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Compare 438 Vacation Homes in Friendship with updated reviews, rates, and availability.

Directly Across from Gate One & Steps from the Waterfront
Private rear courtyard
Directly Across from Gate One & Steps from the Waterfront
10.0 out of 10, Exceptional, (200)
"Incredible location! The process was easy and the house completely suited our needs! We would definitely stay again!"
Directly Across from Gate One & Steps from the Waterfront
Rockhold Creek Cottage, Water Front, Vacation Home, Docks
Grill no longer works
Rockhold Creek Cottage, Water Front, Vacation Home, Docks
9.8 out of 10, Exceptional, (87)
"This lovely home sets in a beautful location. The hosts are available and accommodating. They are definitely available if needed. The house itself is very comfy. All amenities you need are there. "
Rockhold Creek Cottage, Water Front, Vacation Home, Docks
Beautiful family sized townhouse with deck. Close to Washington DC and Baltimore
Living room
Beautiful family sized townhouse with deck. Close to Washington DC and Baltimore
9.8 out of 10, Exceptional, (58)
"Enjoyed these accomodations! Spacious and comfortable. Accessible parking and lovely neighborhood!."
Beautiful family sized townhouse with deck. Close to Washington DC and Baltimore
Bay views with kayaks, bikes, fire pit, crabbing and more
Living room with tv and gas fireplace
Bay views with kayaks, bikes, fire pit, crabbing and more
9.6 out of 10, Exceptional, (17)
"We had a great stay in this beautiful property. Three good size bedrooms and two nice baths. Well equipped kitchen and nice living area. Large yard for kids or dogs and just relaxing. Convenient to restaurants and markets. Hope to visit again soon."
Bay views with kayaks, bikes, fire pit, crabbing and more
Recently Renovated Annapolis Home - Conveniently Located
Single Family Home With Parking for two small or one larger vehicle.
Recently Renovated Annapolis Home - Conveniently Located
10.0 out of 10, Exceptional, (55)
"We had an amazing time at the house and everyone staying with us had nothing but great things to say! Would highly recommend staying here for any occasion bringing you to Annapolis!"
Recently Renovated Annapolis Home - Conveniently Located
3 Story Stunner in Murray Hill <1 mile from USNA!
3 Story Stunner in Murray Hill <1 mile from USNA!
10.0 out of 10, Exceptional, (16)
"Beautiful house in great location! It was the perfect house for our annual trip (group of 10 friends) to Annapolis! It was spacious, clean, and well equipped with everything you need in a rental house. Eric and team were super responsive and accommodating! Highly recommended! Will definitely come back next year!"
The price is SAR 744
SAR 3,264 total
includes taxes & fees
12 Nov - 13 Nov
3 Story Stunner in Murray Hill <1 mile from USNA!
Your Annapolis Adventure Starts Here!!
Annapolis Adventure Awaits - Book Now For March 2023 Festivities!
Your Annapolis Adventure Starts Here!!
10.0 out of 10, Exceptional, (135)
"Joie is a wonderful host!!! Communicating with her was easy & seamless, even as she was on vacation outside the US during our stay!! We attended my 40th reunion at the Naval Academy, and this location was perfect. Easy to get to, very close to grocery stores, etc, and fully stocked!! Highly recommend to others looking to enjoy Annapolis "
Your Annapolis Adventure Starts Here!!
Charming garden row home, easy 4 block walk to the heart of Annapolis.
Amazing Location
Charming garden row home, easy 4 block walk to the heart of Annapolis.
10.0 out of 10, Exceptional, (108)
"We have stayed at this property multiple times since we have a son at the Naval Academy. This place is beautiful, well appointed and comfortable. The hosts are very responsive and they go out of their way to make their guests feel extra special- we will be back. "
Charming garden row home, easy 4 block walk to the heart of Annapolis.
Relaxing oasis 5 min to Navy Stadium, St John’s, Naval Academy & Downtown
Welcome to Annapolis Heron House
Relaxing oasis 5 min to Navy Stadium, St John’s, Naval Academy & Downtown
10.0 out of 10, Exceptional, (70)
"Beautiful clean house close to Annapolis. "
Relaxing oasis 5 min to Navy Stadium, St John’s, Naval Academy & Downtown
Charming Historic Townhouse Steps From USNA
Interior
Charming Historic Townhouse Steps From USNA
10.0 out of 10, Exceptional, (20)
"We had the best time at this rental — it was accessible, cozy, stocked with things like good toilet paper (silly, but we noticed and appreciated!), and in an amazing location! Absolutely recommend! "
Charming Historic Townhouse Steps From USNA
Waterfront Home on the Chesapeake Bay!
Private Pier
Waterfront Home on the Chesapeake Bay!
10.0 out of 10, Exceptional, (23)
"Very nice getaway for a family reunion group of 8 while we visited our son at the USNA. Location is 35 min from US Naval academy; perfect to feel like he's really getting off the Yard. Having such a huge yard really offered lots to do (corn hole, frisbee, etc.). The incredible water views drew us all back home every night, along with the gorgeous sunsets. Had really nice weather so we took advantage of the 3 kayaks and paddled around the marina. Bikes were convenient too, as well as small...
