Cottage vacation rentals in Annapolis

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Top-rated cottage rentals in Annapolis

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Guest favorite

Cottage in North Beach

4.9 out of 5 average rating, 101 reviews

Quiet Coastal Cottage Escape with Water Views

Want to get away? Come relax and escape in our updated bay view cottage. You'll enjoy stunning sunsets, warm surroundings, and all the amenities you could want in our cozy, peaceful cottage home. You'll find plenty of comfortable spots to relax, inside and out. Located on a quiet street, while still close to the small-town charm and offerings of North Beach, Chesapeake Beach, and Herrington Harbor. Walk along the bay, enjoy the local restaurants, and get ready to relax. Stay a week and save!

Guest favorite

A spacious backyard is illuminated by string lights, surrounding a fire pit with seating for six. Adirondeck chairs in various shades are arranged around the fire, and a picnic table is situated nearby on gravel. The cottage's entrance is visible in the background.

Cottage in Rock Hall

4.91 out of 5 average rating, 124 reviews

Cottage with Modern Updates - Walk to Waterfront!

Historic cottage, fully renovated and located in the heart of Rock Hall. Features open living area, modern kitchen, sunny front porch, big fenced backyard, and patio with fire pit and picnic table. Enjoy everything the town has to offer - fishing, boating, festivals, dock bars, restaurants, shopping, & more. Walking distance to Main Street, marina, Harbor Shack, Waterman's Crab House, The Mainstay. A short drive to Eastern Neck National Wildlife Refuge, Washington College, historic Chestertown.

Guest favorite

A breathtaking sunrise is captured over calm waters, creating a stunning reflection of vibrant hues of orange, pink, and purple. The private pier is visible on the right, complementing the serene landscape of trees on the distant shore and a tranquil island in the background.

Cottage in Edgewater

4.99 out of 5 average rating, 153 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!

Guest favorite

Cottage in Rock Hall

4.99 out of 5 average rating, 108 reviews

Cottage by the Bay in Rock Hall, MD

Sunny cottage in quiet waterside town of Rock Hall. Easy walk into downtown: grocery store, cafe, gift shop with beautiful housewares, gifts and jewelry, styling salon, quilt shop, ice cream shop, and local produce market. Gas fireplace, screened porch, stone patio, deck, several bicycles, tv for dvd's. Restaurants, crabs, Eastern Neck Wildlife Refuge, and nearby Tolchester and downtown Chestertown. Public pool, small beach (& picnic gazebos), bike around town...come to relax year round!

Guest favorite

A new wood pier extends over still waters towards a green, tree-lined shore. The pier is flanked by posts, leading to a rocky bank, with a clear view of a nearby cottage among the trees. Sunshine reflects gently off the water.

Cottage in Pasadena

4.97 out of 5 average rating, 172 reviews

Ft. Smallwood Overlook. Waterfront with Kayaks!

Delightful cottage at the confluence of Rock Creek, Patapsco River (Baltimore Inner Harbor) and the Chesapeake Bay. Adjoins Ft. Smallwood Park with its private coves and beaches. Secluded setting features water on 3 sides with beautiful relaxing views. Teeming with wildlife: ducks, geese, egrets, osprey, eagles, deer, foxes and other. Convenient to Annapolis, BWI Airport, Baltimore & Washington, D.C. Walk to the park. Cast a line, catch what you may! Total renovation 2018-2019.

Guest favorite

A wooden dock extends over calm waters, featuring four Adirondack chairs arranged facing the serene view. A light casts a soft glow on the water's edge, and the distant shoreline is lined with trees and structures, hinting at nearby activity.

Cottage in Pasadena

4.88 out of 5 average rating, 124 reviews

Chesapeake Cottages- 2 Quaint Waterfront Retreats

Our tastefully appointed cottages sit on almost an acre of waterfront property. Peaceful and tranquil, yet close to shops and restaurants, this property is perfect for serene getaways and family gatherings. With 2 separate cottages on one property, everyone will enjoy a unique and private space to relax. From peaceful mornings to magical sunsets on the 60-foot pier, this setting will quickly become a family favorite. This area is great for fishing, kayaking and paddle boarding!

Top guest favorite

Two Adirondack chairs are positioned beside a wooden dock, shaded by a large umbrella. The view overlooks calm water surrounded by greenery, creating a serene environment. A small table is present between the chairs, enhancing the inviting outdoor seating area.

Cottage in Easton

5 out of 5 average rating, 102 reviews

Cottage on Solitude Creek, Hot Tub, Pool & Firepit

Cottage on Solitude Creek, Hot Tub (open), Fire Pit, Pool (Not Heated -closed Oct-June) Convenient to St. Michaels, Easton, Oxford - this beautiful cottage has a fully equipped kitchen, patio with private hot tub and gas grill. Waterfront. Host resides on property, but will give you your privacy. *PLEASE NOTE: property complies with zoning of Talbot County which enforces a 3-night minimum and 4 guest max. NO DOGS ALLOWED No Parties #STRN-23-51

Top guest favorite

A serene waterfront view is presented from a patio with two wooden lounge chairs facing the horizon. The setting sun casts warm light over the water, and a private pier extends into the bay, enhancing the tranquil atmosphere.

Cottage in Stevensville

4.95 out of 5 average rating, 155 reviews

Cottage on the Bay - Kent Island

Chesapeake Bay Waterfront home on Kent Island! Enjoy year round big sky and water views from the comfort of the screened porch & family room. Fish & crab from the pier or take a dip in the bay. Open concept living and rear bedroom/rec room are perfect for relaxing and having fun with family & friends. Close to popular wedding venues, local marinas & charter fishing boats, restaurants, Tiki bars, beaches, golfing, parks, & bike trails.

