Holiday rentals in Riva

4.95 out of 5 average rating, 120 reviews

Loft in Riva

New Loft w/South River view from treehouse deck!

Enjoy the quiet Sylvan Shores neighborhood and a view of the South River and bridges in this new modern apartment that has a treehouse style deck for relaxing and enjoying the outside. The unit is served by a separate entrance and free street parking. Bring your kayak or stand-up-paddleboard, or try your luck at fishing! The TV is upgraded to a 55". Downtown Annapolis is just 6 miles away and offers cultural attractions, bars and restaurants, historical tours and access to the Naval Academy.

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, 171 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.

4.92 out of 5 average rating, 131 reviews

Home in Edgewater

Spacious 3 Bedrooms House+Patio+Playground

Spacious 3 bedrooms house with functional patio + private playround located in Edgewater, only 15 mins drive to downtown Annapolis. Fully equipped with designer furnitures, with a sense of home! Huge dining room and fully functional kitchen, perfect to enjoy a great evening with your friends and family! Bedrooms are equipped with your own desks if you want to do some works even in your vacation. Easily fit 2 cars in private driveway. Very quiet neighborhood with proximity to everything!

4.96 out of 5 average rating, 183 reviews

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.

4.89 out of 5 average rating, 35 reviews

Home in Riva

Waterfront Annapolis Getaway!

Escape to this serene waterfront house in Annapolis, perfect for couples seeking a peaceful retreat. Nestled on the picturesque South River, this charming home offers stunning waterfront views and tranquil decks where you can unwind and soak in the beauty. Enjoy cozy evenings by the water, dine alfresco on the deck, and explore nearby attractions. With its serene ambiance and beautiful surroundings, this is the ideal spot for a romantic getaway. Book now for an unforgettable escape!

Superhost

Cottage in Edgewater

4.73 out of 5 average rating, 184 reviews

Waterview Studio on a sunset corner

Book more than 2 days and get up to 15% off. Last painted in June 2021, new toilet and Tempurpedic mattress top. New wood floor installed in 2024. Private and comfortable studio in a centenary house with independent entrance in a quiet neighborhood surrounded by the waters of the South River. The house is divided in two independent and private units. Great for outdoor lovers. Ideal for gate away, temporary stays for work, vacation or relaxing from the stressful life.

5 out of 5 average rating, 34 reviews

Cottage in Riva

The Coral Cottage

Our cozy cottage is the perfect place for a romantic weekend getaway, family vacation, or the annual getaway with your best friends! With so many local Annapolis attractions, access to community piers and views of the South River, and fresh seafood at Mike's Crab House, the Coral Cottage is sure to make your trip to Annapolis a memorable experience. Enjoy the outdoors with the smokeless fire pit, a stroll down to the dock, or cozy up indoors with a good book!

Guest house in Stevensville

4.99 out of 5 average rating, 279 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, 136 reviews

Garden View, a spacious 1 bedroom with loft.

Relax and unwind at this peaceful and charming retreat, nestled in a quiet neighborhood. Located just minutes from Route 50, I-95, and Downtown Annapolis, Garden View is ideally situated for exploring Naval Academy sports, the Renaissance Festival, Boat Shows, and golf at The Preserve. If you prefer staying in, the fully equipped kitchen and free Wi-Fi make it easy to work or cook from the comfort of your space.

4.99 out of 5 average rating, 168 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.

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Other great holiday rentals in Riva

Private room in Annapolis

4.96 out of 5 average rating, 338 reviews

Cape Cod Charm close to USNA & Annapolis - Room 2

UllyRating, 5 stars1 day ago

Michael and Debby's place was a gorgeous house, stylish and very comfortable. The room was cosy and I had everything I needed. Debby and Michael were lovely hosts, so helpful and friendly, and I would have spent time with them and their dog much longer ifvI didn't havd to get back on the road. And I would have enjoyed the pool if it hadn't been for the weather. An exceptional place, I would happily stay there again any time.

4.93 out of 5 average rating, 67 reviews

Guest suite in Riva

2BR Water Privileged Home minutes to Annapolis

GabrielaRating, 5 stars5 months ago

Pink was a great host. Enjoyed the small touches like complimentary snacks, coffee, drinks, etc. The neighborhood home was close to Annapolis- easy to Uber back and forth from.

Private room in Annapolis

4.96 out of 5 average rating, 556 reviews

Chesapeake Mornings

KathleenRating, 5 stars2 weeks ago

Host was waiting for me, door was open, friendly pups to help with acclimating and house tour. The bed was VERY comfortable, the shower water pressure was perfect, the room was quiet, the neighborhood was quiet. The only caution I would make is that if you are a warm person, be sure to request that the A/C be on and running. I loved everything about this home. Neat architecture, off street parking, large work desk just outside the room, strong Wi-Fi, and a VERY comfortable bed. I highly recommend this lovely home!

4.95 out of 5 average rating, 95 reviews

Guest suite in Annapolis

Annapolis Garden Suite

StacyRating, 5 stars1 week ago

Thank you for sharing your beautiful home and charger lol with us ! We will book again

Private room in Glen Burnie

4.82 out of 5 average rating, 753 reviews

Room Near BWI & Baltimore NO Cleaning Fee!

TyRating, 5 stars2 weeks ago

ALL as advertised - which made it perfect for my 12-hour needs, being close to BWI for my 6 AM breakfast at Panera, rental car return, and easily making my 9 AM flight!

5 out of 5 average rating, 16 reviews

Barn in Davidsonville

1bd 1 ba detached guest loft

FredRating, 5 stars1 week ago

Very nice place and Mary was very responsive. Super clean and quiet. Close to Annapolis (10 min drive to downtown) and great restaurants, plus lots of historic sites nearby.

Private room in Annapolis

4.93 out of 5 average rating, 135 reviews

Sandpiper Room - Charming private room, Annapolis

ReneRating, 5 stars1 month ago

Great location. Perfect for a quick visit to see our Midshipman. Would definitely rent again in the future.