Waterfront Home on the Chesapeake Bay!
Edgewater/Mayo Getaway!
Room
Edgewater/Mayo Getaway!
9.8 out of 10, Exceptional, (8)
"A great property for two families with young kids to stay. Children loved the big backyard and there was plenty of space for everyone to have their own place. We loved Beverly Triton Beach and it was easy to get downtown for the Sailboat Show as well."
The price is SAR 883
SAR 2,205 total
includes taxes & fees
18 Nov - 19 Nov
Edgewater/Mayo Getaway!
La Maison - Stunning waterfront views with pool
Tranquil retreat on the South River - private dock
La Maison - Stunning waterfront views with pool
10.0 out of 10, Exceptional, (90)
"Gorgeous, serene and well-appointed property! It was very comfortable for our group of four women. Highly recommend for a family or friends."
La Maison - Stunning waterfront views with pool
Charming brick home with patio, WiFi, AC, & W/D - walk to everything
Charming brick home with patio, WiFi, AC, & W/D - walk to everything
8.8 out of 10, Excellent, (19)
"Loved this location as EVERYTHING is walkable - St John's college, USNA, the capitol and Main Street. One skinny parking place was appreciated and reasonable for a standard size vehicle (not super truck or SUV). Enjoyed the older character of the home and modern conveniences as well as small outdoor space that was very nicely landscaped with flowers. "
Charming brick home with patio, WiFi, AC, & W/D - walk to everything
Walk to Navy stadium and restaurants from Captain’s Crossing Cape with Private deck and backyard
Situated on a quiet street in West Annapolis, the home is walkable to shops, restaurants and Navy Stadium.
Walk to Navy stadium and restaurants from Captain’s Crossing Cape with Private deck and backyard
10.0 out of 10, Exceptional, (16)
"Very clean, great location - easily walkable for a USNA reunion to stadium and alumni center!"
Walk to Navy stadium and restaurants from Captain’s Crossing Cape with Private deck and backyard
Charming Annapolis WaterVIEW Home
3 covered balconies, a ground floor patio, and ceramic and propane grills.
Charming Annapolis WaterVIEW Home
9.6 out of 10, Exceptional, (48)
"This house was perfect for our group of friends especially with infants. Easy check in, comfortable beds and room for pack and plays. Water view is amazing. Definitely worth the rent and would be interested in coming back!"
Charming Annapolis WaterVIEW Home
2-story, riverfront home with private dock, inviting deck & dog-friendly yard
2-story, riverfront home with private dock, inviting deck & dog-friendly yard
9.6 out of 10, Exceptional, (12)
"We appreciate the hospitality and responsiveness of our gracious host. We would stay again and look forward to our next visit. Recommend staying to all looking for a tranquil getaway in the Annapolis area."
2-story, riverfront home with private dock, inviting deck & dog-friendly yard
Fantastic Spacious Eastport Home Easy Walk to Everything & Parking for 6 Cars!
Charming Home in Annapolis, MD !
Fantastic Spacious Eastport Home Easy Walk to Everything & Parking for 6 Cars!
9.6 out of 10, Exceptional, (105)
"The only downside and it was miniscule in relation to the overall experience was the amount of debris on the front porch that came from storms blowing off of the trees. Couldn't really be helped and again very minor issue. The rest of the house was fabulous!!"
Fantastic Spacious Eastport Home Easy Walk to Everything & Parking for 6 Cars!
Charming Cottage with Hot Tub 1 Block from the Bay
Marina
Charming Cottage with Hot Tub 1 Block from the Bay
10.0 out of 10, Exceptional, (8)
"Very clean - well equipped - perfect for our relaxing weekend."
The price is SAR 1,014
SAR 2,180 total
includes taxes & fees
3 Dec - 4 Dec
Charming Cottage with Hot Tub 1 Block from the Bay
Walk to Everything House
Front of House
Walk to Everything House
10.0 out of 10, Exceptional, (72)
"We thoroughly enjoyed the convenience of walking to shops, restaurants, and waterfront! Residence was charming and clean! Only minor issue was we couldn’t locate the iron- just the ironing board! We still had fun but we’re just a bit wrinkled!😁"
Walk to Everything House
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Other property types in Friendship

Directly Across from Gate One & Steps from the Waterfront
Private rear courtyard
Directly Across from Gate One & Steps from the Waterfront
10.0 out of 10, Exceptional, (200)
"Incredible location! The process was easy and the house completely suited our needs! We would definitely stay again!"
Directly Across from Gate One & Steps from the Waterfront
Charming Annapolis WaterVIEW Home
3 covered balconies, a ground floor patio, and ceramic and propane grills.
Charming Annapolis WaterVIEW Home
9.6 out of 10, Exceptional, (48)
"This house was perfect for our group of friends especially with infants. Easy check in, comfortable beds and room for pack and plays. Water view is amazing. Definitely worth the rent and would be interested in coming back!"
Charming Annapolis WaterVIEW Home
Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA
Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA
10.0 out of 10, Exceptional, (202)
"This was a lovely home. I especially appreciated how clean and well-stocked it was. Liz and Tom were very responsive and accommodating! This truly added to a wonderful reunion weekend with friends and family. Thank you!"
Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.