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Chesapeake Bay Vacation Rentals

Find 8,585 available offers from 17 partners
Chesapeake Bay
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Price per night
Up to $100
$100 - $199
From $200
Accommodation types
Condo
House
Farmhouse
Rating
4.5+
4+
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

Save up to 69%

House East Ocean View
Nov 1 - Nov 8
-69%
$690
$216 per night
House ∙ 8 guests ∙ 4 bedrooms
House in East Ocean View with Private Patio + Ocean View
5.0
Outstanding (6 ratings)
East Ocean View, Norfolk, Virginia, United States
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House Cape Charles
Oct 20 - Oct 27
-26%
$182
$134 per night
House ∙ 8 guests ∙ 2 bedrooms
Vacation Home in Cape Charles with Grill
4.8
Outstanding (27 ratings)
Cape Charles, Northampton County, Virginia, United States
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House Lake Shore
Oct 28 - Nov 4
-35%
$650
$425 per night
House ∙ 15 guests ∙ 5 bedrooms
Family Friendly House in Lake Shore with Grill & Yard + Unique View
4.9
Outstanding (64 ratings)
Lake Shore, Anne Arundel County, Maryland, United States
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Find a vacation rental that meets your criteria among the 8,585 welcoming accommodations from 17 partner websites in Chesapeake Bay. HomeToGo instantaneously presents you with the best offers by comparing all of the listed accommodations in Chesapeake Bay from 17 different providers.

Top-Rated Rentals and Accommodations in Chesapeake Bay

Book Vacation Rental Offers with the Highest User Rating

House Cape Saint Claire
Oct 28 - Nov 4
$318 per night
House ∙ 8 guests ∙ 3 bedrooms
Vacation Home in Cape Saint Claire with Pool, Yard & Grill + Peaceful View
5.0
Outstanding (51 ratings)
Cape Saint Claire, Anne Arundel County, Maryland, United States
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House Deal Island
Nov 11 - Nov 18
$137 per night
House ∙ 8 guests ∙ 3 bedrooms
Pleasant Vacation Home in Deal Island with Grill & Jacuzzi + Water Views
4.7
Excellent (40 ratings)
Deal Island, Somerset County, Maryland, United States
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House Ewell
Jul 6 - Jul 13
$169 per night
House ∙ 5 guests ∙ 3 bedrooms
House in Ewell
5.0
Outstanding (1 rating)
Ewell, Smith Island, Maryland, United States
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Recommended Vacation Rentals in Chesapeake Bay

Find your perfect vacation rental in Chesapeake Bay: from $82 per night

House Arundel on the Bay
Dec 30 - Jan 6
$400 per night
House ∙ 13 guests ∙ 5 bedrooms
Beautiful House in Arundel On The Bay with Grill & Yard + Water Views
4.3
Very good (32 ratings)
Arundel on the Bay, Anne Arundel County, Maryland, United States
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House Taylors Island
Apr 13 - Apr 20
-26%
$498
$367 per night
House ∙ 15 guests ∙ 5 bedrooms
Pleasant Vacation Home in Taylors Island with Yard & Grill
4.9
Outstanding (25 ratings)
Taylors Island, Dorchester County, Maryland, United States
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Apartment Earleville
Mar 9 - Mar 16
-26%
$150
$111 per night
Apartment ∙ 3 guests ∙ 1 bedroom
Rental Apartment in Earleville with Free Parking
4.9
Outstanding (11 ratings)
Earleville, Cecilton, Maryland, United States
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House Cape Charles
Oct 14 - Oct 21
-24%
$713
$540 per night
House ∙ 15 guests ∙ 6 bedrooms
House in Cape Charles with Pool & Grill
4.9
Outstanding (51 ratings)
Cape Charles, Northampton County, Virginia, United States
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House Elkton
Oct 31 - Nov 7
-39%
$679
$413 per night
House ∙ 8 guests ∙ 4 bedrooms
House in Elkton with Seasonal Pool + Water Views
4.8
Outstanding (81 ratings)
Elkton, Cecil County, Maryland, United States
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House Cape Charles
Dec 23 - Dec 30
$350 per night
House ∙ 9 guests ∙ 3 bedrooms
Vacation Home in Cape Charles with Yard, Pool & Grill
4.9
Outstanding (10 ratings)
Cape Charles, Northampton County, Virginia, United States
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House Chesapeake City
Mar 2 - Mar 9
$126 per night
House ∙ 2 guests ∙ 1 bedroom
Vacation Home in Chesapeake City with Yard & Grill + Water Views
5.0
Outstanding (24 ratings)
Chesapeake City, Cecil County, Maryland, United States
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House Cape Charles
Dec 23 - Dec 30
-36%
$350
$224 per night
House ∙ 8 guests ∙ 3 bedrooms
Vacation Home in Cape Charles with Large Patio
4.6
Excellent (42 ratings)
Cape Charles, Northampton County, Virginia, United States
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House Reedville
Jul 13 - Jul 20
$228 per night
House ∙ 8 guests ∙ 3 bedrooms
Beautiful Vacation Home in Reedville with Private Parking + Beautiful View
5.0
Outstanding (1 rating)
Reedville, Northumberland County, Virginia, United States
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Budget-friendly Vacation Rentals in Chesapeake Bay

