Holiday Homes in Western Shore of Maryland

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Check prices for these dates

Next weekend
29 Aug - 31 Aug
In two weeks
5 Sept - 7 Sept
In one month
19 Sept - 21 Sept
In two months
17 Oct - 19 Oct

Featured Holiday Homes in Western Shore of Maryland and around

Cozy Private Suite Gated Entry, Driveway Parking & Quiet Stay
Smart TV, fireplace

Cozy Private Suite Gated Entry, Driveway Parking & Quiet Stay

8.0 out of 10, Very good, (1)
"The property itself was very clean and cozy, and having our own private entry was also very nice. Towels and shower supplies were provided, and the bed was nice and comfortable. The host was also very kind and answered any questions we had. However, every morning we were woken up at around 7:30 am by someone (I assume children) stomping around right over our heads. There were also times we didn't really feel comfortable hanging out to watch TV in the living room area, because we could hear the...
The price is €111
includes taxes & fees
21 Aug - 22 Aug
Cozy Private Suite Gated Entry, Driveway Parking & Quiet Stay
Welcoming 4-bedroom house with AC in charming Street

Welcoming 4-bedroom house with AC in charming Street

The price is €539
includes taxes & fees
21 Aug - 22 Aug
Welcoming 4-bedroom house with AC in charming Street
Living in Luxury ..... Where Sophistication meets Elegance
Microwave, oven, stovetop, dishwasher

Living in Luxury ..... Where Sophistication meets Elegance

2.0 star property
The price is €389
includes taxes & fees
25 Aug - 26 Aug
Living in Luxury ..... Where Sophistication meets Elegance
* Lovely Gem w/ Perfect Combo of Flair & Class *
Fridge, microwave, oven, stovetop

* Lovely Gem w/ Perfect Combo of Flair & Class *

10.0 out of 10, Exceptional, (54)
"This little duplex is perfect for a couple of people and those traveling with a pet. The improvements made to the backyard, the parking spot, and the interior were all noticeable investments in comfort for guests. I look forward to my next trip to the area. Would definitely stay again"
The price is €235
includes taxes & fees
27 Aug - 28 Aug
* Lovely Gem w/ Perfect Combo of Flair & Class *
Canton’s Finest Luxury Stay: Walk to Park, Bars!
Interior

Canton’s Finest Luxury Stay: Walk to Park, Bars!

9.8 out of 10, Exceptional, (18)
"The host was great, the place was adorable and perfect for our stay. Very clean, had everything we needed and was close to everything. I highly recommend!"
The price is €225
includes taxes & fees
24 Aug - 25 Aug
Canton’s Finest Luxury Stay: Walk to Park, Bars!
* Beautiful Oasis w/ No Detail Spared *
Smart TV

* Beautiful Oasis w/ No Detail Spared *

9.8 out of 10, Exceptional, (44)
"Enjoyed my stay. Very clean and comfortable and the owners answered all my questions promptly."
The price is €167
includes taxes & fees
24 Aug - 25 Aug
* Beautiful Oasis w/ No Detail Spared *
Hidden Fells Point Gem / Private Courtyard Patio
Marina

Hidden Fells Point Gem / Private Courtyard Patio

9.6 out of 10, Exceptional, (87)
"Property is clean and efficiently designed, tastefully decorated and located in a safe, walkable area.I would recommend this location to anyone wanting to visitBaltimore."
The price is €179
includes taxes & fees
21 Aug - 22 Aug
Hidden Fells Point Gem / Private Courtyard Patio
Lower Level Loft - Adorable Studio Apt. Near BWI
1 bedroom, desk, free WiFi, bed sheets

Lower Level Loft - Adorable Studio Apt. Near BWI

9.4 out of 10, Exceptional, (12)
"This property was perfect for a one night stay. It had everything we needed and was super cozy."
The price is €112
includes taxes & fees
7 Sept - 8 Sept
Lower Level Loft - Adorable Studio Apt. Near BWI
Fox Cottage *Pet Friendly*
2 bedrooms, iron/ironing board, WiFi, bed sheets

Fox Cottage *Pet Friendly*

10.0 out of 10, Exceptional, (42)
"Quiet and beautiful "
The price is €248
includes taxes & fees
28 Aug - 29 Aug
Fox Cottage *Pet Friendly*
Cozy Home in Beautiful Annapolis
Exterior

