Holiday rentals in Mayo Beach

4.97 out of 5 average rating, 185 reviews

Annapolis Area Waterside Retreat

This Rhode River home is your perfect getaway to the Annapolis area - whether you’re looking to get away to a unique home overlooking incredible sunsets, a fun weekend with friends along the water, a family trip to the Chesapeake, or a private work retreat away from the bustle of the city, this home has it all. The house is a short drive from DC or Baltimore and unlike any Airbnb this side of the Chesapeake - it is on a 3 acre marina just minutes from Annapolis but private and away from it all!

4.99 out of 5 average rating, 156 reviews

Cottage in Edgewater

Waterfront Chesapeake Bay Sunrises w/Private PIER!

Gorgeous sunrises and bay breezes await at this newly remodeled Chesapeake Bay waterfront cottage! Catch crabs or fish from your private pier, relax on the furnished deck, or explore Selby Bay with our complimentary canoe. Enjoy water views from the kitchen, dining, living room, and enclosed porch. Just 15 minutes from Annapolis & the Naval Academy, and 45 from DC—peaceful, clean, full of charm. Ideal for USNA families! Unplug, unwind, and make memories on the water—year-round relaxation & fun!

5 out of 5 average rating, 170 reviews

Home in Shady Side

Luxe Modern Chesapeake Waterfront Oasis - 5 Star

The Cottage at Silver Water is a serene 5 Star retreat for those who value tranquility over spectacle. Set along the Chesapeake, it offers front-row seats to breathtaking sunsets—where golden light dances across the water. Inside, Nordic-inspired design meets quiet luxury, featuring award-winning mattresses and bedding that promise restorative sleep. Here, time slows, and luxury isn’t just something you see—it’s something you feel. We invite you to read the reviews of so many happy guests.

4.9 out of 5 average rating, 290 reviews

Calico Cottage Guest House, king bed, free parking

Cute-as-a-bugs ear West Annapolis guest cottage just 1.5 miles from the Navy Stadium and less than 2 miles from Academy's Gate 8. Cottage features: high speed WiFi, EZ free parking, washer & dryer, kitchenette, air conditioning, self check-in and laptop friendly workspace. Park 10 feet from front door. Only 1 step to enter. No stairs to negotiate while carrying luggage! 15 min. walk to Weems Creek with scenic, serene waterviews and a few more minutes walk to popular Bean Rush Cafe.

4.86 out of 5 average rating, 101 reviews

Chesapeake Bay Escape | Cozy Retreat

Welcome to our charming Annapolis retreat! Nestled in a quiet community on the Chesapeake bay, Barefoot Cottage offers a perfect blend of comfort and convenience. Enjoy a stroll around iconic landmarks, savor local cuisine, or unwind with a walk on the beach. Thoughtfully interiors and modern amenities, our Airbnb promises a memorable stay for your solo trip, romantic getaway, sailing enthusiasts or USNA visitor. Book now for an unforgettable experience in this historic maritime city!

4.98 out of 5 average rating, 124 reviews

Luxury Modern Home on Water+Hotub- Annapolis 25min

Waterside mid-century modern home, perfectly appointed. Join with colleagues, family, and friends. Paddleboard, roast marshmallows, watch fireworks, take a hot tub or team building. Our "Flight Deck" is perfect for meetings and retreats. Breathtaking, peaceful grounds with an abundance of space. Approximately 2800 SF sits on a 3/4 acre property - perfect for lawn games and zip lining. 20x20 furnished deck + dock Mayo Beach and Beverly Triton 1 mile away. Within an hour of the DMV

4.91 out of 5 average rating, 107 reviews

Private Cottage on gated estate

Completely remodeled guest cottage on gated, private estate. Home is located just minutes from Eastport, Downtown Annapolis, and the Naval Academy. (4.7 miles to the main gate). We are on a private well but we have installed a state of the art water softener, filtration system, and a blue light bacteria zapper. Home and grounds are kid friendly offering amply outside play space and a multipurpose sports court. Third bedroom of home has a full-sized crib, baby gates, and a twin bed.

Guest house in Galesville

4.95 out of 5 average rating, 170 reviews

Nautical Charm and relaxing waterview!

Our comfortable and relaxing studio is a quiet retreat with a fantastic view while still in close proximity to Washington DC, Annapolis and Baltimore! Situated in a charming waterfront and sailing community, this separate and private unit has: parking, 1 bath, queen bed, kitchen (limited), TV, high speed WiFi and Bluetooth speaker. Wake up to the cluck cluck of our four resident chickens who are tucked away in their attractive coop. Sit on the porch and take in the view!

