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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 av 5 i genomsnittligt betyg, 473 omdömen
Modern Annapolis Getaway - 2 Free Parking Spaces
Modern 2 bedroom, 1 bath home located in the heart of historic Annapolis. Completely remodeled with free off-street parking. Located towards the end of a safe, quiet, dead end road, less than 3 miles from downtown Annapolis, the Naval Academy, the Annapolis Mall, St. John’s College, and the Navy-Marine Corps Memorial Stadium. Walk downtown or to the Annapolis Town Center, restaurants, shops, and so much more! -Wi-Fi -2 free parking spaces -Keurig Coffee -TV -Toothbrushes/Paste -Shampoo/Soaps
5,0 av 5 i genomsnittligt betyg, 123 omdömen
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.
4,9 av 5 i genomsnittligt betyg, 368 omdömen
Lil’ House - A Serene Tiny Home Experience
Newly renovated, immaculate two room tiny home. A stand-alone gem nestled against a wooded backdrop - well back from the main home - and wrapped in a huge, teak-furnished, blue stone patio with fire pit situated in a sunny opening in the mature tree canopy. Super comfy queen Murphy bed offers easy conversion of the well lit and modern main living space from living room & kitchen by day to main sleeping quarters at night. The adjoining room is a well appointed full bath and dressing area.
4,95 av 5 i genomsnittligt betyg, 212 omdömen
Iconic Chesapeake. Unparalleled Luxury.
Autumn at The Cottage at Silver Water is peaceful, cozy, and a little magical. Crisp days invite you to kayak, explore the shoreline, or enjoy the changing colors. Evenings bring golden skies, spectacular sunsets, cool breezes, and fires by the water. Inside, the cottage is warm and inviting, with luxurious bedding, curated art, and thoughtful amenities for a relaxed, memorable stay. Come experience autumn at Silver Water—and see why every guest has given their stay five stars.
5,0 av 5 i genomsnittligt betyg, 217 omdömen
Pet-Friendly King Suite + Kitchen | Near Annapolis
Settle in just minutes from Annapolis in a spacious, pet-friendly guest suite with a king bed, full kitchen, separate living area, and year-round hot tub access. Perfect for couples, families, pet owners, and longer stays, Captain's Quarters sleeps up to 4 with a king bed plus a queen-size LoveSac sofa bed. Located just 4 miles from historic Downtown Annapolis and the U.S. Naval Academy, with private keyless entry, fast Wi-Fi, designated parking, and all the comforts of home.
4,95 av 5 i genomsnittligt betyg, 217 omdömen
Bay View Studio Apartment
Sweeping views of the Chesapeake Bay Bridge may be enjoyed from your apartment with tall windows facing the bay, private patio, or hot tub! 50 ft of waterfront make this private walk-out garden-level apartment nestled in a small wooded oasis near downtown Annapolis a gem. Walk to the marinas or the Sailing School to catch a water taxi to downtown or book a private sail or fishing tour. Walk to Port Annapolis to get some fresh baked goods at Black Market Bakery.
4,97 av 5 i genomsnittligt betyg, 100 omdömen
Annapolis Garden Suite
Welcome to our oasis, tucked away on a forested residential street. ~7 minutes from the Annapolis Towne Centre, ~15m from the coast, and ~30m from Baltimore and DC. Tl;dr: This is a ground-level guest suite. Inside, you’ll find 3 beds, 2 bedrooms, 1 desk, 1 kitchen with a dishwasher, oven, Nespresso/pour over, 2 TVs, a laundry room, fast wifi, a pool, patio and a forest view. We live on the top floor (separated by stairs and a locked door; separate entrances).
4,94 av 5 i genomsnittligt betyg, 147 omdömen
Coastal Waterfront 1 Bedroom Cottage
Enjoy a peaceful waterfront getaway just 2 miles from Historic Downtown Annapolis and the U.S. Naval Academy. Located directly on the South River in a quiet neighborhood, this charming cottage features a full kitchen, 1 bedroom, washer/dryer, and sleeper sofa for up to 4 guests. Relax on the private patio with outdoor seating, grill, and fire pit, or enjoy the beautiful river views. Perfect for exploring Annapolis or simply unwinding by the water.
5,0 av 5 i genomsnittligt betyg, 226 omdömen
The Navy House-Walk or Shuttle Downtown! 3 bd
Your family will be close to everything when you stay at this centrally-located home. 3 blocks from the Navy stadium and walking distance to amazing restaurants! Here is your Annapolis home away from home. Our 3 bedroom 2.5 bath bungalow retreat is perfect for 6-7 people wanting to relax and see all that beautiful Annapolis has to offer. There’s also a free shuttle that takes you downtown to the water. Come, enjoy!
4,93 av 5 i genomsnittligt betyg, 206 omdömen
Garden View, 1 Bedroom and a Loft.
Relax and unwind at this peaceful and charming retreat, nestled in a quiet neighborhood. Located just minutes from Route 50, I-95, and Downtown Annapolis, Garden View is ideally situated for exploring Naval Academy sports, the Renaissance Festival, Boat Shows, and golf at The Preserve. If you prefer staying in, the fully equipped kitchen and free Wi-Fi make it easy to work or cook from the comfort of your space.
4,99 av 5 i genomsnittligt betyg, 167 omdömen
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 av 5 i genomsnittligt betyg, 168 omdömenPopulära bekvämligheter för semesterboenden nära Westfield
Andra populära sevärdheter nära Westfield
Lägenheter med wifi

