Vacation Rentals By Owner In Chesapeake Beach, MD

$381.6
/ Nightly

Private Vacation Home

Mid-Century Modern on Private Beach, Designed by Award Winning Architect!

Chesapeake Beach, Maryland, United States
Come enjoy living in mid-century modern style, with sweeping views of the Chesapeake Bay, all within a short drive from the Washington, DC metropolitan area, Annapolis, Solomons Island, fishing charters and our many local historic sites. This property is also U.S. Army veteran (Afghanistan and Iraq) owned and operated, as well as LGBTQ safe and friendly. brbrAward winning local architect, James William Ritter III, of Ritter-Norton Architecture, located in Alexandria, Virginia, purchased, completely rebuilt and redesigned this home for his wife and himself, when they began their retirement. The architect's son, Mark Ritter, and his spouse, Nicholas Knowlton, now own the home and want to welcome you to enjoy this unique house and its magical setting. https://www.ritternorton.com/jamesbrbrHere, you'll enjoy the true modern ideal of blurring the lines between interior and exterior spaces. Wake up in the morning to the sounds of seabirds calling and waves lapping on the beach. Start your day right, in our open, multi-head, shower stall, with heated floors and protected views of our perennial garden. A huge bank of windows and sliding glass doors makes the Bay the centerpiece of the entire living and kitchen areas. The house draws you outside to enjoy a morning cup of coffee on the veranda, head down the stairs for direct access to a day on the beach or simply enjoy a glass of wine, while relaxing with a book in the hammock. brbrDisclosure: We have hard water. Most of our renters had no complaints or issues, but it has bothered one or two. Therefore, we decided to be upfront about it, rather than have a renter find out upon arrival. Hard water is a problem you’ll unfortunately find in almost any home in this region. We do not provide refunds relating to this issue, given this upfront disclosure.

2
Bed

1
Bath

4
Sleeps

Exceptional(5)

$134.63
/ Nightly

Cottage

Coastal Pet-Friendly Cottage < 1/2 Mi to Beaches

Chesapeake Beach, Maryland, United States
Escape to Chesapeake Beach and relax effortlessly thanks to this 2-bed, 1-bath cottage! Sporting a spacious fenced-in backyard with cushioned patio furniture, this vacation rental is the epitome of seaside living. Spend your days soaking up the sun at Brownie’s Beach or casting off with Reel Attitude Charters! Out-of-towners will love the ability to visit Washington D.C. for the day, and those looking to unwind from every day will simply love beach days filled with sun, family, and friends.brbr-- THE PROPERTY --brbrFree WiFi | Walk to Beaches | Fenced-In BackyardbrbrLounge in a private backyard, on the beach, or visit local attractions, all while enjoying this quaint seaside getaway with the family!brbrBedroom 1: Full Bed | Bedroom 2: Twin Daybed w/ Trundle | Living Room: Sleeper Sofa brbrOUTDOOR LIVING: Partially fenced-in backyard (not fully enclosed), cushioned patio furniture, gas grill, front porchbrINDOOR LIVING: 2 Flat-screen Smart TVs, open main living space, breakfast tablebrKITCHEN: Well equipped w/ cooking basics & spices, coffee maker, toasterbrGENERAL: Linens/towels, free WiFi, complimentary toiletries, trash bags, paper towels, iron/board, washer/dryer, central heating & A/CbrFAQ: Pet fee (paid pre-trip)brPARKING: Free street parking (first-come, first-served)brbr-- THE LOCATION --brbrBEACHES: Chesapeake Beach Veterans Memorial Park (0.1 miles), North Beach Boardwalk/Beach (0.8 miles), Bayfront Park (1.3 miles), Brownie’s Beach (1.5 miles), Breezy Point Beach (6.5 miles)brOUTDOOR RECREATION: Tyler’s Tackle Shop & Crab House (0.2 miles), Reel Attitude Charters (0.6 miles), Katherine Charter Fishing (0.6 miles), Fishing Creek, Chesapeake Beach Maryland (0.7 miles), Chesapeake Beach Fishing (0.7 miles), Chesapeake Adventures Sportfishing (6.6 miles)brATTRACTIONS: Chesapeake Beach Water Park (0.4 miles), Chesapeake Beach Railway Museum (0.7 miles), Jug Bay Wetlands Sanctuary (13.2 miles), Six Flags America (23.8 miles)brNEARBY EATS: Mama Lucia By The Bay (across the street), Traders Seafood Steak & Ale (0.3 miles), Abners Crab House (0.6 miles), Rod ‘N’ Reel Restaurant (0.7 miles), Boardwalk Cafe (0.7 miles)brWASHINGTON D.C. (36.0 miles): United States Capitol, The White House, Lincoln Memorial, National Mall, Smithsonian National Air and Space Museum, attractions, sightseeing, events, nightlife, restaurantsbrAIRPORTS: Ronald Reagan Washington National Airport (37.6 miles), Baltimore/Washington International Thurgood Marshall Airport (54.0 miles)brbr-- REST EASY WITH US --brbrEvolve 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.brbr-- POLICIES --brbr- No smokingbr- Pet friendly w/ $50 fee (+ fees & taxes, 1 pet max)br- No events, parties, or large gatheringsbr- Additional fees and taxes may applybr- Photo ID may be required upon check-inbrbrADDITIONAL INFORMATIONbr- The yard is not completely fenced-in, and pets are not able to run freely without supervision

