Holiday homes & rentals in Chesapeake Bay - HomeToGo base64Hash Holiday homes & rentals in Chesapeake Bay - HomeToGo

Holiday homes & rentals in Chesapeake Bay

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Top 15 Recommended holiday lettings in Chesapeake Bay

Find your perfect holiday home, apartment or cottage in Chesapeake Bay from just £62 per night!

House Willoughby Spit
House ∙ 10 guests ∙ 5 bedrooms

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

Willoughby Spit, Norfolk, Virginia, United States
This house rental in Willoughby Spit accommodates 10 guests, featuring a garden, kitchen, parking, and pet-friendly policies.
from £243
per night
Excellent(32 ratings)
from £243
per night
View deal
House Chesapeake Ranch Estates-Drum Point
House ∙ 8 guests ∙ 4 bedrooms

Family-friendly house with terrace | Pets are welcome

Chesapeake Ranch Estates-Drum Point, Solomons Island, Maryland, United States
This house rental in Chesapeake Ranch Estates-Drum Point accommodates 8, featuring a fireplace, kitchen, parking, and pet-friendly policies.
from £162
per night
Excellent(42 ratings)
from £162
per night
View deal
House Fishing Creek
House ∙ 24 guests ∙ 6 bedrooms

House with barbecue | Sea view

Fishing Creek, Hoopers Island, Maryland, United States
This house rental in Fishing Creek accommodates 16, featuring a kitchen, fireplace, ocean views, and family-friendly space.
from £346
per night
from £346
per night
View deal
House Northeast Virginia Beach
House ∙ 10 guests ∙ 3 bedrooms

Holiday home with BBQ

Northeast Virginia Beach, Virginia Beach, Virginia, United States
This house rental in Northeast Virginia Beach accommodates 10 guests and features convenient parking for a hassle-free stay.
from £184
per night
Outstanding(2 ratings)
from £184
per night
View deal
House Virginia Beach
House ∙ 6 guests ∙ 3 bedrooms

Holiday home with pool & barbecue

Virginia Beach, Virginia, United States
This house rental in Virginia Beach features a pool, parking, and pet-friendly options for up to six guests.
from £83
per night
from £83
per night
View deal
House Kilmarnock
House ∙ 13 guests ∙ 6 bedrooms

Family-friendly holiday home with barbeque, garden & terrace

Kilmarnock, Lancaster County, Virginia, United States
This Kilmarnock house rental features a garden, balcony, and waterside views, perfect for a family getaway with parking for 13.
from £298
per night
Outstanding(25 ratings)
from £298
per night
View deal
Cottage Northeast Virginia Beach
Cottage ∙ 8 guests ∙ 3 bedrooms

Cottage with garden, barbeque & terrace | Nature view

Northeast Virginia Beach, Virginia Beach, Virginia, United States
This family-friendly cottage in Northeast Virginia Beach offers a garden, kitchen, and parking, perfect for up to 8 guests.
from £148
per night
Excellent(75 ratings)
from £148
per night
View deal
House Chesapeake Ranch Estates-Drum Point
House ∙ 8 guests ∙ 3 bedrooms

Fully equipped holiday home with barbecue & terrace

Chesapeake Ranch Estates-Drum Point, Solomons Island, Maryland, United States
This waterside house rental in Chesapeake Ranch Estates-Drum Point features a fireplace, kitchen, and parking for eight guests.
from £212
per night
Outstanding(109 ratings)
from £212
per night
View deal
House Cape Charles
House ∙ 8 guests ∙ 4 bedrooms

House with terrace, pool & garden

Cape Charles, Northampton County, Virginia, United States
This house rental in Cape Charles features a pool, garden, and fireplace, perfect for family gatherings of up to 8 guests.
from £272
per night
Outstanding(14 ratings)
from £272
per night
View deal
House Northeast Virginia Beach
House ∙ 10 guests ∙ 4 bedrooms

