Airbnbs in Chesapeake Bay - HomeToGo base64Hash Airbnbs in Chesapeake Bay - HomeToGo

Airbnbs in Chesapeake Bay

Chesapeake Bay
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Guests
Chesapeake Bay
Anytime
Guests

Choose from a fantastic selection of airbnbs

Price per night
Up to $100
$100 - $199
From $200
Rating
4.5+
4+
Bedrooms
Any
1 bedroom
2+ bedrooms
Show all 9,654 properties

Popular amenities for Airbnbs in Chesapeake Bay

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Pet-Friendly Airbnbs

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Airbnbs with pools

Airbnbs with pools

Airbnbs with air conditioning

Airbnbs with air conditioning

Airbnbs with internet

Airbnbs with internet

Top-rated airbnbs in Chesapeake Bay

Browse our top rated airbnbs offers

Cottage Deal Island
Oct 19 - Oct 26
-18%
$190
$155 per night
Airbnb ∙ 4 guests ∙ 1 bedroom

Cottage in Deal Island with Patio & Grill

5.0
Outstanding (65 ratings)
Deal Island, Somerset County, Maryland, United States
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House Deal Island
May 4 - May 11
$145 per night
Airbnb ∙ 8 guests ∙ 3 bedrooms

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

4.7
Excellent (41 ratings)
Deal Island, Somerset County, Maryland, United States
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House Chesapeake Beach
Mar 1 - Mar 8
-64%
$426
$155 per night
Airbnb ∙ 8 guests ∙ 4 bedrooms

House in Chesapeake Beach with Yard, Patio & Grill

5.0
Outstanding (1 rating)
Chesapeake Beach, Sunderland, Maryland, United States
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Best Deals and Discounts on Airbnbs

Save up to 67%

House Algonquin
May 4 - May 11
-27%
$750
$550 per night
Airbnb ∙ 13 guests ∙ 5 bedrooms

Vacation Home in Algonquin with Grill, Yard & Pool

4.9
Outstanding (14 ratings)
Algonquin, Cambridge, Maryland, United States
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Farmhouse Crisfield
Feb 27 - Mar 5
-49%
$540
$275 per night
Airbnb ∙ 12 guests ∙ 5 bedrooms

Farm in Crisfield with Yard, Patio & Grill + Panoramic Views

4.8
Outstanding (126 ratings)
Crisfield, Somerset County, Maryland, United States
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House Rock Hall
Nov 2 - Nov 9
-67%
$1,199
$399 per night
Airbnb ∙ 16 guests ∙ 6 bedrooms

House in Rock Hall with Grill, Patio & Yard

5.0
Outstanding (61 ratings)
Rock Hall, Edesville, Maryland, United States
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Airbnbs in Chesapeake Bay: Top Accommodations

House Northeast Virginia Beach
Nov 2 - Nov 9
$450 per night
Airbnb ∙ 9 guests ∙ 4 bedrooms

Beautiful Vacation Home in Northeast Virginia Beach with Patio, Grill & Yard

5.0
Outstanding (10 ratings)
Northeast Virginia Beach, Virginia Beach, Virginia, United States
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House Deale
Apr 6 - Apr 13
$450 per night
Airbnb ∙ 10 guests ∙ 3 bedrooms

Vacation Home in Deale with Salt-Water Pool + Water Views

4.9
Outstanding (11 ratings)
Deale, Anne Arundel County, Maryland, United States
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House East Ocean View
Mar 2 - Mar 9
-73%
$351
$95 per night
Airbnb ∙ 4 guests ∙ 2 bedrooms

House in East Ocean View with Patio & Grill + Lake Views

4.3
Very good (19 ratings)
East Ocean View, Norfolk, Virginia, United States
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House Buckroe Beach
May 18 - May 25
$128 per night
Airbnb ∙ 5 guests ∙ 3 bedrooms