2
Bed

1
Bath

6
Sleeps

Exceptional(1)

$416.05
/ Nightly

Cottage

Cliffside Chesapeake Bay Cottage: Pet-friendly, Easy DC Drive

Chesapeake Beach, Maryland, United States
Upscale cottage on a secluded bay front property with stunning water views. Only 45 mins from DC and a quick drive to the beach or dining & shops in Chesapeake Beach and North Beach Maryland. Main room features a double bed, loveseat, streaming TV, desk/workspace, small fridge & microwave. Full bath includes a stand up shower. Patio deck with firepit and another TV. Streaming services include Sling for live TV, Netflix, HBO/Max, Hulu and YouTube. This space is really for the couple or a single person looking for a relaxing bay getaway (and bring along a pet or 2). No kids b/c of the cliff. We love dogs and cats! Two pet max. Dog fence surrounds private small backyard behind the cottage. Unfortunately our insurance won’t allow the following breeds on the property:br-Doberman Pinscherbr-Pit bullbr-Rottweilerbr-Chow Chowbr-Wolf dogs and wolf hybridsbr-Presa Canario (Canary dog)br-Akitabr-German Shepherd -American Bully

1
Bed

1
Bath

2
Sleeps

Select Dates for Price

Private Vacation Home

Waterfront Home On The Chesapeake Bay

Chesapeake Beach, Maryland, United States
Cozy waterfront home. Watch the sunrise on the Chesapeake Bay. 2 bedroom/1 bathroom in the center of town within walking distance to stores, bars and restaurants, only 35 minutes outside of Washington, DC.

2
Bed

1
Bath

4
Sleeps

Exceptional(9)

$905.52
/ Nightly

Private Vacation Home

Indoor pool and spa in contemporary French home secluded in surrounding woods

Chesapeake Beach, Maryland, United States
Contemporary all-brick French manor nestled within 16-acres of secluded woodlands. Indoor pool/spa with waterfall inside a stunning, sunlit atrium. Three bedrooms and three bathrooms accommodate 6-8 people. Centrally located near the Chesapeake Bay where quaint towns include restaurants, antiques, sandy beaches and fishing boat rentals. Centrally located for trips in all directions: Washington, D.C. (35 miles); Annapolis (30 miles) Baltimore (50 miles) and Ocean City (139 miles). Open dining and livingroom area with see through fireplace into large master suite with wood paneled cathedral ceilings.

3
Bed

3
Bath

8
Sleeps

Exceptional(3)

$442.61
/ Nightly

Private Vacation Home

Rising Sun Bay View Cottage W/ Beach Views!

