Holiday lettings & accommodation in Chesapeake Bay - HomeToGo base64Hash Holiday lettings & accommodation in Chesapeake Bay - HomeToGo

Holiday lettings & accommodation in Chesapeake Bay

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Chesapeake Bay
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Chesapeake Bay
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Price per night
Up to £100
£100 - £199
From £200
Accommodation types
House
Apartment
Farmhouse
Rating
4.5+
4+

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.

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Holiday rentals with wifi

Whether it's for working remotely or streaming your favourite shows, internet access can be an indispensable amenity when it comes to choosing a holiday home. Check out HomeToGo's range of holiday lettings with WiFi in Chesapeake Bay and enjoy a fast and reliable internet connection during your stay.

Cottage  Scotland
21 Sept - 28 Sept
£236 per night
Cottage ∙ 8 guests ∙ 3 bedrooms

Cottage in Scotland with Garden, Barbecue & Terrace + Water Views

4.9
Outstanding (16 ratings)
Scotland, St. Inigoes, Maryland, United States
Internet
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House  North
21 Sept - 28 Sept
£542 per night
House ∙ 10 guests ∙ 6 bedrooms

Lovely House in North with Barbecue + Marsh Views

5.0
Outstanding (17 ratings)
North, Petsworth, Virginia, United States
Internet
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House  Buckroe Beach
21 Sept - 28 Sept
£373 per night
House ∙ 10 guests ∙ 4 bedrooms

Holiday Home in Buckroe Beach with Terrace

5.0
Outstanding (23 ratings)
Buckroe Beach, Hampton, Virginia, United States
Internet
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Holiday lettings and apartments with air conditioning

Good weather while on holiday is always great - and it's a plus to be able to control the temperature in your accommodation too. Find holiday homes and apartments in Chesapeake Bay with air conditioning and cooling systems to ensure maximum comfort during your stay.

Cottage  Deltaville
21 Sept - 28 Sept
£201 per night
Cottage ∙ 5 guests ∙ 2 bedrooms

Cottage in Deltaville with Terrace & Barbecue + Water Views

5.0
Outstanding (10 ratings)
Deltaville, Pine Top, Virginia, United States
Air conditioning
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House  Chesapeake Ranch Estates-Drum Point
21 Sept - 28 Sept
-4%
£160
£154 per night
House ∙ 7 guests ∙ 3 bedrooms

Holiday Home in Chesapeake Ranch Estates-Drum Point with Terrace

5.0
Outstanding (47 ratings)
Chesapeake Ranch Estates-Drum Point, Solomons Island, Maryland, United States
Air conditioning
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House  Deale
21 Sept - 28 Sept
£489 per night
House ∙ 10 guests ∙ 3 bedrooms

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

4.9
Outstanding (11 ratings)
Deale, Anne Arundel County, Maryland, United States
Air conditioning
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Apartments and holiday lettings with a kitchen

Looking for self-catering accommodation in Chesapeake Bay? Find the perfect letting for you with our selection of Chesapeake Bay holiday rentals with kitchens. Well-appointed and equipped with plenty of cooking appliances, these holiday homes are great for self-catered stays.

House  Hampton Roads Center
21 Sept - 28 Sept
-7%
£277
£257 per night
House ∙ 8 guests ∙ 4 bedrooms

Holiday Home in Hampton Roads Center with Pool & Barbecue

4.9
Outstanding (14 ratings)
Hampton Roads Center, Hampton, Virginia, United States
Kitchen
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Cottage  Parole
21 Sept - 28 Sept
£152 per night
Cottage ∙ 4 guests ∙ 1 bedroom

Cottage in Parole with Terrace & Garden + Peaceful View

5.0
Outstanding (263 ratings)
Parole, Anne Arundel County, Maryland, United States
Kitchen
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House  Buckroe Beach
21 Sept - 28 Sept
-8%
£198
£183 per night
House ∙ 10 guests ∙ 4 bedrooms

Holiday Home in Buckroe Beach with Garden & Barbecue

5.0
Outstanding (38 ratings)
Buckroe Beach, Hampton, Virginia, United States
Kitchen
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Best holiday rental deals in Chesapeake Bay

Save up to 12%

House Buckroe Beach
21 Sept - 28 Sept
-11%
£242
£215 per night
House ∙ 5 guests ∙ 3 bedrooms

Holiday Home in Buckroe Beach with Garden, Terrace & Barbecue

5.0
Outstanding (41 ratings)
Buckroe Beach, Hampton, Virginia, United States
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House Scotland
21 Sept - 28 Sept
-12%
£511
£452 per night
House ∙ 10 guests ∙ 5 bedrooms

Gorgeous Holiday Home in Scotland with Terrace, Garden & Barbecue + Beautiful Views

4.9
Outstanding (24 ratings)
Scotland, St. Inigoes, Maryland, United States
Details
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You can browse 8,647 unique holiday lettings from 16 providers in Chesapeake Bay, with nightly prices beginning at £53. HomeToGo lets you directly compare the offers for each property from numerous partners to find the best price and save up to 11%.