Vacation Home in Buckroe Beach with Yard, Patio & Grill

5.0
Outstanding (40 ratings)
Buckroe Beach, Hampton, Virginia, United States
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House Gwynn
Feb 8 - Feb 15
$261 per night
Airbnb ∙ 8 guests ∙ 3 bedrooms

House in Gwynn with Yard, Grill & Patio + Beautiful Views

5.0
Outstanding (42 ratings)
Gwynn, Piankatank, Virginia, United States
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House Cape Charles
Dec 7 - Dec 14
$428 per night
Airbnb ∙ 15 guests ∙ 6 bedrooms

House in Cape Charles with Pool & Grill

4.9
Outstanding (57 ratings)
Cape Charles, Northampton County, Virginia, United States
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House North
May 11 - May 18
$525 per night
Airbnb ∙ 10 guests ∙ 6 bedrooms

Lovely House in North with Grill + Marsh Views

5.0
Outstanding (17 ratings)
North, Petsworth, Virginia, United States
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House Taylors Island
Mar 2 - Mar 9
$543 per night
Airbnb ∙ 14 guests ∙ 5 bedrooms

Vacation Home in Taylors Island with Yard & Grill + Story View

5.0
Outstanding (32 ratings)
Taylors Island, Dorchester County, Maryland, United States
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Cabin Lusby
Apr 14 - Apr 21
-37%
$551
$345 per night
Airbnb ∙ 11 guests ∙ 4 bedrooms

Cabin in Lusby with Seasonal Pool + Serene View

5.0
Outstanding (4 ratings)
Lusby, Solomons Island, Maryland, United States
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Budget-friendly airbnbs in Chesapeake Bay

Our top value vacation rentals for airbnbs

House Calvert Beach-Long Beach
Jul 20 - Jul 27
$225 per night
Airbnb ∙ 8 guests ∙ 4 bedrooms

House in Calvert Beach-Long Beach with Patio & Grill + Water Views

5.0
Outstanding (42 ratings)
Calvert Beach-Long Beach, Solomons Island, Maryland, United States
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House Buckroe Beach
May 18 - May 25
$128 per night
Airbnb ∙ 5 guests ∙ 3 bedrooms

Vacation Home in Buckroe Beach with Yard, Patio & Grill

5.0
Outstanding (40 ratings)
Buckroe Beach, Hampton, Virginia, United States
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House Gwynn
Feb 8 - Feb 15
$261 per night
Airbnb ∙ 8 guests ∙ 3 bedrooms

House in Gwynn with Yard, Grill & Patio + Beautiful Views

5.0
Outstanding (42 ratings)
Gwynn, Piankatank, Virginia, United States
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Stay Cool: Airbnbs with Air Conditioning

Cabin  Lusby
Apr 14 - Apr 21
-37%
$551
$345 per night
Airbnb ∙ 11 guests ∙ 4 bedrooms

Cabin in Lusby with Seasonal Pool + Serene View

5.0
Outstanding (4 ratings)
Lusby, Solomons Island, Maryland, United States
Air conditioning
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House  Cambridge
Sep 28 - Oct 5
$865 per night
Airbnb ∙ 22 guests ∙ 8 bedrooms

Beautiful Vacation Home in Cambridge with Yard, Pool & Patio

4.8
Outstanding (91 ratings)
Cambridge, Dorchester County, Maryland, United States
Air conditioning
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House  Tipers
Jul 20 - Jul 27
$250 per night
Airbnb ∙ 8 guests ∙ 3 bedrooms

Nice House in Tipers with Grill, Patio & Yard + Water Views

4.8
Outstanding (72 ratings)
Tipers, Northumberland County, Virginia, United States
Air conditioning
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Stay connected: Airbnbs with internet

