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Check prices for these dates

Next weekend
2 Jum. I - 4 Jum. I
In two weeks
9 Jum. I - 11 Jum. I
In one month
23 Jum. I - 25 Jum. I
In two months
20 Jum. II - 22 Jum. II

Compare 546 Vacation Homes in Friendship with updated reviews, rates, and availability.

Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
Fridge, microwave, oven, stovetop

Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!

10.0 out of 10, Exceptional, (213)
"Great property and location to everything is ideal. Would definitely book this place again. "
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
Beautiful family sized townhouse with deck. Close to Washington DC and Baltimore
Property grounds

Beautiful family sized townhouse with deck. Close to Washington DC and Baltimore

9.6 out of 10, Exceptional, (75)
"Great for the price. The motel of VRBOs would be my best description. Plenty of space for what we needed though and no issues during our stay. "
Beautiful family sized townhouse with deck. Close to Washington DC and Baltimore
The Blue Crab Beach House - Free beach passes
Fridge, microwave, oven, stovetop

The Blue Crab Beach House - Free beach passes

10.0 out of 10, Exceptional, (52)
"We really enjoyed our stay at The Blue Crab Beach House. The home was very clean and well accessorized. The host was very responsive and I would definitely come stay again !"
The Blue Crab Beach House - Free beach passes
Modern Waterfront House with amazing views of the ChesapeakeBay!
Fridge, microwave, oven, stovetop

Modern Waterfront House with amazing views of the ChesapeakeBay!

Modern Waterfront House with amazing views of the ChesapeakeBay!
Historic Annapolis Home 1.5 blocks from center of town.
Terrace/patio

Historic Annapolis Home 1.5 blocks from center of town.

9.8 out of 10, Exceptional, (35)
"This house was in a fantastic location! It is within walking distance to downtown Annapolis and anything you might need or want. It is a cute little home with all of your needed comforts. "
Historic Annapolis Home 1.5 blocks from center of town.
Sweet Bamboo Beach Cottage
Property grounds

Sweet Bamboo Beach Cottage

10.0 out of 10, Exceptional, (73)
"This house was the perfect place to visit old friends. Beds were comfortable, house had everything I needed for a long weekend, and the neighborhood was quiet and friendly. It is walking distance (a few blocks) to the boardwalk and restaurants. "
Sweet Bamboo Beach Cottage
Rockhold Creek Cottage, Water Front, Vacation Home, Docks
Property grounds

Rockhold Creek Cottage, Water Front, Vacation Home, Docks

9.8 out of 10, Exceptional, (88)
"Great house, great location and great host!"
Rockhold Creek Cottage, Water Front, Vacation Home, Docks
Stunning Chesapeake view from almost ever room, private 15 home community beach, fossils, 450 pier
Interior

Stunning Chesapeake view from almost ever room, private 15 home community beach, fossils, 450 pier

10.0 out of 10, Exceptional, (113)
"Location was perfect for what we needed (quiet, on the beach, great views). Family & pup will definitely be back! We wished we could have stayed longer. Owner communication was wonderful, we never needed anything but knew we could reach out if we did. Very comfortable experience throughout. "
Stunning Chesapeake view from almost ever room, private 15 home community beach, fossils, 450 pier
Available for CW 2025 Waterfront Dog-Friendly Oasis with Private Dock, Firepit & Kayaks
Interior

Available for CW 2025 Waterfront Dog-Friendly Oasis with Private Dock, Firepit & Kayaks

2.0 star property
Available for CW 2025 Waterfront Dog-Friendly Oasis with Private Dock, Firepit & Kayaks
Steps to USNA Gate 3 at historic Gatehouse, on-site parking
Fridge, microwave, oven, stovetop

Steps to USNA Gate 3 at historic Gatehouse, on-site parking

2.5 star property
10.0 out of 10, Exceptional, (5)
"We had a wonderful stay in this fabulous property. The location near gate 3 of USNA and the quick walk to downtown made it a perfect spot. The house was impeccably clean, comfortable and roomy. Cathy was exceptionally helpful throughout our booking process and stay. You will absolutely enjoy your stay!"
Steps to USNA Gate 3 at historic Gatehouse, on-site parking
PERFECT LOCATION in the heart of history
Exterior

