Chesapeake Bay Vacation Rentals - HomeToGo base64Hash Chesapeake Bay Vacation Rentals - HomeToGo

Chesapeake Bay Vacation Rentals

Find 9,704 available offers from 33 partners
Chesapeake Bay
Anytime
Guests
Chesapeake Bay
Anytime
Guests

Popular Filters to find the Perfect Home Rental in Chesapeake Bay

2 Adults
1 Bedroom
Pool
House
Pets allowed
4 Adults
Cabin

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.

Show all 9,704 properties

Apartments With Balconies or Patios

Looking for a home with a balcony? Check out these vacation homes in Chesapeake Bay with their own private patios and balconies.

Cottage  Deltaville
Sep 14 - Sep 21
-32%
$304
$206 per night
Cottage ∙ 8 guests ∙ 2 bedrooms

Wonderful Cottage in Deltaville with Patio & Grill

5.0
Outstanding (66 ratings)
Deltaville, Pine Top, Virginia, United States
Balcony/Patio
View deal
View deal
House  Reedville
May 13 - May 20
$201 per night
House ∙ 8 guests ∙ 4 bedrooms

Vacation Home in Reedville with Patio, Yard & Grill

5.0
Outstanding (12 ratings)
Reedville, Northumberland County, Virginia, United States
Balcony/Patio
View deal
View deal
Cottage  East Ocean View
Sep 14 - Sep 21
$54 per night
Cottage ∙ 2 guests ∙ 1 bedroom

Beautiful Cottage in East Ocean View with Grill, Patio & Yard + Ocean View

4.5
Excellent (98 ratings)
East Ocean View, Norfolk, Virginia, United States
Balcony/Patio
View deal
View deal
See all offers

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  East Ocean View
May 13 - May 20
-52%
$686
$329 per night
House ∙ 8 guests ∙ 4 bedrooms

Vacation Home in East Ocean View with Botanical Garden + Ocean View

4.8
Outstanding (56 ratings)
East Ocean View, Norfolk, Virginia, United States
Kitchen
View deal
View deal
House  Ridge
May 3 - May 10
-51%
$1,001
$487 per night
House ∙ 12 guests ∙ 4 bedrooms

House in Ridge with Grill & Yard + Unobstructed Views

5.0
Outstanding (126 ratings)
Ridge, St. Inigoes, Maryland, United States
Kitchen
View deal
View deal
House  Deale
Sep 13 - Sep 20
$316 per night
House ∙ 10 guests ∙ 4 bedrooms

Vacation Home in Deale with Yard, Patio & Grill + Panoramic View

4.9
Outstanding (134 ratings)
Deale, Anne Arundel County, Maryland, United States
Kitchen
View deal
View deal
See all offers

Vacation rentals with Wi-Fi

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

Cottage  White Stone
May 13 - May 20
-33%
$187
$125 per night
Cottage ∙ 6 guests ∙ 2 bedrooms

Rental Cottage in White Stone with Grill & Patio

3.6
Good (155 ratings)
White Stone, Lancaster County, Virginia, United States
Internet
View deal
View deal
House  California
May 2 - May 9
-33%
$505
$338 per night
House ∙ 9 guests ∙ 4 bedrooms

House in California + Water View

4.7
Excellent (60 ratings)
California, Bay, Maryland, United States
Internet
View deal
View deal
House  Easton
Apr 20 - Apr 27
-55%
$507
$230 per night
House ∙ 10 guests ∙ 5 bedrooms

Vacation Home in Easton with Grill, Pool & Yard

3.0
(1 rating)
Easton, Talbot County, Maryland, United States
Internet
View deal
View deal
See all offers

Best Vacation Home Deals in Chesapeake Bay

Save up to 26%

House Saint Michaels
May 20 - May 27
-26%
$700
$518 per night
House ∙ 8 guests ∙ 4 bedrooms

Vacation Home in Saint Michaels with Private Pool

Saint Michaels, St. Michaels, Maryland, United States
View deal
View deal
House Chesapeake Beach
Sep 12 - Sep 19
-24%
$377
$287 per night
House ∙ 8 guests ∙ 4 bedrooms

