9
"Excellent" (74 ratings)
Port Haywood, Chesapeake, Virginia, United States
Internet
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Vacation rentals and apartments with air conditioning

Keep cool during your trip to Chesapeake Bay and book a vacation rental with air conditioning.

House Air conditioning Bay View
Nov 4 - Nov 11
$126 per night
House ∙ 6 guests ∙ 3 bedrooms
Lovely House in Bay View with Grill + Ocean View
4.9
"Excellent" (76 ratings)
Bay View, Norfolk, Virginia, United States
Air conditioning
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House Air conditioning Elkton
Jan 20 - Jan 27
$420 per night
House ∙ 12 guests ∙ 5 bedrooms
Vacation Home in Elkton with Yard & Grill + Fabulous View
5.0
"Excellent" (159 ratings)
Elkton, Cecil County, Maryland, United States
Air conditioning
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Cottage Air conditioning Grimstead
Feb 24 - Mar 2
$226 per night
Cottage ∙ 4 guests ∙ 2 bedrooms
Cottage in Grimstead with Grill & Yard + Expansive Views
5.0
"Excellent" (185 ratings)
Grimstead, Gwynn, Virginia, United States
Air conditioning
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Apartments and vacation rentals with a kitchen

Cook up a feast on your next vacation and book a Chesapeake Bay rental with full kitchen.

House Kitchen Gloucester Courthouse
Sep 2 - Sep 9
$215 per night
House ∙ 8 guests ∙ 3 bedrooms
Vacation Home in Gloucester Courthouse with Yard & Grill
4.9
"Excellent" (155 ratings)
Gloucester Courthouse, Abingdon, Virginia, United States
Kitchen
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House Kitchen Cape Charles
Mar 26 - Apr 2
-21%
$204
$160 per night
House ∙ 6 guests ∙ 3 bedrooms
House in Cape Charles with Grill & Yard
5.0
"Excellent" (209 ratings)
Cape Charles, Northampton County, Virginia, United States
Kitchen
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Condo Kitchen Northeast Virginia Beach
Oct 21 - Oct 28
-52%
$329
$157 per night
Condo ∙ 4 guests ∙ 2 bedrooms
Condo in Northeast Virginia Beach with Indoor Pool + Beach Nearby
4.7
"Outstanding" (106 ratings)
Northeast Virginia Beach, Virginia Beach, Virginia, United States
Kitchen
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Popular Rental Amenities in Chesapeake Bay

  • Internet (9,958)
  • Air conditioning (9,488)
  • TV (9,162)
  • Microwave (8,056)
  • No smoking (7,489)
  • Kitchen (6,735)
  • No pets (6,049)
  • Washer (5,040)
  • Dishwasher (4,490)
  • Pool (4,237)
  • Grill (3,769)
  • Yard (3,374)

Using our filters will help you find the perfect vacation rental in Chesapeake Bay. HomeToGo's data highlights that "Internet" and "Air conditioning" turn out to be the most frequently offered features in Chesapeake Bay. Plan your vacation in advance if you enjoy soaking in the hot tub or you want to sweat it out in a sauna. There are just 232 listed accommodations providing "Hot tub" and 251 properties including "Sauna."

Price and Availability Index in Chesapeake Bay

Vacation Rental Price Information in Chesapeake Bay

The price graph will give you the nightly price average for the upcoming months of the year. Prices in a week of May (5/20 - 5/27) go up to $563 per night, which is the highest average price in the next 12 months. On average, the most interesting prices are in a week of December (12/2 - 12/9) as the average price is only $363 per night.

Rental Availability Information in Chesapeake Bay

Check out the graph above to find out how many accommodations are available in Chesapeake Bay(in %). More people travel to Chesapeake Bay a week in April (4/1 - 4/8). So far, 52% of the rentals are occupied this week. August (8/26 - 9/2) has got the highest percentage of available rentals.

The Weather in Chesapeake Bay

max.
Min.
43°
28°
13 days 13
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45°
30°
13 days 13
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55°
37°
12 days 12
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66°
46°
12 days 12
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75°
59°
13 days 13
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84°
66°
12 days 12
max.
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88°
72°
11 days 11
max.
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84°
68°
13 days 13
max.
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79°
63°
11 days 11
max.
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68°
52°
12 days 12
max.
Min.
57°
41°
9 days 9
max.
Min.
54°
37°
13 days 13
Jan.
Feb.
Mar.
Apr.
May
June
July
Aug.
Sep.
Oct.
Nov.
Dec.
- Rainy days

The above is a climate diagram for Chesapeake Bay. During July, maximum temperatures go up to more than 88° However, temperatures can go lower than 28° in Chesapeake Bay in January. The rainiest month is January while the driest month is November.

