Holiday rentals in Galesville

4.97 out of 5 average rating, 186 reviews

Home in Edgewater

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!

5 out of 5 average rating, 171 reviews

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

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, 107 reviews

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.

Guest house in Galesville

4.95 out of 5 average rating, 172 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, 125 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!

4.99 out of 5 average rating, 215 reviews

Home in Tracys Landing

The Little Gypsy BoHome

Welcome to our Little Gypsy BoHome on the bay! The house is situated in Southern Anne Arundel County, MD in the quaint waterfront town of Tracy's Landing. Our home sits directly on The Chesapeake Bay with breathtaking views from every window. We offer a saltwater swimming pool, two corn hole game sets, a basketball hoop, beach access, canoe, 2 Paddle Boards, a gas grill, and a steam shower, an outdoor redwood panoramic barrel sauna and a redwood cold plunge!

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.

4.91 out of 5 average rating, 621 reviews

Flat in Deale

Romantic Wtrfrnt Flat+Solarium@Chesapeake Paradise

Gift yourself this private, secluded second floor Flat & Solarium Bedroom. Best hideaway to rest, bond, restore, create, or work. A breezy, country-like setting provides space to escape the city hustle! Nearby scenic drives & groceries, or venture to Annapolis TJ/WF or historic walks. Fully relax with pier, kayaks, swings, fire pit, starry nights, sun-drenched loungers, cozy up with books/movies & luxuriate in the deep soaking tub or European shower.

4.99 out of 5 average rating, 146 reviews

Home in Deale

Chesapeake Waterfront-Kayaks-Crab-Fish-FirePit-Spa

There's nothing like being directly on the water! Relax and rejuvenate in this Chesapeake waterfront estate home which includes private pier, hot tub and fire pit. Crab or fish off the pier or take the kayak out to see the Chesapeake bay wildlife. Try out paddle boarding! Sit around the fire pit at night or watch the stars at night while soaking in the hot tub. Make wonderful memories. Great place for families and multi family groups.

4.96 out of 5 average rating, 162 reviews

Cottage in Deale

Chesapeake Bay Cottage

Cottage Located directly on the Chesapeake Bay. Includes sandy beach, yard, a screened in porch and deck. Two Kayaks to enjoy. Two bedroom plus den. Two full baths. Fully equipped kitchen.Kurig coffee maker and regular available. Master bedroom -queen size mattress. Second bedroom -a full-size mattress (double) third bedroom -a twin day bed with twin pullout. Both twin size mattresses.

4.99 out of 5 average rating, 168 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.

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Other great holiday rentals in Galesville

5 out of 5 average rating, 106 reviews

Guest suite in Bowie

Luxury 1BR/1BA Private Suite Close to DC!

ChazRating, 5 stars2 days ago

Carls place is perfect. My fiance and I stayed 7 days and need nothing the entire time. Close to Metro for in and out of the District. Great food around the rental. Carl was super responsive and even left us a welcome care package upon arrival. Super comfortable space. Will book again when I’m in the DMV area no questions asked or hesitation.

4.83 out of 5 average rating, 106 reviews

Guest house in Bowie

Renovated Basement with Private Entrance

AprilRating, 5 stars2 weeks ago

We had a wonderful stay at this Airbnb! The unit was spotless—everything was incredibly clean and well-maintained, including the bathroom. The space itself was cozy and inviting, and we felt right at home, especially in the living room where we spent most of our time relaxing. The host was very responsive and thoughtful—every detail was well considered, and we truly didn’t need for anything. A nice touch was the complimentary water and sodas, which we appreciated after a long trip. One feature we especially liked was the lighting. The lights operated on what we believe were motion sensors, turning on and off automatically. This was both convenient and energy-efficient, especially if we happened to fall asleep with the lights on—they’d shut off on their own. Overall, it was a comfortable and seamless experience. We would absolutely stay again!

4.92 out of 5 average rating, 51 reviews

Cottage in Edgewater

Waterfront Cottage with Private Pier

StephanieRating, 5 stars1 week ago

Beautiful setting. Very cozy house that was well appointed with everything that we needed for a longer stay. I was able to cook full meals in the kitchen with ease and my husband grilled one night. Other than that, there are local restaurants to enjoy as well. During the day my boys had fun fishing and being out on the water and the sunsets over the lake was definitely worth sticking around for. Unfortunately I had to work during the majority of our stay but I was able to do that seamlessly with the desk and reliable internet connection. Overall we had a great time at Miss Kitty’s Place and would love to stay there again someday.

4.96 out of 5 average rating, 55 reviews

The Cottage

DanRating, 5 stars1 month ago

We had a very nice stay. Everything was SO clean! Thank you.

4.9 out of 5 average rating, 42 reviews

Cottage in Shady Side

Luxe Chesapeake Cabin * River View* Fire Pit*

VanessaRating, 5 stars1 month ago

My family and I really loved staying at Jared’s home, not only was it beautiful, but we really liked the fresh air and nature! Jared was very kind, responsive, and was always there to help us with anything we needed. (the best host!!!) We really enjoyed this experience and highly recommend it. Thank you!

4.98 out of 5 average rating, 58 reviews

"Pier Joy!" - 3BR Waterfront Home W/Private Dock

AmandaRating, 5 stars1 month ago

I have stayed at dozens of Airbnb’s and this is in my top 3! The home is perfectly appointed, super clean, well stocked, cozy, and beautifully decorated! The master bathroom is magazine worthy. Jeff was very easy to communicate with and let us check in early. My family plans to make it an annual trip.

Bungalow in Deale

4.85 out of 5 average rating, 394 reviews

Cozy waterfront getaway on the Bay

BillRating, 5 stars2 days ago

The ultimate Maryland water experience. Beautiful house with perfect amenities to enjoy the bay. With the dock, the view, the crabbing, the fishing, and the kayaking, you save time and money by having everything at your fingertips. The hot tub was wonderful even in summer. The house has everything you could want for a relaxing stay. We ate the crabs we caught every night for a week! Plenty to do and see in the area, too. Definitely want to return!

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