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

Chesapeake Bay Vacation Rentals

Find 12,199 available offers from 28 partners
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1 guest
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Recommended vacation rentals in Chesapeake Bay

Find your perfect vacation rental in Chesapeake Bay from just $73 per night!

House Fishing Creek
Mar 15 - Mar 22
House ∙ 14 guests ∙ 6 bedrooms

Vacation Home with Terrace & Barbecue

Fishing Creek, Hoopers Island, Maryland, United States
$341
per night
Excellent(27 ratings)
$341
per night
View deal
Villa Hack Point
May 31 - Jun 7
Villa ∙ 16 guests ∙ 7 bedrooms

Child-Friendly Villa with Barbecue & Pool | Pet-Friendly

Hack Point, Cecil County, Maryland, United States
$1,829
per night
Outstanding(19 ratings)
$1,829
per night
View deal
House Betterton
Jun 14 - Jun 21
House ∙ 11 guests ∙ 6 bedrooms

House with Yard, Barbeque & Terrace

Betterton, Worton (Betterton), Maryland, United States
$355
per night
Outstanding(124 ratings)
$355
per night
View deal
House Cambridge
Mar 13 - Mar 20
House ∙ 17 guests ∙ 6 bedrooms

Family-Friendly Vacation Home with Patio, Grill & Yard | Dogs Allowed

Cambridge, Dorchester County, Maryland, United States
$862
per night
Outstanding(81 ratings)
$862
per night
View deal
House Cape Charles
May 31 - Jun 7
House ∙ 10 guests ∙ 4 bedrooms

House with Barbeque, Garden & Patio | City View

Cape Charles, Northampton County, Virginia, United States
$625
per night
Outstanding(25 ratings)
$625
per night
View deal
House Earleville
Jun 7 - Jun 14
House ∙ 18 guests ∙ 7 bedrooms

Children-Friendly Vacation Home with Terrace, Private Pool & Garden | Nature View | Suitable for Remote Work

Earleville, Cecilton, Maryland, United States
$1,540
per night
Outstanding(17 ratings)
$1,540
per night
View deal
House Shady Side
Feb 16 - Feb 23
House ∙ 6 guests ∙ 3 bedrooms

House with Yard, Barbecue & Terrace | Nature View

Shady Side, Anne Arundel County, Maryland, United States
$260
per night
Outstanding(38 ratings)
$260
per night
View deal
Motel Northwest
-32%
Jan 11 - Jan 18
Motel ∙ 127 guests ∙ 1 bedroom

Motel with Terrace

Northwest, Virginia Beach, Virginia, United States
$107$73
per night
$107$73
per night
View deal
House Cape Charles
-24%
Jan 11 - Jan 18
House ∙ 15 guests ∙ 6 bedrooms

Vacation Home with Heated Pool & Grill

Cape Charles, Northampton County, Virginia, United States
$837$641
per night
Outstanding(64 ratings)
$837$641
per night
View deal
House Riva
-29%
Mar 15 - Mar 22
House ∙ 16 guests ∙ 10 bedrooms

Family-Oriented Big House with Barbecue & Yard | Lake View

Riva, Anne Arundel County, Maryland, United States
$2,878$1,678
per night
Outstanding(23 ratings)
$2,878$1,678
per night
View deal
House Heathsville
-17%
Mar 8 - Mar 15
House ∙ 8 guests ∙ 4 bedrooms

Family-Friendly Charming House with BBQ, Terrace & Yard | Nature View | Perfect for Remote Work | Pet-Friendly

Heathsville, Northumberland County, Virginia, United States
$300$293
per night
Outstanding(129 ratings)
$300$293
per night
View deal
House Chic's Beach
Mar 13 - Mar 20
House ∙ 10 guests ∙ 4 bedrooms

Family-Friendly House with Grill & Terrace | Next to the Beach | Perfect for Remote Work

Chic's Beach, Virginia Beach, Virginia, United States
$334
per night
Outstanding(45 ratings)
$334
per night
View deal
House Heathsville
Mar 1 - Mar 8
House ∙ 16 guests ∙ 7 bedrooms

Vacation Home with Yard, Grill & Private Pool

Heathsville, Northumberland County, Virginia, United States
$1,758
per night
Outstanding(16 ratings)
$1,758
per night
View deal
House Northeast Virginia Beach
-21%
Sep 13 - Sep 20
House ∙ 8 guests ∙ 4 bedrooms

