Vacation rentals & cabins in Chesapeake Bay - HomeToGo base64Hash Vacation rentals & cabins in Chesapeake Bay - HomeToGo

Vacation rentals & cabins in Chesapeake Bay

Find 10,309 available vacation homes 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 $98 per night!

House Shady Side
House ∙ 10 guests ∙ 5 bedrooms

Vacation home with patio & garden | Perfect for remote work

Shady Side, Anne Arundel County, Maryland, United States
from $653
per night
Outstanding(2 ratings)
from $653
per night
View deal
House Reedville
House ∙ 8 guests ∙ 4 bedrooms

Fully equipped big house with garden, terrace & barbecue | Nature view | Suitable for remote work

Reedville, Northumberland County, Virginia, United States
from $536
per night
Outstanding(35 ratings)
from $536
per night
View deal
Condo Northeast Virginia Beach
Condo ∙ 6 guests ∙ 2 bedrooms

Family-oriented condo with private pool & terrace | Close to the beach

Northeast Virginia Beach, Virginia Beach, Virginia, United States
from $133
per night
Outstanding(182 ratings)
from $133
per night
View deal
House Heathsville
House ∙ 10 guests ∙ 3 bedrooms

Fully equipped house with patio, garden & barbecue | Dogs allowed

Heathsville, Northumberland County, Virginia, United States
from $239
per night
Outstanding(58 ratings)
from $239
per night
View deal
House Bay Ridge
House ∙ 14 guests ∙ 5 bedrooms

Children-friendly wonderful house with private pool, terrace & BBQ | Nature view | Pets allowed

Bay Ridge, Northampton County, Virginia, United States
from $639
per night
Outstanding(78 ratings)
from $639
per night
View deal
Cabin White Stone
Cabin ∙ 6 guests ∙ 2 bedrooms

Cottage with grill | Water view

White Stone, Lancaster County, Virginia, United States
from $188
per night
Good(88 ratings)
from $188
per night
View deal
House Cambridge
House ∙ 27 guests ∙ 7 bedrooms

Family-oriented ample vacation home with terrace, grill & private pool | Lake view

Cambridge, Dorchester County, Maryland, United States
from $1,136
per night
Outstanding(47 ratings)
from $1,136
per night
View deal
House Bay View
House ∙ 8 guests ∙ 4 bedrooms

Vacation home with garden, private pool & patio

Bay View, Norfolk, Virginia, United States
from $320
per night
Excellent(11 ratings)
from $320
per night
View deal
House Cape Charles
House ∙ 10 guests ∙ 4 bedrooms

House with patio, yard & barbecue

Cape Charles, Northampton County, Virginia, United States
from $318
per night
Outstanding(113 ratings)
from $318
per night
View deal
House Virginia Beach
House ∙ 10 guests ∙ 3 bedrooms

House with barbeque, private pool & terrace | City view

Virginia Beach, Virginia, United States
from $397
per night
Very good(44 ratings)
from $397
per night
View deal
House Deale
House ∙ 8 guests ∙ 3 bedrooms

Family-oriented vacation home with barbeque, garden & patio | Nature view | Pet-friendly

Deale, Anne Arundel County, Maryland, United States
from $427
per night
Outstanding(96 ratings)
from $427
per night
View deal
House Bay View
House ∙ 9 guests ∙ 4 bedrooms

Fully equipped lovely house with terrace & barbeque | City view

Bay View, Norfolk, Virginia, United States
from $183
per night
Outstanding(54 ratings)
from $183
per night
View deal
House Deale
House ∙ 8 guests ∙ 4 bedrooms

Vacation home with terrace & jacuzzi

Deale, Anne Arundel County, Maryland, United States
from $226
per night
Outstanding(38 ratings)
from $226
per night
View deal
House Heathsville
House ∙ 8 guests ∙ 3 bedrooms

Family-oriented nice vacation home with garden, barbecue & patio | Nature view | Perfect for remote work | Pet-friendly

Heathsville, Northumberland County, Virginia, United States
from $199
per night
Outstanding(139 ratings)
from $199
per night
View deal
House Dam Neck
House ∙ 11 guests ∙ 4 bedrooms

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

Dam Neck, Virginia Beach, Virginia, United States
$233 from $209
per night
Very good(33 ratings)
$233 from $209
per night
View deal

Vacation Rentals With Fireplaces

Cabin  Heathsville
from $239
per night
Cabin ∙ 8 guests ∙ 3 bedrooms

Cottage with jacuzzi, barbeque & patio

5.0
Outstanding(104 ratings)
Heathsville, Northumberland County, Virginia, United States
Fireplace
View deal
House  Tracys Landing
from $1,120
per night
House ∙ 14 guests ∙ 5 bedrooms

Family-oriented charming vacation home with pool, BBQ & patio | Perfect for remote work | Pets allowed

5.0
Outstanding(57 ratings)
Tracys Landing, Anne Arundel County, Maryland, United States
Fireplace
View deal
House  Chesapeake Ranch Estates-Drum Point
from $220
per night
House ∙ 8 guests ∙ 3 bedrooms

Vacation home with terrace, barbeque & yard | Nature view | Suitable for remote work

