Holiday houses 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, 157 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!

4.96 out of 5 average rating, 671 reviews

Guest suite in Arnold

Old Bay Bungalow

This in-law apartment located in the lower level of my occupied home is just moments outside of Annapolis, mere blocks from the Magothy River. I enjoy inviting guests into the space, and take pride in treating new friends like family. Come rest your weary bones in your private retreat with its own separate entrance, relaxing sunporch, and stocked kitchenette. Reach into the fridge and enjoy cold soda or a local beer on me! Sit around our fireplace and relax. Settle into the Old Bay Bungalow!

4.94 out of 5 average rating, 176 reviews

Guest suite in Arnold

Coastal Comfort Suite Near Annapolis, Hottub, EV

Hot tub is open for the season. Pool will be open May 12 through Labor Day weekend. Ideal for a couple's retreat, this king suite guest room has a massive bedroom with a seating area, mounted TV, and coffee bar with microwave/mini-fridge. An ensuite bathroom provides a luxurious shower with dual shower heads and a spacious closet. The pool and hot tub are seasonal. Please don’t hesitate to reach out with any questions, concerns, or expectations so that we can address them prior to your stay.

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

Guesthouse in Annapolis

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.

4.98 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

Guesthouse in Annapolis

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.

4.95 out of 5 average rating, 171 reviews

Guesthouse in Galesville

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!

4.98 out of 5 average rating, 124 reviews

Home in West River

Cozy waterview home in West River!

Your family will be close to everything when you stay at this centrally-located place. This home is located just 15 miles to Annapolis, 18 miles to the Naval Academy, and 30 miles to the heart of Washington, DC. Less then 8 miles to Rt 214, providing direct access to beltway, and other major highways. This charming home has as spacious fenced in yard, High Speed Internet, TV (Netflix & Hulu), outdoor seating and a fire pit. Want to get away? Bring the whole family!

Guesthouse 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.

4.99 out of 5 average rating, 168 reviews

Guesthouse in Annapolis

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.

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Other great holiday rentals in Mayo Beach

4.99 out of 5 average rating, 75 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, 7 reviews

Edgewater's Shelby on the Bay

AldonaRating, 5 stars3 days ago

We stayed at Danielle's Airbnb for a family get together. There was plenty of room in the house for the six of us staying there and the rooms were comfortable and clean. View from the second story balcony was amazing - that evening we watched the thunderstorm from there. The rest of our family joined us at the house the next day. There were 2 picnic tables on the side of the house where there was adequate room for us to eat, though the grill provided was very small. Spent time around the fire pit on the front lawn in the evening. The property, itself is small, so there is no backyard space to offer privacy. The grassy expanse and water across the road provided a feeling of openness to the area. We reached out to Danielle with several issues which she responded to immediately. She's very easy to work with and wants to make your stay as nice as possible.

Guesthouse in Stevensville

5 out of 5 average rating, 34 reviews

Private | Near BayBridge | Wedding Venue Proximity

MeganRating, 5 stars3 days ago

Great hosts! Super responsive, friendly and flexible. Place was clean and perfect for wedding venue nearby. Would absolutely stay here again and HIGHLY recommend

4.93 out of 5 average rating, 44 reviews

Apartment 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!

4.98 out of 5 average rating, 59 reviews

Entire Beach House with Pool and Hot Tub

LisaRating, 5 starstoday

Peggy’s house is beautiful! The inside and the outside are just wonderful! The pool, hot tub are just perfect! Wishing only that the house could sleep 6 adults plus a couple of kids. The location is just perfect!

5 out of 5 average rating, 28 reviews

Guest suite in Annapolis

Pristine, Private 1 Bed/1 Bath Guest Apartment

DaniellaRating, 5 stars2 weeks ago

Fox Haven is heaven on earth. So quaint, so clean, so many thoughtful extras including a healthy snack basket, toiletry items, and personal touches throughout the apartment. The location is outstanding with a short walk to historic downtown Annapolis. Lenetta is one of the most responsive and personable Air B&B owners we've ever experienced. We will be back for sure! Highly recommend Fox Haven to everyone!

4.93 out of 5 average rating, 15 reviews

Guest suite in Riva

Cozy one bedroom appt on the water

ChristelRating, 5 stars4 months ago

I had a lovely time at Zelda’s. Her home is beautiful and cosy and it’s really pleasant to be able to walk around and enjoy the river. This is definitely my go to place for the holidays.