66 Results
Cancel Clear Filters Apply Filters

Price Per Week

$ $

Sleeps

Bedrooms

Bathrooms

Booking Options

Property Type

Condos
Cottages
Estates
Homes
Lodges
Studios
Townhomes
Villas
Apartments
Barns
Boats
Bungalows
Cabins
Castles
Chalets
Farmhouses
Hotels
Yachts

Booking Options

Location Type

Even More Filters

Features

Managed By

66 Results
Cancel Clear Filters Apply Filters
Use filters to narrow your search results!

Annapolis Pet Friendly Vacation Rentals(66)

66 Results
  • 6 BR,
  • 4 BA,
  • 1 HF BA,
  • Sleeps 15
4 night min stay
(58)
  • 3 BR,
  • 2 BA,
  • Sleeps 8
2 night min stay
(47)
  • 5 BR,
  • 3 BA,
  • Sleeps 21
2 - 7 night min stay
(65)
$425 - $550
per night
2 - 5 night min stay
  • 2 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 6
2 - 5 night min stay
(9)
$400
per night
2 night min stay
  • 3 BR,
  • 2 BA,
  • Sleeps 8
2 night min stay
(45)
$400 - $975
per night
2 - 4 night min stay
  • 5 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 15
2 - 4 night min stay
(15)
  • 4 BR,
  • 4 BA,
  • Sleeps 12
2 night min stay
(28)
$425
per night
1 - 3 night min stay
  • 2 BR,
  • 2 BA,
  • Sleeps 7
1 - 3 night min stay
(5)
  • 7 BR,
  • 5 BA,
  • 1 HF BA,
  • Sleeps 14
(8)
$550
per night
3 night min stay
  • 5 BR,
  • 2 BA,
  • Sleeps 12
3 night min stay
$450 - $500
per night
3 night min stay
  • 4 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 10
3 night min stay
(35)
  • 2 BR,
  • 2 BA,
  • Sleeps 8
2 night min stay
(40)
  • 4 BR,
  • 3 BA,
  • Sleeps 12
2 - 5 night min stay
(36)
$260 - $643
per night
2 - 7 night min stay
  • 3 BR,
  • 3 BA,
  • Sleeps 8
2 - 7 night min stay
(3)
  • 3 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 6
3 - 7 night min stay
1 Review
  • 5 BR,
  • 4 BA,
  • 1 HF BA,
  • Sleeps 12
2 - 7 night min stay
1 Review
$700
per night
5 night min stay
  • 3 BR,
  • 2 BA,
  • Sleeps 6
5 night min stay
  • 3 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 8
2 night min stay
(28)
$275 - $350
per night
2 - 7 night min stay
  • 2 BR,
  • 1 BA,
  • 1 HF BA,
  • Sleeps 6
2 - 7 night min stay
2 Reviews
  • 2 BR,
  • 1 BA,
  • 1 HF BA,
  • Sleeps 4
$350 - $750
per night
2 - 6 night min stay
  • 4 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 10
2 - 6 night min stay
  • 2 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 8
2 night min stay
(24)
$355 - $620
per night
2 - 6 night min stay
  • 4 BR,
  • 2 BA,
  • Sleeps 9
2 - 6 night min stay
1 Review
  • 2 BR,
  • 2 BA,
  • Sleeps 4
7 night min stay
1 Review
$220 - $350
per night
3 night min stay
  • 3 BR,
  • 2 BA,
  • Sleeps 6
3 night min stay
  • 2 BR,
  • 1 BA,
  • Sleeps 6
2 night min stay
2 Reviews
  • 5 BR,
  • 2 BA,
  • Sleeps 15
4 night min stay
(5)
$300
per night
2 - 4 night min stay
  • 6 BR,
  • 3 BA,
  • Sleeps 15
2 - 4 night min stay
  • 3 BR,
  • 2 BA,
  • Sleeps 8
37 more choices from the HomeAway Network
  • 4 BR,
  • 2 BA,
  • Sleeps 10
3 night min stay
 View map Map
Advertisement
 

Recent Annapolis Reviews

Steffan Point rental

5 of 5
Our stay at Steffan point was a great weekend. We arrived to a clean house with a great layout and fun decor. We used the fire pit in the evenings and enjoyed some great food made in the spacious kitchen. The owner texted to check on things several times to make sure all was well. The house is well cared for and in great shape. I would suggest a larger grill, considering how many people the house sleeps, but it all worked out. Thanks for a great stay.
  • Submitted: Apr 27, 2015
  • Stayed: Apr 2015

Lovely, clean, comfortable, and convenient!

5 of 5
This home was just as described and perfect for a group of multiple couples or families. The renovated interior has handcrafted charm, the beds are very comfortable (including a wonderful Murphy bed), and everything was clean and in working order. The hosts were gracious, welcoming and knowledgeable about the area, and immediately responsive to our questions and needs. They are in the starting phase of a family-owned hydroponic farm for locally-sourced herbs, and they are happy to show their greenhouse to interested parties. This location was perfect for day trips in and around Annapolis, DC, and Baltimore! Will definitely stay here again the next time we will be in the area.
  • Submitted: Apr 8, 2015
  • Stayed: Apr 2015

Perfect Stay!

5 of 5
The Carriage House was the perfect spot for our girls weekend. Jane is wonderful to work with and met all of our needs. The place is beautifully decorated down to the smallest details. The kitchen is well appointed though we found little need to cook with such easy access to the restaurants in Annapolis. She has stocked all the basics making it a very easy and comfortable rental. I only wish we could have had some warmer weather, but that means we will just have to return. It is truly a perfect spot for a getaway with family or friends.
  • Submitted: Mar 24, 2015
  • Stayed: Mar 2015