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Luxe Chesapeake Bay Getaway < 20 Mi to Annapolis!

your current months are December, 2024 and January, 2025.
December 2024
January 2025

Photo gallery for Luxe Chesapeake Bay Getaway < 20 Mi to Annapolis!

Interior
Beach
Property grounds
Beach
TV

Reviews

9.8 out of 10

Exceptional

Entire home

3 bedrooms2 bathroomsSleeps 6153 sq m

Popular amenities

  • Beach view
    Beach view
  • Parking available
    Parking available
  • Outdoor space
    Outdoor space
  • Kitchen
    Kitchen
  • Air conditioning
    Air conditioning

Explore the area

Map
Shady Side, Maryland
  • Shadyside Park
    7 min drive
  • Captain Avery Museum
    8 min drive
  • U.S. Naval Academy
    33 min drive
  • Washington, DC (DCA-Ronald Reagan Washington National)
    53 min drive

Room options

Similar properties

Private kitchen

The Cottage

Washer
Dryer
Pet-friendly
Free WiFi
5.0 out of 5, Exceptional, (1)
The price is AU$667
for 1 night
includes taxes & fees
7 Dec - 8 Dec
The Cottage

About the area

Shady Side

Located in Shady Side, this vacation home is a 5-minute drive from Franklin Point State Park and 7 minutes from Shadyside Park. .This vacation home is 20.7 mi (33.2 km) from U.S. Naval Academy and 2.9 mi (4.7 km) from Captain Avery Museum.
View more Holiday homes in Shady SideOpens in a new window

What's nearby

  • Westfield Annapolis Mall - 28 min drive - 28.6 km
  • Navy-Marine Corps Memorial Stadium - 30 min drive - 30.9 km
  • Annapolis City Dock - 32 min drive - 32.8 km
  • U.S. Naval Academy - 33 min drive - 33.3 km
  • Maryland Quiet Waters Park - 37 min drive - 34.0 km

Getting around

  • Fort Meade, MD (FME-Tipton) - 46 min drive

Restaurants

  • ‪Pirates Cove Restaurant - ‬14 min drive
  • ‪Skippers Pier - ‬13 min drive
  • ‪Happy Harbor Inn - ‬12 min drive
  • ‪Petie Greens - ‬12 min drive
  • ‪Old Stein Inn - ‬22 min drive

About this property

Entire place

You'll have the entire home to yourself and will only share it with other guests in your party.

Luxe Chesapeake Bay Getaway < 20 Mi to Annapolis!

A quiet, seaside escape awaits at this Shady Side vacation rental, hosting 3 bedrooms, 2 baths, at-home comforts and access to the neighborhood’s amenities - including a boat launch, pier, and more! Enjoy peaceful mornings strolling along the shore, then venture only minutes to explore unique attractions in this quaint bay town. Opt for a day trip to Annapolis, Baltimore, or D.C., then return home and relax by whipping up a home-cooked meal and sharing a family movie night.

-- THE PROPERTY --

STR-000026 | Bayfront Destination | Private Community | Contemporary Design

With access to Columbia Beach amenities and proximity to the historic area’s best sites, this home-away-from-home offers an ideal East Coast retreat for families and groups of friends.

Bedroom 1: King Bed | Bedroom 2: Queen Bed | Bedroom 3: Queen Bed

OUTDOOR LIVING: Private yard & waterfront, gas grill, community basketball court, playground, boat launch & pier
KITCHEN: Fully equipped, tile floors, built-in counter stovetop, stainless steel refrigerator, coffee maker, convection oven, microwave, toaster, cooking essentials, knife set, dishware, glassware, silverware
INTERIOR FEATURES: Smart TVs, large picture windows, sliding doors accessing stairs to yard, spiral staircase, laundry machines, 2 shower/tub combos
GENERAL: Free WiFi, central heat & A/C, iron & ironing board, hair dryers, essentials like toiletries, trash bags, etc
FAQ: Fireplace is only decorative
PARKING: Driveway (2 vehicles)

-- THE LOCATION --

LOCAL FUN: The Corner Grill (1.3 miles), Renno's Quality Food Market (1.5 miles), Brick House Restaurant (1.9 miles), Sandra Lee Charters (2.1 miles), Franklin Point State Park (2.3 miles), Drift Wood Diner (2.4 miles), John Marshall Park (2.9 miles), Chesapeake Yacht Club (3.0 miles), Captain Salem Avery Museum (3.0 miles), Miss Edie Chesapeake Bay Fishing Charters (4.4 miles), Chalk Point Marine (4.5 miles)
NEARBY: Annapolis (19.7 miles), Kent Island (35.8 miles), Washington D.C. (36.8 miles), Baltimore (43.5 miles)
AIRPORTS: Ronald Reagan Washington National Airport (38.3 miles), Baltimore/Washington International Thurgood Marshall Airport (38.5 miles)

-- REST EASY WITH US --

Evolve makes it easy to find and book properties you'll never want to leave. You can relax knowing that our properties will always be ready for you and that we'll answer the phone 24/7. Even better, if anything is off about your stay, we'll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you.

