Holiday houses in Edgewater

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.

4.97 out of 5 average rating, 186 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!

4.94 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.

4.98 out of 5 average rating, 179 reviews

Bungalow in Edgewater

Peaceful Setting with Chic, Thoughtful Style

Settle down for a peaceful night's sleep in the four-poster bed at this tranquil cottage in the woods. The soft gray color palette along with beautiful hardwood floors creates a calm, fresh feel, while the screen porch offers a quiet spot for restful afternoons. This serene retreat sits minutes away from Annapolis. The waterfront community has a beach a short walk away for launching kayaks and taking relaxing strolls. There is also easy access to Baltimore, Washington, and the Eastern Shore.

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.

4.92 out of 5 average rating, 131 reviews

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

Guesthouse 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

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.

Guesthouse 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, 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 Edgewater

4.9 out of 5 average rating, 158 reviews

Cabin in Gambrills

Relaxing Cabin Get Away Near Annapolis & DC

RebeccaRating, 5 stars1 week ago

What a gem! This cabin hidden in the woods is a perfect getaway location! The cabin itself has great heat and A/C (I got to experience both over 3+ weeks!), excellent hot water pressure in the shower, and the most comfortable bed! In addition, it's fully equipped with everything you could possibly need! Beyond the cabin, the woods are so peaceful, with deer, foxes, squirrels, and badgers! The dogs and I loved our multiple walks per day with not a person in sight. To top it off, Ted is the nicest host I've ever had! So wonderfully friendly and responsive. I hope to stay here again soon!

Superhost

5 out of 5 average rating, 7 reviews

Edgewater's Shelby on the Bay

AldonaRating, 5 stars5 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.

4.92 out of 5 average rating, 48 reviews

Apartment in Annapolis

Tranquil apartment in the woods

SummerRating, 5 stars5 months ago

My husband and I stayed here with my parents and it was a great stay. The place was very clean, easy to find and Ken was a great host. There was plenty of space for four people. I would recommend this location to anyone!

4.96 out of 5 average rating, 26 reviews

Home in Shady Side

Ruby Of The Bay

StarlaRating, 5 stars2 weeks ago

Can’t say enough good things about our stay! Beautiful place with everything we could possibly need. The kitchen was well stocked and our host had thought of everything! Clear instructions, great recommendations for local spots etc. And the huge backyard and deck was perfect for us and our pups. Very comfortable beds and pillows too! Finally, host communicated so well and was incredibly accommodating.

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!

4.89 out of 5 average rating, 344 reviews

Apartment in Annapolis

Private Annapolis Inlaw Apartment

MegRating, 5 stars3 days ago

It was beautiful! And the nicest, most well appointed AB&B yet! And I’ve been to a LOT! Especially grateful for the spices and condiments, full set of good knives, and well laid out kitchen. Best was having so many towels! We went to lots of events, involved lots of showers, and it was towel heaven! Finally, that SUPER bed!!! Wow! So comfy! And BIG! THANK YOU!

4.98 out of 5 average rating, 54 reviews

Home in Shady Side

Sunset Cottage

Michelle EllenRating, 5 stars5 days ago

Nicole was a great host. Her place was nice — uncluttered, kitchen had everything you need, it was nice sitting on the sofa and looking out at the water. The beds we very comfortable.