Best & Cheap Romantic Getaways in Annapolis, MD

Compare romantic getaways, From $21/night

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ACCOMMODATION TYPES

Best & Cheap Romantic Getaways in Annapolis, MD: Top Deals

Large modern in wooded privacy
Guest Suite · 2 Guests · 6 Bedrooms
Large modern in wooded privacy
4.8 (12 reviews)
This Guest Suite is located in a wooded area, just outside of Washington D.C., offering guests a tranquil and private getaway. Nearby restaurants include the Red Horse Tavern, The Melting Pot, and Rí Rá Irish Pub & Restaurant. Popular activities in the area include exploring the Oxon Cove Park & Oxon Hill Farm and taking a hike along the Billy Goat Trail.
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$697 /night*
Lots free parking, hot tub, tree house, outdoor oasis - NOT party house
Guest Suite · 2 Guests · 4 Bedrooms
Lots free parking, hot tub, tree house, outdoor oasis - NOT party house
4.8 (13 reviews)
This Guest Suite is a perfect spot for those looking for a peaceful outdoor escape. Located just a short distance away from popular restaurants, activities, and trails, guests can enjoy the hot tub, tree house, and outdoor oasis without having to worry about noise or overcrowding. Nearby popular restaurants include Pusser's Caribbean Grille, Iron Bridge Wine Co., and The Point at Kent Narrows. Popular activities in the area include kayaking, paddle boarding, and visiting Chesapeake Beach Water Park. Nature lovers can explore nearby trails such as Maryland State Forest Trail, Chesapeake Bay Environmental Center, and Matapeake Beach & Fishing Pier.
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$683 /night*
Adorable waterside cottage with pool Beach community
Guest Suite · 8 Guests · 2 Bedrooms
Adorable waterside cottage with pool Beach community
4.6 (28 reviews)
This Guest Suite is an adorable waterside cottage located in a beach community that can accommodate up to 8 people and allows pets. Nearby popular restaurants include Captain Chuck-A-Mucks, Brass Cannon Brewing, and The Pier Restaurant & Lounge. Popular activities nearby include fishing, kayaking, and paddle boarding. Additionally, there are several trails for hiking and biking nearby, including the Cedar Creek Trail, the Chesapeake Beach Railway Trail, and the Cross Island Trail.
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$342 /night*
Crowne Plaza Annapolis, an IHG Hotel
Hotel
Crowne Plaza Annapolis, an IHG Hotel
4.3 (690 reviews)
This Hotel is located in Annapolis, Maryland and offers a convenient location near popular attractions such as the US Naval Academy, Sandy Point State Park, and Quiet Waters Park. The nearby restaurants include Carrol's Creek Cafe, Galway Bay Irish Pub & Restaurant, and Lemongrass Asian Bistro. There are also plenty of activities to enjoy such as shopping at Westfield Annapolis Mall, visiting the Annapolis Maritime Museum, or exploring nature on the Baltimore and Annapolis Trail. Pets are not allowed.
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$98 /night
Country Inn & Suites by Radisson, Annapolis, MD
Villa
Country Inn & Suites by Radisson, Annapolis, MD
This Villa is located in Annapolis, Maryland and offers pet-friendly accommodations. Popular nearby restaurants include Chick & Ruth's Delly, Red Red Wine Bar, and Tsunami Sushi & Lounge. For activities, visitors can explore the historic streets of downtown Annapolis or take a trip to Sandy Point State Park for trails, beaches, and waterfront views.
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$105.6 /night
Annapolis Area Private, 3 Bedroom Pool, Jacuzzi & Sauna & Casino-Like Game Room
Guest Suite · 2 Guests · 3 Bedrooms
Annapolis Area Private, 3 Bedroom Pool, Jacuzzi & Sauna & Casino-Like Game Room
4.7 (27 reviews)
This luxurious Guest Suite in the Annapolis area is perfect for a weekend getaway. It features a private 3-bedroom pool, jacuzzi, sauna and a casino-like game room. The suite can sleep up to 2 people and pets are not allowed. Popular local attractions include the Sandy Point State Park, the Annapolis Maritime Museum, and the historic William Paca Garden. There are also various restaurants nearby such as Cantler's Riverside Inn, Pusser's Caribbean Grille, and The Iron Rooster.
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$1345 /night*
Waterfront Kent Island home with Hot Tub!
Guest Suite · 8 Guests · 4 Bedrooms
Waterfront Kent Island home with Hot Tub!
5.0 (1 review)
This Guest Suite is a waterfront home located in Kent Island, Maryland. It offers amenities such as a hot tub and can comfortably sleep 8 people. Popular restaurants nearby include Hemingway's Restaurant & Lounge, Mears Great Oak Landing, and The Jetty Dock Bar. Other activities to enjoy include fishing at Matapeake Park, hiking the Chesapeake Bay Environmental Center trails, and boating on Eastern Bay.
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$774 /night*
Annapolis Entertainment Complex
Guest Suite · 2 Guests · 4 Bedrooms
Annapolis Entertainment Complex
4.9 (56 reviews)
This Annapolis Entertainment Complex is a well-equipped Guest Suite located in the heart of Annapolis, Maryland. It can accommodate up to two people and even allows pets! Popular restaurants nearby include Carrol's Creek Café, Blackwall Hitch, and Tsunami Sushi Bar & Lounge. Other activities close by include sailing at Annapolis Harbor, biking along the B&A Trail, and visiting the U.S. Naval Academy Museum. With so much to do in the area, this Guest Suite is the perfect place for an unforgettable adventure.
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$697 /night*
Charming Annapolis WaterVIEW Home
Guest Suite · 2 Guests · 5 Bedrooms
Charming Annapolis WaterVIEW Home
4.7 (23 reviews)
This Charming Annapolis WaterVIEW Home is a pet-friendly guest suite that can accommodate up to two people. Located near the waterfront in Annapolis, it's close to popular restaurants like Carrol's Creek Cafe, McGarvey's Saloon & Oyster Bar, and Chick & Ruth's Delly, as well as outdoor activities such as biking or walking along Spa Creek Trail, kayaking on the Severn River, and sightseeing at the United States Naval Academy.
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$653 /night*
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Which Price Range Is Considered As A Good Deal in Annapolis, MD Area?
Vacation House & Apartment Rental Price Information in Annapolis, MD
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The graph shows the percentages of vacation homes in each price bucket. Annapolis has the largest percentage (19.76%) of homes in $500+ price range.
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How Many Accommodations Are Pets Allowed in Annapolis, MD?
Percentage of Pet Friendly Rental Properties in Annapolis, MD
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21.53% of vacation homes in Annapolis are pet friendly. If you have pet allergies, make sure to check the home property and see whether it is a pet-friendly vacation home or not.
Where are the best romantic restaurants in Annapolis, MD?
Romantic Restaurants in Annapolis
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Annapolis is a great place to celebrate your special occasion. Here are some of the most romantic restaurants in the area, perfect for honeymoons and anniversaries alike.