-- POLICIES --

- No smoking
- No pets allowed
- No events, parties or large gatherings
- NOTE: The fireplaces are not available for guest use
- Must be at least 25 years old to book
- Additional fees and taxes may apply
- Photo ID may be required upon check-in
Make yourself comfortable in this air-conditioned vacation home, featuring a kitchen with a refrigerator and a stovetop. Conveniences include a microwave and a coffee/tea maker.
Guests will find features like wireless internet access and onsite parking.

Property manager

Evolve

Languages

English, French, German, Spanish

Property amenities

Internet

  • WiFi available

Parking and transport

  • On-site parking

Kitchen

  • Fridge
  • Stovetop
  • Microwave
  • Dishwasher
  • Spices
  • Coffee/tea maker
  • Cookware/dishes/utensils
  • Toaster

Bedrooms

  • 3 bedrooms

Bathrooms

  • 2 bathrooms
  • Hairdryer

Living spaces

  • Dining room

Entertainment

  • TV with cable/satellite service

Outdoor areas

  • Garden

Comfort

  • Air conditioning
  • Heating

Pets

  • No pets allowed

Suitability/Accessibility

  • Smoke-free property

Services and conveniences

  • Iron/ironing board

Location highlights

  • Near the bay

Things to do

  • Basketball nearby
  • Power boating nearby

Safety features

  • Carbon monoxide detector installed (host has indicated that there is a carbon monoxide detector on the property)
  • Smoke detector installed (host has indicated that there is a smoke detector on the property)
  • First aid kit

General

  • Unit size: 1650 sq ft (153 sq m)
  • Property does not allow children

Policies

Check-in

Check-in time starts at 3:00 PM
Minimum check-in age: 25

Check-out

Check-out before 10:00 AM

Special check-in instructions

You will receive an email from the host with check-in and check-out instructions

Pets

Pets not allowed

Children and extra beds

This property does not allow children

Important information

You need to know

Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card, or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
Onsite parties or group events are strictly prohibited
Host has indicated there is a carbon monoxide detector on the property
Host has indicated there is a smoke detector on the property
Safety features at this property include a first aid kit
This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation
Property Registration Number STR 26;STR 26

Property is also known as

440816
NEW! Chesapeake Bay Getaway < 20 Mi to Annapolis!
Luxe Chesapeake Bay Getaway < 20 Mi to Annapolis! Shady Side

Luxe Chesapeake Bay Getaway < 20 Mi to Annapolis! Reviews

Reviews

9.8

Exceptional

Rating 10 - Excellent. 48 out of 54 reviews" "
Rating 8 - Good. 6 out of 54 reviews" "
Rating 6 - Okay. 0 out of 54 reviews" "
Rating 4 - Poor. 0 out of 54 reviews" "
Rating 2 - Terrible. 0 out of 54 reviews" "

9.8/10

Cleanliness

Reviews

10/10 Excellent

Susana B.

Liked: Cleanliness
Relaxation Heaven
This house was so bright and happy! Right on the bay. Nothing more relaxing than listening to waves when you are going to bed or first thing in the morning.
Stayed 3 nights in Oct 2024

10/10 Excellent

Tim Y.

Liked: Cleanliness
Great Family Getaway Spot
Wonderful jewel of a place!! Perfect for a family getaway over Labor Day Weekend! Lovely and clean, incredibly well-stocked kitchen, and great outdoor space for relaxing. We loved our time here!!
Stayed 3 nights in Aug 2024

10/10 Excellent

Gregory H.

Liked: Cleanliness
Nice house, beautiful view, friendly owners
Nice house, beautiful view, & friendly owners. Only thing is circular stairs were taller than regular stairs, so make sure you hold on the rail. House was extremely clean so we left a tip for the cleaning crew. They did a great job. Saw a fox, osprey bird, and some skates in the water. Would definitely go back again. Had lunch at Ketch22 at Harrington Harbor about 20 min away. Strongly recommend going there. Very happy with long weekend there.
Stayed 3 nights in Jul 2024

10/10 Excellent

Bevi P.