5.0
Outstanding(24 ratings)
Chesapeake Ranch Estates-Drum Point, Solomons Island, Maryland, United States
Fireplace
View deal
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Vacation rentals and apartments with air conditioning

House  Port Republic
from $151
per night
House ∙ 6 guests ∙ 3 bedrooms

Family-friendly vacation home with terrace, yard & grill | Nature view

4.8
Outstanding(23 ratings)
Port Republic, Solomons Island, Maryland, United States
Air conditioning
View deal
House  Scotland
from $752
per night
House ∙ 14 guests ∙ 7 bedrooms

Spacious vacation home with barbecue | Pets are welcome

4.8
Outstanding(116 ratings)
Scotland, St. Inigoes, Maryland, United States
Air conditioning
View deal
House  Lusby
from $166
per night
House ∙ 8 guests ∙ 4 bedrooms

Family-friendly vacation home with patio | Pets are welcome

4.7
Excellent(25 ratings)
Lusby, Solomons Island, Maryland, United States
Air conditioning
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Vacation houses with Balconies or Patios

House  Northeast Virginia Beach
from $387
per night
House ∙ 9 guests ∙ 3 bedrooms

Child-friendly pleasant vacation home with barbeque, patio & garden | Dogs allowed

4.9
Outstanding(227 ratings)
Northeast Virginia Beach, Virginia Beach, Virginia, United States
Balcony/Patio
View deal
House  Virginia Beach
from $345
per night
House ∙ 12 guests ∙ 4 bedrooms

Child-friendly spacious vacation home with barbecue, yard & terrace | Nature view | Good for workation | Pets are welcome

4.9
Outstanding(208 ratings)
Virginia Beach, Virginia, United States
Balcony/Patio
View deal
House  Chesapeake Beach
from $210
per night
House ∙ 11 guests ∙ 4 bedrooms

Vacation home with barbeque, patio & hot tub

4.0
Very good(2 ratings)
Chesapeake Beach, Sunderland, Maryland, United States
Balcony/Patio
View deal
See all offers

Budget-friendly Vacation Rentals in Chesapeake Bay

Find Fantastic yet Inexpensive Offers

House Pasadena
from $503
per night
House ∙ 14 guests ∙ 5 bedrooms

Child-friendly house with terrace & yard | Lake view

4.7
Excellent(97 ratings)
Pasadena, Anne Arundel County, Maryland, United States
View deal
House Reedville
from $224
per night
House ∙ 6 guests ∙ 3 bedrooms

Family-oriented vacation home with barbeque

5.0
Outstanding(6 ratings)
Reedville, Northumberland County, Virginia, United States
View deal
House Lusby
from $421
per night
House ∙ 11 guests ∙ 4 bedrooms

Child-friendly house with BBQ & pool | Water view | Pets are welcome

5.0
Outstanding(2 ratings)
Lusby, Solomons Island, Maryland, United States
View deal

Top-Rated Rentals and Accommodations in Chesapeake Bay

Book Vacation Rental Offers with the Highest User Rating

House West Ocean View
from $380
per night
House ∙ 10 guests ∙ 4 bedrooms

Vacation home with hot tub, yard & grill

4.6
Excellent(19 ratings)
West Ocean View, Norfolk, Virginia, United States
View deal
House Perryville
from $723
per night
House ∙ 16 guests ∙ 5 bedrooms

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

5.0
Outstanding(19 ratings)
Perryville, Cecil County, Maryland, United States
View deal
House Chesapeake Ranch Estates-Drum Point
from $421
per night
House ∙ 8 guests ∙ 4 bedrooms

Children-friendly house with patio | Good for workation

4.8
Outstanding(18 ratings)
Chesapeake Ranch Estates-Drum Point, Solomons Island, Maryland, United States
View deal

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Popular Rental Amenities in Chesapeake Bay

  • Pet-friendly (3,214)
  • Pool (4,393)
  • Air conditioning (9,930)
  • WiFi (9,924)
  • Fishing (2,614)
  • TV (9,041)
  • Balcony/patio (3,651)
  • Grill (3,346)
  • Kitchen (6,244)
  • Parking (864)
  • No smoking (9,426)
  • Hot tub (714)

Finding a vacation rental with a pool shouldn't be too difficult in Chesapeake Bay. Nearly half 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 more than 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 June (6/20 – 6/27) that you will find the highest prices for the next 12 months. The most affordable accommodation prices can be found in September (9/13 – 9/20).

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 May (5/2 – 5/9). Only 8% of the rentals are still available. People tend to travel less to Chesapeake Bay during a week in August (8/30 – 9/6) when only 29% 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 10,309 rentals
🌙 Nightly prices starting at $98
⭐ Popular amenities Pets allowed, Pool and Air conditioning
🐾 Pet friendly homes 3,219 homes
🏊 Vacation rentals with pools 4,395 homes

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 $98. $632 is the average nightly price for house rentals in Chesapeake Bay. Apartment rentals in Chesapeake Bay cost $399 per night on average.

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

Currently there are 10,309 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 4,395 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 - 31% 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 $98.

Find the perfect accommodation to stay in Chesapeake Bay

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