Guest house in Stevensville

4.99 out of 5 average rating, 278 reviews

Waterfront Getaway - View of bay from your bed

Enjoy this newly renovated, waterfront private studio apartment with a beautiful view of the Chesapeake Bay. It's a perfect getaway for anyone looking for rest and relaxation amidst a quiet, breath-taking location. Enjoy swimming in the pool, fishing off the point, sitting around an evening gas fire, visiting any of the local sandy beaches, or simply watching stunning sunsets from a private patio. Ample parking, WiFi, TV, boat-ramp access. One pet is welcome.

Superhost

Flat in Annapolis

4.77 out of 5 average rating, 264 reviews

Charming Eastport

Who needs a boat to stay at a marina? Eastport Yacht Center has a quaint one bedroom apartment located in charming Eastport, within walking distance to Downtown Annapolis and the U.S. Naval Academy. Conveniently located next to the Annapolis Maritime Museum. (Two guests maximum) If this apartment isn't available for your time period check out our other studio apartment listed under "NEW lovely studio apartment with onsite parking".

4.99 out of 5 average rating, 167 reviews

Coastal Waterfront 1 Bedroom Cottage

This waterfront cottage is located 2 miles from Historic Downtown Annapolis and the United States Naval Academy, making it easy to plan your visit. It is located right on the South River in a quiet neighborhood. There is a full outdoor seating and patio area with a grill and fire pit. It has a full kitchen, 1 bedroom, washer/dryer and can sleep up to 4 with the pull-out sleeper couch.

4.9 out of 5 average rating, 515 reviews

Guest suite in Edgewater

South River Park Apartment

Located minutes from Annapolis, the in-law apartment offers access to Baltimore and DC in under an hour. The apartment offers its own entrance, full kitchen, one bathroom, one bedroom, tile floors, pullout sofa, Wifi, and parking. The apartment is registered with the Anne Arundel County Dept. of Inspections & Permits, #STR-15, for short term rentals.

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Other great holiday rentals in Mayo Beach

4.99 out of 5 average rating, 74 reviews

Home in Annapolis

Captain’s Retreat! Newly Renovated - Beach House!

LisaRating, 5 stars3 weeks ago

plenty of towels. Great accomodations for a family wedding. Cards and games were available and appreciated.

Superhost

5 out of 5 average rating, 6 reviews

Edgewater's Shelby on the Bay

RebeccaRating, 5 stars1 month ago

The house is absolutely wonderful. The park and beach are just across the street which was perfect for the kids to play at throughout the day. No mosquitos in late-April! There is a surprising amount of space. Two of the bedrooms are very spacious and the kids’ bedroom is perfect for young families.

5 out of 5 average rating, 53 reviews

Flat in Davidsonville

Aspen Woods

Gina MichelleRating, 5 stars2 weeks ago

I have nothing but good things to say about Donna and Ken. When we arrived, it was pouring rain. We had a long trailer with us and we needed to park it. Ken already had the doors open for us and helped my husband get the trailer parked in the rain. Then the next morning, he helped my husband get it backed out. The garage apartment was perfect. It was clean and felt like home. I absolutely love their place. It has everything that you need while you are there. It definitely is home away from home. The area that it is in is very nice. They have several nice restaurants. We plan on coming back in the future but without the trailer. Donna and Ken are wonderful host. Thank you so much for loaning your place out for others to enjoy.

4.93 out of 5 average rating, 44 reviews

Flat in Annapolis

Annapolis Charmer! 2BR Bright BSMT APT 3 mi to DT

KatieRating, 5 stars2 weeks ago

Linda's place was great! Easy to find, great location, very clean! A little bit away from downtown Annapolis but easy to get to. Would stay again!

5 out of 5 average rating, 9 reviews

Cottage in Annapolis

Wonderful Cottage Nestled On Chesapeake Bay

EdmondRating, 5 stars2 weeks ago

The cottage looks just like the photos. Very quiet and peaceful location. They provided a binder that catalogs anything you may need during your stay. EXCELLENT communication. Easiest Check out EVER. Would certainly book again if we return to the area.

4.98 out of 5 average rating, 58 reviews

Entire Beach House with Pool and Hot Tub

ParsaRating, 5 stars6 days ago

We had a wonderful experience staying at Peggy’s place. It is as pristine as it looks in the photos and is peaceful and relaxing. We especially loved the pool. We would definitely book again

4.98 out of 5 average rating, 52 reviews

Home in Annapolis

Annapolis Retreat - Near DTA with Tons of Parking!

BrandiRating, 5 stars2 weeks ago

Ronny’s place was more than enough space for our family. Ronny was responsive and even offered early check-in, even though I didn’t end up using it. One thing to note is that the basement room is extremely cold, we think because it’s not carpeted and it has a door that leads right outside. We ended up sleeping in the basement living room after we found out it had a fireplace and the couch was a pull-out sofa.