Recommended holiday lettings in Chesapeake Bay

Rent a holiday home, apartment or cottage in Chesapeake Bay from just £53 per night

House Saint Michaels
£431 per night
House ∙ 8 guests ∙ 4 bedrooms

House in Saint Michaels with Private Pool

Saint Michaels, St. Michaels, Maryland, United States
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House Easton
£255 per night
House ∙ 10 guests ∙ 5 bedrooms

House in Easton with Barbecue, Pool & Garden

3.0
(1 rating)
Easton, Talbot County, Maryland, United States
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House Deal Island
£111 per night
House ∙ 8 guests ∙ 3 bedrooms

Pleasant House in Deal Island with Barbecue, Hot Tub & Terrace + Water Views

4.7
Excellent (41 ratings)
Deal Island, Somerset County, Maryland, United States
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Cabin Lusby
£329 per night
Cabin ∙ 11 guests ∙ 4 bedrooms

Cabin in Lusby with Seasonal Pool + Serene View

5.0
Outstanding (5 ratings)
Lusby, Solomons Island, Maryland, United States
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House Algonquin
£532 per night
House ∙ 13 guests ∙ 5 bedrooms

Holiday Home in Algonquin with Barbecue, Garden & Pool

4.9
Outstanding (14 ratings)
Algonquin, Cambridge, Maryland, United States
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House Chesapeake Beach
£140 per night
House ∙ 8 guests ∙ 4 bedrooms

Holiday Home in Chesapeake Beach with Garden, Terrace & Barbecue

5.0
Outstanding (1 rating)
Chesapeake Beach, Sunderland, Maryland, United States
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House Bay View
£90 per night
House ∙ 10 guests ∙ 4 bedrooms

Beautiful Holiday Home in Bay View with Terrace, Garden & Barbecue + Ocean View

4.5
Excellent (12 ratings)
Bay View, Norfolk, Virginia, United States
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Cottage Port Republic
21 Sept - 28 Sept
£330 per night
Cottage ∙ 4 guests ∙ 2 bedrooms

Cottage in Port Republic with Terrace & Barbecue

4.9
Outstanding (149 ratings)
Port Republic, Solomons Island, Maryland, United States
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House Taylors Island
£478 per night
House ∙ 14 guests ∙ 5 bedrooms

House in Taylors Island with Garden & Barbecue + Story View

5.0
Outstanding (32 ratings)
Taylors Island, Dorchester County, Maryland, United States
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Budget-friendly Holiday Homes in Chesapeake Bay

Find Fantastic yet Cheap Lettings

Cottage Deal Island
£132 per night
Cottage ∙ 4 guests ∙ 1 bedroom

Cottage in Deal Island with Terrace & Barbecue

5.0
Outstanding (65 ratings)
Deal Island, Somerset County, Maryland, United States
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House North Beach
21 Sept - 28 Sept
-4%
£384
£369 per night
House ∙ 6 guests ∙ 3 bedrooms

Beautiful Holiday Home in North Beach with Terrace, Barbecue & Garden + Water Views + Close to Beach

4.9
Outstanding (60 ratings)
North Beach, Sunderland, Maryland, United States
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House White Stone
£281 per night
House ∙ 6 guests ∙ 2 bedrooms

Whole Holiday Home in White Stone with Barbecue & Terrace + Amazing Views

5.0
Outstanding (10 ratings)
White Stone, Lancaster County, Virginia, United States
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Top-Rated Lettings and Properties in Chesapeake Bay

Book Holiday Letting Offers with the Highest User Rating

Cottage Wenona
£78 per night
Cottage ∙ 8 guests ∙ 4 bedrooms

Wonderful Cottage in Wenona with Garden, Barbecue & Terrace

4.7
Excellent (79 ratings)
Wenona, Deal Island, Maryland, United States
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Cottage New Point
21 Sept - 28 Sept
£367 per night
Cottage ∙ 6 guests ∙ 2 bedrooms

Beachfront Cottage in New Point with Barbecue, Terrace & Garden

4.9
Outstanding (77 ratings)
New Point, Chesapeake, Virginia, United States
Details
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House Virginia Beach
£187 per night
House ∙ 10 guests ∙ 3 bedrooms

House in Virginia Beach with Terrace, Barbecue & Garden

5.0
Outstanding (3 ratings)
Virginia Beach, Virginia, United States
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Popular holiday rental amenities in Chesapeake Bay

  • Pool (4,122)
  • WiFi (9,208)
  • Pet-friendly (1,820)
  • Air conditioning (9,214)
  • Parking (697)
  • Kitchen (5,790)
  • TV (8,485)
  • Washing machine (5,264)
  • Balcony/patio (3,368)
  • Dishwasher (3,764)
  • Grill (3,185)
  • Garden (2,680)

Nearly half of the holiday rentals offer a pool, which makes Chesapeake Bay the ideal destination for travellers looking to spend their holidays poolside. Also, more hotel room have pools than any other accommodation type. They are a great choice if you go in a group of 10, as that is the number of people they can most often accommodate. Among these properties, more than half are within 2 kilometres of water.