Chesapeake Beach, Maryland, United States
Welcome to Your Chesapeake Bay Retreat!brbrWe`re thrilled to have you at our waterfront home! Enjoy stunning Bay views, a spacious layout, and a private beach just steps away. Relax on the screened porch, unwind on the deck, or explore the nearby attractions and local dining.brbrPlease stay within the designated rope line for your safety when near the water. If you need anything during your stay, feel free to reach out—we`re here to help!brbrEnjoy your time here and create lasting memories by the beautiful Chesapeake Bay!br1) Non-Smoking Property and No Pets Allowed.br2) Check-in time is 4pm or later on your arrival date. Want to check-in early We`ll let you check-in two hours before the scheduled check-in time! 2pm check in $30 or 11am $60. This fee goes to our amazing cleaners! This must be agreed to and paid for before your stay.br3) Check-out time is 10 am. Need some time to sleep in Go for it! With late check-out we`ll give you two more more hours from the scheduled checkout time before you have to go! 12pm check out fee is $30 or 1pm check out fee is $50. This fee goes to our amazing cleaners. This must be agreed to and paid before your stay. The house must be vacated by check out time and doors locked. The house should be left clean, and all trash should be removed and placed in the receptacles. All bags must be placed in the rolling blue bin, and the bin placed at the top of the driveway, or the trash company will not pick it up. br4) Maximum occupancy of the property is listed on contract and MUST not be exceeded. Guest agrees that exceeding maximum occupancy is a material breach of this Agreement and will result in immediate removal and forfeiture of all monies paid. brbr5) No Bachelor, Bachelorette, Sorority or Fraternity parties chaperoned or not, are permitted. ABSOLUTELY NO HOUSE PARTIES ALLOWED. Violation is a material breach of this Agreement and will result in the immediate termination of the Guest’s visit without refund, with no exceptions. brbr6) Locked areas for which the Guest is not provided a key, such as the owner`s personal storage areas, are exempt from this Agreement and are off-limits to the Guest. Forced entry into these areas is cause for immediate eviction and Guest will be charged for any damaged or missing items.brbr7) House comes equipped with internet access. If any charges occur on the owner’s Internet service, Guests will be billed for the charges, plus a $100.00 collection fee. brbr8) House comes equipped with furniture, kitchen appliances, pots and pans, dishes, glassware, silverware, pillows, towels, linens, blankets, bedspreads and basic housekeeping items. Guests will be furnished with a starter amount of bathroom, kitchen, and laundry products unless otherwise indicated in the description of the house. Guest agrees to use bed linens (sheets and pillowcases) on all bedding being used during their stay. Cribs are not provided.brbr9) Guest shall not deliberately or negligently destroy, deface, damage or remove any part of the premises, nor render inoperable the smoke detectors provided by the Owner, or knowingly permit any person to do so. Guest must notify Owner of the need for replacement of or repairs to the smoke detectors. brbr10) Owner is not responsible for items left by Guests. brbr11) This house is a non-smoking house. Smoke only outside and properly dispose of the butts. If you smoke in the house, you will be charged an additional $400.00 for cleaning of the house entirely to rid it of smoke.

3
Bed

4
Bath

6
Sleeps

Exceptional(22)

$427.35
/ Nightly

Private Vacation Home

Charming 4 Bdr 3 Bath Chesapeake Beach Home 2 king beds, a queen and bunk bed

Chesapeake Beach, Maryland, United States
4 bedroom home with 3 full baths that can comfortably sleep 9 in Chesapeake Beach, MD. Less than a mile from the bay. This split level house has a full kitchen, dining room, large deck, family room and a kids bedroom with Captain's Bed (bunk bed with twin over full). It is located on a quiet, partially wooded property. Just 4 miles from Herrington on the Bay and North Beach, 3 miles from the Chesapeake Beach boat docks and Rod 'N' Reel Resort, and 31 miles from Annapolis, MD, 39 miles from Washington, DC and 55 miles from Baltimore, MD.brbrHome features 4 bedrooms, 3 full baths and can comfortably sleep 9 guests. Upstairs you’ll find a king bed and full bath in bedroom 1, a queen bed in bedroom 2, and a captain’s bed with twin over full in bedroom 3. There is a second full bath upstairs. Downstairs you’ll find a king bed in bedroom 4 and 3rd full bathroom. brNewly updated custom kitchen with cookware and dishes. There is also an outdoor grill and a patio set on the deck for days you want to stay at home, dine outside and enjoy the peace of the partially wooded property. A great living area to connect with family and friends. brWiFi, cable TV, smart TV to easily watch your favorite streaming service, and Blu-ray player.brAll linens provided. brTrash bags, toilet paper and a roll of paper towels provided.brbrSuperHost with nearly 90 5* listings on Aiirbnb.

4
Bed

3
Bath

9
Sleeps

Exceptional(22)

$416.05
/ Nightly

Cottage

Cliffside Chesapeake Bay Cottage: Pet-friendly, Easy DC Drive

Chesapeake Beach, Maryland, United States

1
Bed

1
Bath

2
Sleeps

Exceptional(22)

$427.35
/ Nightly

Private vacation home

Charming 4 Bdr 3 Bath Chesapeake Beach Home 2 king beds, a queen and bunk bed

Chesapeake Beach, Maryland, United States

4
Bed

3
Bath

9
Sleeps

Exceptional(22)

$905.52
/ Nightly

Private vacation home

Indoor pool and spa in contemporary French home secluded in surrounding woods

Chesapeake Beach, Maryland, United States

3
Bed

3
Bath

8
Sleeps

Exceptional(22)

$442.61
/ Nightly

Private vacation home

Rising Sun Bay View Cottage W/ Beach Views!

Chesapeake Beach, Maryland, United States

3
Bed

4
Bath

6
Sleeps

Exceptional(22)

$134.63
/ Nightly

Cottage

Coastal Pet-Friendly Cottage < 1/2 Mi to Beaches

Chesapeake Beach, Maryland, United States

2
Bed

1
Bath

6
Sleeps

Exceptional(22)

$381.60
/ Nightly

Private vacation home

Mid-Century Modern on Private Beach, Designed by Award Winning Architect!

Chesapeake Beach, Maryland, United States

2
Bed

1
Bath

4
Sleeps