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Vacation rentals in Annapolis

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Quick stats about vacation rentals in Annapolis

  • Total vacation rentals

    Explore 650 vacation rentals in Annapolis

  • Nightly prices starting at

    Annapolis vacation rentals start at $14 CAD per night before taxes and fees

  • Verified guest reviews

    Over 32,300 verified reviews to help you choose

  • Family-friendly vacation rentals

    450 properties offer extra space and kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 230 rentals that welcome pets

  • Vacation rentals with a pool

    30 properties feature pools

  • Rentals with dedicated workspaces

    350 properties have a dedicated workspace

  • Wifi availability

    650 of Annapolis vacation rentals include wifi access

  • Popular amenities for guests

    Guests love Monthly stays, Self check-in, and Gym across Annapolis rentals

  • 4.9 Average rating

    Annapolis stays are highly rated by guests—averaging 4.9 out of 5!

Top-rated vacation rentals in Annapolis

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Top guest favourite
A spacious living area features large windows that allow natural light to fill the space, showcasing views of the surrounding greenery. Comfortable seating is arranged around a low table, with a television mounted on the wall, and decorative shelves filled with various items.
Cottage in Annapolis

Relaxing Water Views - Mill Creek Cottage

Eclectic three level water view cottage in unique wooded location overlooking beautiful Mill Creek. Minutes from downtown Annapolis and the US Naval Academy; walk to Cantler’s Riverside Inn for crabs, convenient to US 50 and the Bay Bridge and Eastern Shore. Due to the stairs and loft, this accommodation may not be appropriate for toddlers and the mobility challenged Parties are not permitted. Please note that there is no water access on the property, but there is nearby public water access.

4.97 out of 5 average rating, 470 reviews
Top guest favourite
The exterior of a charming historic building features a welcoming front porch adorned with seating. Lush green trees and blooming flowers enhance the inviting atmosphere. American flags are displayed, highlighting the traditional character of the neighborhood.
Home in Annapolis

Elegant & Authentic Annapolis

Enjoy comfortable elegance in this historic beauty on one of the prettiest streets in Downtown Annapolis--Main Street and the Water only 2 blocks away. This private unit is the full main level with its own eat-in kitchen, living room, front porch and back patio. Bedroom features queen size bed, dresser and walk-in closet. Bathroom has shower/tub and counterspace for your comfort. Street parking is available or public garage parking is a short stroll away. Relish this quiet & convenient location.

4.99 out of 5 average rating, 156 reviews
Top guest favourite
The exterior of a historic townhome is showcased, featuring red brick walls and black shutters. Lush greenery and colorful flowers enhance the garden area. A flag may be seen hanging from the building, set against a clear blue sky.
Townhouse in Annapolis

Historic 3 Bedroom Downtown Annapolis Townhome

Be close to everything when you stay at this centrally-located, historic townhome! Located steps from the Naval Academy, Downtown Restaurants, Bars, Shopping, and Festivals. Enjoy and relax on your large private, fenced-in patio or in your modern living room. While the restaurant scene is mouth-watering in Annapolis, you can also stay "home" and cook in your gourmet kitchen. Explore all that Annapolis has to offer from the comfort of your home away from home! No on-site parking but lots of off.

4.95 out of 5 average rating, 213 reviews
Top guest favourite
A screened porch features a hanging bench swing with cushions in shades of blue and nautical motifs. A small chair stands nearby, adorned with a decorative pillow. Tall curtains frame the space, providing a relaxed and inviting atmosphere surrounded by greenery.
Cottage in Annapolis

Charming City Oasis. Walk to harbor, eateries.USNA

As many others over the past decade, you will enjoy the year-round charm & convenience of this cottage. Just blocks from shops, restaurants, pubs.. Free parking. Enjoy a secluded patio oasis for family gatherings, a chimnea & blankets to wrap up in, furnishings from Robert Redford's Sundance, modern appliances, ceiling fans, AC/heat, bathrooms with comfort-height toilets & grab bars, original pine floors. Corn Hole boards available. Game on. Open USNA '28, '29 Com Wk. 6-night min applies.

