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

Chesapeake Bay Vacation Rentals

Find 12,555 available house rentals from 33 partners
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Top 15 Recommended vacation rentals in Chesapeake Bay

Find your perfect vacation rental in Chesapeake Bay from just $91 per night!

House Bay View
-47%
Feb 21 - Feb 28
Free cancellation
House ∙ 8 guests ∙ 4 bedrooms

Family-friendly house with pool, grill & garden | Pets allowed

Bay View, Norfolk, Virginia, United States
$556$293
per night
$556$293
per night
View deal
House Lake Shore
Jul 19 - Jul 26
House ∙ 15 guests ∙ 7 bedrooms

House with grill & yard

Lake Shore, Anne Arundel County, Maryland, United States
$450
per night
Outstanding(79 ratings)
$450
per night
View deal
House Ridge
-58%
Jun 1 - Jun 8
House ∙ 11 guests ∙ 5 bedrooms

Family-friendly pleasant house with pool, barbeque & hot tub

Ridge, St. Inigoes, Maryland, United States
$1,397$587
per night
Outstanding
$1,397$587
per night
View deal
House Perryville
Aug 23 - Aug 30
House ∙ 16 guests ∙ 5 bedrooms

Vacation home with hot tub, garden & grill | Nature view

Perryville, Cecil County, Maryland, United States
$728
per night
Outstanding(12 ratings)
$728
per night
View deal
House Cape Charles
May 5 - May 12
House ∙ 9 guests ∙ 4 bedrooms

Fully equipped pleasant vacation home with pool & barbecue | Good for workation

Cape Charles, Northampton County, Virginia, United States
$500
per night
Excellent(7 ratings)
$500
per night
View deal
House Cape Charles
May 5 - May 12
House ∙ 16 guests ∙ 6 bedrooms

Vacation home with pool, barbecue & patio | Lake view

Cape Charles, Northampton County, Virginia, United States
$486
per night
Outstanding(32 ratings)
$486
per night
View deal
House Camellia Shores
Oct 18 - Oct 25
House ∙ 12 guests ∙ 4 bedrooms

Family-friendly vacation home with garden, terrace & barbeque | Lake view | Suitable for remote work

Camellia Shores, Norfolk, Virginia, United States
$259
per night
Outstanding(49 ratings)
$259
per night
View deal
House Port Republic
-51%
Apr 23 - Apr 30
House ∙ 5 guests ∙ 1 bedroom

House with garden, barbecue & pool | Good for workation | Dogs allowed

Port Republic, Solomons Island, Maryland, United States
$426$209
per night
Outstanding(8 ratings)
$426$209
per night
View deal
House Heathsville
-55%
Apr 26 - May 3
House ∙ 11 guests ∙ 4 bedrooms

Child-friendly vacation home with grill | Water view | Dogs allowed

Heathsville, Northumberland County, Virginia, United States
$530$237
per night
Outstanding(2 ratings)
$530$237
per night
View deal
House Dam Neck
-62%
May 17 - May 24
House ∙ 11 guests ∙ 4 bedrooms

Family-oriented vacation home with BBQ & patio | Beach nearby | Pets allowed

Dam Neck, Virginia Beach, Virginia, United States
$404$153
per night
Very good(32 ratings)
$404$153
per night
View deal
House Northeast Virginia Beach
Aug 23 - Aug 30
House ∙ 9 guests ∙ 4 bedrooms

Child-friendly vacation home with yard, barbeque & patio | Close to the beach

Northeast Virginia Beach, Virginia Beach, Virginia, United States
$450
per night
Outstanding(20 ratings)
$450
per night
View deal
House Chesapeake Ranch Estates-Drum Point
-25%
May 17 - May 24
House ∙ 11 guests ∙ 5 bedrooms

House with BBQ, patio & garden | Suitable for remote work | Pets allowed

Chesapeake Ranch Estates-Drum Point, Solomons Island, Maryland, United States
$373$278
per night
Outstanding(22 ratings)
$373$278
per night
View deal
House Palmer
Apr 26 - May 3
House ∙ 14 guests ∙ 4 bedrooms