Holiday home with barbecue, terrace & garden

Northeast Virginia Beach, Virginia Beach, Virginia, United States
This house rental in Northeast Virginia Beach accommodates 10 guests and features a kitchen, garden, and family-friendly amenities.
from £407
per night
Excellent(32 ratings)
from £407
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, garden, and parking, perfect for families seeking adventure.
from £173
per night
Outstanding(58 ratings)
from £173
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 accommodates 10, featuring a kitchen, fireplace, parking, and welcomes pets for family fun.
from £193
per night
Outstanding(58 ratings)
from £193
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 offers a kitchen, fireplace, and parking, perfect for a family getaway with pets.
from £129
per night
Outstanding(34 ratings)
from £129
per night
View deal
House Buckroe Beach
House ∙ 8 guests ∙ 3 bedrooms

House with BBQ, pool & terrace

Buckroe Beach, Hampton, Virginia, United States
This house rental at Buckroe Beach features a pool, fireplace, kitchen, and garden, accommodating up to 8 guests by the water.
from £336
per night
Outstanding(44 ratings)
from £336
per night
View deal
House Cape Charles
House ∙ 9 guests ∙ 3 bedrooms

Children-friendly holiday home with garden, pool & barbecue | Perfect for remote work | Pets are welcome

Cape Charles, Northampton County, Virginia, United States
This Cape Charles house rental features a pool, fireplace, and garden, perfect for families and pets, accommodating up to 9 guests.
from £169
per night
Very good(26 ratings)
from £169
per night
View deal

Holiday lettings and apartments with air conditioning

House  Scotland
from £518 per night
House ∙ 14 guests ∙ 7 bedrooms

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

5.0
Outstanding(23 ratings)
Scotland, St. Inigoes, Maryland, United States
Air conditioning
View deal
Cottage  Northeast Virginia Beach
from £123 per night
Cottage ∙ 4 guests ∙ 2 bedrooms

Nice cottage | Next to the beach | Pets are welcome

5.0
Outstanding(6 ratings)
Northeast Virginia Beach, Virginia Beach, Virginia, United States
Air conditioning
View deal
House  Bohannon
from £331 per night
House ∙ 12 guests ∙ 6 bedrooms

Child-friendly big house with barbeque, terrace & garden | Pet-friendly

5.0
Outstanding(217 ratings)
Bohannon, Westville, Virginia, United States
Air conditioning
View deal
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Best holiday homes with a patio or terrace

House  Cape Leonard
from £424 per night
House ∙ 15 guests ∙ 6 bedrooms

House with barbeque, terrace & garden

4.7
Excellent(48 ratings)
Cape Leonard, Calvert County, Maryland, United States
Balcony/Patio
View deal
House  Northeast Virginia Beach
from £284 per night
House ∙ 12 guests ∙ 4 bedrooms

Holiday home with terrace, barbecue & garden

5.0
Outstanding(214 ratings)
Northeast Virginia Beach, Virginia Beach, Virginia, United States
Balcony/Patio
View deal
House  Havre de Grace
from £74 per night
House ∙ 3 guests ∙ 2 bedrooms

House with garden & terrace | City view | Good for workation

4.8
Outstanding(85 ratings)
Havre de Grace, Harford County, Maryland, United States
Balcony/Patio
View deal
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Holiday homes and cottages with a garden

House  Dam Neck
from £468 per night
House ∙ 13 guests ∙ 5 bedrooms

Family-friendly pleasant holiday home with garden, terrace & barbeque | Nature view | Close to the beach | Perfect for remote work | Dogs allowed

4.0
Very good(147 ratings)
Dam Neck, Virginia Beach, Virginia, United States
Garden
View deal
Villa  Rock Hall
from £1,247 per night
Villa ∙ 28 guests ∙ 9 bedrooms

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

4.9
Outstanding(50 ratings)
Rock Hall, Edesville, Maryland, United States
Garden
View deal
House  Northeast Virginia Beach
from £406 per night
House ∙ 9 guests ∙ 4 bedrooms

Child-friendly holiday home with garden, barbeque & terrace | Close to the beach

4.9
Outstanding(23 ratings)
Northeast Virginia Beach, Virginia Beach, Virginia, United States
Garden
View deal
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Budget-friendly Holiday Homes in Chesapeake Bay

