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Holiday Homes in Chesapeake Beach

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Check prices for these dates

Next weekend
24 Oct - 26 Oct
In two weeks
31 Oct - 2 Nov
In one month
14 Nov - 16 Nov
In two months
12 Dec - 14 Dec

Featured Holiday Homes in Chesapeake Beach

Pool
Beach Front, Bay View, Fishing, chesapeake,Family Getaway
Beach Front, Bay View, Fishing, chesapeake,Family Getaway
9.0 out of 10, Wonderful, (6)
"Everything was great. The owner was extremely helpful. Couldn't ask for anything better."
United States
Bryan P.
The price is AU$703
includes taxes & fees
18 Nov - 19 Nov
Beach Front, Bay View, Fishing, chesapeake,Family Getaway
Marina
Relax on Kent Island in 3 Bedroom Home w/Waterview
Relax on Kent Island in 3 Bedroom Home w/Waterview
9.8 out of 10, Exceptional, (41)
"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 AU$488
includes taxes & fees
16 Nov - 17 Nov
Relax on Kent Island in 3 Bedroom Home w/Waterview
TV
Relaxing Getaway w/ Huge Lounge and Bedroom
Relaxing Getaway w/ Huge Lounge and Bedroom
2.0 star property
The price is AU$244
includes taxes & fees
22 Oct - 23 Oct
Relaxing Getaway w/ Huge Lounge and Bedroom
Interior
Beautiful Waterfront Retreat in Cambridge!
Beautiful Waterfront Retreat in Cambridge!
10.0 out of 10, Exceptional, (48)
"Property was as listed. We enjoyed are stay."
United States
Jennifer S.
The price is AU$611
includes taxes & fees
22 Oct - 23 Oct
Beautiful Waterfront Retreat in Cambridge!
Beach nearby
Walk to Beach! King Bed & Free Beach Passes
Walk to Beach! King Bed & Free Beach Passes
10.0 out of 10, Exceptional, (16)
"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 AU$540
includes taxes & fees
20 Oct - 21 Oct
Walk to Beach! King Bed & Free Beach Passes
Terrace/patio
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
10.0 out of 10, Exceptional, (10)
"Very clean - well equipped - perfect for our relaxing weekend."
United States
Chris J.
The price is AU$736
includes taxes & fees
27 Oct - 28 Oct
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
Microwave, oven, stovetop, dishwasher
Annapolis Retreat - 7 mins from downtown Annapolis!
Annapolis Retreat - 7 mins from downtown Annapolis!
10.0 out of 10, Exceptional, (3)
"Great house in cute neighborhood. Thanks for a very comfortable stay!"
United States
Paul C.
The price is AU$862
includes taxes & fees
11 Nov - 12 Nov
Annapolis Retreat - 7 mins from downtown Annapolis!
Marina
London Towne Bungalow w/Loft - Walk to the Beach!
London Towne Bungalow w/Loft - Walk to the Beach!
8.0 out of 10, Very good, (2)
"The water that comes out of the house tastes bad."
United States
Mario A.
The price is AU$728
includes taxes & fees
30 Oct - 31 Oct
London Towne Bungalow w/Loft - Walk to the Beach!
Exterior
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
10.0 out of 10, Exceptional, (3)
"Very comfortable bedrooms and sitting area. Perfect location for the event we were attending. Very clean. Friendly host. "
United States
Mark E.
The price is AU$661
includes taxes & fees
20 Oct - 21 Oct
Peaceful 2-bedroom / 2-bathroom house with WiFi and AC in serene Shady Side
Beach nearby, sun-loungers, beach towels
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants
10.0 out of 10, Exceptional, (30)
"Absolutely beautiful and spacious home perfectly located in North Beach. Very peaceful area and close to the beach, restaurants and shopping. We really enjoyed our stay and hope to visit again in the future. "
United States
Vicki K.
The price is AU$642
includes taxes & fees
20 Oct - 21 Oct
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants
Fridge, microwave, oven, stovetop
Edgewater/Mayo Gateaway w/ Hot Tub
Edgewater/Mayo Gateaway w/ Hot Tub
9.8 out of 10, Exceptional, (23)
"Very clean, had everything we needed for our stay!"
United States
Jackie R.
The price is AU$894
includes taxes & fees
22 Oct - 23 Oct
Edgewater/Mayo Gateaway w/ Hot Tub
TV, books, offices
Holly Hill Haven - Sleeps 10
Holly Hill Haven - Sleeps 10
10.0 out of 10, Exceptional, (3)
