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

Vacation rentals in Chesapeake Bay

Browse 9,960 available vacation homes and compared across 32 trusted partners
Anytime
Guests
Anytime
Guests

  • Price per night

    • Up to $100
    • $100 - $199
    • From $200

  • Accommodation types

    • Condo
    • House
    • Farmhouse

  • Rating

    • 4.5+
    • 4+

  • Booking Options

    • Instant Booking

  • Services

    • Pool
    • Air conditioning
    • WiFi
    • TV
    • Balcony/patio
    • Kitchen
    • Parking
    • Hot tub
    • Fireplace
    • Washing machine
    • Microwave
    • Dishwasher
    • Yard
    • Crib
    Show more

  • Accommodation type

    • Pet-friendly
    • No smoking
    • Wheelchair access
    • No pets

  • Activities

    • Fishing
    • Grill

Top 15 most Recommended Vacation Rentals in Chesapeake Bay

Discover your ideal Chesapeake Bay vacation rental with real-time comparisons of 9,960 properties, featuring recommended options based on the property location, value for money, and verified guest reviews.

House Fishing Creek
House ∙ 15 guests ∙ 7 bedrooms

House with barbecue, yard & patio | Water view

Fishing Creek, Hoopers Island, Maryland, United States
This waterfront house rental in Fishing Creek features a kitchen, balcony, yard, and sea view, perfect for family gatherings.
from $347
per night
Excellent(55 ratings)
from $347
per night
View deal
House Cape Charles
House ∙ 14 guests ∙ 6 bedrooms

Children-friendly beautiful vacation home with pool, patio & barbecue | Nature view

Cape Charles, Northampton County, Virginia, United States
This house rental in Cape Charles features a pool, fireplace, and beach access, perfect for families up to 14 guests.
from $638
per night
Outstanding(28 ratings)
from $638
per night
View deal
House Northeast Virginia Beach
House ∙ 9 guests ∙ 4 bedrooms

Children-friendly beautiful vacation home with patio, garden & grill | Beach nearby

Northeast Virginia Beach, Virginia Beach, Virginia, United States
This waterfront house rental in Northeast Virginia Beach offers a kitchen, yard, and parking, perfect for families of up to nine.
from $541
per night
Outstanding(15 ratings)
from $541
per night
View deal
House Northeast Virginia Beach
House ∙ 10 guests ∙ 3 bedrooms

Vacation home with grill

Northeast Virginia Beach, Virginia Beach, Virginia, United States
This house rental in Northeast Virginia Beach offers parking and space for 10 guests, perfect for your next getaway.
from $167
per night
from $167
per night
View deal
House Northeast Virginia Beach
House ∙ 18 guests ∙ 8 bedrooms

Wonderful house with patio | Dogs allowed

Northeast Virginia Beach, Virginia Beach, Virginia, United States
This house rental in Northeast Virginia Beach accommodates 18 guests, features a kitchen, and welcomes pets for a memorable getaway.
from $1,135
per night
Excellent(14 ratings)
from $1,135
per night
View deal
House Fox Hill - Grandview
House ∙ 12 guests ∙ 4 bedrooms

Children-friendly vacation home with barbeque, private pool & hot tub | Beach nearby

Fox Hill - Grandview, Hampton, Virginia, United States
This Fox Hill house rental features a private pool, hot tub, and fireplace, perfect for families seeking a memorable getaway.
from $558
per night
Excellent(61 ratings)
from $558
per night
View deal
House Bay View
House ∙ 10 guests ∙ 4 bedrooms

Family-friendly house with grill & terrace | Suitable for remote work | Pets allowed

Bay View, Norfolk, Virginia, United States
This Bay View house rental offers waterfront access, a kitchen, and a balcony, making it perfect for family getaways with pets.
from $180
per night
Very good(56 ratings)
from $180
per night
View deal
House Ocean View
House ∙ 8 guests ∙ 4 bedrooms

Child-friendly house with garden & barbecue | Next to the beach

Ocean View, Norfolk, Virginia, United States
This ocean view house rental features a fireplace, kitchen, and yard, welcoming up to 8 guests for an unforgettable getaway.
from $188
per night
Outstanding(57 ratings)
from $188
per night
View deal
House Bohannon
House ∙ 12 guests ∙ 6 bedrooms