PERFECT LOCATION in the heart of history

10.0 out of 10, Exceptional, (197)
"Great weekend at this property in Annapolis! Location is within walking distance to restaurants and shopping!"
PERFECT LOCATION in the heart of history
The Lazy Crab Beach House - Free beach passes
Exterior

The Lazy Crab Beach House - Free beach passes

10.0 out of 10, Exceptional, (47)
"Would stay again."
The Lazy Crab Beach House - Free beach passes
Relax on Kent Island in 3 Bedroom Home w/Waterview
Smart TV

Relax on Kent Island in 3 Bedroom Home w/Waterview

9.8 out of 10, Exceptional, (34)
"Owner was very welcoming and left a bottle of wine as a nice gesture. Excellent communication."
The price is SAR 256
SAR 908 total
includes taxes & fees
28 Apr - 29 Apr
Relax on Kent Island in 3 Bedroom Home w/Waterview
The Cottage
Exterior

The Cottage

10.0 out of 10, Exceptional, (4)
"Beautiful, beautiful, beautiful! Haley was a wonderful host! "
The Cottage
7 mins away from Downtown Annapolis
Fridge, microwave, oven, coffee/tea maker

7 mins away from Downtown Annapolis

9.8 out of 10, Exceptional, (15)
"A warm and cozy property that can hold that big holiday gathering you want. Well stocked, comfortable, and full of what you need."
7 mins away from Downtown Annapolis
Renovated Row Home in the heart of Downtown Annapolis.Two blocks to everything
3 bedrooms, iron/ironing board, travel crib, WiFi

Renovated Row Home in the heart of Downtown Annapolis.Two blocks to everything

9.8 out of 10, Exceptional, (16)
"Loved the stay, easy and functional for a larger group to get together in Annapolis. "
Renovated Row Home in the heart of Downtown Annapolis.Two blocks to everything
Walk to Everything House
Smart TV

Walk to Everything House

10.0 out of 10, Exceptional, (78)
"Clean and nice place to stay"
Walk to Everything House
Charming garden row home, easy 4 block walk to the heart of Annapolis.
Exterior

Charming garden row home, easy 4 block walk to the heart of Annapolis.

10.0 out of 10, Exceptional, (111)
"I visited my midshipman and I couldn’t have asked for a better place! Very comfortable & spacious-yet not too big. It was as if we were home. Location was awesome. Mike was great with immediate communication-especially in preparing us with info well before our check in day! I would definitely stay here again! "
Charming garden row home, easy 4 block walk to the heart of Annapolis.
Recently Renovated Annapolis Home - Conveniently Located
Exterior

Recently Renovated Annapolis Home - Conveniently Located

10.0 out of 10, Exceptional, (59)
"Great location! Beautifully furnished! I stayed here for a month and loved it. The property manager is awesome. Responds to requests within minutes. Book it you won’t be disappointed!"
Recently Renovated Annapolis Home - Conveniently Located
Private Waterview Estate with 4 bedroom Suites, game room and Hot Tub
Fridge, microwave, oven, stovetop

Private Waterview Estate with 4 bedroom Suites, game room and Hot Tub

9.6 out of 10, Exceptional, (24)
"Great location and house! We all had a great time!"
Private Waterview Estate with 4 bedroom Suites, game room and Hot Tub
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

Beautiful family sized townhouse with deck. Close to Washington DC and Baltimore
Property grounds

Beautiful family sized townhouse with deck. Close to Washington DC and Baltimore

9.6 out of 10, Exceptional, (75)
"Great for the price. The motel of VRBOs would be my best description. Plenty of space for what we needed though and no issues during our stay. "
Beautiful family sized townhouse with deck. Close to Washington DC and Baltimore
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
Fridge, microwave, oven, stovetop

Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!

10.0 out of 10, Exceptional, (213)
"Great property and location to everything is ideal. Would definitely book this place again. "
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
The Blue Crab Beach House - Free beach passes
Fridge, microwave, oven, stovetop

The Blue Crab Beach House - Free beach passes

10.0 out of 10, Exceptional, (52)
"We really enjoyed our stay at The Blue Crab Beach House. The home was very clean and well accessorized. The host was very responsive and I would definitely come stay again !"
The Blue Crab Beach House - Free beach passes
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.