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Holiday Homes in Chesapeake Beach

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Featured Holiday Homes in Chesapeake Beach and around

Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife
Fridge, microwave, oven, stovetop
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife
9.8 out of 10, Exceptional, (27)
"The house was perfect for our needs. It has a cute, fenced in yard so our 2 dogs could hang outside. It had everything we needed for a wonderful weekend birthday celebration!"
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife
Breathtaking Views, 450 pier, kayaks, fossils, priv beach, 45 min to D.C.
3 bedrooms, desk, iron/ironing board, free WiFi
Breathtaking Views, 450 pier, kayaks, fossils, priv beach, 45 min to D.C.
10.0 out of 10, Exceptional, (102)
"Loved the house!"
Breathtaking Views, 450 pier, kayaks, fossils, priv beach, 45 min to D.C.
Jackson's Bunker in Eastport with fenced-in backyard
Property grounds
Jackson's Bunker in Eastport with fenced-in backyard
10.0 out of 10, Exceptional, (7)
"This home has a fenced-in backyard and is dog-friendly, making it a good spot for visiting Annapolis with a dog in tow. Along with being a five-minute drive to downtown Annapolis, this home is also close to Quiet Waters Park. Sean is terrific at communicating; the complimentary wine and coffee were appreciated!"
Jackson's Bunker in Eastport with fenced-in backyard
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Eastport Cottage .5 mi from Downtown Annapolis
Exterior
Eastport Cottage .5 mi from Downtown Annapolis
10.0 out of 10, Exceptional, (52)
"Small but mighty Eastport house, super convenient to all thing Annapolis. Clean, equipped, comfortable. Mark is great at all things communication. Stay here….just not on the dates that I need it!"
Eastport Cottage .5 mi from Downtown Annapolis
NEW, cozy, waterfront, 5BR 4BA house w 2 decks near USNA & downtown
Fridge, microwave, oven, stovetop
NEW, cozy, waterfront, 5BR 4BA house w 2 decks near USNA & downtown
10.0 out of 10, Exceptional, (9)
"Our stay in Annapolis was a short and sweet 3-day visit for a wedding--my original focus was to have enough space for everyone to get ready without waiting in line. The property provided so much more than enough room. The entire house was very clean, well-appointed, and smartly laid out. The kitchen was stock with a wide range of food to get the weekend started off without the need to spend hours in the local grocery store. Throw in a great ping-pong table to make it even more fun. My only two...
NEW, cozy, waterfront, 5BR 4BA house w 2 decks near USNA & downtown
Waterfront Cambridge Gem w/ Hot Tub, Pool & Dock!
Fridge, microwave, stovetop, dishwasher
Waterfront Cambridge Gem w/ Hot Tub, Pool & Dock!
9.6 out of 10, Exceptional, (4)
"We extremely enjoyed our stay. The house was beautiful, kitchen was well equipped and the view was spectacular, especially with the Eagles that have nested on the 32 acre property. However was disappointed in the fact that the fire places were not in working conditions and rooms should have been number. We enjoy kayaking up and down the bay and taking it all in. I would definitely stay again."
Waterfront Cambridge Gem w/ Hot Tub, Pool & Dock!
Waterfront, dog-friendly home with private dock, kayaks, firepit & amazing yard
Property grounds
Waterfront, dog-friendly home with private dock, kayaks, firepit & amazing yard
9.6 out of 10, Exceptional, (12)
"Our stay in Oyster Harbor was very nice. The weather didn't cooperate but the house itself was very nice and I would certainly stay there again. It's about a 10 minute drive to downtown Annapolis so that made it convenient as well!"
Waterfront, dog-friendly home with private dock, kayaks, firepit & amazing yard
The Lazy Crab Beach House - Free beach passes
Property grounds
The Lazy Crab Beach House - Free beach passes
10.0 out of 10, Exceptional, (26)
"This wonderful property is a short walk to both the beach and restaurants. The check in and checkout process was smooth, the property was clean and stocked with necessary amenities (toiletries/kitchen products/ beach chairs and umbrella), and communication with the host was stellar. We will definitely be back!"
The Lazy Crab Beach House - Free beach passes
Dee's Lounge, Your Relaxation Oasis
Pool
Dee's Lounge, Your Relaxation Oasis
9.8 out of 10, Exceptional, (7)
"This home was beautiful and very accommodating for my guest and I. It was nice, cozy and clean and I didn’t need anything because she had it there. I will definitely book this again when I’m in the area. Thank you for your hospitality."
Dee's Lounge, Your Relaxation Oasis
The Hidaway on the Patuxent River<br>Children allowed and welcomed to stay.
3 bedrooms, iron/ironing board, WiFi, bed sheets
The Hidaway on the Patuxent River<br>Children allowed and welcomed to stay.
9.2 out of 10, Wonderful, (9)
"Got to go fishing, kayaking, and swimming in the pool. Had a great time, views are wonderful and it’s a peaceful environment. 10/10 would stay again."
The price is €459
per night
2 Jul - 3 Jul
The Hidaway on the Patuxent River<br>Children allowed and welcomed to stay.
The Normandy Cottage ~ Charming Getaway ~ On The Shores Of The Chesapeake!
Beach nearby
The Normandy Cottage ~ Charming Getaway ~ On The Shores Of The Chesapeake!
9.6 out of 10, Exceptional, (35)
"Great place for a short moms getaway. Walking distances to many things. Heard live music from the porch. House is spacious and extremely clean"
The Normandy Cottage ~ Charming Getaway ~ On The Shores Of The Chesapeake!
Spacious River Front Home - 90 minutes from DC with Dock, Kayaks & Paddleboards
Fridge, microwave, oven, stovetop
Spacious River Front Home - 90 minutes from DC with Dock, Kayaks & Paddleboards
9.8 out of 10, Exceptional, (15)
"The house was incredible. My husband loved the master shower! The kids enjoyed the beach and swimming. Our youngest son (39) paddled the creek in the kayak. Our oldest son was able to dock his boat. The house had so many amenities. The kitchen was well stocked. There were games and books for all ages. We hope this home is available whenever we go back to visit family. Thank you, Victoria, for being so gracious!"
Spacious River Front Home - 90 minutes from DC with Dock, Kayaks & Paddleboards
Large RENOVATED 6 bedroom 5 bath private home with LOTS of space!
Fridge, microwave, oven, stovetop
Large RENOVATED 6 bedroom 5 bath private home with LOTS of space!
9.6 out of 10, Exceptional, (24)
"If you have a big group this is the place for you! We had a great time!!"
Large RENOVATED 6 bedroom 5 bath private home with LOTS of space!
Blocks to the Boardwalk!
Beach nearby, sun-loungers, beach towels
Blocks to the Boardwalk!
9.8 out of 10, Exceptional, (28)
"Tammy was a great host and accomadated us in every way. Always available to answer any questions. It was pleasant and close to the boardwalk. It was perfect place for long term. It was easy process to check in and out."
Blocks to the Boardwalk!
Private Waterview Estate with 4 bedroom Suites & Hot Tub
Fridge, microwave, oven, stovetop
Private Waterview Estate with 4 bedroom Suites & Hot Tub
9.8 out of 10, Exceptional, (18)
"Great location and house! We all had a great time!"
Private Waterview Estate with 4 bedroom Suites & Hot Tub
Shewell’s Rambler in the Chesapeake Ranch Estates
View from property
Shewell’s Rambler in the Chesapeake Ranch Estates
9.2 out of 10, Wonderful, (19)
"Nice and super clean. Nice location. We will stay again next time we visit family. "
Shewell’s Rambler in the Chesapeake Ranch Estates
Grace Cottage, Saint Michaels Walk to everything!
Property grounds
Grace Cottage, Saint Michaels Walk to everything!
10.0 out of 10, Exceptional, (1)
"Beautiful house. Great location. Host was very responsive to questions. Thanks for a great stay"
Grace Cottage, Saint Michaels Walk to everything!
Hudson Creek Retreat, 5 Acre Waterfront Home, Pool, Pier, Fishing & Crabbing
6 bedrooms, iron/ironing board, WiFi, bed sheets
Hudson Creek Retreat, 5 Acre Waterfront Home, Pool, Pier, Fishing & Crabbing
Hudson Creek Retreat, 5 Acre Waterfront Home, Pool, Pier, Fishing & Crabbing
The SPOT In the Gleneagle community of Waldorf Maryland near St. Charles Mall
Fridge, microwave, oven, stovetop
The SPOT In the Gleneagle community of Waldorf Maryland near St. Charles Mall
10.0 out of 10, Exceptional, (3)
"Great Hospitality "
The SPOT In the Gleneagle community of Waldorf Maryland near St. Charles Mall
2 blocks from Bay! Private beach! Boat launch! Kayak! Hike! No cleaning fee!
Beach
2 blocks from Bay! Private beach! Boat launch! Kayak! Hike! No cleaning fee!
2 blocks from Bay! Private beach! Boat launch! Kayak! Hike! No cleaning fee!
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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.

