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

Holiday homes & rentals in Chesapeake Bay

Find 10,132 available offers from 34 partners
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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 £59 per night!

House Northeast Virginia Beach
House ∙ 9 guests ∙ 4 bedrooms

Family-oriented charming holiday home with garden, barbecue & terrace | Close to the beach

Northeast Virginia Beach, Virginia Beach, Virginia, United States
from £393
per night
Excellent(43 ratings)
from £393
per night
View deal
Cabin Port Republic
Cabin ∙ 5 guests ∙ 2 bedrooms

Cabin with garden, terrace & pool | Nature view

Port Republic, Solomons Island, Maryland, United States
from £96
per night
Outstanding(206 ratings)
from £96
per night
View deal
Cottage Churchton
Cottage ∙ 8 guests ∙ 3 bedrooms

Family-friendly nice cottage with jacuzzi, garden & barbeque | Lake view | Pets allowed

Churchton, Deale, Maryland, United States
from £177
per night
Outstanding(92 ratings)
from £177
per night
View deal
House Elkton
House ∙ 12 guests ∙ 5 bedrooms

House with terrace & barbeque

Elkton, Cecil County, Maryland, United States
from £355
per night
Outstanding(213 ratings)
from £355
per night
View deal
House Northwest
House ∙ 8 guests ∙ 3 bedrooms

Family-oriented house with terrace | Close to the beach | Good for workation

Northwest, Virginia Beach, Virginia, United States
from £95
per night
Outstanding(85 ratings)
from £95
per night
View deal
House Wythe
House ∙ 8 guests ∙ 4 bedrooms

Child-friendly ample house with barbecue & terrace | Good for workation | Dogs allowed

Wythe, Hampton, Virginia, United States
from £237
per night
Outstanding(18 ratings)
from £237
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
from £131
per night
Outstanding(34 ratings)
from £131
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
from £144
per night
Excellent(31 ratings)
from £144
per night
View deal
House Shady Side
House ∙ 6 guests ∙ 3 bedrooms

House with terrace | Nature view

Shady Side, Anne Arundel County, Maryland, United States
from £139
per night
Excellent(15 ratings)
from £139
per night
View deal
House Shady Side
House ∙ 8 guests ∙ 4 bedrooms

Holiday home with garden, terrace & barbeque | Nature view

Shady Side, Anne Arundel County, Maryland, United States
from £319
per night
Outstanding(39 ratings)
from £319
per night
View deal
House Madison
House ∙ 18 guests ∙ 7 bedrooms

House with garden, barbecue & private pool | Lake view | Perfect for remote work

Madison, Dorchester County, Maryland, United States
from £602
per night
Outstanding(84 ratings)
from £602
per night
View deal
House Tracys Landing
House ∙ 8 guests ∙ 3 bedrooms

Children-friendly holiday home with barbecue & terrace

Tracys Landing, Anne Arundel County, Maryland, United States
from £207
per night
Excellent(38 ratings)
from £207
per night
View deal
House Deale
House ∙ 8 guests ∙ 3 bedrooms

Family-oriented house with barbeque, terrace & garden | Nature view | Pet-friendly

Deale, Anne Arundel County, Maryland, United States
from £358
per night
Outstanding(96 ratings)
from £358
per night
View deal
House Shady Side
House ∙ 8 guests ∙ 3 bedrooms

Child-friendly charming house with barbeque, terrace & garden | Nature view | Pets are welcome

Shady Side, Anne Arundel County, Maryland, United States
from £117
per night
Outstanding(31 ratings)
from £117
per night
View deal
Villa Earleville
Villa ∙ 16 guests ∙ 7 bedrooms

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

Earleville, Cecilton, Maryland, United States
from £826
per night
Outstanding(33 ratings)
from £826
per night
View deal

Holiday homes and cottages with a garden

House  Madison
from £854 per night
House ∙ 24 guests ∙ 10 bedrooms

Holiday home with terrace, garden & private pool | Good for workation

5.0
Outstanding(76 ratings)
Madison, Dorchester County, Maryland, United States
Garden
View deal
House  Pasadena
from £374 per night
House ∙ 14 guests ∙ 5 bedrooms

Child-friendly house with garden & terrace | Lake view

4.7
Excellent(99 ratings)
Pasadena, Anne Arundel County, Maryland, United States
Garden
View deal
House  Reedville
from £622 per night
House ∙ 16 guests ∙ 6 bedrooms

Child-friendly charming house with terrace, hot tub & garden | Suitable for remote work | Dogs allowed

Reedville, Northumberland County, Virginia, United States
Garden
View deal
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Holiday lettings and apartments with air conditioning