Find Fantastic yet Inexpensive Offers

House Hollywood
Aug 3 - Aug 10
$105 per night
House ∙ 2 guests ∙ 1 bedroom
Vacation Home in Hollywood with Grill & Yard
4.6
Excellent (39 ratings)
Hollywood, Patuxent, Maryland, United States
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House Willoughby Spit
Oct 7 - Oct 14
-18%
$725
$595 per night
House ∙ 12 guests ∙ 5 bedrooms
House in Willoughby Spit with Yard & Grill + Ocean View
4.6
Excellent (76 ratings)
Willoughby Spit, Norfolk, Virginia, United States
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House Olde Hampton
Mar 16 - Mar 23
$246 per night
House ∙ 9 guests ∙ 3 bedrooms
Vacation Home in Olde Hampton
4.7
Excellent (6 ratings)
Olde Hampton, Hampton, Virginia, United States
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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 Cape Charles
Mar 9 - Mar 16
-62%
$436
$166 per night
House ∙ 9 guests ∙ 2 bedrooms
House in Cape Charles with Yard & Grill
5.0
Outstanding (19 ratings)
Cape Charles, Northampton County, Virginia, United States
Air conditioning
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House Scotland
Dec 1 - Dec 8
-21%
$336
$265 per night
House ∙ 6 guests ∙ 3 bedrooms
House in Scotland with Grill
4.9
Outstanding (87 ratings)
Scotland, St. Inigoes, Maryland, United States
Air conditioning
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Cottage Elkton
Dec 2 - Dec 9
-27%
$236
$172 per night
Cottage ∙ 8 guests ∙ 3 bedrooms
Cottage in Elkton with Grill & Yard + Water Views
5.0
Outstanding (55 ratings)
Elkton, Cecil County, Maryland, 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 Annapolis
Dec 2 - Dec 9
$232 per night
House ∙ 10 guests ∙ 3 bedrooms
House in Annapolis with Free Parking
5.0
Outstanding (6 ratings)
Annapolis, Anne Arundel County, Maryland, United States
Kitchen
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House Cape Charles
Dec 16 - Dec 23
-78%
$563
$127 per night
House ∙ 4 guests ∙ 1 bedroom
Vacation Home in Cape Charles with Yard & Grill
5.0
Outstanding (22 ratings)
Cape Charles, Northampton County, Virginia, United States
Kitchen
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House Hampton Roads Center
Nov 11 - Nov 18
$196 per night
House ∙ 8 guests ∙ 4 bedrooms
Vacation Home in Hampton Roads Center with Pool & Grill
5.0
Outstanding (8 ratings)
Hampton Roads Center, Hampton, Virginia, United States
Kitchen
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Vacation Rentals With Fireplaces

Get warm and cozy on cold winter nights in Chesapeake Bay by booking a vacation home with a fireplace.

