Chesapeake Bay holiday lettings and accommodation - HomeToGo base64Hash Chesapeake Bay holiday lettings and accommodation - HomeToGo

Chesapeake Bay holiday lettings and accommodation

Find 12,594 available offers from 32 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 £60 per night!

House Northeast Virginia Beach
House ∙ 9 guests ∙ 4 bedrooms

House with garden, barbecue & terrace | City view

Northeast Virginia Beach, Virginia Beach, Virginia, United States
from £172
per night
Outstanding(54 ratings)
Vrbo
from £172
per night
View deal
Vrbo
House Bay View
House ∙ 8 guests ∙ 4 bedrooms

Holiday home with garden, terrace & private pool

Bay View, Norfolk, Virginia, United States
from £277
per night
Excellent(10 ratings)
Vrbo
from £277
per night
View deal
Vrbo
House White Stone
House ∙ 13 guests ∙ 5 bedrooms

Family-friendly holiday home with barbeque & terrace

White Stone, Lancaster County, Virginia, United States
from £273
per night
Very good(1 rating)
Vrbo
from £273
per night
View deal
Vrbo
House Chic's Beach
House ∙ 10 guests ∙ 4 bedrooms

Fully equipped nice holiday home with terrace & barbecue | Beach nearby | Pet-friendly

Chic's Beach, Virginia Beach, Virginia, United States
from £148
per night
Outstanding(18 ratings)
Vrbo
from £148
per night
View deal
Vrbo
House Virginia Beach
House ∙ 32 guests ∙ 8 bedrooms

Holiday home with barbecue, sauna & jacuzzi

Virginia Beach, Virginia, United States
from £323
per night
Very good(75 ratings)
Vrbo
from £323
per night
View deal
Vrbo
House Port Haywood
House ∙ 8 guests ∙ 4 bedrooms

Child-friendly wonderful house with terrace, garden & barbeque | Nature view | Dogs allowed

Port Haywood, Chesapeake, Virginia, United States
from £188
per night
Outstanding(161 ratings)
Vrbo
from £188
per night
View deal
Vrbo
Villa Rock Hall
Villa ∙ 25 guests ∙ 9 bedrooms

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

Rock Hall, Edesville, Maryland, United States
from £848
per night
Outstanding(45 ratings)
Vrbo
from £848
per night
View deal
Vrbo
Apartment Northeast Virginia Beach
Apartment ∙ 8 guests ∙ 3 bedrooms

Pleasant flat | Next to the beach

Northeast Virginia Beach, Virginia Beach, Virginia, United States
from £324
per night
Excellent(7 ratings)
Vrbo
from £324
per night
View deal
Vrbo
House Palmer
House ∙ 12 guests ∙ 3 bedrooms

Family-oriented spacious holiday home with BBQ, terrace & garden | Suitable for remote work | Pets are welcome

Palmer, Lancaster County, Virginia, United States
from £345
per night
Outstanding(59 ratings)
Vrbo
from £345
per night
View deal
Vrbo
House Bay View
House ∙ 9 guests ∙ 4 bedrooms

Fully equipped lovely holiday home with terrace & barbeque | City view

Bay View, Norfolk, Virginia, United States
from £129
per night
Outstanding(54 ratings)
Vrbo
from £129
per night
View deal
Vrbo
House West Ocean View
House ∙ 16 guests ∙ 5 bedrooms

Children-friendly big house with garden & BBQ | City view | Beach nearby

West Ocean View, Norfolk, Virginia, United States
from £250
per night
Excellent(14 ratings)
Vrbo
from £250
per night
View deal
Vrbo
House Churchton
House ∙ 13 guests ∙ 6 bedrooms

House with BBQ, hot tub & garden | Lake view

Churchton, Deale, Maryland, United States
from £657
per night
Excellent(19 ratings)
Vrbo
from £657
per night
View deal
Vrbo
House Deale
House ∙ 10 guests ∙ 3 bedrooms

Holiday home with hot tub, private pool & terrace

Deale, Anne Arundel County, Maryland, United States
from £364
per night
Outstanding(26 ratings)
Vrbo
from £364
per night
View deal
Vrbo
House Cape Charles
House ∙ 16 guests ∙ 4 bedrooms

Holiday home with terrace, pool & barbecue | Lake view

Cape Charles, Northampton County, Virginia, United States
from £422
per night
Outstanding(32 ratings)
Vrbo
from £422
per night
View deal
Vrbo
House Arnold
House ∙ 14 guests ∙ 6 bedrooms

House with terrace, garden & barbecue | Pets allowed

Arnold, Anne Arundel County, Maryland, United States
from £852
per night
Outstanding(1 rating)
Vrbo
from £852
per night
View deal
Vrbo

Holiday homes and cottages with a garden

House  Cambridge
from £562 per night
House ∙ 14 guests ∙ 7 bedrooms

House with BBQ, private pool & terrace | Perfect for remote work

5.0
Outstanding(31 ratings)
Cambridge, Dorchester County, Maryland, United States
Garden
Vrbo
View deal
House  Heathsville
from £213 per night
House ∙ 10 guests ∙ 3 bedrooms