Liked: Cleanliness
Postcard Views from this Vacation Gem!
This beautiful waterfront home offered our family the peaceful respite from hectic schedules. The calming water views and warmth of the decor were a welcomed setting for a wonderful family get-away. The kitchen was generously stocked. The beds were comfortable, and the living room offered an area for many conversations and laughter. We enjoyed a quick trip to Annapolis, a day at North Beach and meals at our local favorites - Ledo Pizza, Ketch 22 at Herrington Harbor and Hook and Vine. We were sad that the Bakist Bakery was closed for this trip but we will catch them the next stay. We spent some fun-filled hours cooling off at the community beach - a very small and private inlet. There are lots of options within driving distance at this quiet and peaceful location. We will be back!
Stayed 4 nights in Jun 2024

10/10 Excellent

Allison S.

Liked: Cleanliness
Perfect birthday stay
I chose this house for the family to gather to celebrate my husband’s 65th birthday and it was perfect: immaculate, well stocked, comfortable, beautiful views of the water, nice neighborhood for walking. My husband says he couldn’t imagine a better birthday.
Stayed 4 nights in May 2024

10/10 Excellent

Kimberly H.

Liked: Cleanliness
Home away from home
The home is just right for what we were looking for and stocked with more than you'll need of everything you have at home. The host is warm and responsive.
Stayed 6 nights in Mar 2024

8/10 Good

Francisco A.

Liked: Cleanliness
Amazing home
This house was exactly as advertised. If you're looking for a quiet, relaxing getaway, book this home. Joy was amazing and even reached out personally before check in to ensure we had everything we needed. It's a bit of a hike to get to decent restaurants and such, but so worth it for this view every morning and the peace and quiet. Home was comfortable, clean, and had everything we needed and more. Would absolutely stay again.
Stayed 3 nights in Mar 2024

8/10 Good

Ilona M.

Liked: Cleanliness
Summer weekend
It was nice relaxing place near water
Stayed 3 nights in Jul 2023

10/10 Excellent

Elena P.

Liked: Cleanliness
Great stay (but for the rain)
Really enjoyed the home. Quiet, clean with everything we needed for a 3-day stay. On the Bay for wonderful views and the sound of the waves breaking on the shore. Clear instructions received in advance. Only minor issue is that if possible, the Wi-Fi should be upgraded. It could not handle three computers at once)))). Overall, we love this place. Thank you!
Stayed 3 nights in Jun 2023

10/10 Excellent

John T.

Liked: Cleanliness
Very nice stay
Impeccably clean, well designed home. Really a top notch home to stay,
Stayed 4 nights in May 2023

10/10 Excellent

Greg B.

Liked: Cleanliness
Great stay & wonderful views
We had a great time at the home. Everything was just as it was shown online. Both Joy and the listing service were very responsive to our questions and accommodating. The neighborhood was quite and friendly. This was a great location for us and had a great time fishing the Chesapeake! We will return!! gb
Stayed 3 nights in May 2023

10/10 Excellent

Joseph G.

Liked: Cleanliness
Paradise awaits your arrival!
This place is beautiful!! Clean and picturesque! Right on the Chesapeake Bay and and a view that captivates!!! So much so that we never turned the tv on once!! The owner is excellent and super friendly with clear directions to get to the house. We were in awe with the beauty of the house, the community pier and the sheer beauty of the location!! We will definitely be making a return visit!!
Stayed 3 nights in Mar 2023

8/10 Good

Rhonda J.

Liked: Cleanliness
Overall, very nice property
The house itself is a gem. The water view from the living room/kitchen/eating area is stunning and it's the same gorgeous view from the master bedroom, which has a lovely sitting area. Perfect for sipping coffee and watching the sun rise in the morning and set in the evening. It was nice to have a small balcony and yard to sit outside. The furniture is very comfortable, the home is stocked with the essentials and a few extra goodies, and the owner is wonderful to communicate with. Just a few small things - First, the neighborhood is just okay. Even though this is a gated community, the houses are in various states, with some being run down and in disrepair. Though people seemed friendly enough and waived as we passed them in the car, we wouldn't go walking around at night and there weren't any nice places to eat within a short driving distance. Also, the water in the shower on the main level had a strong sulfur smell, the air filters and vents on the main level and 2nd level looked like they hadn't been changed/cleaned in years, and the refrigerator and ceiling in the kitchen could have been a bit cleaner. All in all, given the price point of this home in Shady Side, it's definitely worth considering. We enjoyed our stay.
Stayed 4 nights in Dec 2022

10/10 Excellent

Ramon C.