Family-Friendly House with Grill & Garden | Close to the Beach | Good for Workation | Dogs Allowed

Northeast Virginia Beach, Virginia Beach, Virginia, United States
$807$637
per night
Excellent(40 ratings)
$807$637
per night
View deal
House West Ocean View
-38%
Apr 12 - Apr 19
House ∙ 4 guests ∙ 3 bedrooms

Children-Friendly Pleasant Vacation Home with Garden, Terrace & BBQ | Pet-Friendly

West Ocean View, Norfolk, Virginia, United States
$243$157
per night
Outstanding(18 ratings)
$243$157
per night
View deal

Vacation rentals and apartments with air conditioning

House  Carvel Beach
Dec 31 - Jan 7
$409
per night
House ∙ 10 guests ∙ 5 bedrooms

Vacation Home with Yard, Terrace & Grill | Nature View

5.0
Outstanding(34 ratings)
Carvel Beach, Riviera Beach, Maryland, United States
Air conditioning
View deal
House  Cape Charles
Oct 4 - Oct 11
-18%
$345
$287
per night
House ∙ 8 guests ∙ 3 bedrooms

Children-Friendly Lovely House with BBQ, Patio & Yard | City View | Pets Are Welcome

4.9
Outstanding(49 ratings)
Cape Charles, Northampton County, Virginia, United States
Air conditioning
View deal
Motel  Northwest
Jan 4 - Jan 11
$73
per night
Motel ∙ 127 guests ∙ 1 bedroom

Motel with Terrace

3.0
Northwest, Virginia Beach, Virginia, United States
Air conditioning
View deal
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Vacation homes and rentals with a yard

House  Annapolis
Jul 5 - Jul 12
$415
per night
House ∙ 14 guests ∙ 4 bedrooms

Vacation Home with Barbeque, Patio & Garden | Suitable for Remote Work

5.0
Outstanding(11 ratings)
Annapolis, Anne Arundel County, Maryland, United States
Yard
View deal
House  Wenona
Jun 21 - Jun 28
$263
per night
House ∙ 8 guests ∙ 4 bedrooms

House with Barbeque, Terrace & Garden | Nature View | Good for Workation

5.0
Outstanding(23 ratings)
Wenona, Deal Island, Maryland, United States
Yard
View deal
House  Riva
Jul 26 - Aug 2
$1,678
per night
House ∙ 16 guests ∙ 10 bedrooms

Family-Oriented Big House with Barbecue & Yard | Lake View

4.8
Outstanding(23 ratings)
Riva, Anne Arundel County, Maryland, United States
Yard
View deal
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Best Vacation Home Deals in Chesapeake Bay

Save up to 49%

House Annapolis
Feb 1 - Feb 8
-31%
$248
$170
per night
House ∙ 14 guests ∙ 7 bedrooms

Family-Friendly Vacation Home with Garden & Barbecue | Perfect for Remote Work | Dogs Allowed

5.0
Outstanding(36 ratings)
Annapolis, Anne Arundel County, Maryland, United States
View deal
House Reedville
Jun 1 - Jun 8
-18%
$543
$447
per night
House ∙ 11 guests ∙ 4 bedrooms

House with Garden, Patio & BBQ | Nature View

5.0
Outstanding(3 ratings)
Reedville, Northumberland County, Virginia, United States
View deal
House Edgewater
Mar 15 - Mar 22
-49%
$459
$233
per night
House ∙ 10 guests ∙ 3 bedrooms

Vacation Home with Barbeque, Patio & Yard | Nature View

4.7
Excellent(23 ratings)
Edgewater, Anne Arundel County, Maryland, United States
View deal

Find the ideal vacation rental from $73 per night by searching and comparing the 12,199 rentals available in Chesapeake Bay. Using HomeToGo you can easily search and compare the offers of each listed property to find the best deal and save up to 54%.

