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Vacation Homes in Annapolis

Point Arena Lighthouse

3.0 star property
9.6 out of 10, Exceptional, (109)
"Was very quaint and quiet"
$223 nightly
The price is $245
Oct 2 - Oct 3
Total with taxes and fees
Point Arena Lighthouse

Dog-friendly home with private hot tub, ocean/meadow views & shared pools

9.6 out of 10, Exceptional, (120)
"Spacious house with enough room for a larger family group, comfortable furnishings and great views! Also love being so close to our favorite beach sites, Walk-on and Tide Pool."
Dog-friendly home with private hot tub, ocean/meadow views & shared pools

Wildwood Gardens Scenic Rustic Vacation Retreat on the River

9.6 out of 10, Exceptional, (191)
"My husband and I enjoyed our stay in this home on the river. The decks, and large, private, river front yard were beautiful. "
Wildwood Gardens Scenic Rustic Vacation Retreat on the River

Gorgeous Esherick home with ocean views, hot tub, and trail to Black Point Beach

9.0 out of 10, Wonderful, (57)
"Lovely home, location and space with nice views of the sunset and stars. Overall great stay!"
Gorgeous Esherick home with ocean views, hot tub, and trail to Black Point Beach

Sibley | Beautiful Ocean Views & Hot Tub!

2.0 star property
9.4 out of 10, Exceptional, (46)
"Sea Ranch is so special. We had a wonderful stay! The house was very clean and comfortable. We enjoyed the ocean views from the deck. The house is just a short walk to the Bluff Trail for beautiful sunsets and ocean views. As always, we enjoyed the community pool and sauna. Great communication with the host company, too. Very well-planned with our parking and pool passes available when we arrived. We would definitely stay here again! "
Sibley | Beautiful Ocean Views & Hot Tub!

Oceanfront home with private hot tub, views, & close beach access

9.2 out of 10, Wonderful, (97)
"What a wonderful experience we had with my family we enjoyed our stay every day. We promised to come back and stay to the house."
Oceanfront home with private hot tub, views, & close beach access

Asti Estate Enchanting Wine Country Farm

10.0 out of 10, Exceptional, (3)
"To say this is a fabulous colonial-style farmhouse would be an understatement. The entire property is wonderful, and the main house is magnificent as you drive in. The kitchen literally took my breath away, as did the master suite. All of the rooms are great, and so many spaces to hang out in. The hosts were so gracious, we luckily were there in tomato and basil season, and they left some for us to cook with. Highly recommended!"
Asti Estate Enchanting Wine Country Farm

Oceanfront home with panoramic ocean views, pool, & private hot tub

8.8 out of 10, Excellent, (177)
"We loved being by the ocean. And the proximity to town was nice for shopping."
Oceanfront home with panoramic ocean views, pool, & private hot tub

Beautiful home w/sweeping estuary, water views, Wifi, private grill & wood stove

9.0 out of 10, Wonderful, (13)
"The home was ideally placed. Fantastic views and close to the beach and beach-town food. Most relaxing place I've been. We loved it."
Beautiful home w/sweeping estuary, water views, Wifi, private grill & wood stove

~Riverfront 3 Bed 2 Bath w/Gas Fireplace Hot Tub Dock & Boats. 3/4 mile to town~

10.0 out of 10, Exceptional, (90)
"Lovely, relaxing home"
~Riverfront 3 Bed 2 Bath w/Gas Fireplace Hot Tub Dock & Boats. 3/4 mile to town~

OCEAN FRONT-WHITE WATER VU from every room - above Del Mar Cove

10.0 out of 10, Exceptional, (276)
"The only place we like to stay at sea ranch!"
OCEAN FRONT-WHITE WATER VU from every room - above Del Mar Cove

RIGHT ON THE OCEAN BLUFF with Romance and Luxury: When ONLY THE BEST Will Do..

10.0 out of 10, Exceptional, (254)
"Beautiful view"
RIGHT ON THE OCEAN BLUFF with Romance and Luxury: When ONLY THE BEST Will Do..

Dog-Friendly Home with WiFi, Ocean Views, Shared Pool, & Prime Location

8.8 out of 10, Excellent, (109)
"Simple home without the frills."
Dog-Friendly Home with WiFi, Ocean Views, Shared Pool, & Prime Location

Dog-friendly home with a deck, hot tub, washer/dryer - golf nearby

8.8 out of 10, Excellent, (19)
"Perfect for our weekend schedule thank you"
Dog-friendly home with a deck, hot tub, washer/dryer - golf nearby

Cozy Sea Ranch hideaway, dog friendly near hiking trails, shared amenities

2.0 star property
9.2 out of 10, Wonderful, (7)
"We loved this home. So many top-quality features with the decor, bedding and furniture. It's like staying in a tree house and so very quiet. A perfect place to relax and unwind. It's very close to the Sea Ranch Lodge. If you're up for it, there are pickleball courts close by as well. We will definitely book this home again! Loved it!"
Cozy Sea Ranch hideaway, dog friendly near hiking trails, shared amenities

Luxurious Large Home, Beautiful Pool, Extensive Gardens

9.8 out of 10, Exceptional, (155)
"We had a great time hanging out at the pool with the family,"
Luxurious Large Home, Beautiful Pool, Extensive Gardens

Private Courtyard with Hot Tub... Ocean View...2 min. walk to bluff

10.0 out of 10, Exceptional, (160)
"Great location, great hiking, views. "
Private Courtyard with Hot Tub... Ocean View...2 min. walk to bluff

Riverfront Home, close to beach and restaurants

10.0 out of 10, Exceptional, (113)
"Perfectly located, right on the river. Close to restaurants and fun things to do. Loved it—we will definitely try to return to this property."
Riverfront Home, close to beach and restaurants

Renovated Vineyard Home - 4 BR/4 BA - Solar Pool, Spa, Views

10.0 out of 10, Exceptional, (152)
"The photos do not do this place justice! The pool and yard are absolutely magical. Each room has been thoughtfully updated. Would definitely stay again."
Renovated Vineyard Home - 4 BR/4 BA - Solar Pool, Spa, Views

The Cliff House: Panoramic Oceanfront Views by Famed Architect Carson Bowler.

2.0 star property
9.8 out of 10, Exceptional, (14)
"We thoroughly enjoyed this house. The location is perfect. The decoration and linens were all of high quality. Great stay for us!"
The Cliff House: Panoramic Oceanfront Views by Famed Architect Carson Bowler.
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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Top Annapolis Hotel Reviews

Find out more about Annapolis

Find out more about Annapolis

Annapolis Vacation Homes information

Number of reviews
1,575
Accommodation
650 Vacation Homes
Lowest Price
$245
Highest Price
$245

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