Holiday houses in Annapolis

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Popular amenities for Annapolis holiday rentals

Other great holiday rentals in Annapolis

Guest favourite
Home in Ste. Genevieve
5 out of 5 average rating, 70 reviews

Secluded Private Cabin with Pool, hot tub, firepla

EmmaRating, 5 stars3 weeks ago
This property exceeds 5 stars without a doubt - our only complaint is that we didn’t plan to stay longer!!! We were stopping through on a 5,000 mile road trip & it was like a spot of sheer relaxation & amazingness with something for everyone. The meticulousness of the property was amazing - from the helpful labels to the abundance of towels (for outside & inside) - this property exceeds allll expectations.
Guest favourite
Holiday home in Eminence
4.95 out of 5 average rating, 20 reviews

Pet friendly Beautiful 4 bedroom home in eminence

PhillipRating, 5 stars8 months ago
Enjoyed being walking distance too town. And ending our float right by house was nice
Top Guest favourite
Cabin in Van Buren
5 out of 5 average rating, 7 reviews

Wagnon's Landing

KristenRating, 5 stars1 month ago
Our family had a wonderful stay at the house. The kitchen was so well stocked, best I’ve seen at a rental house. The location is beautiful, views of the river from the house are amazing. We would definitely stay again!
Superhost
Home in Annapolis
5 out of 5 average rating, 4 reviews

3 bedroom 2.5 bath

DaveRating, 5 stars6 months ago
Lucy was very communicative abouts the house and activities and attractions nearby. She was very responsive. The house worked very well for our family of 5 with the three baths and two full showers. Nice deck off the back of the house with a couch, table and umbrella and gas grill. We really enjoyed the nice fire pit and big yard and my kids loved the cows right across the street!
Superhost
Farm stay in Davisville
4.91 out of 5 average rating, 11 reviews

Pine Valley at Dillard Mill - The Farm

JasonRating, 5 stars8 months ago
This place is amazing and we definitely want to come back. Jay was very hospitable and responsive. As others mentioned in their reviews, the professional kitchen in the common area really is great. We came down to Pine Valley with a big group for a float trip. Its was a huge relief that this property had everything we needed and more so we could just focus on spending time with each other. Oh, and we found a full size cornhole game with sandbags we played with too. Fun.
Superhost
Home in Ironton
4.87 out of 5 average rating, 239 reviews

Mountain Cabin, Wow Views, King Bed, Hiking+

JoshRating, 5 stars1 month ago
Really enjoyed our stay! Everything was as described.
Superhost
Home in Saint Mary
4.79 out of 5 average rating, 24 reviews

Ste. Genevieve Co. House w/ HOT TUB!

JohnRating, 5 stars2 days ago
What a great experience. Charming home away from home, opportune for making it our own, accommodated our family, while we each had our individual space. It’s clear that this family ranch was well preserved and host many positive memories. A coveted sprawling ranch cabin in the woods. ❤️
Guest favourite
Cabin in Silva
5 out of 5 average rating, 17 reviews

The Cozy Cabin

DanielRating, 5 stars3 weeks ago
The Cozy Cabin is amazing! The home is beautiful, and the setting is great. We were well pleased with our stay. We would very happily stay there again!

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