Child-friendly big vacation home with barbeque, patio & garden | Pet-friendly

Bohannon, Westville, Virginia, United States
This waterfront house rental in Bohannon features a yard, beach access, and space for 12, perfect for family gatherings.
from $446
per night
Outstanding(212 ratings)
from $446
per night
View deal
Houseboat Havre de Grace
Houseboat ∙ 10 guests ∙ 4 bedrooms

Children-friendly beautiful boat with terrace & BBQ | Pets are welcome

Havre de Grace, Harford County, Maryland, United States
This houseboat in Havre de Grace offers a kitchen, fireplace, and parking, accommodating up to 10 guests with pets welcome.
from $247
per night
Outstanding(57 ratings)
from $247
per night
View deal
Cabin Deal Island
Cabin ∙ 9 guests ∙ 3 bedrooms

Family-oriented cottage with BBQ | Water view | Dogs allowed

Deal Island, Somerset County, Maryland, United States
This waterfront cabin on Deal Island accommodates up to 9 guests, featuring a kitchen, sea views, and pet-friendly facilities.
from $222
per night
Outstanding(6 ratings)
from $222
per night
View deal
House Willoughby Spit
House ∙ 4 guests ∙ 1 bedroom

House with grill | Pets are welcome

Willoughby Spit, Norfolk, Virginia, United States
This house rental at Willoughby Spit offers beach access, a kitchen, parking, and is pet-friendly for a memorable stay.
from $146
per night
from $146
per night
View deal
House Elkton
House ∙ 12 guests ∙ 5 bedrooms

Vacation home with patio & barbeque | Nature view

Elkton, Cecil County, Maryland, United States
This Elkton house rental offers waterfront access, a kitchen, a fireplace, and space for 12, perfect for family gatherings.
from $484
per night
Outstanding(222 ratings)
from $484
per night
View deal
Villa Rock Hall
Villa ∙ 28 guests ∙ 9 bedrooms

Family-oriented nice villa with patio, sauna & BBQ | Suitable for remote work

Rock Hall, Edesville, Maryland, United States
This waterfront villa in Rock Hall features a private heated pool, sauna, hot tub, and ample space for 28 guests to unwind.
from $1,202
per night
Outstanding(50 ratings)
from $1,202
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
This waterfront house rental in Heathsville features a yard, fireplace, and a kitchen, making it perfect for family gatherings.
from $207
per night
Outstanding(146 ratings)
from $207
per night
View deal

Vacation rentals and apartments with air conditioning

House Northeast Virginia Beach
from $548
per night
House ∙ 9 guests ∙ 4 bedrooms

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

4.9
Outstanding(23 ratings)
Northeast Virginia Beach, Virginia Beach, Virginia, United States
Air conditioning
View deal
Houseboat Solomons
from $216
per night
Houseboat ∙ 2 guests ∙ 1 bedroom

Nice boat with patio | City view | Pet-friendly

5.0
Outstanding(9 ratings)
Solomons, Solomons Island, Maryland, United States
Air conditioning
View deal
House Cape Charles
from $358
per night
House ∙ 11 guests ∙ 4 bedrooms

House with patio, garden & grill | Nature view | Perfect for remote work

4.8
Outstanding(22 ratings)
Cape Charles, Northampton County, Virginia, United States
Air conditioning
View deal
See all offers

Vacation houses with Balconies or Patios

House Northeast Virginia Beach
from $533
per night
House ∙ 9 guests ∙ 4 bedrooms

Family-oriented charming house with patio, garden & barbecue | Close to the beach

4.7
Excellent(44 ratings)
Northeast Virginia Beach, Virginia Beach, Virginia, United States
Balcony/Patio
View deal
House Churchton
from $571
per night
House ∙ 13 guests ∙ 6 bedrooms

House with hot tub, grill & garden | Lake view

4.7
Excellent(22 ratings)
Churchton, Deale, Maryland, United States
Balcony/Patio
View deal
House Cape Charles
from $342
per night
House ∙ 10 guests ∙ 4 bedrooms

Family-friendly house with terrace, barbeque & yard | Nature view | Perfect for remote work

5.0
Outstanding(75 ratings)
Cape Charles, Northampton County, Virginia, United States
Balcony/Patio
View deal
See all offers