House in Chesapeake Beach with Yard, Patio & Grill

5.0
Outstanding (1 rating)
Chesapeake Beach, Sunderland, Maryland, United States
View deal
View deal
House Heathsville
Apr 15 - Apr 22
-17%
$300
$250 per night
House ∙ 8 guests ∙ 3 bedrooms

Nice Vacation Home in Heathsville with Patio, Yard & Grill

5.0
Outstanding (108 ratings)
Heathsville, Northumberland County, Virginia, United States
View deal
View deal

Find a vacation rental that meets your criteria among the 9,704 welcoming accommodations from 33 partner websites in Chesapeake Bay. HomeToGo instantaneously presents you with the best offers by comparing all of the listed accommodations in Chesapeake Bay from 33 different providers.

Recommended Vacation Rentals in Chesapeake Bay

Find your perfect vacation rental in Chesapeake Bay: from $37 per night

House East Ocean View
Aug 24 - Aug 31
$457 per night
House ∙ 8 guests ∙ 4 bedrooms

Entire House in East Ocean View with Private Balcony + Ocean View

5.0
Outstanding (2 ratings)
East Ocean View, Norfolk, Virginia, United States
View deal
View deal
Apartment Buckroe Beach
Apr 20 - Apr 27
$79 per night
Apartment ∙ 4 guests ∙ 2 bedrooms

Rental Apartment in Buckroe Beach with Patio, Grill & Yard

4.5
Excellent (27 ratings)
Buckroe Beach, Hampton, Virginia, United States
View deal
View deal
House Foster
Aug 17 - Aug 24
$499 per night
House ∙ 10 guests ∙ 6 bedrooms

Charming Vacation Home in Foster with Grill & Yard + Water Views

5.0
Outstanding (54 ratings)
Foster, Westville, Virginia, United States
View deal
View deal
House North Beach
Sep 14 - Sep 21
$120 per night
House ∙ 3 guests ∙ 1 bedroom

Wonderful Vacation Home in North Beach with Secret Garden

4.8
Outstanding (42 ratings)
North Beach, Sunderland, Maryland, United States
View deal
View deal
Cottage Scotland
Aug 24 - Aug 31
$550 per night
Cottage ∙ 8 guests ∙ 3 bedrooms

Cottage in Scotland with Yard, Grill & Patio + Water Views

4.9
Outstanding (17 ratings)
Scotland, St. Inigoes, Maryland, United States
View deal
View deal
House North
Sep 12 - Sep 19
$525 per night
House ∙ 10 guests ∙ 6 bedrooms

Lovely House in North with Grill + Marsh Views

5.0
Outstanding (18 ratings)
North, Petsworth, Virginia, United States
View deal
View deal
Cottage Exmore
Apr 20 - Apr 27
$144 per night
Cottage ∙ 6 guests ∙ 2 bedrooms

Cottage in Exmore with Yard, Patio & Grill

5.0
Outstanding (28 ratings)
Exmore, Northampton County, Virginia, United States
View deal
View deal
House Reedville
Jul 8 - Jul 15
$390 per night
House ∙ 6 guests ∙ 2 bedrooms

House in Reedville with Yard, Grill & Pool

4.8
Outstanding (109 ratings)
Reedville, Northumberland County, Virginia, United States
View deal
View deal
Cabin Lusby
May 2 - May 9
$262 per night
Cabin ∙ 11 guests ∙ 4 bedrooms

Cabin in Lusby with Seasonal Pool + Serene View

5.0
Outstanding (5 ratings)
Lusby, Solomons Island, Maryland, United States
View deal
View deal
See all offers

Budget-friendly Vacation Rentals in Chesapeake Bay

Find Fantastic yet Inexpensive Offers

House Chestertown
Jun 1 - Jun 8
$286 per night
House ∙ 10 guests ∙ 4 bedrooms

Vacation Home in Chestertown with Yard, Grill & Patio

5.0
Outstanding (20 ratings)
Chestertown, Kent County, Maryland, United States
View deal
View deal
House Willoughby Spit
Aug 17 - Aug 24
$661 per night
House ∙ 12 guests ∙ 5 bedrooms

House in Willoughby Spit with Yard, Grill & Patio + Ocean View

4.7
Excellent (79 ratings)
Willoughby Spit, Norfolk, Virginia, United States
View deal
View deal
House Exmore
May 4 - May 11
$658 per night
House ∙ 12 guests ∙ 5 bedrooms