Cozy Home in Beautiful Annapolis

10.0 out of 10, Exceptional, (13)
"Great property and very clean!"
The price is €252
includes taxes & fees
25 Aug - 26 Aug
Cozy Home in Beautiful Annapolis
family-friendly 2-bedroom home in Baltimore with WiFi, AC, Pool table, Poker
Fridge, microwave, oven, stovetop

family-friendly 2-bedroom home in Baltimore with WiFi, AC, Pool table, Poker

2.0 star property
10.0 out of 10, Exceptional, (2)
"Crystal responded very quickly (within an hour) to provide me with check-in instructions. The place looks exactly like the pictures, smelled amazing, and was very clean. I had a small get together for my partner’s birthday and we played pool as well as card games at the poker table. Everyone kept saying how much fun they were having at her place so I definitely recommend. 10/10 Crystal thank you so much!"
The price is €234
includes taxes & fees
2 Sept - 3 Sept
family-friendly 2-bedroom home in Baltimore with WiFi, AC, Pool table, Poker
Beach Home with King Bed and Beach Passes in a Cute Town
Beach nearby

Beach Home with King Bed and Beach Passes in a Cute Town

10.0 out of 10, Exceptional, (16)
"Excellent"
The price is €300
includes taxes & fees
24 Aug - 25 Aug
Beach Home with King Bed and Beach Passes in a Cute Town
Beach Front, Bay View, Fishing, chesapeake,Family Getaway
Pool

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."
The price is €350
includes taxes & fees
15 Sept - 16 Sept
Beach Front, Bay View, Fishing, chesapeake,Family Getaway
Parkside Gem: Luxe & Roomy by Historic Druid Hill l WIFI l Entire Unit
Exterior

Parkside Gem: Luxe & Roomy by Historic Druid Hill l WIFI l Entire Unit

The price is €210
includes taxes & fees
22 Aug - 23 Aug
Parkside Gem: Luxe & Roomy by Historic Druid Hill l WIFI l Entire Unit
Charming Pet-Friendly Stay - Near Bay & Beaches.
Interior

Charming Pet-Friendly Stay - Near Bay & Beaches.

10.0 out of 10, Exceptional, (3)
"Tons of space with lots of amenities! Super nice neighbor hood and neighbors. Very clean as well!"
The price is €446
includes taxes & fees
24 Aug - 25 Aug
Charming Pet-Friendly Stay - Near Bay & Beaches.
Charming Annapolis Beach Cottage by the Bay with Hot Tub, Gourmet Kitchen & Pier
Terrace/patio

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

10.0 out of 10, Exceptional, (9)
"Very clean - well equipped - perfect for our relaxing weekend."
The price is €418
includes taxes & fees
25 Aug - 26 Aug
Charming Annapolis Beach Cottage by the Bay with Hot Tub, Gourmet Kitchen & Pier
Cute bungalow blocks to Stadium
Fridge, microwave, oven, stovetop

Cute bungalow blocks to Stadium

10.0 out of 10, Exceptional, (5)
"We loved the layout, location, and porch- quality time with family with plenty to do and close USNA. We will stay here again!"
The price is €480
includes taxes & fees
21 Aug - 22 Aug
Cute bungalow blocks to Stadium
Cozy Baltimore Townhome
Fridge, microwave, oven, stovetop

Cozy Baltimore Townhome

9.6 out of 10, Exceptional, (14)
"Great Place"
The price is €271
includes taxes & fees
27 Aug - 28 Aug
Cozy Baltimore Townhome
The Cottage
Exterior

The Cottage

10.0 out of 10, Exceptional, (7)
"Beautiful, beautiful, beautiful! Haley was a wonderful host! "
The price is €412
includes taxes & fees
25 Aug - 26 Aug
The Cottage
Holly Hill Haven - Sleeps 10
TV, books, offices

Holly Hill Haven - Sleeps 10

10.0 out of 10, Exceptional, (3)
"House was clean and comfortable. Great layout. "
The price is €478
includes taxes & fees
22 Aug - 23 Aug
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 Western Shore of Maryland Hotel Reviews

Graduate by Hilton Annapolis

Graduate by Hilton Annapolis

10/10 Excellent
"Cool place, cool vibe! Loved all the pictures and the strong decor. Front desk check in and out was quick & efficient. The parking valets were quick and very friendly. Walking distance to shopping, restaurants and bars! The bed was super comfy! We would definitely stay here again!"
Hollie 1-night trip
Posted 9 hours ago
Graduate by Hilton Annapolis