Family-oriented spacious vacation home with BBQ, terrace & garden | Suitable for remote work | Pets are welcome

Palmer, Lancaster County, Virginia, United States
$418
per night
Outstanding(59 ratings)
$418
per night
View deal
Cottage Scotland
-30%
May 11 - May 18
Cottage ∙ 12 guests ∙ 6 bedrooms

Family-oriented wonderful cottage with terrace, jacuzzi & yard | Nature view | Pet-friendly

Scotland, St. Inigoes, Maryland, United States
$904$633
per night
Outstanding(9 ratings)
$904$633
per night
View deal
House Earleville
May 3 - May 10
House ∙ 18 guests ∙ 7 bedrooms

Children-friendly vacation home with terrace, jacuzzi & private pool | Nature view | Perfect for remote work

Earleville, Cecilton, Maryland, United States
$1,350
per night
Outstanding(19 ratings)
$1,350
per night
View deal

Vacation rentals and apartments with air conditioning

House  Heathsville
Apr 26 - May 3
-55%
$485
$217
per night
House ∙ 11 guests ∙ 6 bedrooms

Fully equipped house with barbecue & patio | Pets allowed

5.0
Outstanding(16 ratings)
Heathsville, Northumberland County, Virginia, United States
Air conditioning
View deal
House  Bay View
Sep 6 - Sep 13
$321
per night
House ∙ 8 guests ∙ 5 bedrooms

Vacation home with garden, private pool & patio

4.5
Excellent(8 ratings)
Bay View, Norfolk, Virginia, United States
Air conditioning
View deal
House  Chic's Beach
Jun 6 - Jun 13
$810
per night
House ∙ 21 guests ∙ 8 bedrooms

Vacation home with terrace, BBQ & garden | Perfect for remote work

4.9
Outstanding(70 ratings)
Chic's Beach, Virginia Beach, Virginia, United States
Air conditioning
View deal
See all offers

Vacation houses with Balconies or Patios

House  Annapolis
Aug 9 - Aug 16
$675
per night
House ∙ 12 guests ∙ 6 bedrooms

House with patio, yard & barbeque | City view

5.0
Outstanding(77 ratings)
Annapolis, Anne Arundel County, Maryland, United States
Balcony/Patio
View deal
House  Northeast Virginia Beach
Aug 16 - Aug 23
$405
per night
House ∙ 9 guests ∙ 4 bedrooms

Fully equipped charming house with patio, garden & barbecue | Close to the beach

4.7
Excellent(35 ratings)
Northeast Virginia Beach, Virginia Beach, Virginia, United States
Balcony/Patio
View deal
House  Cape Charles
Apr 26 - May 3
-20%
$500
$400
per night
House ∙ 8 guests ∙ 4 bedrooms

House with terrace, pool & BBQ | Nature view

4.9
Outstanding(7 ratings)
Cape Charles, Northampton County, Virginia, United States
Balcony/Patio
View deal
See all offers

Vacation homes and rentals with a yard

House  Heathsville
Feb 21 - Feb 28
-42%
$417
$244
per night
House ∙ 8 guests ∙ 4 bedrooms

Child-friendly vacation home with barbecue & garden | Water view

5.0
Outstanding(1 rating)
Heathsville, Northumberland County, Virginia, United States
Free cancellation
Yard
View deal
House  Pasadena
May 13 - May 20
$435
per night
House ∙ 14 guests ∙ 6 bedrooms

Child-friendly house with terrace & yard | Lake view

4.7
Excellent(97 ratings)
Pasadena, Anne Arundel County, Maryland, United States
Yard
View deal
House  Cape Charles
Sep 14 - Sep 21
-43%
$350
$199
per night
House ∙ 9 guests ∙ 3 bedrooms

Children-friendly vacation home with garden, pool & barbecue | Perfect for remote work | Pets are welcome

4.7
Excellent(9 ratings)
Cape Charles, Northampton County, Virginia, United States
Yard
View deal
See all offers

Best Vacation Home Deals in Chesapeake Bay

Save up to 57%

House Saint Michaels
Oct 10 - Oct 17
-24%
$1,229
$940
per night
House ∙ 12 guests ∙ 6 bedrooms