House in Exmore with Yard, Patio & Grill + Water Views

4.9
Outstanding (43 ratings)
Exmore, Northampton County, Virginia, United States
View deal
View deal

Top-Rated Rentals and Accommodations in Chesapeake Bay

Book Vacation Rental Offers with the Highest User Rating

House Chesapeake Ranch Estates-Drum Point
Sep 13 - Sep 20
-18%
$442
$360 per night
House ∙ 13 guests ∙ 5 bedrooms

House in Chesapeake Ranch Estates-Drum Point with Hot Tub & Grill

4.5
Excellent
Chesapeake Ranch Estates-Drum Point, Solomons Island, Maryland, United States
View deal
View deal
House Norfolk Garden
Aug 24 - Aug 31
$96 per night
House ∙ 5 guests ∙ 3 bedrooms

Beautiful Vacation Home in Norfolk Garden with Botanical Garden

4.9
Outstanding (13 ratings)
Norfolk Garden, Norfolk, Virginia, United States
View deal
View deal
House Deltaville
Jun 8 - Jun 15
$395 per night
House ∙ 8 guests ∙ 3 bedrooms

Family Friendly House in Deltaville with Grill + Panoramic Views

5.0
Outstanding (22 ratings)
Deltaville, Pine Top, Virginia, United States
View deal
View deal
2024-americas-best-customer-service-newsweek-statista-award

Popular Rental Amenities in Chesapeake Bay

  • Pet-friendly (1,933)
  • Pool (4,245)
  • Air conditioning (9,399)
  • WiFi (9,425)
  • Fishing (2,633)
  • TV (8,650)
  • Balcony/patio (3,478)
  • Grill (3,232)
  • Kitchen (5,764)
  • Parking (725)
  • No smoking (9,233)
  • Hot tub (537)

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'd like to have a fenced-in yard or you need a crib for your baby. There are just 390 listed accommodations providing "Fenced" and 1,804 properties including "Crib."

Price and Availability Index in Chesapeake Bay

Click on any bar to see price and availability information

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 August (8/24 – 8/31) go up to $516 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 (12/7 – 12/14) as the average price is only $326 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 January (1/25 – 2/1). So far, 96% of the rentals are occupied this week. May (5/11 – 5/18) 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

Mon, 15 Apr
64°
60°

0%

5 h

4 mi/h

Tue, 16 Apr
59°
57°

10%

3 h

11 mi/h

Wed, 17 Apr
62°
60°

15%

0 h

12 mi/h

Thu, 18 Apr
66°
64°

15%

2 h

10 mi/h

Fri, 19 Apr
57°
53°

0%

2 h

11 mi/h

Sat, 20 Apr
57°
55°

0%

6 h

16 mi/h

Sun, 21 Apr
50°
50°

15%

0 h

9 mi/h

Accommodations for your vacation in Chesapeake Bay

2,434 out of the 9,704 listed properties in Chesapeake Bay are house rental. They account for more than half of the properties in this destination (56.33%). Additionally, these accommodations have an average size of 232 m² as well as a median price of $625 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 562 properties to compare. These accommodations cost $291 per night on average and have an average size of 77 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 9,704 rentals
💳 Possible discounts up to 51%
🌙 Nightly prices starting at $37
⭐ Popular amenities Pets allowed, Pool and Air conditioning
🐾 Pet friendly homes 1,934 homes
🏊 Vacation rentals with pools 4,227 homes
14 reviews
Chesapeake Bay vacation rentals have an average rating of 3.7/5 on 14 reviews left by travelers.

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 $37. If you would like to stay in a house rental, the average price is $625 per night. A apartment rental Chesapeake Bay will cost $291 per night on average.

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

There are currently 9,704 rentals from 33 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 4,227 vacation homes across 33 providers in Chesapeake Bay.

Are dogs allowed in vacation rentals in Chesapeake Bay?

If you are traveling with a dog in Chesapeake Bay - 20% 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.

Find the perfect Chesapeake Bay home to match your style

Top cities to visit

Show more

Top Vacation Ideas

Explore More Vacation Ideas

Show more

More popular destinations in Chesapeake Bay

Other nearby destinations in Chesapeake Bay

Show more
image-tag