Annapolis Vacation Rentals

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Browse Select Annapolis Vacation Homes

Starlight Reach | Private Hot Tub

2.0 star property
10.0 out of 10, Exceptional, (13)
"We had such a wonderful time at this rental! It was clean, well stocked, and just as advertised. It was beautifully located and we had such a great weekend relaxing. Would definitely recommend! "
Starlight Reach | Private Hot Tub

Point Arena Lighthouse

3.0 star property
9.6 out of 10, Exceptional, (106)
"The 2 bedroom house was newly remodeled. Very comfortable. Our window overlooked the ocean, front and back and the lighthouse."
The price is CA $247
CA $315 total
includes taxes & fees
Aug 18 - Aug 19
Point Arena Lighthouse

Ocean Bungalow | Tesla EV Station & Near Trails!

2.0 star property
9.8 out of 10, Exceptional, (42)
"House was spacious, great views from the living room."
Ocean Bungalow | Tesla EV Station & Near Trails!

Dreamy lodging with hot tub, pool, beach access, furnished patio

9.0 out of 10, Wonderful, (50)
"Had a great stay, well equipped house, could use an update on fixtures in bathrooms."
Dreamy lodging with hot tub, pool, beach access, furnished patio

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

9.0 out of 10, Wonderful, (55)
"The property is comfy & spacious and has 2 enclosed areas which our dog loves. Also easy access to the bluffs and black-point beach."
Gorgeous Esherick home with ocean views, hot tub, and trail to Black Point Beach

Vineyard cottage with a hot tub, fireplace, washer/dryer & vineyard views

8.4 out of 10, Very good, (27)
"Cute cottage. The outdoor chairs in front were very old and worn out. The furniture by the hot tub was dirty from being under the trees but we used one of the sheets and it was fine. was dirty"
Vineyard cottage with a hot tub, fireplace, washer/dryer & vineyard views

Wildwood Gardens Scenic Rustic Vacation Retreat on the River

9.6 out of 10, Exceptional, (187)
"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

Luxurious Large Home, Beautiful Pool, Extensive Gardens

9.8 out of 10, Exceptional, (153)
"The property is stunning, the house has everything you need, the kitchen was fully equipped with every gadget required for a gourmet meal. The pool was amazing to have, the hot tub was a killer, the outdoor space was stunning. All in all an incredible experience. The costs do start to add up with pool heating, dogs, etc. so make sure to read the listing in its entirety before committing. The host was very communicative and respectful. Highly recommend this stay! "
Luxurious Large Home, Beautiful Pool, Extensive Gardens

Luxury 3-bedroom Estate surrounded by a 20-acre vineyard and 30-mile views.

10.0 out of 10, Exceptional, (6)
"We had a pleasant stay at the property over the Memorial Day weekend. It’s away from the crowds but yet 15 mins from Sonoma Lake for water sports and 30 mins from Healdsburg. Amazing view and great time in the pool. "
Luxury 3-bedroom Estate surrounded by a 20-acre vineyard and 30-mile views.

Dog-friendly beach house with private hot tub, indoor pool, WiFi & ocean views

9.0 out of 10, Wonderful, (51)
"Excellent location with stunning ocean views. Ideal for family vacations."
Dog-friendly beach house with private hot tub, indoor pool, WiFi & ocean views

Sea Pine | Hot Tub with Ocean View

2.0 star property
9.2 out of 10, Wonderful, (53)
"Great, cozy home right on the bluffs. We loved the hot tub and well-stocked kitchen! "
Sea Pine | Hot Tub with Ocean View

Valley Vista | Complimentary wine tasting at Croix Estate included!

10.0 out of 10, Exceptional, (78)
"Lovely house with everything needed for a wonderful stay. Truly a tree top paradise!"
Valley Vista | Complimentary wine tasting at Croix Estate included!

PERFECT LOCATION Private+Spacious-2block to Town/River/Beach+SPA+Tennis/Kid Park

9.8 out of 10, Exceptional, (276)
"Excellent location and a very nice house for a family reunion."
PERFECT LOCATION Private+Spacious-2block to Town/River/Beach+SPA+Tennis/Kid Park

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

8.8 out of 10, Excellent, (19)
"Very nice property, tucked away surrounded by redwoods and ferns. The hot tub was probably our favorite amenity."
Dog-friendly home with a deck, hot tub, washer/dryer - golf nearby

Unique Sea Ranch Binker Barn with amazing ocean views & private hot tub

9.2 out of 10, Wonderful, (12)
"We enjoyed the views and the comfort of this home!"
Unique Sea Ranch Binker Barn with amazing ocean views & private hot tub

Beautiful Ocean Bluff Retreat with Private Hot Tub, Sauna, & Shared Pool

9.2 out of 10, Wonderful, (125)
"Love this property, will visit agin!"
Beautiful Ocean Bluff Retreat with Private Hot Tub, Sauna, & Shared Pool

Fern Woods-Sprawling DECKS!Enchanting Redwood Cabin- Redwoods- HtTb/WiFi/Pup

9.8 out of 10, Exceptional, (17)
"Incredible property and kids had fun in the loft. "
Fern Woods-Sprawling DECKS!Enchanting Redwood Cabin- Redwoods- HtTb/WiFi/Pup

MagicMadrone- Astonishing Views! Stunner Home Top of Redwoods! HotTub / WiFi

9.8 out of 10, Exceptional, (7)
"We spent the week at this beautiful home nestled among the redwoods. Beautiful views with great attention to detail. House was very well appointed and we would definitely stay here again. "
MagicMadrone- Astonishing Views! Stunner Home Top of Redwoods! HotTub / WiFi

Pelican's Landing | Amazing Views & Hot Tub!

2.0 star property
9.2 out of 10, Wonderful, (38)
"This was our fourth rental at Sea Ranch and our first right on the coast. The stormy waves were LOUD, but we really enjoyed this different and up-close vantage on the sea. The house is spacious and spectacular, the kitchen was well-stocked, and the beds were comfortable. We hope to come back!"
Pelican's Landing | Amazing Views & Hot Tub!

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

9.2 out of 10, Wonderful, (96)
"The view and sound of the ocean cannot be beat! House was very clean at check-in. The beds were very comfortable."
Oceanfront home with private hot tub, views, & close beach access
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