Vacation Rentals With Fireplaces

House Ridge
from $588
per night
House ∙ 12 guests ∙ 4 bedrooms

Vacation home with yard, barbecue & patio | Beach view

5.0
Outstanding(251 ratings)
Ridge, St. Inigoes, Maryland, United States
Fireplace
View deal
House Northeast Virginia Beach
from $897
per night
House ∙ 12 guests ∙ 6 bedrooms

Vacation home with 6 rooms for 12 persons

5.0
Outstanding(7 ratings)
Northeast Virginia Beach, Virginia Beach, Virginia, United States
Fireplace
View deal
House Annapolis
from $255
per night
House ∙ 9 guests ∙ 5 bedrooms

Fully equipped house with grill

5.0
Outstanding(7 ratings)
Annapolis, Anne Arundel County, Maryland, United States
Fireplace
View deal
See all offers

Budget-friendly rental options

Enjoy affordable vacation rentals in Chesapeake Bay offering exceptional value for money

House Lusby
from $428
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
Villa Earleville
from $1,279
per night
Villa ∙ 16 guests ∙ 7 bedrooms

Children-friendly villa with jacuzzi, pool & barbeque | Dogs allowed

4.9
Outstanding(36 ratings)
Earleville, Cecilton, Maryland, United States
View deal
House Cape Charles
from $403
per night
House ∙ 13 guests ∙ 4 bedrooms

Child-friendly nice vacation home with patio, grill & pool | Nature view

5.0
Outstanding(28 ratings)
Cape Charles, Northampton County, Virginia, United States
View deal

Top-Rated Vacation rentals in Chesapeake Bay

Book the highest-rated Chesapeake Bay vacation rentals, rated by real guests for comfort, location, cleanliness, services and value for money

House Virginia Beach
from $312
per night
House ∙ 12 guests ∙ 4 bedrooms

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

4.9
Outstanding(221 ratings)
Virginia Beach, Virginia, United States
View deal
House Annapolis
from $154
per night
House ∙ 10 guests ∙ 5 bedrooms

Fully equipped vacation home with barbeque, terrace & yard | City view

4.9
Outstanding(191 ratings)
Annapolis, Anne Arundel County, Maryland, United States
View deal
Apartment Annapolis
from $251
per night
Apartment ∙ 4 guests ∙ 2 bedrooms

Holiday apartment with barbecue & private pool | City view

5.0
Outstanding(99 ratings)
Annapolis, Anne Arundel County, Maryland, United States
View deal

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Trust in the quality and comfort of your stay with verified guest reviews.

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Spend your budget exactly as planned by comparing thousands of providers.

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Find your dream stay

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

Popular Features & Amenities in Chesapeake Bay

  • Pet-friendly (3,299)
  • Pool (4,245)
  • Air conditioning (9,692)
  • WiFi (9,614)
  • Fishing (2,500)
  • TV (8,949)
  • Balcony/patio (3,479)
  • Grill (3,169)
  • Kitchen (6,090)
  • Parking (812)
  • No smoking (9,171)
  • Hot tub (593)

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 4 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 (6/27 – 7/4) that you will find the highest prices for the next 12 months. The most affordable accommodation prices can be found in January (1/17 – 1/24).

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 (11/14 – 11/21). Only 3% of the rentals are still available. People tend to travel less to Chesapeake Bay during a week in January (1/10 – 1/17) when only 24% 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 9,960 rentals
🌙 Nightly prices starting at $77
⭐ Popular amenities Pets allowed, Pool and Air conditioning
🐾 Pet friendly homes 3,283 homes
🏊 Vacation rentals with pools 4,235 homes

Frequently Asked Questions

What is the average price per night for a vacation home in Chesapeake Bay?

The price of a night's stay in Chesapeake Bay starts at $77. Average prices for house rentals are $656 per night. Apartment rentals in Chesapeake Bay cost on average $381 per night.

How many vacation rentals are available for booking in Chesapeake Bay?

Currently there are 9,960 vacation homes in Chesapeake Bay to browse and book for your upcoming trip.

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

The most popular amenities for vacation home rentals in Chesapeake Bay include accommodations with: Pets allowed, Pool, and Air conditioning.

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

Chesapeake Bay has 4,235 Hotel room and Condo available for renting.

Are pets allowed in vacation rentals in Chesapeake Bay?

If traveling with a dog in Chesapeake Bay, 33% of vacation rentals are pet-friendly.

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