Chesapeake Beach Holiday Rentals

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Check prices for these dates

In two weeks
20 Feb - 22 Feb
In two months
3 Apr - 5 Apr
In three months
1 May - 3 May
In four months
29 May - 31 May

Our top choices for Chesapeake Beach holiday rentals

Exterior

Relax on Kent Island in a 4 Bedroom Home w/Waterview!

Relax on Kent Island in a 4 Bedroom Home w/Waterview!
Stevensville
9.8 out of 10, Exceptional, (43 reviews)
"We had a great stay! The property has everything we needed and host was easy to communicate with "
United States
Stephanie S.
The price is HK$751
HK$2,179 total
includes taxes & fees
17 Feb - 18 Feb
Relax on Kent Island in a 4 Bedroom Home w/Waterview!
Beach nearby

Walk to Beach! King Bed & Free Beach Passes

Walk to Beach! King Bed & Free Beach Passes
North Beach
10.0 out of 10, Exceptional, (18 reviews)
"We loved our stay! The property was just as advertised and had everything we needed. Quiet area and felt very safe. The owners provided excellent communication as well!"
United States
Jennifer B.
The price is HK$664
HK$2,596 total
includes taxes & fees
16 Feb - 17 Feb
Walk to Beach! King Bed & Free Beach Passes
Outdoor dining

Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants

Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants
North Beach
10.0 out of 10, Exceptional, (31 reviews)
"Perfect place to spend quality time with our three adult children and their significant others. "
United States
Malarkey F.
The price is HK$775
HK$3,185 total
includes taxes & fees
11 Feb - 12 Feb
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants
Dining

Haven 2

Haven 2
2.5 star property
Waldorf
The price is HK$357
HK$787 total
includes taxes & fees
12 Feb - 13 Feb
Haven 2
Fridge, microwave, oven, stovetop

Beautiful Waterfront Retreat in Cambridge!

Beautiful Waterfront Retreat in Cambridge!
Cambridge
10.0 out of 10, Exceptional, (50 reviews)
"The house was completely spotless - the location was perfect! And the host included a s'mores kit, and baited crab traps and had them waiting with crabs in them when we arrived! This was an excellent weekend - we would recommend Hudson House to anyone!"
United States
Elizabeth G.
The price is HK$1,934
HK$3,764 total
includes taxes & fees
9 Feb - 10 Feb
Beautiful Waterfront Retreat in Cambridge!
Sun-loungers

Cottage Located on the Patuxent River!

Cottage Located on the Patuxent River!
Prince Frederick
10.0 out of 10, Exceptional, (42 reviews)
"The accommodations were superb and being on the water was amazing!"
United States
Daniel P.
The price is HK$2,074
HK$2,480 total
includes taxes & fees
8 Feb - 9 Feb
Cottage Located on the Patuxent River!
Marina

Bay Ridge unit by Downtown Annapolis and Quiet Waters Park

Bay Ridge unit by Downtown Annapolis and Quiet Waters Park
Annapolis
8.8 out of 10, Excellent, (3 reviews)
"The place is very nice and comfortable inside. Quiet. Great place to sleep - no noise."
United States
William
The price is HK$1,347
HK$3,789 total
includes taxes & fees
8 Feb - 9 Feb
Bay Ridge unit by Downtown Annapolis and Quiet Waters Park
Smart TV

Peaceful 2-bedroom / 2-bathroom house with WiFi and AC in serene Shady Side

Peaceful 2-bedroom / 2-bathroom house with WiFi and AC in serene Shady Side
Shady Side
10.0 out of 10, Exceptional, (4 reviews)
"Would stay here again "
United States
Thomas D.
The price is HK$1,195
HK$3,438 total
includes taxes & fees
8 Feb - 9 Feb
Peaceful 2-bedroom / 2-bathroom house with WiFi and AC in serene Shady Side
Property grounds

Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.

Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.
Benedict
9.0 out of 10, Wonderful, (8 reviews)
"Just the perfect place I needed for a personal retreat. It is quiet, peaceful and serene. I would definitely visit again. "
United States
Berenice N.
The price is HK$1,406
HK$2,338 total
includes taxes & fees
8 Feb - 9 Feb
Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.
Beach nearby, sun-loungers, beach towels

Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach

Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
Arundel on the Bay
9.8 out of 10, Exceptional, (11 reviews)
"Great communication with the host, easy check in.. nice property. "
United States
Henry P.
The price is HK$1,723
HK$4,030 total
includes taxes & fees
9 Feb - 10 Feb
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
Beach

2 blocks from Bay! Community beach! Boat launch! Kayak! Hike! Fossil Hunt!

2 blocks from Bay! Community beach! Boat launch! Kayak! Hike! Fossil Hunt!
Prince Frederick
10.0 out of 10, Exceptional, (8 reviews)
"Such a cool neighborhood! Easy walk to an amazing private beach. Would love to stay again. "
United States
Olivia M.
The price is HK$1,563
HK$3,040 total
includes taxes & fees
9 Feb - 10 Feb
2 blocks from Bay! Community beach! Boat launch! Kayak! Hike! Fossil Hunt!
Beach

Charming 3-bedroom house with AC, WiFi in tranquil Edgewater on the bay .

Charming 3-bedroom house with AC, WiFi in tranquil Edgewater on the bay .
Edgewater
10.0 out of 10, Exceptional, (4 reviews)
"Great location, easy check in/out. Everything we needed was available! Very comfortable bed, super cute property. "
United States
MJ S.
The price is HK$1,758
HK$2,797 total
includes taxes & fees
8 Feb - 9 Feb
Charming 3-bedroom house with AC, WiFi in tranquil Edgewater on the bay .
Outdoor spa tub

London Towne Bungalow w/Loft - Walk to the Beach!