House  Northeast Virginia Beach
from £763 per night
House ∙ 18 guests ∙ 8 bedrooms

Wonderful house with terrace | Dogs allowed

4.6
Excellent(12 ratings)
Northeast Virginia Beach, Virginia Beach, Virginia, United States
Air conditioning
View deal
Apartment  Annapolis
from £217 per night
Apartment ∙ 4 guests ∙ 2 bedrooms

Holiday apartment with barbecue & private pool | City view

5.0
Outstanding(95 ratings)
Annapolis, Anne Arundel County, Maryland, United States
Air conditioning
View deal
House  Buckroe Beach
from £170 per night
House ∙ 10 guests ∙ 3 bedrooms

House with garden, terrace & BBQ | Perfect for remote work

4.8
Outstanding(60 ratings)
Buckroe Beach, Hampton, Virginia, United States
Air conditioning
View deal
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Best holiday homes with a patio or terrace

House  Cape Charles
from £332 per night
House ∙ 10 guests ∙ 3 bedrooms

Family-oriented holiday home with barbeque, pool & terrace | Nature view | Pets allowed

4.8
Outstanding(7 ratings)
Cape Charles, Northampton County, Virginia, United States
Balcony/Patio
View deal
House  Edgewood
from £470 per night
House ∙ 12 guests ∙ 5 bedrooms

Family-oriented house with BBQ & terrace | Nature view | Good for workation

4.9
Outstanding(32 ratings)
Edgewood, Abingdon, Maryland, United States
Balcony/Patio
View deal
House  Scotland
from £505 per night
House ∙ 14 guests ∙ 7 bedrooms

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

5.0
Outstanding(18 ratings)
Scotland, St. Inigoes, Maryland, United States
Balcony/Patio
View deal
See all offers

Budget-friendly Holiday Homes in Chesapeake Bay

Find Fantastic yet Cheap Lettings

House Northeast Virginia Beach
from £488 per night
House ∙ 9 guests ∙ 3 bedrooms

House with private pool

Northeast Virginia Beach, Virginia Beach, Virginia, United States
View deal
House Northeast Virginia Beach
from £312 per night
House ∙ 13 guests ∙ 6 bedrooms

House with barbeque & garden | Good for workation

5.0
Outstanding(16 ratings)
Northeast Virginia Beach, Virginia Beach, Virginia, United States
View deal
House East Ocean View
from £102 per night
House ∙ 10 guests ∙ 4 bedrooms

Holiday home with jacuzzi & barbecue

4.8
Outstanding(82 ratings)
East Ocean View, Norfolk, Virginia, United States
View deal

Top-Rated Lettings and Properties in Chesapeake Bay

Book Holiday Letting Offers with the Highest User Rating

House Northeast Virginia Beach
from £146 per night
House ∙ 9 guests ∙ 4 bedrooms

Children-friendly beautiful holiday home with terrace, barbecue & garden | Beach nearby

5.0
Outstanding(15 ratings)
Northeast Virginia Beach, Virginia Beach, Virginia, United States
View deal
House Woolford
from £246 per night
House ∙ 18 guests ∙ 6 bedrooms

House with barbeque, terrace & garden | Nature view

4.8
Outstanding(31 ratings)
Woolford, Madison, Maryland, United States
View deal
House Tracys Landing
from £1,031 per night
House ∙ 20 guests ∙ 7 bedrooms

Family-friendly holiday home with BBQ, terrace & garden | Lake view | Perfect for remote work | Pets are welcome

4.9
Outstanding(71 ratings)
Tracys Landing, Anne Arundel County, Maryland, United States
View deal

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Find your dream stay

Find your dream stay

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

Popular holiday rental amenities in Chesapeake Bay

  • Pool (4,356)
  • WiFi (9,746)
  • Pet-friendly (3,210)
  • Air conditioning (9,515)
  • Parking (833)
  • Kitchen (5,967)
  • TV (8,836)
  • Washing machine (5,694)
  • Balcony/patio (3,626)
  • Dishwasher (3,717)
  • Grill (3,201)
  • Garden (2,935)

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 4 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 more than 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 June (20/06 – 27/06). In November (22/11 – 29/11), prices will hit an average low of £270 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 October, as it is the busiest week of the next 6 months (24/10 – 31/10). November (22/11 – 29/11) 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 10,132 rentals
🌙 Nightly prices from £59
⭐ Popular amenities Pool, Internet and Pets allowed
🐾 Pet friendly rentals 3,217 properties
🏊 Holiday rentals with pools 4,381 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 £59. 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 10,132 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 4,381 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 £59 - 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 10,132 deals from 34 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 9671 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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