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

Chesapeake Bay Vacation Rentals

Find 12,447 available house rentals from 29 partners
Anytime
1 guest
Anytime
1 guest

Top 15 Recommended vacation rentals in Chesapeake Bay

Find your perfect vacation rental in Chesapeake Bay from just $89 per night!

House Cape Charles
May 31 - Jun 7
House ∙ 8 guests ∙ 4 bedrooms

Vacation Home with Yard, Terrace & Barbeque | City View

Cape Charles, Northampton County, Virginia, United States
$380
per night
Outstanding(81 ratings)
$380
per night
View deal
House Stevensville
-17%
Jul 19 - Jul 26
House ∙ 10 guests ∙ 6 bedrooms

Child-Friendly Wonderful House with Private Pool, Barbeque & Patio | Good for Workation | Pet-Friendly

Stevensville, Kent Island, Maryland, United States
$1,526$880
per night
Outstanding(2 ratings)
$1,526$880
per night
View deal
House Betterton
May 10 - May 17
House ∙ 11 guests ∙ 6 bedrooms

House with Yard, Barbeque & Terrace

Betterton, Worton (Betterton), Maryland, United States
$353
per night
Outstanding(127 ratings)
$353
per night
View deal
House Chic's Beach
Mar 22 - Mar 29
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
$278
per night
Outstanding(45 ratings)
$278
per night
View deal
House Cape Charles
-20%
Apr 5 - Apr 12
House ∙ 8 guests ∙ 4 bedrooms

House with Barbeque, Garden & Patio | City View

Cape Charles, Northampton County, Virginia, United States
$625$500
per night
Outstanding(13 ratings)
$625$500
per night
View deal
House Northeast Virginia Beach
Apr 12 - Apr 19
House ∙ 9 guests ∙ 4 bedrooms

Fully Equipped Wonderful Vacation Home with Grill, Yard & Terrace | Beach Nearby

Northeast Virginia Beach, Virginia Beach, Virginia, United States
$498
per night
Excellent(35 ratings)
$498
per night
View deal
House Cape Charles
-33%
Apr 5 - Apr 12
House ∙ 9 guests ∙ 4 bedrooms

House with Grill, Yard & Terrace

Cape Charles, Northampton County, Virginia, United States
$649$444
per night
Outstanding(44 ratings)
$649$444
per night
View deal
House West Ocean View
-43%
Oct 4 - Oct 11
House ∙ 4 guests ∙ 3 bedrooms

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

West Ocean View, Norfolk, Virginia, United States
$289$202
per night
Outstanding(18 ratings)
$289$202
per night
View deal
House Northside
Mar 1 - Mar 8
House ∙ 2 guests ∙ 2 bedrooms

Family-Friendly House with Patio & BBQ | Dogs Allowed

Northside, Norfolk, Virginia, United States
$151
per night
Outstanding(39 ratings)
$151
per night
View deal
House Cape Charles
Apr 5 - Apr 12
House ∙ 12 guests ∙ 6 bedrooms

Vacation Home with Yard, Patio & Private Pool | Lake View

Cape Charles, Northampton County, Virginia, United States
$788
per night
Outstanding(46 ratings)
$788
per night
View deal
House Cape Charles
Jul 5 - Jul 12
House ∙ 12 guests ∙ 6 bedrooms

Fully Equipped Vacation Home with Barbeque, Garden & Terrace | Nature View | Pets Are Welcome

Cape Charles, Northampton County, Virginia, United States
$397
per night
Outstanding(97 ratings)
$397
per night
View deal
House Dam Neck
-53%
Sep 20 - Sep 27
House ∙ 10 guests ∙ 5 bedrooms

Family-Friendly House with Barbeque & Terrace | Beach Nearby

Dam Neck, Virginia Beach, Virginia, United States
$955$529
per night
Very good(24 ratings)
$955$529
per night
View deal
House Northampton County
Aug 16 - Aug 23
House ∙ 6 guests ∙ 3 bedrooms

Child-Friendly House with Pool, Terrace & Yard | Nature View | Pets Allowed

Northampton County, Virginia, United States
$204
per night
Outstanding(31 ratings)
$204
per night
View deal
House Northeast Virginia Beach
Dec 21 - Dec 28
House ∙ 9 guests ∙ 4 bedrooms

Vacation Home with Barbeque, Patio & Garden | City View

Northeast Virginia Beach, Virginia Beach, Virginia, United States
$585
per night
Outstanding(54 ratings)
$585
per night
View deal
House Cambridge
-39%
Feb 22 - Mar 1
House ∙ 27 guests ∙ 7 bedrooms

Family-Oriented Lovely Vacation Home with Grill, Private Pool & Jacuzzi | Lake View

Cambridge, Dorchester County, Maryland, United States
$1,574$986
per night
Outstanding(5 ratings)
$1,574$986
per night
View deal