  • Harry Browne's Restaurant: This cozy eatery serves up delicious American fare with a French twist. Enjoy views of Spa Creek as you savor their signature dishes including crab cakes, steak frites, and shrimp scampi.
  • Carrol's Creek Cafe: This waterfront restaurant offers an extensive seafood menu with a few steaks and chicken dishes sprinkled in. The outdoor seating is especially popular during sunset when the view of the Chesapeake Bay can be appreciated.
  • The Boatyard Bar & Grill: This casual restaurant boasts incredible views of the harbor along with a variety of grilled favorites. Visitors rave about the seafood mac and cheese, crab cakes, burgers, and other classic dishes.
What activities can couples enjoy in Annapolis?
Romantic Activities in Annapolis
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Annapolis has plenty of activities for couples to enjoy together. From walking tours to boat rides, here are some of the best romantic activities in the city.

  • Annapolis City Walking Tour: Take a leisurely stroll through historic streets and learn about the city's nautical history, architecture, and culture. This tour is particularly special at sunset when the buildings and monuments glow golden.
  • Harbor Queen Cruises: Set sail on the Harbor Queen for a romantic cruise around the bay. During the ride, admire the stunning scenery and spot local wildlife such as dolphins, ospreys, and bald eagles.
  • Tall Ships Cruise: Enjoy a majestic Tall Ships cruise on the Severn River. Watch the tall ships fly by as you sip champagne and take in the beautiful sights of Annapolis.
Best Tourist Attractions in Annapolis, MD?
Top Rated Places to Visit in Annapolis, MD
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What are the Airports in Annapolis, MD?
Suggested Airports in Annapolis, MD
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