Liked: Cleanliness
Very nice place to stay!
Nice and cozy Home near to the water with beautiful views, very peaceful, quiet and confortable. Definitely will come back. Thank you to the property owner to let us enjoy their beautiful place.
Stayed 4 nights in Nov 2022

10/10 Excellent

Anna M.

Liked: Cleanliness
Excellent
Our time at this house was wonderful. We are able to rest, recharge and enjoy the beautiful views of the bay. The house was clean and had everything we needed. Look forward to being back.
Stayed 4 nights in Oct 2022

10/10 Excellent

Steve H.

Liked: Cleanliness
Came for the U of H vs Navy game.
The house furnishings and view are better than described. 3 comfortable beds and a fully stocked kitchen. The view from both upstairs and downstairs was so relaxing. This is the best VRBO home overall that we have stayed at will definitely stay again when in the area
Stayed 4 nights in Oct 2022

10/10 Excellent

Mitchell B.

Liked: Cleanliness
Wonderful place to stay for quiet getaway on the bay
We visited Maryland for the Annapolis sailboat show. As far as the drive from this BNB to Annapolis it was a little further than we would’ve liked (round 35 minutes). So if your doing the same make sure you bring what’s needed to be away from the house for the day cause once you find parking in Annapolis you won’t wanna to find it again. On the upside of the location there are a few very nice small towns in the surrounding area such as Shady Side and Deale if your looking to just hangout in the area for the day. The house is RIGHT (like 15 yards from the water)on the bay which made for spectacular views of the sunrise and passing sailboats in the distance. There is a great peer just a short walk away for an even better view. Our one complaint was the guest bed upstairs was very hard so we ended up staying in the downstairs bedroom which was great. Our friends stayed in the master bedroom which faced the bay and has great views and big windows that can be opened to let in the breeze from the sea. The neighborhood is very quiet and the few people we saw were very nice. All in all we had a wonderful experience and would rent the home again if we decide to go back to the area.
Stayed 3 nights in Oct 2022

10/10 Excellent

Zach G.

Liked: Cleanliness
Perfection
It was a perfect escape for our honeymoon. Everything in the photos were a great representation of the place, except there's no way to capture how beautiful the sunrise is in person. From the master bedroom, it's great, from the benches by the fishing pier, it's breathtaking. Annapolis is great, but don't miss the great local restaurants in Deale. So happy we took the kayaks and fishing rods. Had so much fun, and feel so relaxed. We would love to go back with friends some time.
Stayed 5 nights in Sep 2022

10/10 Excellent

CeCe G.

Liked: Cleanliness
Beautiful home in the most peaceful location
Stunning views of the bay. Meticulously clean home. Kind and warm hosts. Very peaceful stay. My soul has been restored after this wonderful retreat.
Stayed 3 nights in Aug 2022

10/10 Excellent

Kathryn P., Emerald Hills

Liked: Cleanliness
Fun on Chesapeake Bay
My two sisters and I spent a week at this property. The size was perfect for us with 2 bedrooms upstairs and 1 downstairs. Kitchen was a bit small but certainly adequate. Loved the sound of the water at night. Right on the water but you need to go to a beach if you wish to swim. The neighborhood was very quiet. We went into Annapolis 3 times...takes about 35 min. We loved our week here which included lots of good seafood.
Stayed 7 nights in Aug 2022

10/10 Excellent

Jessica L.

Liked: Cleanliness
Loved it
We loved staying here! Such a beautiful area and having the water right out of the back door was amazing. The property is just as described, comfortable, and the neighborhood was great.
Stayed 4 nights in Jul 2022

10/10 Excellent

Steve R.

Liked: Cleanliness
Wonderful Time
Property was as advertised. Right on the bay and very peaceful. Spent a great deal of time just watching and listening to the water. Very relaxing. Would return in the fall when it is not so hot and humid.
Stayed 8 nights in Jul 2022

10/10 Excellent

Julie Ann M.

Liked: Cleanliness
Incredible!
Everything it says it is and more! Little touches make it feel like home—a magical getaway!
Stayed 5 nights in Jun 2022

10/10 Excellent

Malissa P.

Liked: Cleanliness
We loved it!
Walking into the house we were just blown away of the view!! We enjoyed just sitting outside every single day. It made our visit very relaxing. House was amazing as well. Had everything we could need.
Stayed 3 nights in May 2022

10/10 Excellent

Sam B.

Liked: Cleanliness
lovely PROPERTY
great trip AND PROPERTY AND LOVELY VIEW VERY QUIET AND PEACEFUL.
Stayed 5 nights in Jun 2022