1st Floor Condo in Annapolis
4,96 av 5 i genomsnittligt betyg, 180 omdömen
Funky Uptown Apt meets Downtown - Hist District
4,96 av 5 i genomsnittligt betyg, 128 omdömen
New Downtown Annapolis Condo With Free Parking
4,98 av 5 i genomsnittligt betyg, 166 omdömen
Renovated Apt In Historic Dist w/2 Parking Spots
4,94 av 5 i genomsnittligt betyg, 455 omdömen
Anchors Away
4,85 av 5 i genomsnittligt betyg, 110 omdömen
Captains Quarters | Waterfront & Pool
4,98 av 5 i genomsnittligt betyg, 124 omdömen
Annapolis @Gate 1 steps to the Harbor Free parking
4,91 av 5 i genomsnittligt betyg, 153 omdömen
Capts Qrtrs - Awesome downtown Annapolis location!
4,86 av 5 i genomsnittligt betyg, 193 omdömenFamiljevänliga hus

Luxury Modern Home on Water+Hotub- Annapolis 25min
4,99 av 5 i genomsnittligt betyg, 145 omdömen
Waterfront Sanctuary only 50 Min. From DC/Balt.
4,97 av 5 i genomsnittligt betyg, 113 omdömen
Kent Island Waterfront Home with Amazing Sunsets
4,99 av 5 i genomsnittligt betyg, 152 omdömen
Captain’s Retreat! Newly Renovated - Beach House!
4,98 av 5 i genomsnittligt betyg, 109 omdömen
Large Home w/ Pool, Gym, 7 Bedrooms, Sleeps 21
4,86 av 5 i genomsnittligt betyg, 228 omdömen
Downtown Annapolis Luxury House
4,98 av 5 i genomsnittligt betyg, 102 omdömen
Waterfront Chesapeake Bay Sunrises & Fishing Dock!
4,98 av 5 i genomsnittligt betyg, 185 omdömen
Beach Access, Hot Tub, Pet Friendly, Fully Fenced
4,99 av 5 i genomsnittligt betyg, 142 omdömenLägenheter med luftkonditionering

Charming, Chic Downtown Annapolis Apartment #1
4,9 av 5 i genomsnittligt betyg, 125 omdömen
Just Like Home - Private Entrance Apt in DMV Area
4,94 av 5 i genomsnittligt betyg, 176 omdömen
Charming Navy-Themed Townhome | Walk to USNA & DTA
4,93 av 5 i genomsnittligt betyg, 118 omdömen
Perfect Eastport location
4,98 av 5 i genomsnittligt betyg, 148 omdömen
Gybeset Eastport Inn
4,88 av 5 i genomsnittligt betyg, 307 omdömen
Pet Friendly Garden Apartment Near Annapolis
4,91 av 5 i genomsnittligt betyg, 476 omdömen
CIRCA 1885-Historic Annapolis-USNA GATE 1
4,99 av 5 i genomsnittligt betyg, 133 omdömen
King George Downtown Annapolis Getaway
4,85 av 5 i genomsnittligt betyg, 129 omdömenAndra bra semesterboenden nära Westfield

Miller Cottage - near Navy Stadium
4,99 av 5 i genomsnittligt betyg, 164 omdömen
Step Out to Main Street From a Chic Loft
4,92 av 5 i genomsnittligt betyg, 1143 omdömen
Charming Detached Studio w/ easy walk to Downtown.
4,96 av 5 i genomsnittligt betyg, 230 omdömen
Annapolis Guesthouse - Completely Separate Space
4,88 av 5 i genomsnittligt betyg, 219 omdömen
Waterfront-View of Bay from your Bed
4,99 av 5 i genomsnittligt betyg, 371 omdömen
Serene Hideaway
5,0 av 5 i genomsnittligt betyg, 43 omdömen
Welcome to Heron House! Annapolis Waterfront Oasis
4,98 av 5 i genomsnittligt betyg, 43 omdömen
CJ's Cottage
4,95 av 5 i genomsnittligt betyg, 84 omdömenDestinationer att utforska
- M&T Bank Stadium
- National Mall
- Vita huset
- Walter E Washington Convention Center
- Nationalparken
- Johns Hopkinsuniversitetet
- FedExField
- Oriole Park at Camden Yards
- Federal Hill Park
- Capital One Arena
- Georgetown Waterfront Park
- Howard University
- Arlington National Cemetery
- Betterton Beach
- Washingtonmonumentet
- National Harbor
- Nationalmuseum för afroamerikansk historia och kultur
- Baltimore Convention Center
- CFG Bank Arena
- Smithsonian National Zoological Park
- Bibelmuseet
- Smithsonian National Air and Space Museum
- Nationella akvariet
- Smithsonian American Art Museum





