Airbnbs in Chesapeake Bay

Chesapeake Bay

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$100 - $199

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Popular amenities for Airbnbs in Chesapeake Bay

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Airbnbs with pools

Airbnbs with air conditioning

Airbnbs with internet

Top-rated airbnbs in Chesapeake Bay

Browse our top rated airbnbs offers

Dec 23 - Dec 30

$137 per night

Airbnb ∙ 8 guests ∙ 3 bedrooms

Pleasant Vacation Home in Deal Island with Grill & Jacuzzi + Water Views

4.7

Excellent (36 ratings)

Deal Island, Somerset County, Maryland, United States

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Jun 7 - Jun 14

$903 per night

Airbnb ∙ 12 guests ∙ 6 bedrooms

Vacation Home in Madison with Yard, Pool & Grill + Water Views

5.0

Outstanding (30 ratings)

Madison, Dorchester County, Maryland, United States

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Nov 11 - Nov 18

-28%

$201

$146 per night

Airbnb ∙ 8 guests ∙ 2 bedrooms

Vacation Home in Cape Charles with Grill

4.8

Outstanding (25 ratings)

Cape Charles, Northampton County, Virginia, United States

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Best Deals and Discounts on Airbnbs

Save up to 62%

Mar 16 - Mar 23

-26%

$150

$111 per night

Airbnb ∙ 3 guests ∙ 1 bedroom

Rental Apartment in Earleville with Free Parking

4.9

Outstanding (9 ratings)

Earleville, Cecilton, Maryland, United States

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Oct 29 - Nov 5

-39%

$679

$413 per night

Airbnb ∙ 8 guests ∙ 4 bedrooms

House in Elkton with Seasonal Pool + Water Views

4.8

Outstanding (80 ratings)

Elkton, Cecil County, Maryland, United States

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Dec 2 - Dec 9

-62%

$339

$130 per night

Airbnb ∙ 6 guests ∙ 3 bedrooms

Vacation Home in Reedville with Grill

5.0

Outstanding (8 ratings)

Reedville, Northumberland County, Virginia, United States

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Airbnbs in Chesapeake Bay: Top Accommodations

Jul 13 - Jul 20

$169 per night

Airbnb ∙ 5 guests ∙ 3 bedrooms

House in Ewell

Ewell, Smith Island, Maryland, United States

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Sep 26 - Oct 3

$105 per night

Airbnb ∙ 2 guests ∙ 1 bedroom

Vacation Home in Hollywood with Grill & Yard

4.6

Excellent (38 ratings)

Hollywood, Patuxent, Maryland, United States

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Dec 2 - Dec 9

-62%

$339

$130 per night

Airbnb ∙ 6 guests ∙ 3 bedrooms

Vacation Home in Reedville with Grill

5.0

Outstanding (8 ratings)

Reedville, Northumberland County, Virginia, United States

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Oct 28 - Nov 4

-35%

$650

$425 per night

Airbnb ∙ 15 guests ∙ 5 bedrooms

Family Friendly House in Lake Shore with Grill & Yard + Unique View

4.9

Outstanding (58 ratings)

Lake Shore, Anne Arundel County, Maryland, United States

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Nov 10 - Nov 17

-37%

$713

$450 per night

Airbnb ∙ 15 guests ∙ 6 bedrooms

House in Cape Charles with Pool & Grill

4.9

Outstanding (51 ratings)

Cape Charles, Northampton County, Virginia, United States

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Jan 6 - Jan 13

-44%

$1,202

$669 per night

Airbnb ∙ 14 guests ∙ 5 bedrooms

Charming Vacation Home in Tracys Landing with Private Pool

5.0

Outstanding (6 ratings)

Tracys Landing, Anne Arundel County, Maryland, United States

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Sep 14 - Sep 21

$157 per night

Airbnb ∙ 4 guests ∙ 2 bedrooms

Apartment in Bay View

4.1

Very good (27 ratings)