Other property types in Chesapeake Beach

Beach Front, Bay View, Fishing, chesapeake,Family Getaway
Pool
Beach Front, Bay View, Fishing, chesapeake,Family Getaway
10.0 out of 10, Exceptional, (1)
"The house was clean and quiet. The hosts were helpful and available for communication. This is a lovely house for a vacation away from crowds and by the beach."
The price is €913
per night
12 Jul - 13 Jul
Beach Front, Bay View, Fishing, chesapeake,Family Getaway
Mid-Century Modern and Marvelous on the Bay
Property grounds
Mid-Century Modern and Marvelous on the Bay
10.0 out of 10, Exceptional, (62)
"The house is a perfect retreat! I watched the sunrise from my bedroom and porch with my coffee each day of our stay. My parents live just 2 doors down. I have been coming to this neighborhood since the 70's. I still love hunting for fossils on the beach. Thank you for allowing us to book this spot!"
Mid-Century Modern and Marvelous on the Bay
Pool and Bay Views on wrap around deck in Kent Island
Outdoor pool
Pool and Bay Views on wrap around deck in Kent Island
9.6 out of 10, Exceptional, (21)
"Everyone really loved the house and the location. The pool was great"
Pool and Bay Views on wrap around deck in Kent Island
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.

Chesapeake Beach Holiday Homes information

Number of reviews
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 Holiday Homes
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Recent Reviews in Chesapeake Beach
Expedia verified reviews

Econo Lodge Andrews Air Force Base

Econo Lodge Andrews Air Force Base

5/5 Excellent
"It was relaxing "
A verified traveller stayed at Econo Lodge Andrews Air Force Base
Posted 2 days ago
Econo Lodge Andrews Air Force Base