Price and Availability Index for Chesapeake Bay

Click on any bar to see price and availability information

Holiday Letting Price Information in Chesapeake Bay

The graph shows the average holiday accommodation prices for the next twelve months in Chesapeake Bay. Prices reach their peak during one week in August. The price per night for a stay in a holiday letting in Chesapeake Bay during this week (24/08 – 31/08) is £403 on average. Prices are at their lowest in January (25/01 – 01/02).

Rental availability information in Chesapeake Bay

The availability graph shows the percentage of available holiday homes in Chesapeake Bay. The most challenging week to find a letting in the next twelve months is in January (25/01 – 01/02). It is easier to find a rental during one week of May (25/05 – 01/06), when only 26% of the holiday lettings on offer are booked.

The Weather in Chesapeake Bay

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Jan.
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Mar.
Apr.
May
June
July
Aug.
Sep.
Oct.
Nov.
Dec.
- Rainy days

Check out our climate diagram to find the perfect month for your holiday. During July, maximum temperatures climb above 31°. On the other hand, you could have temperatures dropping under -2° in January. November is the driest month of the year.

7-Day Weather Forecast in Chesapeake Bay

Mon, 4 Mar
12°
11°

0%

1 h

5 km/h

Tue, 5 Mar
10°
10°

15%

0 h

16 km/h

Wed, 6 Mar
13°
12°

15%

0 h

33 km/h

Thu, 7 Mar
11°
11°

0%

1 h

30 km/h

Fri, 8 Mar

0%

2 h

17 km/h

Sat, 9 Mar

15%

0 h

32 km/h

Sun, 10 Mar

15%

0 h

24 km/h

Accommodation options for your holiday in Chesapeake Bay

More than half of the accommodation options (57.55%) in Chesapeake Bay are house rentals. They are the most prevalent holiday rentals there. These types of accommodation have an average size of 221 m² and a median price of £491 per night. Furthermore, these properties are a great option if you're going in a group of 8, since that's the average number of holidaymakers that house rentals are able to accommodate in Chesapeake Bay. Travellers looking for an alternative to a house rentals can, with HomeToGo's great range, also find a perfect apartment rental for them. This property type is the second most popular kind of accommodation in Chesapeake Bay. Apartment rental in Chesapeake Bay are 74 m² on average, with an average price of £215 per night.
What is the weather like in Chesapeake Bay?

Ideal time to visit Chesapeake Bay

The peak season for travellers to Chesapeake Bay is the summer period between June and August. Thousands of holidaymakers visit during this time for the hot weather and fun water-sports, including fishing, boating, and swimming.

If you specifically want to avoid the peak crowds, travel to Chesapeake Bay in either spring (March to May) or fall (September to November). During these seasons, you will be able to observe dolphins, explore salt marshes, and go hiking.

What are the best events and festivals in Chesapeake Bay?

Festivals in Chesapeake Bay

Chesapeake Bay Blues Festival is an annual event that takes place in Annapolis, Maryland. Spanning a weekend, this festival raises millions of dollars for charity. Attend this event and you can enjoy some of the world's best blues artists accompanied by gorgeous beachside views and amazing food.

Maryland Seafood Festival is held to celebrate the state's signature blue crabs. This festival also takes place in Annapolis and features numerous vendors selling crab cakes, steamed crab, and cream of crab soup, as well as braided crab pretzels.

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 8,647 rentals
💳 Discounts available up to 11%
🌙 Nightly prices from £53
⭐ Popular amenities Pool, Internet and Pets allowed
🐾 Pet friendly rentals 1,692 properties
🏊 Holiday rentals with pools 3,695 properties
12 reviews
Chesapeake Bay holiday rentals have an average rating of 3.5/5 across 12 reviews left by travellers.

Frequently Asked Questions

How many accommodation are available to book in Chesapeake Bay?

There are currently 8,647 holiday apartments in Chesapeake Bay to choose from and book for your next 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 homes with pools are 43 of all offers in Chesapeake Bay with an average rate of £319 per night.

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

Book your Chesapeake Bay holiday in November or July to avoid a washout; these are the months with the least amount of rain.

Can you get deals on holiday homes in Chesapeake Bay?

You can get brilliant bargains on holiday homes in Chesapeake Bay with the nightly price of a let beginning at £53 - and HomeToGo has introduced plenty of filters that make it quick and simple to locate some outstanding offers. When choosing the dates for a trip, you can use HomeToGo's flexible dates technology to scan for low-price timings and see savings of up to 11%. In addition, HomeToGo's 'distance from' filter makes it easy to discover top quality accommodation offers in great value, under-the-radar locales with good proximity to your desired destination, whether that's a beach, lake, ski region or city centre. Book early to make the most of the greatest variety of options and the best deals - and do so free from stress by utilising HomeToGo's 'free cancellation' filter when you search.

What are the pros of choosing a holiday rental in Chesapeake Bay with HomeToGo?

From increased privacy away from the crowds to plenty of room to enjoy with your loved ones, holiday lettings in Chesapeake Bay bring a variety of benefits. HomeToGo surfaces real reviews written by previous guests, and searching is safe, easy, and stress-free - so with 8,647 offers from 16 providers in the area, you're bound to uncover the ideal place to stay with all of the amenities you need in Chesapeake Bay.

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