Cottage  Grimstead
Apr 8 - Apr 15
$183 per night
Airbnb ∙ 4 guests ∙ 2 bedrooms

Cottage in Grimstead with Grill, Yard & Patio + Expansive Views

5.0
Outstanding (217 ratings)
Grimstead, Gwynn, Virginia, United States
Internet
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Apartment  Northeast Virginia Beach
Apr 13 - Apr 20
-68%
$650
$210 per night
Airbnb ∙ 11 guests ∙ 4 bedrooms

Pleasant Rental Apartment in Northeast Virginia Beach with Outdoor Pool + Ocean Views

Northeast Virginia Beach, Virginia Beach, Virginia, United States
Internet
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House  Reedville
Oct 19 - Oct 26
$390 per night
Airbnb ∙ 6 guests ∙ 2 bedrooms

House in Reedville with Yard, Grill & Pool

4.8
Outstanding (109 ratings)
Reedville, Northumberland County, Virginia, United States
Internet
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Airbnbs with kitchens

House  Buckroe Beach
Nov 2 - Nov 9
$314 per night
Airbnb ∙ 10 guests ∙ 4 bedrooms

Vacation Home in Buckroe Beach with Patio

4.9
Outstanding (22 ratings)
Buckroe Beach, Hampton, Virginia, United States
Kitchen
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House  Buckroe Beach
Mar 9 - Mar 16
-64%
$305
$111 per night
Airbnb ∙ 8 guests ∙ 3 bedrooms

House in Buckroe Beach with Yard + Beautiful Views

5.0
Outstanding (1 rating)
Buckroe Beach, Hampton, Virginia, United States
Kitchen
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Cottage  Parole
Mar 19 - Mar 26
$150 per night
Airbnb ∙ 4 guests ∙ 1 bedroom

Cottage in Parole with Patio & Yard + Peaceful View

5.0
Outstanding (262 ratings)
Parole, Anne Arundel County, Maryland, United States
Kitchen
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Airbnbs with Hot Tubs

Rentals Featuring Jacuzzis and Whirlpools

Cottage Northeast Virginia Beach
Jul 27 - Aug 3
$400 per night
Airbnb ∙ 8 guests ∙ 3 bedrooms

Cottage in Northeast Virginia Beach with Vegetable Garden

4.6
Excellent (52 ratings)
Northeast Virginia Beach, Virginia Beach, Virginia, United States
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House Chesapeake City
Jul 27 - Aug 3
$306 per night
Airbnb ∙ 8 guests ∙ 3 bedrooms

House in Chesapeake City with Large Whirlpool + Water Views

5.0
Outstanding (45 ratings)
Chesapeake City, Cecil County, Maryland, United States
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House Virginia Beach
Dec 7 - Dec 14
$658 per night
Airbnb ∙ 32 guests ∙ 8 bedrooms

House in Virginia Beach with Large Whirlpool

4.3
Very good (77 ratings)
Virginia Beach, Virginia, United States
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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. January is the most affortable time to stay in Chesapeake Bay with a large group, when nightly prices for Airbnbs will range from $310 to $526 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 $273 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 January with prices starting at $86 per night. Search HomeToGo's best Airbnbs for romantic retreats in Chesapeake Bay today!
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Information about Airbnbs in Chesapeake Bay

💳 Highest rates in August
🥳 Busiest month January
🛏️ Popular home types Apartment rental and House rental
🌡️ Hottest months July and June
❄️ Coldest months 28 °F in January and February
🌧️ Rainiest months January and February

Frequently Asked Questions

What types of vacation homes can i book for Airbnbs in Chesapeake Bay?

We would advice browsing our incredible selection of Apartment rental and House rental for Airbnbs in Chesapeake Bay.

Airbnbs in Chesapeake Bay: How much does a stay cost?

The average cost for a vacation rental in Chesapeake Bay is usually between $310 and $526 per night.

Can I find a vacation home for a group for Airbnbs in Chesapeake Bay?

Usually the size of a House rental is 220 m² and may fit 8 guests on average which is great for large groups.

Searching for something else?

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