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

Vacation rentals in Chesapeake Bay

Browse 10,141 available vacation homes and compared across 26 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+

  • 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 10,141 properties, featuring recommended options based on the property location, value for money, and verified guest reviews.

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 $426
per night
Good(57 ratings)
from $426
per night
View deal
Cabin Willoughby Spit
Cabin ∙ 12 guests ∙ 3 bedrooms

Children-friendly wonderful cottage with yard, barbeque & terrace | Pet-friendly

Willoughby Spit, Norfolk, Virginia, United States
This waterfront cabin at Willoughby Spit features a kitchen, balcony, and yard, welcoming up to 12 guests and pets.
from $326
per night
(48 ratings)
from $326
per night
View deal
Cabin Deal Island
Cabin ∙ 9 guests ∙ 3 bedrooms

Cottage with terrace & grill | Suitable for remote work

Deal Island, Somerset County, Maryland, United States
This Deal Island cabin offers a waterfront location, a fireplace, kitchen, pet-friendly policies, and parking for nine guests.
from $197
per night
Outstanding(19 ratings)
from $197
per night
View deal
House Calvert Beach-Long Beach
House ∙ 6 guests ∙ 3 bedrooms

Family-friendly house with terrace & BBQ | Good for workation | Dogs allowed

Calvert Beach-Long Beach, Solomons Island, Maryland, United States
This house rental in Calvert Beach-Long Beach features a kitchen, fireplace, and space for pets, perfect for family getaways.
from $171
per night
Outstanding(35 ratings)
from $171
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 $252
per night
Outstanding(57 ratings)
from $252
per night
View deal
House Chesapeake Ranch Estates-Drum Point
House ∙ 8 guests ∙ 4 bedrooms

Family-friendly vacation home with patio | Pets are welcome

Chesapeake Ranch Estates-Drum Point, Solomons Island, Maryland, United States
This house rental in Chesapeake Ranch Estates-Drum Point welcomes up to 8 guests and features a kitchen, fireplace, and pet-friendly options.
from $232
per night
Excellent(43 ratings)
from $232
per night
View deal
House Chesapeake Ranch Estates-Drum Point
House ∙ 8 guests ∙ 3 bedrooms

Fully equipped vacation home with barbecue & terrace

Chesapeake Ranch Estates-Drum Point, Solomons Island, Maryland, United States
This waterfront house in Chesapeake Ranch Estates-Drum Point features a fireplace, kitchen, and parking, accommodating up to 8 guests.
from $281
per night
Outstanding(109 ratings)
from $281
per night
View deal
House Cape Charles
House ∙ 14 guests ∙ 6 bedrooms

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

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 $913
per night
Outstanding(33 ratings)
from $913
per night
View deal
House Virginia Beach
House ∙ 12 guests ∙ 4 bedrooms

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

Virginia Beach, Virginia, United States
This Virginia Beach house rental features a private pool, sauna, hot tub, and ample space for 12, perfect for family getaways.
from $262
per night
Outstanding(225 ratings)
from $262
per night
View deal
House Windsor Woods
House ∙ 12 guests ∙ 4 bedrooms

Child-friendly house with jacuzzi, private pool & BBQ | Good for workation | Pets are welcome

Windsor Woods, Virginia Beach, Virginia, United States
This house in Windsor Woods offers a private pool, hot tub, and space for 12, perfect for family getaways with pets.
from $184
per night
from $184
per night
View deal
House Buckroe Beach
House ∙ 8 guests ∙ 3 bedrooms

House with pool, terrace & grill

Buckroe Beach, Hampton, Virginia, United States
This waterfront house at Buckroe Beach features a pool, fireplace, kitchen, and a yard, perfect for family fun and relaxation.
from $447
per night
Outstanding(44 ratings)
from $447
per night
View deal
House Reedville
House ∙ 9 guests ∙ 4 bedrooms

Child-friendly nice vacation home with patio & BBQ | Perfect for remote work

Reedville, Northumberland County, Virginia, United States
This waterfront house in Reedville offers a fireplace, kitchen, balcony, and parking, perfect for a family getaway for nine.
from $417
per night
Outstanding(23 ratings)
from $417
per night
View deal
House Scotland
House ∙ 14 guests ∙ 7 bedrooms

House with terrace, barbecue & garden | Nature view | Good for workation

Scotland, St. Inigoes, Maryland, United States
This house rental in Scotland features a kitchen, yard, balcony, and parking, perfect for family gatherings of up to 14.
from $773
per night
Outstanding(25 ratings)
from $773
per night
View deal
House Bay View
House ∙ 9 guests ∙ 4 bedrooms

Family-friendly pleasant vacation home with terrace, barbecue & yard | Pets allowed

Bay View, Norfolk, Virginia, United States
from $220
per night
Very good(32 ratings)
from $220
per night
View deal
House Chesapeake Ranch Estates-Drum Point
House ∙ 8 guests ∙ 4 bedrooms

Children-friendly house with patio | Good for workation

Chesapeake Ranch Estates-Drum Point, Solomons Island, Maryland, United States
This waterfront house rental in Chesapeake Ranch Estates-Drum Point offers a fireplace, kitchen, and parking for a family of 8.
from $426
per night
Outstanding(32 ratings)
from $426
per night
View deal

