Vacation rentals in Galesville

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Top-rated vacation rentals in Galesville

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Top guest favorite

An open living space features large windows allowing natural light and views of the outdoor scenery. A gray sofa faces a stone coffee table with a round design. Two chairs surround a small table, complemented by a wall-mounted television. The flooring consists of slate tiles.

Home in Edgewater

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!

Guest favorite

Cottage in Edgewater

4.99 out of 5 average rating, 157 reviews

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!

Top guest favorite

Home in Shady Side

5 out of 5 average rating, 170 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.

Guest favorite

A wooden sign displaying the name 'bean rush café' is mounted on a white fence. The café entrance is visible in the background, along with a flag displayed on the porch. Green foliage surrounds the sign, contributing to a welcoming neighborhood vibe.

Guesthouse in Annapolis

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.

Guest favorite

Guesthouse in Galesville

4.95 out of 5 average rating, 171 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!

Superhost

A spacious studio layout is visible, featuring a comfortable bed, small kitchenette area, and distinct seating. Natural light filters through multiple windows, enhancing the neutral-colored walls. A cozy atmosphere is conveyed through simple furnishings and decorative accents, creating a welcoming space for relaxation.

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.

Top guest favorite

The kitchen features white cabinetry and stainless steel appliances, including a dishwasher and stove. A spacious countertop offers ample workspace, illuminated by natural light from the nearby window. The adjacent dining area is visible, showcasing a table and chairs.

Home in West River

4.98 out of 5 average rating, 124 reviews

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!

Top guest favorite

A dining area is framed by large windows, providing expansive views of the Chesapeake Bay and nearby greenery. A rustic table with weathered wood complements the inviting atmosphere. Natural light fills the space, enhancing the connection to the outdoor scenery.

Home in Tracys Landing

4.99 out of 5 average rating, 214 reviews

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!

Top guest favorite

Home in Deale

4.99 out of 5 average rating, 145 reviews

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.

Guest favorite

Cottage in Deale

4.82 out of 5 average rating, 182 reviews

Watrfnt Cottage @ChesapeakeParadise Kayaks/Dogs OK

Savor our three-bedroom Cottage in this peaceful western shore spot, enjoy two acres of green space, the pier, kayaks, swings, fire pit, shady lawns & sun-drenched loungers, local waterfront dining or eat in, close to Washington, D.C., Annapolis, & Baltimore at this honeymoon-worthy country-like micro-resort. Due to the current COVID-19 situation, we have offered SPECIAL discounts for longer-term rentals

Guest favorite

A screened-in porch is captured, featuring a comfortable seating area with light-colored cushions. The view includes the Chesapeake Bay, with gently crashing waves and a cloudy sky in the background. A small round table is positioned beside the seating area.

Cottage in Deale

4.96 out of 5 average rating, 160 reviews

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.

Top guest favorite

A bright kitchen is oriented towards waterfront views, featuring white cabinetry and a spacious island. Two bar stools are positioned at the island, while a seating area with a light-colored couch is visible. Natural light floods the space through sliding glass doors, enhancing the airy atmosphere.

Guesthouse in Annapolis

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 vacation rentals in Galesville

Top guest favorite

A modern kitchen features sleek cabinetry and a white countertop. Glass pendant lights illuminate the space, highlighting the greenery on the wall with the words 'Taste Love' in neon. Kitchen appliances and dishes are neatly arranged, adding to the tidy appearance.

Guest suite in Bowie

5 out of 5 average rating, 105 reviews

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

AdrienneRating, 5 stars1 week ago

This is my husband’s and I second time staying at Carls place. We absolutely love this spot and he is such a great host!! We give him 100 out of 5 stars ⭐️

Top guest favorite

The living room is furnished with a spacious grey sectional sofa, complemented by a warm brown wood floor. A mounted flat-screen TV is positioned above an electric fireplace. An open kitchenette is visible in the background, enhancing the inviting and functional layout.

Guest suite in Upper Marlboro

4.92 out of 5 average rating, 37 reviews

Private Lower Level Suite

MiriamRating, 5 stars1 month ago

I enjoyed my stay here. The sofa was very comfortable and I was able to get a good night rest in the bed. The location felt safe and was located near stores and eateries. The host was very responsive and accommodating. Thanks!

Guest favorite

A serene waterfront scene features colorful Adirondack chairs set on a lush green lawn. The calm waters of Rockhold Creek reflect the greenery and nearby docks, creating a tranquil atmosphere. Trees provide shade, enhancing the inviting outdoor space perfect for relaxation.

Cottage in Deale

4.9 out of 5 average rating, 166 reviews

Rockhold Creek Cottage

ShamsRating, 5 stars2 months ago

We stayed at Richard's house for 3 nights in late Spring. Its an amazing place, with great views from the rooms. There were lots of great places to see nearby.

A brown chicken is positioned at the entrance of a green coop, with its body partially visible. The open door offers a glimpse of the coop's interior, characterized by simple, clean lines and a spacious structure, ensuring a comfortable environment for the bird.

Guest suite in Dunkirk

5 out of 5 average rating, 4 reviews

Pool-side chickens between D.C. and Chesapeake Bay

RyanRating, 5 stars1 week ago

Great stay for our large family! Booked for pool, and we swam every day! Also my kids thoroughly enjoyed the Atari! Was great getting to meet Luis and Laura and their son! Talked about booking next year!

Top guest favorite

A dining area is presented with a large wooden table surrounded by four black chairs and a matching bench. Natural light enters through a window, illuminating the space. A small decorative piece sits on the table, while a console table is positioned in the corner.

Barn in Davidsonville

5 out of 5 average rating, 15 reviews

1bd 1 ba detached guest loft

CharlesRating, 5 stars2 weeks ago

Mary was an excellent host. Any question I had she responded in great time. Mary's place is set up great. Had everything you need. Super peaceful and quiet. Would stayed longer if I could have. Recommend to anyone.

Guest favorite

Home in Shady Side

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.

Guest favorite

A comfortable gray sectional sofa sits against a light gray wall, accented by plush throw pillows. A stylish coffee table made of white marble-like material is positioned on a geometric area rug. Tall light fixtures provide soft illumination, and a decorative plant adds a touch of greenery.

Cottage in Shady Side

4.9 out of 5 average rating, 42 reviews

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!

A silhouette of an osprey is perched on its nest as the sun sets in the background, creating a warm glow against the horizon. The nest is supported by a pole, surrounded by a backdrop of trees and a colorful sky.

Bungalow in Deale

4.85 out of 5 average rating, 393 reviews

Cozy waterfront getaway on the Bay

MichaelRating, 5 stars1 month ago

This place is awesome!!! Very quiet and nice neighborhood. This was the place that I chose for our 11 th wedding anniversary and could not ask for a better experience. The kitchen is what I loved the most . Many places to eat near by and the Chesapeake bay is right there.

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Vacation rentals in Galesville

Top-rated vacation rentals in Galesville

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