Guest favorite

Cottage in Deale

4.82 out of 5 average rating, 178 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 sandy beach stretches along the Chesapeake Bay, where two colorful lounge chairs are positioned near the water's edge. Lush greenery and a manicured lawn are visible in the background, complemented by nearby cottages that offer a serene atmosphere.

Cottage in Deale

4.96 out of 5 average rating, 158 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

An outdoor dining area features a large wooden table surrounded by matching chairs, set on a stone patio. The view extends over the peaceful Chesapeake Bay, framed by bare trees and a clear blue sky.

Cottage in North Beach

4.97 out of 5 average rating, 324 reviews

Waterfront Cottage Near Herrington and North Beach

Escape to Osprey Cottage, a renovated oasis overlooking the Chesapeake Bay. Our home is a 1930s bungalow that has been tastefully updated with modern sensibility, while still preserving its original charm. Streamlined decor, gleaming wood floors, and stunning views from the common spaces, deck, and hot tub invite you to simply relax.

Guest favorite

A screened porch features comfortable seating and a ceiling fan, offering a shaded area to enjoy views of Rockhold Creek. Vibrant chairs in blue and orange are positioned nearby, surrounded by lush greenery and inviting outdoor space.

Cottage in Deale

4.9 out of 5 average rating, 165 reviews

Rockhold Creek Cottage

The Perfect rock fishing and crabbing cottage in Deale, Maryland right on Rockhold Creek, with docks and spectacular views! The waterfowl are mesmerizing to watch. Just 1/2 block from Happy Harbor and Fishing Charters! No need to make that drive at 4am, you can stay the night before and after for maximum enjoyment!

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What guests are saying

Cozy Off-street Cottage Maryland

4.96 out of 5 average rating, 27 reviews2 weeks ago

Denise’s place was wonderful. It was clean, spacious and peaceful. I was able to work remotely and relax afterwards. I visit the area often and was looking for a place to go that was peaceful and private and this place was just that . Would definitely return. If you need to get away to relax this is the place for you . There are many things to do close by but I didn’t take advantage of them this time. Denise’s communication and responsive was also a bonus and much appreciated

Cottage in Bowie

What guests are saying

The Middle Point Cottage at Saint Michaels

4.87 out of 5 average rating, 141 reviews3 months ago

We had a delightful stay at Nick’s place. The interior is unbelievably charming- it is clear that they have an eye for interior design! There were plenty of towels, a well stocked kitchen, and plenty of basic necessities. The beds were comfortable and the host left helpful instructions for the area and home. 10/10 we would come back again!

Cottage in Neavitt

What guests are saying

Full house rental in Twin Beach. 1 bk from the Bay

4.86 out of 5 average rating, 174 reviews6 months ago

Had to visit for an extended period of time for a family-related health issue. Having a place to go back to during my long stay and work was super important to me and this place delivered. What I wasn’t expecting was it’s outstanding location in the heart of North Beach (less than a block away from several restaurants and a 3 minute walk to the boardwalk), as well as it’s off-street parking which has been traditionally rare in North Beach when I’ve stayed at other airbnb’s. The house was clean, quiet, and convenient. I especially appreciated the small study where I was able to work remote during my stay. All in all, this made my stay far more pleasant than I was expecting and I definitely recommend it to anyone staying in North Beach for sure.

Cottage in North Beach

What guests are saying

Peaceful Escape: Bay Ridge Cottage by the Bay

4.93 out of 5 average rating, 73 reviews3 weeks ago

We had a great stay at Tiffany’s cottage which was close to the Chesapeake Bay for walking and close to Annapolis for everything we wanted to do while staying at the cottage. The house was very clean with all the amenities and clear instructions about the stay. Enjoyed it!

Cottage in Annapolis

What guests are saying

The Little House of Rockaway Beach, Maryland

5 out of 5 average rating, 43 reviews1 month ago

There are no words to express our gratitude 🙏 !! We absolutely loved “the little house” on rockaway beach…It was truly a healing home…we went to Baltimore for my husband’s ankle replacement surgery..this home could not be any more perfect for us…we can’t wait to come back….thank you again and again Brent & Jennifer!! ❤️❤️❤️❤️❤️❤️Casandra Amazing sunrises on the Potomac, close to Baltimore/Washington DC/Annapolis &more, nestled in the charming Rockaway Beach in Essex… The Little House is a comfortable & welcoming retreat. Me on my knee scooter, rolling into the kitchen, bedroom, bathroom and shower. Brent & Jennifer are Super Hosts for good reason, their warm hospitality and impeccable curated beach cottage make for the perfect Maryland getaway, no matter the season. We’ll be back! Scott 😍😍

Cottage in Essex

What guests are saying

Waterfront Cottage with Private Pier

4.91 out of 5 average rating, 47 reviews1 month ago

The pictures of Melissa’s house and the surrounding areas does it no justice. You have to be there to experience this beautiful home. The ambience and atmosphere were amazing. Melissa went above and beyond to make you feel at home. From activities to great places to eat. I definitely will come back again.

Cottage in Edgewater

What guests are saying

Duck Cove Waterfront Cottage

4.98 out of 5 average rating, 55 reviews6 months ago

The cottage was a perfect place for a relaxing anniversary getaway. Beautiful views, peaceful setting. House is very well maintained, clean and comfortable. Easy to launch canoe /kayaks from the dock, campfire by the water watching the moonrise over the water. Perfect, would love to return. Highly recommend.

Cottage in Neavitt