Family-friendly wonderful holiday home with garden, BBQ & terrace | Nature view

4.8
Outstanding(42 ratings)
Heathsville, Northumberland County, Virginia, United States
Garden
Vrbo
View deal
House  Virginia Beach
from £372 per night
House ∙ 10 guests ∙ 3 bedrooms

House with barbeque, private pool & terrace | City view

4.3
Very good(44 ratings)
Virginia Beach, Virginia, United States
Garden
Vrbo
View deal
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Holiday lettings and apartments with air conditioning

House  Dam Neck
from £195 per night
House ∙ 11 guests ∙ 4 bedrooms

Fully equipped house with terrace & BBQ | Nature view | Beach nearby | Pets allowed

4.2
Very good(32 ratings)
Dam Neck, Virginia Beach, Virginia, United States
Air conditioning
Vrbo
View deal
House  Cape Charles
from £505 per night
House ∙ 10 guests ∙ 3 bedrooms

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

Cape Charles, Northampton County, Virginia, United States
Air conditioning
Vrbo
View deal
House  Heathsville
from £268 per night
House ∙ 8 guests ∙ 5 bedrooms

Children-friendly holiday home with private pool, garden & terrace | Nature view | Perfect for remote work

4.9
Outstanding(94 ratings)
Heathsville, Northumberland County, Virginia, United States
Air conditioning
Vrbo
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Best holiday homes with a patio or terrace

House  Chesapeake Beach
from £159 per night
House ∙ 11 guests ∙ 4 bedrooms

Holiday home with barbeque, hot tub & terrace

4.0
Very good(2 ratings)
Chesapeake Beach, Sunderland, Maryland, United States
Balcony/Patio
Vrbo
View deal
House  Northeast Virginia Beach
from £393 per night
House ∙ 9 guests ∙ 4 bedrooms

Fully equipped charming holiday home with garden, barbecue & terrace | Close to the beach

4.7
Excellent(35 ratings)
Northeast Virginia Beach, Virginia Beach, Virginia, United States
Balcony/Patio
Vrbo
View deal
House  Cape Charles
from £351 per night
House ∙ 10 guests ∙ 5 bedrooms

House with terrace, barbeque & garden

4.8
Outstanding(30 ratings)
Cape Charles, Northampton County, Virginia, United States
Balcony/Patio
Vrbo
View deal
See all offers

Budget-friendly Holiday Homes in Chesapeake Bay

Find Fantastic yet Cheap Lettings

House Virginia Beach
from £336 per night
House ∙ 13 guests ∙ 5 bedrooms

Children-friendly holiday home with private pool, barbeque & terrace | Suitable for remote work

4.4
Very good(52 ratings)
Virginia Beach, Virginia, United States
Vrbo
View deal
House Northeast Virginia Beach
from £449 per night
House ∙ 9 guests ∙ 3 bedrooms

House with private pool

Northeast Virginia Beach, Virginia Beach, Virginia, United States
Vrbo
View deal
House Buckroe Beach
from £449 per night
House ∙ 14 guests ∙ 6 bedrooms

Children-friendly charming house with barbeque & terrace | Next to the beach

4.8
Outstanding(9 ratings)
Buckroe Beach, Hampton, Virginia, United States
Vrbo
View deal

Top-Rated Lettings and Properties in Chesapeake Bay

Book Holiday Letting Offers with the Highest User Rating

House Cambridge
from £232 per night
House ∙ 7 guests ∙ 3 bedrooms

Holiday home with private pool & BBQ

5.0
Outstanding(2 ratings)
Cambridge, Dorchester County, Maryland, United States
Vrbo
View deal
House White Stone
from £178 per night
House ∙ 8 guests ∙ 3 bedrooms

Holiday home with terrace & pool

5.0
Outstanding(1 rating)
White Stone, Lancaster County, Virginia, United States
Vrbo
View deal
House Dam Neck
from £546 per night
House ∙ 12 guests ∙ 5 bedrooms

Family-friendly lovely holiday home with garden, BBQ & terrace | Nature view | Next to the beach | Suitable for remote work

4.9
Outstanding(77 ratings)
Dam Neck, Virginia Beach, Virginia, United States
Vrbo
View deal

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Spend your budget exactly as planned by comparing thousands of providers.

Smart search made simple

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Transform holiday planning into a joy with advanced, AI-powered search tools.

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 (4,708)
  • WiFi (12,043)
  • Pet-friendly (3,761)
  • Air conditioning (11,826)
  • Parking (1,014)
  • Kitchen (8,341)
  • TV (10,716)
  • Washing machine (7,132)
  • Balcony/patio (3,663)
  • Dishwasher (4,083)
  • Grill (3,449)
  • Garden (4,058)

Many holidaymakers would like to find a holiday rental that includes a pool. One-third 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 August (02/08 – 09/08). In September (13/09 – 20/09), prices will hit an average low of £279 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 April, as it is the busiest week of the next 6 months (18/04 – 25/04). September (06/09 – 13/09) 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 12,594 rentals
🌙 Nightly prices from £60
⭐ Popular amenities Pool, Internet and Pets allowed
🐾 Pet friendly rentals 3,759 properties
🏊 Holiday rentals with pools 4,708 properties

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 £60. The average cost of apartment rental is £301 per night. House rentals will cost £462 per night on average.

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

There are currently 12,594 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 37 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 £60 - 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 10%. 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 12,594 offers from 32 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.

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