Holiday rentals in Rhode River

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, 169 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, 288 reviews

Guest house 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.

4.96 out of 5 average rating, 106 reviews

Home in Shady Side

Waterfront w/ Private Pier, 35 Mins to Annapolis

Located 35 minutes from Annapolis and 45 minutes from Washington DC, Shady Side is a quaint town. This waterfront home is perfect for families or small groups looking to enjoy a relaxing getaway on the Chesapeake Bay. Enjoy the large wrap-around screened in porch and private pier with ladder for easy access for swimming. Large yard, and an incredible view of the Bay Bridge. Free public boat ramp 5 min away in Parish Creek. Listed for 8 people max but contact us for approval of 1-2 more.

4.96 out of 5 average rating, 183 reviews

Guest house in Annapolis

Lil’ House - A Serene Tiny Home Experience

Newly renovated, immaculate two room tiny home. A stand-alone gem nestled against a wooded backdrop - well back from the main home - and wrapped in a huge, teak-furnished, blue stone patio with fire pit situated in a sunny opening in the mature tree canopy. Super comfy queen Murphy bed offers easy conversion of the well lit and modern main living space from living room & kitchen by day to main sleeping quarters at night. The adjoining room is a well appointed full bath and dressing area.

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

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!

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!

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.

4.99 out of 5 average rating, 167 reviews

Guest house 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.

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 Rhode River

4.99 out of 5 average rating, 76 reviews

Houseboat in Baltimore

Flohom 1 | Breathtaking Skyline 360° Views

MackenzieRating, 5 stars3 weeks ago

Overall this rental was a great stay! The furniture was comfortable and the environment was very nice. It’s an absolute beautiful location and all the windows make it feel like you’re on a serene vacation. It was clean and the hosts gave very clear check in and check out instructions. The rooftop fireplace and all the other ammenities made it feel luxurious, but it still had a homey feel. The only “downside” I would say is that it’s a bit pricey, and the cleaners were leaving right at 3:00 as we were arriving, but I would definitely recommend FloHom to a friend!!

4.91 out of 5 average rating, 46 reviews

Sundrenched waterview primo family holiday retreat

JulieRating, 5 stars2 weeks ago

We appreciated the opportunity to stay in this home during our son's Commissioning Week. The drive to USNA was easy and it was nice having a quiet location not too far away from Annapolis. Plenty of grocery shopping, restaurants, etc nearby. We would definitely rent this home again or recommend it to others!

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.

4.96 out of 5 average rating, 28 reviews

Flat in Annapolis

Bayside Retreat

CaitlinRating, 5 stars5 days ago

Fantastic getaway, perfect for a couples trip! Kathleen’s attention to detail was unlike any other Airbnb host I’ve experienced - from a stocked fridge, binder of recommendations, bathroom essentials, and more - she truly thought of everything! We would absolutely stay again. The home was spotless and the small beach in the neighborhood is lovely to spend a sunny day outside!

Superhost

4.82 out of 5 average rating, 22 reviews

South River Beach Front House

Katherine Rating, 5 stars3 weeks ago

I stayed here the week of my wedding and it was absolutely perfect! From waking up each morning to have coffee on the dock with my pups and husband, to the beautiful views from each room in the house, we truly had a lovely time and chose the right Airbnb for such a special week in our lives.

5 out of 5 average rating, 27 reviews

Guest suite in Annapolis

Pristine, Private 1 Bed/1 Bath Guest Apartment

MieRating, 5 stars3 weeks ago

When you book Fox Haven, you not only get a tranquil sanctuary, but the most gracious and communicative host who anticipates your every possible need. The space is thoughtfully designed and equipped for convenience and is located at the end of dead end street in a quiet residential area in the middle of all the action. A friend who came to visit me was so impressed that she was voluntarily raving about the place to others. I look forward to returning time and again.