Vacation homes and rentals with a yard

House Heathsville
from $209
per night
House ∙ 10 guests ∙ 5 bedrooms

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

4.8
Outstanding(68 ratings)
Heathsville, Northumberland County, Virginia, United States
Yard
View deal
House Kilmarnock
from $397
per night
House ∙ 13 guests ∙ 6 bedrooms

Family-friendly vacation home with patio, barbeque & yard

4.8
Outstanding(26 ratings)
Kilmarnock, Lancaster County, Virginia, United States
Yard
View deal
House Dam Neck
from $607
per night
House ∙ 13 guests ∙ 5 bedrooms

Family-friendly pleasant vacation home with terrace, yard & barbeque | Close to the beach | Perfect for remote work | Dogs allowed

4.0
Very good(146 ratings)
Dam Neck, Virginia Beach, Virginia, United States
Yard
View deal
See all offers

Vacation houses with Balconies or Patios

House Virginia Beach
from $179
per night
House ∙ 8 guests ∙ 4 bedrooms

Vacation home with patio | Good for workation

4.3
Very good(31 ratings)
Virginia Beach, Virginia, United States
Balcony/Patio
View deal
House Ocean View
from $186
per night
House ∙ 6 guests ∙ 3 bedrooms

House with terrace & garden | Suitable for remote work

4.9
Outstanding(22 ratings)
Ocean View, Norfolk, Virginia, United States
Balcony/Patio
View deal
House East Ocean View
from $246
per night
House ∙ 8 guests ∙ 4 bedrooms

Fully equipped house with terrace | Dogs allowed

5.0
Outstanding(6 ratings)
East Ocean View, Norfolk, Virginia, United States
Balcony/Patio
View deal
See all offers

Vacation rentals and apartments with air conditioning

House Stevensville
from $573
per night
House ∙ 10 guests ∙ 4 bedrooms

House with yard, grill & terrace

5.0
Outstanding(5 ratings)
Stevensville, Kent Island, Maryland, United States
Air conditioning
View deal
House Cape Charles
from $362
per night
House ∙ 8 guests ∙ 4 bedrooms

House with terrace, pool & garden

5.0
Outstanding(14 ratings)
Cape Charles, Northampton County, Virginia, United States
Air conditioning
View deal
House Northeast Virginia Beach
from $462
per night
House ∙ 8 guests ∙ 4 bedrooms

Vacation home with barbecue

5.0
Outstanding(4 ratings)
Northeast Virginia Beach, Virginia Beach, Virginia, United States
Air conditioning
View deal
See all offers

Budget-friendly rental options

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

House Cambridge
from $557
per night
House ∙ 12 guests ∙ 5 bedrooms

Fully equipped ample house with barbecue, pool & patio | Dogs allowed

4.6
Excellent(25 ratings)
Cambridge, Dorchester County, Maryland, United States
View deal
House Talbot County
from $793
per night
House ∙ 8 guests ∙ 4 bedrooms

Fully equipped charming house with private pool, grill & garden | Pet-friendly

5.0
Outstanding(52 ratings)
Talbot County, Maryland, United States
View deal
House Ocean View
from $205
per night
House ∙ 8 guests ∙ 4 bedrooms

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

5.0
Outstanding(58 ratings)
Ocean View, Norfolk, 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 Willoughby Spit
from $279
per night
House ∙ 10 guests ∙ 5 bedrooms

Child-friendly pleasant house with garden & terrace | Perfect for remote work | Pet-friendly

4.7
Excellent(32 ratings)
Willoughby Spit, Norfolk, Virginia, United States
View deal
House Cape Charles
from $450
per night
House ∙ 13 guests ∙ 4 bedrooms

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

5.0
Outstanding(28 ratings)
Cape Charles, Northampton County, Virginia, United States
View deal
House Northeast Virginia Beach
from $539
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
View deal

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

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Popular Features & Amenities in Chesapeake Bay

  • Pet-friendly (3,309)
  • Pool (4,303)
  • Air conditioning (9,753)
  • WiFi (9,679)
  • Fishing (2,519)
  • TV (9,015)
  • Balcony/patio (3,480)
  • Grill (3,171)
  • Kitchen (6,131)
  • Parking (816)
  • No smoking (9,214)
  • Hot tub (599)

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 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 (7/4 – 7/11) that you will find the highest prices for the next 12 months. The most affordable accommodation prices can be found in September (9/19 – 9/26).

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 (4/24 – 5/1). Only 9% of the rentals are still available. People tend to travel less to Chesapeake Bay during a week in May (5/30 – 6/6) when only 23% 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 10,141 rentals
🌙 Nightly prices starting at $87
⭐ Popular amenities Pets allowed, Pool and Air conditioning
🐾 Pet friendly homes 3,351 homes
🏊 Vacation rentals with pools 4,387 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 $87. Average prices for house rentals are $710 per night. Apartment rentals in Chesapeake Bay cost on average $388 per night.

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

Currently there are 10,141 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 4,387 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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