7-Day Weather Forecast in Chesapeake Bay

Tue, 21 Mar
50°
41°

0%

7 h

11 mi/h

Wed, 22 Mar
50°
46°

15%

0 h

13 mi/h

Thu, 23 Mar
57°
50°

15%

4 h

11 mi/h

Fri, 24 Mar
64°
55°

15%

5 h

15 mi/h

Sat, 25 Mar
59°
50°

15%

4 h

22 mi/h

Sun, 26 Mar
53°
46°

0%

10 h

8 mi/h

Mon, 27 Mar
50°
44°

15%

2 h

22 mi/h

Accommodations for your vacation in Chesapeake Bay

3,490 out of the 10,842 listed properties in Chesapeake Bay are house rental. They account for many of the properties in this destination (60.28%). Additionally, these accommodations have an average size of 228 m² as well as a median price of $677 per night. Moreover, if you are going in a group of 8, house rental are the perfect accommodation type in Chesapeake Bay, as they usually welcome this exact group size. You can also search and find other accommodation types in Chesapeake Bay. Apartment rental are, for example, another popular accommodation option there with 858 properties to compare. These accommodations cost $304 per night on average and have an average size of 97 m².
What is the weather like in Chesapeake Bay?

Ideal time to visit Chesapeake Bay

The peak season for travelers to Chesapeake Bay is the summer period between June and August. Thousands of holidaymakers visit during this time for the hot weather and fun water-sports, including fishing, boating, and swimming.

If you specifically want to avoid the peak crowds, travel to Chesapeake Bay in either spring (March to May) or fall (September to November). During these seasons, you will be able to observe dolphins, explore salt marshes, and go hiking.

What are the best events and festivals in Chesapeake Bay?

Festivals in Chesapeake Bay

Chesapeake Bay Blues Festival is an annual event that takes place in Annapolis, Maryland. Spanning a weekend, this festival raises millions of dollars for charity. Attend this event and you can enjoy some of the world's best blues artists accompanied by gorgeous beachside views and amazing food.

Maryland Seafood Festival is held to celebrate the state's signature blue crabs. This festival also takes place in Annapolis and features numerous vendors selling crab cakes, steamed crab, and cream of crab soup, as well as braided crab pretzels.

What are the must-see attractions in Chesapeake Bay?

Iconic attractions in Chesapeake Bay

Chesapeake Bay Bridge-Tunnel

Located on US Route 13, Chesapeake Bay Bridge-Tunnel is a fixed link crossing in Virginia. This bridge-tunnel includes two mile-long tunnels and was opened in 1964. The structure is one of only ten bridge-tunnel constructions in the world.

Thomas Point Shoal Light

Thomas Point Shoal Light is the most popular lighthouse in Maryland. Built in 1825, it was listed on the National Register of Historic Places in 1975. It is open to the public for just 3 months in the year.

Susquehanna

Susquehanna is the longest river in the continental US, and the Chesapeake Bay is actually the ria of this river. The Susquehanna River and the Chesapeake Bay are essentially part of one ecosystem.

Chesapeake Bay Bridge

Chesapeake Bay Bridge is an important link along US Routes 50 and 301. This bridge spans Chesapeake Bay in its entirety and connects the metropolitan Western Shore to the rural Eastern Shore in Maryland.

Kent Island

Situated at the base of Chesapeake Bay Bridge, Kent Island is home to beautiful views and numerous dining options. Kent Narrows is a small water channel that separates this island from the mainland.

Information about vacation rentals in Chesapeake Bay

🏡 Vacation rentals 10,842 properties
💳 Possible discounts up to 60%
🌙 Nightly prices starting at $90
⭐ Popular amenities Internet, Air conditioning and TV
🐾 Pet friendly accommodations 2,247 properties
🏊 Vacation rentals with pools 4,638 properties

Frequently Asked Questions

What is the average price per night for a vacation home in Chesapeake Bay?

The price of a night's stay in Chesapeake Bay starts at $90. If you are looking for a house rental, the nightly price is $677 on average. A apartment rental Chesapeake Bay will cost $304 per night on average.

How many vacation rentals are available to book in Chesapeake Bay?

There are currently 10,842 rentals available for booking for your trip.

What amenities are most popular for vacation rentals in Chesapeake Bay?

Travelers look for Air conditioning, Internet, and TV when booking a vacation rental in Chesapeake Bay.

How many vacation rentals with a pool are in Chesapeake Bay?

There are 4,638 rentals across 11 providers in Chesapeake Bay.

Are dogs allowed in vacation rentals in Chesapeake Bay?

If traveling with a dog in Chesapeake Bay, 20% of vacation rentals allow pets.

What's the best time of year to travel to Chesapeake Bay?

Chesapeake Bay has its warmest time of year around July and June, with average nightly prices being around $90.

We list offers from thousands of providers, including:

Booking.com Vacation Rentals in Chesapeake Bay TripAdvisor Vacation Rentals in Chesapeake Bay Vrbo Vacation Rentals in Chesapeake Bay VacationRentals.com Vacation Rentals in Chesapeake Bay HouseTrip Vacation Rentals in Chesapeake Bay FlipKey Vacation Rentals in Chesapeake Bay Homestay.com Vacation Rentals in Chesapeake Bay Only-apartments Vacation Rentals in Chesapeake Bay Interhome Vacation Rentals in Chesapeake Bay Novasol Vacation Rentals in Chesapeake Bay HomeEscape Vacation Rentals in Chesapeake Bay

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