Find Fantastic yet Cheap Lettings

House Lusby
from £265 per night
House ∙ 8 guests ∙ 4 bedrooms

Holiday home with BBQ | Water view

5.0
Outstanding(3 ratings)
Lusby, Solomons Island, Maryland, United States
View deal
House Willoughby Spit
from £329 per night
House ∙ 8 guests ∙ 4 bedrooms

Child-friendly wonderful house with barbecue, garden & terrace | Pets allowed

5.0
Outstanding(12 ratings)
Willoughby Spit, Norfolk, Virginia, United States
View deal
Villa Earleville
from £973 per night
Villa ∙ 16 guests ∙ 7 bedrooms

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

4.8
Outstanding(41 ratings)
Earleville, Cecilton, Maryland, United States
View deal

Top-Rated Lettings and Properties in Chesapeake Bay

Book Holiday Letting Offers with the Highest User Rating

House Elkton
from £923 per night
House ∙ 16 guests ∙ 7 bedrooms

House with private pool, barbecue & terrace | Nature view

4.8
Outstanding(176 ratings)
Elkton, Cecil County, Maryland, United States
View deal
House Cape Charles
from £255 per night
House ∙ 9 guests ∙ 5 bedrooms

Family-oriented house with barbeque & terrace | Pets allowed

4.9
Outstanding(121 ratings)
Cape Charles, Northampton County, Virginia, United States
View deal
House Cape Saint Claire
from £695 per night
House ∙ 18 guests ∙ 6 bedrooms

Holiday home with pool, terrace & barbeque

5.0
Outstanding(80 ratings)
Cape Saint Claire, Anne Arundel County, Maryland, United States
View deal

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Find your dream stay

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

Popular holiday rental amenities in Chesapeake Bay

  • Pool (4,303)
  • WiFi (9,679)
  • Pet-friendly (3,309)
  • Air conditioning (9,753)
  • Parking (816)
  • Kitchen (6,131)
  • TV (9,015)
  • Washing machine (5,572)
  • Balcony/patio (3,480)
  • Dishwasher (3,786)
  • Grill (3,171)
  • Garden (2,913)

Many holidaymakers would like to find a holiday rental that includes a pool. Nearly half of the rentals in Chesapeake Bay have this amenity. Interestingly, our data show that more hotel room provide pools than condo. Additionally, they're able to welcome 10 holidaymakers, on average, while condo with pools can host an average of 5 people. You could also rent accommodation offering a pool near the water, which is the case for nearly half of the properties there.

Price and Availability Index for Chesapeake Bay

Click on any bar to see price and availability information

Holiday Letting Price Information in Chesapeake Bay

We summarised price information data in the above graph to give you more insights as to costs in Chesapeake Bay. The most expensive dates to travel to Chesapeake Bay are in July (04/07 – 11/07). In April (11/04 – 18/04), prices will hit an average low of £310 per night.

Rental availability information in Chesapeake Bay

This graph shows the holiday letting availability rate for the next twelve months. Be careful if you plan to go to Chesapeake Bay in March, as it is the busiest week of the next 6 months (20/03 – 27/03). June (06/06 – 13/06) has got the highest percentage of available rentals.

Revel in the laidback atmosphere of Chesapeake Bay holiday lettings

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 holiday homes are available in different types and sizes. From luxury townhouses and waterfront cottages to apartments and farmhouses, holiday lettings 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 holiday rentals in Chesapeake Bay

🏡 Holiday homes available 10,472 rentals
🌙 Nightly prices from £62
⭐ Popular amenities Pool, Internet and Pets allowed
🐾 Pet friendly rentals 3,366 properties
🏊 Holiday rentals with pools 4,519 properties

Frequently Asked Questions

What is the average nightly price for a holiday home in Chesapeake Bay?

Nightly rates for holiday rentals in Chesapeake Bay start from around £62. Whether you're after something simple or more luxurious, there's a wide range available. HomeToGo helps you filter by price to match your budget.

