Annapolis Romantic Hotels, Maryland: Annapolis Hotel Guide

A historic town street at dusk with a prominent church dome, brick buildings, and a yellow fire hydrant.

Change your mind
Book hotels with free cancellation
Treat yourself
Sign in to save 10% or more on thousands of hotels
Sign in
Be picky
Search almost a million properties worldwide

Check availability on Annapolis Romantic Hotels

Tonight

Tomorrow

This weekend

Next weekend

Our top choices for Annapolis romantic hotels

A wooden dock extending into a calm body of water with boats docked at the end.

A modern living room with a white sofa, a coffee table, and a potted plant.

A two-story house with a porch, a flag, and a welcome sign.

A kitchen with wooden flooring, stainless steel appliances, a white door, and a white dining table with chairs.

1. Cozy 2br home w/ parking in downtown Annapolis

Historic District

Nancy N.

€389

includes taxes & fees

5 Oct - 6 Oct

A house with a red door, a small porch, and a view of a river with a bridge in the background.

A wooden picnic table with checkered tablecloths, set on a wooden deck.

A two-story building with a covered outdoor area, a staircase, and trees with autumn leaves.

A cozy living room with a bed, a television, a coffee table, and a sofa.

2. Your Annapolis Waterfront retreat for a weekend or any-day getaway!

West Annapolis

Jill R.

A wooden dock with Adirondack chairs and a ladder, overlooking a calm body of water with a distant shoreline.

A house with a large lawn, a dock, and a tree.

A dock with a boat and a house in the background.

A modern kitchen with white cabinets, a wooden dining table, stainless steel appliances, and a window providing natural light.

3. Chesapeake Cottages- 2 Quaint Waterfront Retreats

Pasadena

Buu T.

€579

includes taxes & fees

28 Sept - 29 Sept

Three birds perched on a wooden structure by the water.

A beach with a thatched-roof hut, a white building with a red roof, and a wooden structure with a curved roof.

A wooden deck with picnic tables and umbrellas, a covered seating area with chairs, and a house with large windows.

A cozy living room with a ceiling fan, a dining area with chairs and a table, and large windows offering a view of the outdoors.

4. Waterview Home! Beach Volleyball! Near Wedding Venues! Walk to Bar & Restaurant!

Stevensville

barbara s.

€1,155

includes taxes & fees

27 Sept - 28 Sept

A waterfront with a docked boat, a water taxi, and a historic building with a clock tower.

A kitchen with wooden cabinets, a microwave, a coffee maker, and a dishwasher.

A living room with a brick wall, leather sofa, a small table with a lamp, and a TV mounted on the wall.

A neatly made bed with striped bedding and two bedside tables with lamps.

5. Cozy Fells Point Gem / In The Heart of Fells Point

Fells Point

Tammy

€221

includes taxes & fees

4 Oct - 5 Oct

A two-story house with a backyard swimming pool, surrounded by trees and a well-maintained lawn.

A spacious living room with a large window, a ceiling fan, and a sofa.

A kitchen with white cabinets, a central island with stools, a dining area with a table and chairs, and a view through the glass doors.

A dining area with a white table, a vase of flowers, and a staircase.

6. 4 Bedroom Waterview - MD Chesapeake Bay! Walk to Marina, Beach Bar & Restaurant!

Stevensville

David R.

€1,245

includes taxes & fees

27 Sept - 28 Sept

View all properties

Top Annapolis Hotel Reviews

Graduate by Hilton Annapolis

10/10 Excellent

"I love the Graduate Hotel and it is very convenient. But please fix the parking garage gate 😬! It’s terrible!"

DoubleTree by Hilton Hotel Annapolis

10/10 Excellent

"We were comfortable, very comfortable actually and this hotel had everything we needed to get our son off to college."

Annapolis Waterfront Hotel, Autograph Collection

8/10 Good

"The view from our room was incredible. The property is clean and the beds comfortable. For the price, however, the only thing that justifies it is the view and location. There are 2 restaurants- Marmo was disappointing and overpriced. The cantina was great. Unfortunately, they take up all of the waterfront dock area, so there is really nowhere else to gather in the hotel to enjoy the water if you just want to sit and visit or play a game, or some such. (The balconies were too small for anything except a cup of coffee). And since the restaurants are open to the public the area is packed all the time. Otherwise, being an older hotel, there really aren't any special amenities. No spa or pool. nothing else special about it. And those terrible nespresso machines in the room. I just want a regular cup of coffee. Parking is overpriced- we hoofed it to a garage a few blocks away for significantly less per day."

Best Western Annapolis

10/10 Excellent

"The room was clean and well maintained. The lobby was pleasant, and the staff was friendly and attentive. The breakfast was excellent for this price point, with a wide selection of hot and cold items."

The Westin Annapolis

10/10 Excellent

"Only used the valet parking."

Frequently asked questions

Searching for romantic hotels in Annapolis?

If you and your partner need a romantic holiday, we've got just the thing. Couples choose Annapolis for its top-notch restaurants, major shopping area and interesting historical sites. If you want to spend some time strolling through captivating scenery with your love, you might make a visit to Maryland Quiet Waters Park, Ellen O. Moyer Nature Park at Back Creek or Helen Avalynne Tawes Garden. Whether you'd like to soak in a hot tub or watch the sunset from your balcony, you'll be sure to find accommodation in Annapolis to make for a relaxing weekend away.

When is the best time of year for a romantic getaway to Annapolis?

If you're hoping to get lost in the rain on your romantic getaway, take a look at these details about year-round temperatures in Annapolis: The hottest months are usually July and August, with an average temperature of 24°C, while the coldest months are January and February, with an average of 4°C. Average annual precipitation for Annapolis is 1318 mm.

What is there to do in Annapolis?

There's nothing better than wandering around a new destination with your sweetheart, so consider taking time to discover all that Annapolis has to offer. If you're hoping to see some of the area's cultural attractions, you and your partner will love Annapolis for its major shopping area and interesting historical sites. You might think about stopping by William Paca House, Annapolis City Dock or Navy-Marine Corps Memorial Stadium while you're seeing the sights.

What's the best way to get to Annapolis and around town during my romantic getaway?

This information about transportation options in Annapolis might help your romantic getaway go off without a hitch: To get to Annapolis, you can fly into Fort Meade, MD (FME-Tipton), which is the closest major airport, located 16.2 mi (26.1 km) from the city centre. If you'd like to venture out around the area, consider renting a car to explore more sights.

Explore a world of travel with Expedia

Maryland Holiday Rentals

Things to do in Maryland

Annapolis Hotel Guide - Romantic Hotels in Annapolis, Maryland

Change your mind

Treat yourself

Be picky

Check availability on Annapolis Romantic Hotels

Our top choices for Annapolis romantic hotels

1. Cozy 2br home w/ parking in downtown Annapolis

2. Your Annapolis Waterfront retreat for a weekend or any-day getaway!

3. Chesapeake Cottages- 2 Quaint Waterfront Retreats

4. Waterview Home! Beach Volleyball! Near Wedding Venues! Walk to Bar & Restaurant!

5. Cozy Fells Point Gem / In The Heart of Fells Point

6. 4 Bedroom Waterview - MD Chesapeake Bay! Walk to Marina, Beach Bar & Restaurant!

Top Annapolis Hotel Reviews

Graduate by Hilton Annapolis

DoubleTree by Hilton Hotel Annapolis

Annapolis Waterfront Hotel, Autograph Collection

Best Western Annapolis

The Westin Annapolis

Frequently asked questions

Explore a world of travel with Expedia