Bay View, Norfolk, Virginia, United States

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Mar 9 - Mar 16

$125 per night

Airbnb ∙ 6 guests ∙ 2 bedrooms

House in Havre De Grace

4.8

Outstanding (17 ratings)

Havre de Grace, Harford County, Maryland, United States

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Dec 9 - Dec 16

$162 per night

Airbnb ∙ 5 guests ∙ 3 bedrooms

Rustic Vacation Home in Buckroe Beach with Yard & Grill

4.9

Outstanding (71 ratings)

Buckroe Beach, Hampton, Virginia, United States

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Budget-friendly airbnbs in Chesapeake Bay

Our top value vacation rentals for airbnbs

Dec 2 - Dec 9

-20%

$246

$196 per night

Airbnb ∙ 9 guests ∙ 3 bedrooms

Vacation Home in Olde Hampton

4.7

Excellent (6 ratings)

Olde Hampton, Hampton, Virginia, United States

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Jan 6 - Jan 13

-60%

$374

$150 per night

Airbnb ∙ 4 guests ∙ 2 bedrooms

Pleasant Boat in Kent Narrows with Patio + Magnificent View

5.0

Outstanding (112 ratings)

Kent Narrows, Kent Island, Maryland, United States

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Sep 23 - Sep 30

$400 per night

Airbnb ∙ 13 guests ∙ 5 bedrooms

Beautiful House in Arundel On The Bay with Grill & Yard + Water Views

4.4

Very good (29 ratings)

Arundel on the Bay, Anne Arundel County, Maryland, United States

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Airbnbs with Kitchens

Dec 17 - Dec 24

-69%

$431

$132 per night

Airbnb ∙ 4 guests ∙ 1 bedroom

Vacation Home in Cape Charles with Yard & Grill

5.0

Outstanding (19 ratings)

Cape Charles, Northampton County, Virginia, United States

Kitchen

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Dec 2 - Dec 9

$166 per night

Airbnb ∙ 8 guests ∙ 4 bedrooms

Nice Vacation Home in Reedville with Grill & Yard

4.7

Excellent (63 ratings)

Reedville, Northumberland County, Virginia, United States

Kitchen

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Nov 3 - Nov 10

-68%

$673

$216 per night

Airbnb ∙ 8 guests ∙ 4 bedrooms

House in East Ocean View with Private Patio + Ocean View

5.0

Outstanding (6 ratings)

East Ocean View, Norfolk, Virginia, United States

Kitchen

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Stay Cool: Airbnbs with Air Conditioning

Nov 25 - Dec 2

$295 per night

Airbnb ∙ 12 guests ∙ 6 bedrooms

House in Deltaville with Yard, Pool & Grill

5.0

Outstanding (14 ratings)

Deltaville, Pine Top, Virginia, United States

Air conditioning

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Dec 23 - Dec 30

-36%

$350

$224 per night

Airbnb ∙ 8 guests ∙ 3 bedrooms

Vacation Home in Cape Charles with Large Patio

4.6

Excellent (42 ratings)

Cape Charles, Northampton County, Virginia, United States

Air conditioning

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Sep 24 - Oct 1

$266 per night

Airbnb ∙ 6 guests ∙ 3 bedrooms

House in Grimstead with Grill & Yard

5.0

Outstanding (7 ratings)

Grimstead, Gwynn, Virginia, United States

Air conditioning

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Soak Up the Sun: Airbnbs with Patios

Sep 28 - Oct 5

$126 per night

Airbnb ∙ 2 guests ∙ 1 bedroom

Vacation Home in Chesapeake City with Yard & Grill + Water Views

5.0

Outstanding (24 ratings)

Chesapeake City, Cecil County, Maryland, United States

Balcony/Patio

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Dec 9 - Dec 16

-24%

$225

$172 per night

Airbnb ∙ 8 guests ∙ 3 bedrooms

Cottage in Elkton with Grill & Yard + Water Views

5.0

Outstanding (53 ratings)