Vacation homes and rentals with a yard

House  Wenona
Jun 21 - Jun 28
$234
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  Northeast Virginia Beach
Oct 4 - Oct 11
-39%
$849
$543
per night
House ∙ 8 guests ∙ 4 bedrooms

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

4.7
Excellent(40 ratings)
Northeast Virginia Beach, Virginia Beach, Virginia, United States
Yard
View deal
Condo  Northeast Virginia Beach
Jul 26 - Aug 2
$738
per night
Condo ∙ 15 guests ∙ 7 bedrooms

Condo with Yard, Grill & Terrace

5.0
Outstanding(47 ratings)
Northeast Virginia Beach, Virginia Beach, Virginia, United States
Yard
View deal
See all offers

Best Vacation Home Deals in Chesapeake Bay

Save up to 54%

House Cape Charles
Jan 11 - Jan 18
-24%
$850
$675
per night
House ∙ 12 guests ∙ 5 bedrooms

Family-Friendly Charming House with Garden, Patio & Barbecue | City View | Suitable for Remote Work

5.0
Outstanding(96 ratings)
Cape Charles, Northampton County, Virginia, United States
View deal
House Northeast Virginia Beach
Mar 1 - Mar 8
-54%
$1,069
$1,040
per night
House ∙ 13 guests ∙ 6 bedrooms

Vacation Home with Garden & BBQ | Perfect for Remote Work

5.0
Outstanding(15 ratings)
Northeast Virginia Beach, Virginia Beach, Virginia, United States
View deal
House Chesapeake Ranch Estates-Drum Point
Jan 25 - Feb 1
-51%
$433
$268
per night
House ∙ 11 guests ∙ 4 bedrooms

House with Barbecue & Garden | Water View

Chesapeake Ranch Estates-Drum Point, Solomons Island, Maryland, United States
View deal

Find the ideal vacation rental from $89 per night by searching and comparing the 12,447 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 Virginia Beach
Aug 9 - Aug 16
$174
per night
House ∙ 4 guests ∙ 3 bedrooms

House with 3 Rooms for 4 Persons

Virginia Beach, Virginia, United States
View deal
Cottage Lusby
Mar 29 - Apr 5
$91
per night
Cottage ∙ 3 guests ∙ 1 bedroom

Cottage with Patio, BBQ & Garden | Nature View | Good for Workation

5.0
Outstanding(26 ratings)
Lusby, Solomons Island, Maryland, United States
View deal
Condo Northeast Virginia Beach
May 17 - May 24
$738
per night
Condo ∙ 15 guests ∙ 7 bedrooms

Condo with Yard, Grill & Terrace

5.0
Outstanding(47 ratings)
Northeast Virginia Beach, Virginia Beach, Virginia, 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
Mar 1 - Mar 8
$394
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 Chesapeake
Feb 7 - Feb 14
-74%
$661
$488
per night
House ∙ 11 guests ∙ 6 bedrooms

Fully Equipped House with Terrace & BBQ | Pet-Friendly

5.0
Outstanding(15 ratings)
Chesapeake, Virginia, United States
View deal
Condo Northeast Virginia Beach
Mar 1 - Mar 8
-71%
$732
$274
per night
Condo ∙ 8 guests ∙ 3 bedrooms

Condo | Beach Nearby

4.9
Outstanding(13 ratings)
Northeast Virginia Beach, Virginia Beach, Virginia, United States
View deal

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

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Find your dream stay

Find your dream stay

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

Popular Rental Amenities in Chesapeake Bay

  • Pet-friendly (3,930)
  • Pool (4,626)
  • Air conditioning (11,783)
  • WiFi (11,967)
  • Fishing (3,346)
  • TV (10,671)
  • Balcony/patio (3,532)
  • Grill (3,389)
  • Kitchen (8,178)
  • Parking (1,070)
  • No smoking (11,207)
  • Hot tub (833)

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 November (11/29 – 12/6) that you will find the highest prices for the next 12 months. The most affordable accommodation prices can be found in February (2/15 – 2/22).

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 (11/8 – 11/15). Only 6% of the rentals are still available. People tend to travel less to Chesapeake Bay during a week in June (6/7 – 6/14) 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 12,448 rentals
💳 Possible discounts up to 54%
🌙 Nightly prices starting at $89
⭐ Popular amenities Pets allowed, Pool and Air conditioning
🐾 Pet friendly homes 3,944 homes
🏊 Vacation rentals with pools 4,618 homes
2,419,645 reviews
Chesapeake Bay vacation rentals have an average rating of 4.2/5 on 2,419,645 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 $89. $613 is the average nightly price for house rentals in Chesapeake Bay. Apartment rentals in Chesapeake Bay cost $344 per night on average.

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

Currently there are 12,448 vacation rentals from 29 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 4,618 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 $89.

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