4.87 out of 5 average rating, 116 reviews
Top guest favourite
A wooden dock extends over calm waters, leading to a charming home surrounded by trees. The house, featuring large windows, is illuminated as dusk approaches. Adirondack chairs are placed along the shoreline, inviting relaxation in the natural setting.
Home in Stevensville

Kent Island Waterfront Home with Amazing Sunsets

Relax with the whole family at this peaceful and beautiful home on Thompson Creek! Enjoy the gorgeous sunsets all year-long. Bring your boat, fishing gear or other watercraft and discover Kent Island! Thompson Creek is accessible to the Chesapeake Bay and a short ride to discover Annapolis, The Kent Narrows or St. Michaels. In the mornings, sip coffee on the screened-in porch and bring a book - you may be there for a while! Our home feels remote but is accessible to convenient shopping.

4.99 out of 5 average rating, 149 reviews
Top guest favourite
Home in Shady Side

Iconic Chesapeake. Unparalleled Luxury.

Summer at The Cottage at Silver Water is effortless and indulgent. A sweeping waterfront lawn leads to a private shoreline for swimming, kayaking, and long days in the sun. Evenings bring golden skies, spectacular sunsets, and fires by the water’s edge. Inside, the cottage is beautifully designed with luxurious bedding, curated art, and thoughtful amenities that make every stay relaxed, refined, and unforgettable. See why all our guests only have a 5-Star experience.

5.0 out of 5 average rating, 214 reviews
Top guest favourite
A living area features a gray couch adorned with decorative pillows against a light wall. A recliner is positioned nearby, and a wall-mounted Smart TV is visible. A dresser with a plant sits below the TV. Natural light streams in through nearby windows.
Condo in Annapolis

1st Floor Condo in Annapolis

This newly renovated, 1st floor studio is perfectly located just across Spa Creek from historic Annapolis in Eastport. Within easy walking distance of restaurants (3 min), Main Street/City Dock (10 min) & USNA's Gate 1 entrance (14 min), our studio includes a full kitchen, high-speed wifi, free onsite parking lot, a secure building entrance, dock (limited access) and a rooftop patio (with a seasonal pool) that offers beautiful views of downtown Annapolis.

4.96 out of 5 average rating, 172 reviews
Top guest favourite
The front exterior of the home features vibrant, blooming flowerbeds with a variety of blue and pink flowers. Two hanging planters with yellow flowers adorn the entryway, while a charming red door stands out against the yellow walls. A small seating area with dark chairs is visible on the porch.
Home in Annapolis

Historic & sunny home steps from USNA/downtown

This beautiful and cozy 3-bedroom, 2.5 bath home built in 1900 is located on Prince George Street, one block from Annapolis City Dock and Gate 1 (main gate) of the US Naval Academy. Filled with sunlit, spacious rooms and equipped with numerous amenities (incl. gas fireplace), this home can sleep up to 8 (on 4 beds in the 3 bedrooms and 1 futon in a private room in the basement) and offers a combination of location and charm that is hard to beat!

5.0 out of 5 average rating, 202 reviews
Top guest favourite
A modern kitchen is highlighted by sleek white cabinetry and a large island with seating for four. Stainless steel appliances are positioned for convenience, and natural light fills the space through a window overlooking the backyard.
Townhouse in Annapolis

Beautiful Downtown Annapolis Townhome!

Beautiful Remodeled Townhome ! We have thought of everything you will need for an amazing stay. Fully loaded kitchen , 3 and 1/2 Baths , Wonderful Upgraded Mattresses that will ensure a great nights sleep, Big screen TV's Back yard courtyard with gas firepit. And the best part....... Walking distance to Downtown Annapolis with Shopping , Dining and much more bring the whole family to this great place with lots of room for fun.

5.0 out of 5 average rating, 119 reviews
Top guest favourite
A spacious great room features large windows that offer sweeping views of the water. Comfortable seating arrangements with soft furnishings are complemented by a working fireplace. A staircase is visible in the background, leading to additional living spaces.
Home in Shady Side

Waterfront Sanctuary only 50 Min. From DC/Balt.

