Holiday lettings & accommodation in Chesapeake Bay - HomeToGo base64Hash

Holiday lettings & accommodation in Chesapeake Bay

Find 9,184 available offers from 27 partners

Popular Filters to discover the perfect holiday home in Chesapeake Bay

Holiday rentals with wifi

Apartments and holiday lettings with a kitchen

Best holiday homes with a patio or terrace

Best holiday rental deals in Chesapeake Bay

Save up to 34%

Browse 9,184 rentals listed in Chesapeake Bay and discover the ideal place to stay for your next holiday. Our algorithm instantly evaluates all the accommodation options to help you save up to 57%.

Recommended holiday lettings in Chesapeake Bay

Rent a holiday home, apartment or cottage in Chesapeake Bay from just £62 per night

Budget-friendly Holiday Homes in Chesapeake Bay

Find Fantastic yet Cheap Lettings

Top-Rated Lettings and Properties in Chesapeake Bay

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Popular holiday rental amenities in Chesapeake Bay

Pool (4,029)
WiFi (9,025)
Pet-friendly (3,024)
Air conditioning (8,939)
Parking (722)
Kitchen (5,648)
TV (8,278)
Washing machine (5,297)
Balcony/patio (3,377)
Dishwasher (3,590)
Grill (3,141)
Garden (2,923)

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 6 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 May (17/05 – 24/05). In January (04/01 – 11/01), prices will hit an average low of £229 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 February, as it is the busiest week of the next 6 months (22/02 – 01/03). October (12/10 – 19/10) has got the highest percentage of available rentals.

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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	9,317 rentals
💳 Discounts available	up to 68%
🌙 Nightly prices from	£62
⭐ Popular amenities	Pool, Internet and Pets allowed
🐾 Pet friendly rentals	3,016 properties
🏊 Holiday rentals with pools	4,065 properties

12 reviews

Chesapeake Bay holiday rentals have an average rating of 3.5/5 across 12 reviews left by travellers.

Frequently Asked Questions

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

The average price per night in Chesapeake Bay is around £62. The average cost of apartment rental is £204 per night. House rentals will cost £470 per night on average.

How many holiday apartments are available to rent in Chesapeake Bay?

There are currently 9,317 holiday apartments in Chesapeake Bay to browse and book for your upcoming trip.

What is the most searched holiday home amenity in Chesapeake Bay?

Travellers planning trips to Chesapeake Bay most often look for Pool, Internet, and Pets allowed when it comes to holiday rental amenities.

How many holiday rentals in Chesapeake Bay have a pool?

Holiday rentals with pools are 44 of all offers in Chesapeake Bay.

What is the best time of year to travel to Chesapeake Bay?

Sun lovers should visit Chesapeake Bay in July and June to enjoy the warmest weather.

Can you get deals on holiday accommmodation in Chesapeake Bay?

You can get great value holiday rentals in Chesapeake Bay with the nightly price of a let beginning at £62 - and HomeToGo has launched a range of filters that make it a piece of cake to see some awesome offers. If you're still selecting dates for your break, try a search using HomeToGo's flexible dates technology to scan for low-price time periods and see discounts of up to 68%. In addition, HomeToGo's 'distance from' filter makes it easy to discover top quality accommodation offers in great value, under-the-radar spots with good proximity to your desired destination, whether that's a beach, lake, ski region or city centre. Start searching with time to spare to take advantage of good availability and the best deals - and do so free from stress by ticking HomeToGo's 'free cancellation' filter when you search.

What are the benefits of finding a holiday rental in Chesapeake Bay with HomeToGo?

From serenity away from the crowds to plenty of room in which to have fun with your family, friends or partner, holiday lets in Chesapeake Bay bring plenty of advantages. HomeToGo shows you genuine ratings written by previous guests, and searching is safe, easy, and stress-free - so with 9,317 offers from 28 providers in the vicinity, you're guaranteed to locate the right place to stay with the amenities and features to suit you in Chesapeake Bay.

We list offers from thousands of providers, including

Holiday lettings & accommodation in Chesapeake Bay

Popular Filters to discover the perfect holiday home in Chesapeake Bay

Holiday rentals with wifi

Holiday Home in Betterton with Garden, Terrace & Barbecue

Pleasant Holiday Home in Elkton with Pool, Garden & Barbecue

Cottage in Deal Island with Barbecue

Apartments and holiday lettings with a kitchen

Cottage in Heathsville with Barbecue, Hot Tub

House in Buckroe Beach

House in Buckroe Beach with Garden & Barbecue

Best holiday homes with a patio or terrace

Rental Cottage in White Stone with Terrace & Barbecue

Lovely House in Willoughby Spit with Barbecue + Water Views

Cottage in Deltaville with Garden

Best holiday rental deals in Chesapeake Bay

Motel in Northwest with Terrace

Recommended holiday lettings in Chesapeake Bay

House in Kilmarnock with Barbecue & Garden

House in Reedville with Barbecue, Garden & Terrace

Holiday Home in Buckroe Beach

House in Stevensville with Barbecue, Garden & Terrace + Beautiful Views

Holiday Home in Fishing Creek with Terrace & Barbecue

Family Friendly Holiday Home in Dam Neck with Garden, Terrace & Barbecue

House in Reedville

Pleasant House in Rock Hall with Large Patio + Waterfront Views

Holiday Home in Cape Saint Claire with Pool, Barbecue & Terrace