London Towne Bungalow w/Loft - Walk to the Beach!
Edgewater
8.8 out of 10, Excellent, (3 reviews)
"Very cute house. It was exactly what I was looking for. "
United States
Collin G.
The price is HK$1,086
HK$3,705 total
includes taxes & fees
8 Feb - 9 Feb
London Towne Bungalow w/Loft - Walk to the Beach!
Interior

Annapolis Retreat - 7 mins from downtown Annapolis!

Annapolis Retreat - 7 mins from downtown Annapolis!
Hillsmere
10.0 out of 10, Exceptional, (5 reviews)
"Great house in cute neighborhood. Thanks for a very comfortable stay!"
United States
Paul C.
The price is HK$1,242
HK$4,035 total
includes taxes & fees
9 Feb - 10 Feb
Annapolis Retreat - 7 mins from downtown Annapolis!
Interior

Lakefront Log Cabin Retreat w/ Hot tub + Kayaks!

Lakefront Log Cabin Retreat w/ Hot tub + Kayaks!
3.0 star property
Lusby
The price is HK$1,617
HK$4,103 total
includes taxes & fees
8 Feb - 9 Feb
Lakefront Log Cabin Retreat w/ Hot tub + Kayaks!
Fridge, microwave, oven, stovetop

Annapolis Gem: Stylish and Cozy

Annapolis Gem: Stylish and Cozy
Eastport
10.0 out of 10, Exceptional, (3 reviews)
"Great spot"
United States
Brian F.
The price is HK$1,934
HK$3,782 total
includes taxes & fees
8 Feb - 9 Feb
Annapolis Gem: Stylish and Cozy
Dining

Charming 3-bedroom in Upper Marlboro - Minutes from Washington, DC

Charming 3-bedroom in Upper Marlboro - Minutes from Washington, DC
Upper Marlboro
Charming 3-bedroom in Upper Marlboro - Minutes from Washington, DC
Smart TV

WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8

WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8
Cambridge
10.0 out of 10, Exceptional, (14 reviews)
"Amazing news out of the back.Great for kayaking.We brought our own kayaksAnd also use yoursThere were four of usWe also took a nice trip over to Saint Michael’s"
United States
Sandy S.
The price is HK$2,050
HK$4,127 total
includes taxes & fees
9 Feb - 10 Feb
WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8
Fridge, microwave, oven, stovetop

Golden Anchor Retreat; Lux Living! - Sleeps 7

Golden Anchor Retreat; Lux Living! - Sleeps 7
Edgewater
10.0 out of 10, Exceptional, (2 reviews)
"The property was beautiful with plenty of space to have a getaway with friends. The host was super communicative when we had issues with check in. Would highly recommend staying here!"
United States
Sam A.
The price is HK$1,555
HK$5,255 total
includes taxes & fees
8 Feb - 9 Feb
Golden Anchor Retreat; Lux Living! - Sleeps 7
TV, books, offices

Holly Hill Haven - Sleeps 10

Holly Hill Haven - Sleeps 10
Edgewater
10.0 out of 10, Exceptional, (3 reviews)
"House was clean and comfortable. Great layout. "
United States
Kristin G.
Holly Hill Haven - Sleeps 10
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Chesapeake Beach Hotel Reviews

Sonesta ES Suites Annapolis

Sonesta ES Suites Annapolis

10/10 Excellent
"We were happy to stay at this place. Very beautiful, warm, comfortable ❤️❤️❤️"
Olga 3-night trip
Posted 4 days ago
Sonesta ES Suites Annapolis

Find out more about Chesapeake Beach

Search for holiday rentals in Chesapeake Beach on Expedia! You can easily find your home rentals, villas, holiday apartments in Chesapeake Beach using one of the methods below:

  • View our selection of featured holiday rentals in Chesapeake Beach
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  • Enter your travel dates to view the best deals on holiday rentals in Chesapeake Beach while they last

Look no further and take a look at our great range of rental properties in Chesapeake Beach!

Frequently asked questions

Can I find a holiday rental in Chesapeake Beach?

Yes, there are holiday rentals in Chesapeake Beach close to Chesapeake Beach Water Park, or you can select a more secluded option if you're looking for a relaxing stay. Discover why Chesapeake Beach is known for its spas and beaches. While you're here, grab a bite or have a drink at the restaurants.

What are some of the best holiday rentals that Chesapeake Beach has to offer?

Mid-Century Modern on Private Beach, Designed by Award Winning Architect!: This highly rated holiday home rental in Chesapeake Beach is located on the beach, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. Kick off your shoes and enjoy yourself with a private garden and a selection of games.

How many holiday rentals will I find in Chesapeake Beach?

With 6 Expedia holiday rentals, you're guaranteed to find just the right place for your Chesapeake Beach stay.

What’s there to see and do in Chesapeake Beach?

Family-friendly attractions include Chesapeake Beach Water Park and Chesapeake Beach Railway Museum, whereas Breezy Point Beach and Northern Chesapeake Bay are a couple of great spots to enjoy the outdoors. Other places in town to visit include Rod n Reel Charter Fishing and Chesapeake Bay.

What’s a holiday rental in Chesapeake Beach like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Chesapeake Beach. Holiday rentals provide amenities like kitchens and laundry facilities so your stay will be comfortable. If you're concerned about cleanliness, a holiday rental can provide a sense of privacy away from public hotel lifts and busy front desks while still allowing you the enjoyment of travel. You'll also find more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a great option for small groups.