New full home renovation with gourmet kitchen, wide open floor plan, multiple guests rooms, and a bunk room that accommodates 12. An inviting space that welcomes any couple or a large extended family. This home sits with only three other homes on a private peninsula and has water access on both sides. It is conveniently located less than an hour from DC and Baltimore on the west coast of the Bay (no need to cross the Bay Bridge).

4.97 out of 5 average rating, 110 reviews
Top guest favourite
Cottage in Annapolis

Weems Creek Cottage, Annapolis Waterfront

(August, 2025) Jim is the best host we’ve ever had. Super responsive, reached out to let us know the place was ready and we could check in early. The house is perfect size for 2 adults and a kid. Beautiful view and really comfortable. We loved the screened in porch. We walked to breakfast at the smoothie place and had a great walk down to the naval academy. We would definitely stay here again.

4.98 out of 5 average rating, 164 reviews
Top guest favourite
Apartment in Annapolis

Charming, Chic Downtown Annapolis Apartment #1

In the heart of Downtown Annapolis. One block from Main Street/West Street/Church Circle. Close proximity to USNA, Ego Alley, Eastport, State House, shops, galleries, restaurants/bars and all other DTA amenities. This private apartment has an open floor plan and is elegantly decorated (with a modern twist). One Full Bathroom with tiled shower. One Bedroom with walk-in closet (with W/D).

4.91 out of 5 average rating, 120 reviews

Popular amenities for Annapolis vacation rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Stay near Annapolis's top sights

Downtown Annapolis Partnership

57 locals recommend

United States Naval Academy

121 locals recommend

Quiet Waters Park

166 locals recommend

Rams Head Tavern

127 locals recommend

Westfield

124 locals recommend

Annapolis Maritime Museum & Park

96 locals recommend

Other great vacation rentals in Annapolis

Guest favourite
The exterior of a charming two-story row house is presented, featuring light blue siding and black shutters. A pink front door is framed by decorative greenery, while a small bench sits on the red brick walkway. Potted plants add a welcoming touch to the entrance.
Home in Annapolis

Charming Renovated Historic Home Downtown wParking

4.91 out of 5 average rating, 241 reviews
Top guest favourite
An inviting front yard is presented, featuring a pathway of round stones leading to the entrance of a two-story guesthouse. Lush greenery is framed by ornamental plants and mulched beds, creating a serene outdoor setting surrounded by trees.
Home in Annapolis

Quiet Waterfront

4.98 out of 5 average rating, 189 reviews
Top guest favourite
Cottage in Annapolis

Charming Cottage 2 parking spot easy walk downtown

4.94 out of 5 average rating, 214 reviews
Top guest favourite
Home in Annapolis

Sailing Off Gloucester

5.0 out of 5 average rating, 19 reviews
Top guest favourite
Apartment in Annapolis

The Sail Loft

5.0 out of 5 average rating, 43 reviews
Top guest favourite
The exterior of a charming, single-story house is depicted, featuring a well-maintained lawn bordered by trees and shrubs. A vibrant red door provides a welcoming focal point. The pathway leads to the entrance, complemented by stairs on either side, indicating accessibility.
Home in Annapolis

The Red Door Cottage - Pet-Friendly!

5.0 out of 5 average rating, 41 reviews
Top guest favourite
Home in Annapolis

The Anchored Stay: Spacious, Walkable & Parking

5.0 out of 5 average rating, 18 reviews
Top guest favourite
A welcoming living space is highlighted by natural light streaming through large windows. A light beige sofa is positioned alongside a wooden dining table with a yellow décor piece. A bright yellow door provides a striking focal point, complementing the greenery in the room.
Home in Annapolis

Historic + Modern Home | Just Steps to Waterfront

5.0 out of 5 average rating, 52 reviews

When is the best time to visit Annapolis?

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Frequently Asked Questions

  • What are the best places to stay in Annapolis?

    Many guests choose accommodations in the Historic District for walkable access to waterfront sights, local shops, and dining. Eastport, just across the harbor, has a laid-back vibe and maritime charm that is often recommended.