Elkton, Cecil County, Maryland, United States

Balcony/Patio

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Oct 21 - Oct 28

$225 per night

Airbnb ∙ 5 guests ∙ 2 bedrooms

Vacation Home in Rock Hall with Grill & Yard

5.0

Outstanding (64 ratings)

Rock Hall, Edesville, Maryland, United States

Balcony/Patio

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Airbnbs with Hot Tubs

Rentals Featuring Jacuzzis and Whirlpools

Sep 23 - Sep 30

-56%

$370

$163 per night

Airbnb ∙ 6 guests ∙ 2 bedrooms

House in Willow Oaks with Private Balcony

Willow Oaks, Hampton, Virginia, United States

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May 4 - May 11

-59%

$529

$215 per night

Airbnb ∙ 8 guests ∙ 2 bedrooms

Vacation Home in Mayo with Pool, Hot Tub & Grill + Panoramic View

4.6

Excellent (44 ratings)

Mayo, Anne Arundel County, Maryland, United States

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Jan 6 - Jan 13

-65%

$2,214

$783 per night

Airbnb ∙ 14 guests ∙ 5 bedrooms

House in Tracys Landing with Electric Fireplace

Tracys Landing, Anne Arundel County, Maryland, United States

Free cancellation

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Airbnbs in Chesapeake Bay for Any Type of Traveler

Traveling with a group of eight or more people in Chesapeake Bay?

HomeToGo offers numerous Airbnbs in Chesapeake Bay with eight or more bedrooms and eight or more bathrooms. Find amazing Airbnbs for big groups in Chesapeake Bay, complete with private pool, big kitchen, and plenty of space to enjoy. November is the most affortable time to stay in Chesapeake Bay with a large group, when nightly prices for Airbnbs will range from $362 to $516 per night. Start searching our top Airbnbs for large groups and plan the perfect trip!

Planning a big family getaway in Chesapeake Bay?

Browse HomeToGo's offers of large Airbnbs in Chesapeake Bay, perfect for a big family with six or more beds and lots of washrooms. Chesapeake Bay has lots of fun family-friendly activities to try, including hiking, swimming, biking, and many other activities. You will find lots of Airbnbs in Chesapeake Bay have family-friendly features, including hot tubs, private pool, TV, games, and many others. Most Airbnbs in Chesapeake Bay will cost around $256 per night for a family of 4 people but there are lots of affordable options in Chesapeake Bay to choose from. Start browsing for family-friendly Airbnbs now!

Booking a remote vacation in Chesapeake Bay with your partner?

Find cozy Airbnbs in Chesapeake Bay for a romantic getaway, complete with hot tub, spa, and a picturesque view of Chesapeake Bay's surrounding scenery. There are lots of fun activities to try with your partner during your couples trip, including swimming, hiking, biking, and many other outdoor activities. The most affordable time to book is November with prices starting at $83 per night. Search HomeToGo's best Airbnbs for romantic retreats in Chesapeake Bay today!

Information about Airbnbs in Chesapeake Bay

💳 Highest rates	in June
😎 Least busy month	September
🛏️ Popular home types	House rental and Apartment rental
🌡️ Hottest months	88 °F in July and June
❄️ Coldest months	January and February
🌧️ Rainiest months	January and February

Frequently Asked Questions

What types of vacation homes are available for Airbnbs in Chesapeake Bay?

You can choose from 2,224 House rental and 488 Apartment rental for Airbnbs in Chesapeake Bay right here on HomeToGo.

Airbnbs in Chesapeake Bay: What is the vacation rental cost in Chesapeake Bay?

The average rate for a vacation rental in Chesapeake Bay is between $362 and $516 per night.

Can I find a vacation rental for a group of guests for Airbnbs in Chesapeake Bay?

The average size for a House rental is 224 m² and can fit 8 guests on average which is great for large groups.

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