"House was clean and comfortable. Great layout. "
United States
Kristin G.
The price is AU$765
includes taxes & fees
3 Nov - 4 Nov
Holly Hill Haven - Sleeps 10
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!
10.0 out of 10, Exceptional, (7)
"Clean and easy "
United States
Robert R.
The price is AU$565
includes taxes & fees
26 Oct - 27 Oct
2 blocks from Bay! Community beach! Boat launch! Kayak! Hike! Fossil Hunt!
Smart TV
WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8
WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8
10.0 out of 10, Exceptional, (14)
"Second time staying at this lovely, serene home/property. It’s the perfect getaway if you’re looking to escape into some peace! Highly recommend "
United States
Jill C.
The price is AU$871
includes taxes & fees
21 Oct - 22 Oct
WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8
3 bedrooms, iron/ironing board, WiFi, bed sheets
Welcoming 3-bedroom townhome with AC in Waldorf
Welcoming 3-bedroom townhome with AC in Waldorf
10.0 out of 10, Exceptional, (1)
"When we walked in, the host had the dining room table set nicely. We thought, "Wow, this place is fancy." We enjoyed the ping pong table and plenty of rooms for our family gathering. "
United States
Keith A.
The price is AU$487
includes taxes & fees
2 Nov - 3 Nov
Welcoming 3-bedroom townhome with AC in Waldorf
Interior
Golden Anchor Retreat; Lux Living! - Sleeps 7
Golden Anchor Retreat; Lux Living! - Sleeps 7
10.0 out of 10, Exceptional, (2)
"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 AU$996
includes taxes & fees
5 Nov - 6 Nov
Golden Anchor Retreat; Lux Living! - Sleeps 7
Fridge, microwave, oven, stovetop
Tranquil Modern Farmhouse
Tranquil Modern Farmhouse
9.4 out of 10, Exceptional, (6)
"This property was super gorgeous and spacious so we were able to relax. Guests had more than enough space and didn’t feel like they were on top of each other sleeping wise! We were able to just have dinner and feel safe! The owner answered any questions we had within 15 minutes, which was super helpful! "
United States
khaddija j.
The price is AU$822
includes taxes & fees
28 Oct - 29 Oct
Tranquil Modern Farmhouse
Terrace/patio
2BR, 1BA Boutique Brick Beauty located in historic Eastport.
2BR, 1BA Boutique Brick Beauty located in historic Eastport.
The price is AU$559
includes taxes & fees
20 Oct - 21 Oct
2BR, 1BA Boutique Brick Beauty located in historic Eastport.
3 bedrooms, iron/ironing board, travel cot, free WiFi
Kick back and enjoy the Chesapeake & this 3-bedroom, relaxing, stylish space.
Kick back and enjoy the Chesapeake & this 3-bedroom, relaxing, stylish space.
9.4 out of 10, Exceptional, (3)
"We had a short stay after a sporting event in DC, it was a little less than an hour away. Convenient location and a very clean house. Kitchen was well stocked. There was little communication with the owner, which was nice vs a long list of rules, but we would have liked to know any of their local specific favorite spots or more detailed check in/check out. Worked out nicely for our family. "
United States
Carrie K.
The price is AU$623
includes taxes & fees
3 Nov - 4 Nov
Kick back and enjoy the Chesapeake & this 3-bedroom, relaxing, stylish space.
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 .
The price is AU$602
includes taxes & fees
2 Nov - 3 Nov
Charming 3-bedroom house with AC, WiFi in tranquil Edgewater on the bay .
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
"The 2 bedroom suite was wonderful, and loved the fact that each room had its own bathroom. The kitchenette was great also. Only drawback was getting back later in the evening after a concert, was a bit sketchy as there was a woman just hanging around outside the building, unsure if homeless or not but more security in the evenings would be a good thing"
Patricia 2-night trip
Posted 21 hours ago
Sonesta ES Suites Annapolis

Find out more about Chesapeake Beach

Chesapeake Beach Holiday Homes information

Number of reviews
204
Accommodation
402 Holiday Homes
Lowest Price
AU$244
Highest Price
AU$996