  • What are the best things to do in Annapolis with kids?

    Families frequently explore the U.S. Naval Academy, visit local museums, or enjoy sailing lessons around the harbor. Parks and waterfront trails also provide space for outdoor play and discovery.

  • What are some of the best things to do in Annapolis?

    Explore historic sites like the Maryland State House, wander local marina areas, and discover galleries and cafes in the Historic District. Sailing or taking guided boat tours is often suggested for experiencing the city’s maritime culture.

  • How is the weather in Annapolis?

    Annapolis has crisp winters around 25–43°F (-4–6°C) and warm, humid summers between 68–89°F (20–32°C). Rain is fairly consistent year-round, so packing layers and a rain jacket is helpful.

  • What are the best places to visit in Annapolis?

    Explore the U.S. Naval Academy’s historic grounds, the Maryland State House, and quiet corners of the Historic District. City Dock is frequently suggested for people-watching, local snacks, and harbor views.

  • What are some hiking trails in Annapolis?

    Quiet Waters Park has wooded trails, art installations, and water views, making it a favorite for walkers and nature lovers. Greenbury Point is another area with paths winding through natural habitats near the water.

  • What are some family activities we can do in Annapolis?

    Families often enjoy exploring interactive exhibits at local museums, sailing or kayaking together, and strolling city parks for outdoor fun. Many neighborhoods have playgrounds and green spaces for all ages.

  • What are some of the best day trip ideas from Annapolis?

    Explore vibrant waterfront towns on the Chesapeake Bay, discover local wineries and farms around the region, or visit natural preserves just outside the city. State parks and small historic communities are also frequently suggested.

  • Are there any pet friendly accommodations available in Annapolis?

    Many rentals in the Historic District and Eastport area welcome pets, making it easy to explore the city’s parks and waterfront trails together. Some hosts provide amenities for pets, such as bowls and outdoor spaces.

  • What are some local tips for visiting Annapolis?

    Walking is a great way to explore narrow historic streets and see waterfront sights. Trying a sailing experience, sampling local crab dishes, and checking out neighborhood art galleries help connect with Annapolis’s distinct maritime culture.

  • What is Annapolis known for?

    Annapolis is known for its maritime heritage, historic architecture, and the presence of the U.S. Naval Academy. The city has a vibrant sailing culture, colonial-era sites, and crab-focused cuisine.

  • What are the best hidden gems to explore in Annapolis?

    Artists’ studios in West Annapolis, cozy bookshops in the historic area, and small galleries along quaint side streets allow visitors to connect with the local creative community. The Kunta Kinte-Alex Haley Memorial offers space for reflection near the water.

  • What are the best foods to try in Annapolis?

    Annapolis has Maryland blue crab specialties such as crab cakes and creamy crab soup, along with fresh oysters and locally made ice cream. You’ll also find regional dishes rooted in Chesapeake Bay traditions.

  • What should I bring for a trip to Annapolis?

    Pack comfortable walking shoes, layered clothing, and a rain jacket for changing weather. A wide-brim hat and sunscreen are useful for sunny days spent exploring the waterfront or hopping on boat tours.

  • What is the nightlife in Annapolis like?

    Annapolis has lively bars, local breweries, and music venues clustered around the Historic District and Eastport. Jazz nights, open mics, and waterfront pubs create a relaxed evening atmosphere.

  • What are the most popular events or festivals in Annapolis?

    The city hosts boat shows in spring and fall, and the Maryland Renaissance Festival takes place nearby in late summer and early fall. Local parades and seafood celebrations add to the festive calendar.

  • Are there family friendly vacation rentals in Annapolis?

    Vacation rentals in neighborhoods like the Historic District and Eastport often have kid-friendly sleeping arrangements and amenities such as kitchens and outdoor spaces. Many hosts are welcoming to families and provide helpful local tips.

  • When is the best time to visit Annapolis?

    Late spring through early fall is often recommended for milder temperatures and frequent waterfront events. The changing leaves in autumn create pleasant scenery for city walks and harbor outings.

Destinations to explore