Budget-friendly Vacation Rentals in Chesapeake Bay

Find Fantastic yet Inexpensive Offers

House Reedville
Mar 1 - Mar 8
$450
per night
House ∙ 14 guests ∙ 5 bedrooms

Family-Oriented Pleasant Vacation Home with Barbecue, Terrace & Yard | Perfect for Remote Work | Pet-Friendly

5.0
Outstanding(92 ratings)
Reedville, Northumberland County, Virginia, United States
View deal
House Annapolis
Jun 21 - Jun 28
$234
per night
House ∙ 12 guests ∙ 5 bedrooms

House with Patio

4.6
Excellent(5 ratings)
Annapolis, Anne Arundel County, Maryland, United States
View deal
House Red Point
Jul 19 - Jul 26
$1,235
per night
House ∙ 24 guests ∙ 11 bedrooms

Family-Friendly Vacation Home with Yard, Barbeque & Terrace | Lake View

5.0
Outstanding(20 ratings)
Red Point, Cecil County, Maryland, United States
View deal

Top-Rated Rentals and Accommodations in Chesapeake Bay

Book Vacation Rental Offers with the Highest User Rating

House Northeast Virginia Beach
Aug 16 - Aug 23
$470
per night
House ∙ 9 guests ∙ 4 bedrooms

Vacation Home with Yard, Grill & Terrace

4.9
Outstanding(77 ratings)
Northeast Virginia Beach, Virginia Beach, Virginia, United States
View deal
House Northeast Virginia Beach
Jul 19 - Jul 26
$552
per night
House ∙ 9 guests ∙ 4 bedrooms

Family-Oriented Vacation Home with Barbeque, Yard & Terrace | Close to the Beach

4.8
Outstanding(20 ratings)
Northeast Virginia Beach, Virginia Beach, Virginia, United States
View deal
House Mechanicsville
Jun 20 - Jun 27
$435
per night
House ∙ 6 guests ∙ 4 bedrooms

Children-Friendly Big House with Grill & Patio | Good for Workation

5.0
Outstanding(15 ratings)
Mechanicsville, Chaptico, Maryland, United States
View deal

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Explore 15 million+ rentals, the world’s biggest selection of vacation homes.

Popular Rental Amenities in Chesapeake Bay

  • Pet-friendly (3,858)
  • Pool (4,616)
  • Air conditioning (11,544)
  • WiFi (11,744)
  • Fishing (3,537)
  • TV (10,423)
  • Balcony/patio (3,472)
  • Grill (3,305)
  • Kitchen (7,939)
  • Parking (1,098)
  • No smoking (11,131)
  • Hot tub (873)

Finding a vacation rental with a pool shouldn't be too difficult in Chesapeake Bay. One-third of the properties have pools. Interestingly, HomeToGo's data shows that more hotel room offer a pool than condo. Also, they can host 10 people, on average, while condo with pools can host an average of 5 people. You can also compare and find an accommodation offering a pool near the water, which is the case for nearly half of the rentals there.

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 show you the average nightly price in Chesapeake Bay for the upcoming months of the year. It is during a week of September (9/27 – 10/4) that you will find the highest prices for the next 12 months. The most affordable accommodation prices can be found in January (1/4 – 1/11).

Rental availability information in Chesapeake Bay

Find out how busy the upcoming months are going to be in Chesapeake Bay with our availability graph. The week with the highest booking rate is in November (11/1 – 11/8). Only 6% of the rentals are still available. People tend to travel less to Chesapeake Bay during a week in June (6/14 – 6/21) when only 44% of the rentals are booked.

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.

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 12,199 rentals
💳 Possible discounts up to 54%
🌙 Nightly prices starting at $73
⭐ Popular amenities Pets allowed, Pool and Air conditioning
🐾 Pet friendly homes 3,856 homes
🏊 Vacation rentals with pools 4,638 homes
2,443,813 reviews
Chesapeake Bay vacation rentals have an average rating of 4.2/5 on 2,443,813 reviews left by travelers.

Frequently Asked Questions

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

The nightly price of accommodations in Chesapeake Bay starts at $73. $604 is the average nightly price for house rentals in Chesapeake Bay. Apartment rentals in Chesapeake Bay cost $334 per night on average.

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

Currently there are 12,199 vacation rentals from 28 different providers in Chesapeake Bay.

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

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

How many vacation rentals with pools are there in Chesapeake Bay?

Browse 4,638 vacation rentals available to book in Chesapeake Bay.

Are pets allowed in vacation rentals in Chesapeake Bay?

If you are traveling with a pet in Chesapeake Bay - 32% of vacation homes allow pets.

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

Chesapeake Bay has its warmest time of year around July and June, with average nightly prices around $73.

Find the perfect Chesapeake Bay home to match your style

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