House Tracys Landing
Jan 6 - Jan 13
-47%
$1,262
$669 per night
House ∙ 14 guests ∙ 5 bedrooms
Charming Vacation Home in Tracys Landing with Private Pool
5.0
Outstanding (13 ratings)
Tracys Landing, Anne Arundel County, Maryland, United States
Fireplace
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House Fishing Creek
Oct 14 - Oct 21
-58%
$629
$262 per night
House ∙ 12 guests ∙ 4 bedrooms
Charming Vacation Home in Fishing Creek with Yard & Grill + Water Views
5.0
Outstanding (18 ratings)
Fishing Creek, Hoopers Island, Maryland, United States
Fireplace
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House Buckroe Beach
Jan 13 - Jan 20
$314 per night
House ∙ 10 guests ∙ 4 bedrooms
Vacation Home in Buckroe Beach
4.9
Outstanding (12 ratings)
Buckroe Beach, Hampton, Virginia, United States
Fireplace
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Popular Rental Amenities in Chesapeake Bay

  • Pet-friendly (1,529)
  • Pool (3,932)
  • Air conditioning (8,301)
  • WiFi (8,470)
  • Fishing (2,488)
  • TV (7,867)
  • Balcony/patio (1,456)
  • Grill (3,131)
  • Kitchen (5,233)
  • Parking (698)
  • No smoking (6,007)
  • Hot tub (339)

Using our filters will help you find the perfect vacation rental in Chesapeake Bay. HomeToGo's data highlights that "Pets allowed" and "Pool" turn out to be the most frequently offered features in Chesapeake Bay. Plan your vacation in advance if you need a fenced-in backyard or you want a rental providing a crib. There are just 354 listed accommodations providing "Fenced" and 1,252 properties including "Crib."

Price and Availability Index in Chesapeake Bay

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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 (5/25 - 6/1) go up to $577 per night, which is the highest average price in the next 12 months. On average, the most interesting prices are in a week of February (2/17 - 2/24) 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 August (8/31 - 9/7). So far, 75% of the rentals are occupied this week. October (10/28 - 11/4) has got the highest percentage of available rentals.

The Weather in Chesapeake Bay

max.
Min.
43°
28°
13 days 13
max.
Min.
45°
30°
13 days 13
max.
Min.
55°
37°
12 days 12
max.
Min.
66°
46°
12 days 12
max.
Min.
75°
59°
13 days 13
max.
Min.
84°
66°
12 days 12
max.
Min.
88°
72°
11 days 11
max.
Min.
84°
68°
13 days 13
max.
Min.
79°
63°
11 days 11
max.
Min.
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

Wed, 27 Sep
71°
64°

10%

3 h

16 mi/h

Thu, 28 Sep
71°
64°

10%

5 h

16 mi/h

Fri, 29 Sep
73°
68°

15%

2 h

18 mi/h

Sat, 30 Sep
73°
62°

5%

9 h

13 mi/h

Sun, 1 Oct
75°
64°

0%

11 h

7 mi/h

Mon, 2 Oct
75°
66°

0%

11 h

8 mi/h

Tue, 3 Oct
69°
64°

10%

11 h

13 mi/h

Accommodations for your vacation in Chesapeake Bay

2,221 out of the 8,585 listed properties in Chesapeake Bay are house rental. They account for more than half of the properties in this destination (58%). Additionally, these accommodations have an average size of 227 m² as well as a median price of $609 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 464 properties to compare. These accommodations cost $238 per night on average and have an average size of 81 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 available 8,585 homes
💳 Possible discounts up to 69%
🌙 Nightly prices starting at $82
⭐ Popular amenities Pets allowed, Pool and Air conditioning
🐾 Pet friendly homes 1,473 homes
🏊 Vacation rentals with pools 3,895 homes

Frequently Asked Questions

What is the typical nightly price for a vacation rental in Chesapeake Bay?

The nightly price of accommodations in Chesapeake Bay starts at $82. If you would like to stay in a house rental, the average price is $609 per night. A apartment rental Chesapeake Bay will cost $238 per night on average.

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

There are currently 8,585 rentals from 17 different providers in Chesapeake Bay.

What are the most popular amenities for vacation homes in Chesapeake Bay?

Most travelers look for Pool, Pets allowed, and Air conditioning when booking a vacation rental in Chesapeake Bay.

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

There are 3,895 vacation homes across 17 providers in Chesapeake Bay.

Are dogs allowed in vacation rentals in Chesapeake Bay?

If you are traveling with a dog in Chesapeake Bay - 17% of vacation homes allow pets.

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

When looking for a vacation rental in Chesapeake Bay, consider that rainy season is typically in January or February, with November often being the driest.

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