Vacation home with jacuzzi & private pool | Nature view

5.0
Outstanding(2 ratings)
Saint Michaels, St. Michaels, Maryland, United States
View deal
House Bohannon
May 5 - May 12
-57%
$272
$117
per night
House ∙ 6 guests ∙ 3 bedrooms

Vacation home | Water view

3.4
(3 ratings)
Bohannon, Westville, Virginia, United States
View deal
House Cape Charles
Dec 6 - Dec 13
-30%
$468
$326
per night
House ∙ 9 guests ∙ 5 bedrooms

House with barbecue & patio

4.9
Outstanding(78 ratings)
Cape Charles, Northampton County, Virginia, United States
Free cancellation
View deal

Find the ideal vacation rental from $91 per night by searching and comparing the 12,555 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 36%.

Budget-friendly Vacation Rentals in Chesapeake Bay

Find Fantastic yet Inexpensive Offers

House Cambridge
Jul 5 - Jul 12
$445
per night
House ∙ 13 guests ∙ 8 bedrooms

House with yard, patio & grill | Suitable for remote work

5.0
Outstanding(6 ratings)
Cambridge, Dorchester County, Maryland, United States
View deal
House Northside
Apr 30 - May 7
$156
per night
House ∙ 6 guests ∙ 4 bedrooms

Family-oriented big vacation home with yard, pool & patio | Nature view | Suitable for remote work

4.9
Outstanding(25 ratings)
Northside, Norfolk, Virginia, United States
View deal
House Cape Charles
May 17 - May 24
$561
per night
House ∙ 8 guests ∙ 3 bedrooms

Beautiful vacation home with pool | Nature view | Pets allowed

Cape Charles, Northampton County, Virginia, United States
View deal

Top-Rated Rentals and Accommodations in Chesapeake Bay

Book Vacation Rental Offers with the Highest User Rating

House Cape Charles
Oct 18 - Oct 25
$799
per night
House ∙ 12 guests ∙ 5 bedrooms

Vacation home with private pool, patio & BBQ | Nature view

5.0
Outstanding(64 ratings)
Cape Charles, Northampton County, Virginia, United States
View deal
House Cape Charles
Oct 18 - Oct 25
-20%
$500
$400
per night
House ∙ 8 guests ∙ 4 bedrooms

Vacation home with yard, barbecue & patio | City view

5.0
Outstanding(26 ratings)
Cape Charles, Northampton County, Virginia, United States
View deal
House Taylors Island
Jun 28 - Jul 5
$410
per night
House ∙ 9 guests ∙ 7 bedrooms

Children-friendly vacation home with terrace & barbeque | Perfect for remote work | Dogs allowed

5.0
Outstanding(20 ratings)
Taylors Island, Dorchester County, 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 (3,832)
  • Pool (4,689)
  • Air conditioning (11,851)
  • WiFi (12,069)
  • Fishing (3,492)
  • TV (10,660)
  • Balcony/patio (3,587)
  • Grill (3,426)
  • Kitchen (8,412)
  • Parking (989)
  • No smoking (11,322)
  • Hot tub (917)

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 July (7/5 – 7/12) that you will find the highest prices for the next 12 months. The most affordable accommodation prices can be found in April (4/19 – 4/26).

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 April (4/4 – 4/11). Only 13% of the rentals are still available. People tend to travel less to Chesapeake Bay during a week in August (8/23 – 8/30) 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 12,555 rentals
💳 Possible discounts up to 36%
🌙 Nightly prices starting at $91
⭐ Popular amenities Pets allowed, Pool and Air conditioning
🐾 Pet friendly homes 3,827 homes
🏊 Vacation rentals with pools 4,678 homes
2,362,622 reviews
Chesapeake Bay vacation rentals have an average rating of 4.3/5 on 2,362,622 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 $91. $630 is the average nightly price for house rentals in Chesapeake Bay. Apartment rentals in Chesapeake Bay cost $377 per night on average.

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

Currently there are 12,555 vacation rentals from 33 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 4,678 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 - 30% 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 $91.

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