How many holiday homes are available to book in Chesapeake Bay? And what are the most popular types of holiday lets?

There are 10,472 holiday apartments in Chesapeake Bay to choose from and book for your next trip. Holiday homes in Chesapeake Bay often include spacious house rentals and apartment rental. They’re ideal whether you’re planning a romantic escape or a group getaway. Discover the most booked options quickly with HomeToGo’s smart filters.

What is the most popular holiday apartment amenity in Chesapeake Bay?

When choosing a holiday rental in Chesapeake Bay, consider looking for a place with Pool, Internet, or Pets allowed, which are the three most popular amenities for this destination.

Do you offer holiday homes with a swimming pool in Chesapeake Bay?

Yes, 43% of holiday lettings in Chesapeake Bay include access to a swimming pool. Enjoy your own private swim spot by browsing one of the 4,519 properties with a pool available. Use the 'pool' filter on HomeToGo to see your options.

What's the perfect time to travel to Chesapeake Bay?

November and July are the months with the least amount of rain in Chesapeake Bay.

How do I find deals on holiday accommmodation in Chesapeake Bay?

You can get fabulous discounts on holiday homes in Chesapeake Bay with the cost per night for a let beginning at £62 - and HomeToGo has introduced a range of features that make it easy to find the best offers. If you're still selecting dates for your break, search with HomeToGo's flexible dates technology to quickly locate great value time periods and get discounts of up to 10%. Furthermore, HomeToGo's 'distance from' filter can help you locate top quality accommodation offers in great value, under-the-radar spots with good proximity to the area of your choice, whether that's sand and sea, a mountain for snowboarding, or a city's urban hub. Start searching with time to spare to get the best of good availability and the best deals - and do so free from stress by ticking HomeToGo's 'free cancellation' filter when searching for holiday accommodation.

What are the pros of finding a holiday letting in Chesapeake Bay with HomeToGo?

From increased privacy away from the crowds to plenty of room for relaxing with your loved ones, holiday lets in Chesapeake Bay bring many advantages. HomeToGo shows you real reviews from verified visitors, and searching is secure, simple, and stress-free - so with 10,472 deals from 27 providers in the region, you're guaranteed to uncover the ideal type of accommodation with all of the amenities to suit you in Chesapeake Bay.

Do you offer holiday accommodation for couples in Chesapeake Bay?

There are lovely holiday homes in Chesapeake Bay designed with couples in mind. Whether you're after a quiet countryside cottage or a city-centre flat, there’s something to suit your style. HomeToGo helps you discover the best spots for two.

Can I book a waterfront holiday rental in Chesapeake Bay?

You can book one of 9983 waterfront holiday homes in Chesapeake Bay for a truly scenic break. These spots are perfect for a morning coffee with a view or lazy days by the water. Use HomeToGo’s "Near the water" filter to find your perfect waterfront holiday let.

Why should I book my holiday rental with HomeToGo?

From seaside cottages to city apartments, HomeToGo has the best holiday rentals out there. Our smart search makes it easy to find what suits you. Try HomeToGo and discover how easy it is to plan your perfect holiday letting.

Can I find family-friendly holiday lettings in Chesapeake Bay?

Yes, many holiday homes in Chesapeake Bay are ideal for families, with plenty of space and useful amenities. Many come with space for large groups and practical features like kitchens and gardens. Start your search with HomeToGo for a stress-free getaway.

Can I cancel my holiday rental booking for free?

Yes, many holiday lettings on HomeToGo offer free cancellation. This gives you flexibility in case your travel plans change.

Is it possible to rent a holiday home for a weekend getaway in Chesapeake Bay?

Yes, many holiday lets in Chesapeake Bay offer flexible booking options, including weekend stays. It’s perfect for a quick break without using too many holiday days. Discover your ideal holiday home with ease on HomeToGo.

Are there any last-minute holiday rental deals in Chesapeake Bay?

Need a quick break? Last-minute holiday is just a few clicks away in Chesapeake Bay. Perfect for a spur-of-the-moment trip — especially with savings of up to 10%. Use HomeToGo’s filters to see what’s available right now.

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