Annapolis Vacation Rentals

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In two weeks
Sep 19 - Sep 21
In two months
Oct 31 - Nov 2
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Nov 28 - Nov 30
In four months
Dec 26 - Dec 28

Vacation Rentals in Annapolis

Our top choices for Annapolis vacation rentals

The Ranch at Lake Sonoma
Front of property

The Ranch at Lake Sonoma

1.0 star property
10.0 out of 10, Exceptional, (1)
"The location is fantastic, with a spectacular view on the lake if you choose a lakeview. A very genuine welcome from The Ranch team, with all detailed explanations, a map to help you to navigate around. For our first time going camping, we want definitely to come back there !"
The price is ￥8,742
￥9,965 total
includes taxes & fees
Sep 27 - Sep 28
The Ranch at Lake Sonoma
Point Arena Lighthouse
Family House, 3 Bedrooms, Kitchen, Ocean View (Pet Friendly) | Dining room

Point Arena Lighthouse

3.0 star property
9.6 out of 10, Exceptional, (107)
"The 2 bedroom house was newly remodeled. Very comfortable. Our window overlooked the ocean, front and back and the lighthouse."
The price is ￥26,324
￥33,673 total
includes taxes & fees
Sep 16 - Sep 17
Point Arena Lighthouse
Incredibly Beautiful, Private, Unique Home Perched On The Bluff At Ocean's Edge!
Smart TV, fireplace, DVD player, books

Incredibly Beautiful, Private, Unique Home Perched On The Bluff At Ocean's Edge!

10.0 out of 10, Exceptional, (393)
"Absolutely amazing definitely plan on going back"
Incredibly Beautiful, Private, Unique Home Perched On The Bluff At Ocean's Edge!
Riverfront Cottage in Wine Country - Seasonal River Access - Dogs Stay for Free!
Terrace/patio

Riverfront Cottage in Wine Country - Seasonal River Access - Dogs Stay for Free!

9.8 out of 10, Exceptional, (336)
"We've rented Jujube each year for over 10 years now. It is our favorite place. Right on the river, huge deck, cute, cozy, fully stocked, etc.. Each year, Bridgette has added something new that makes our stay even more enjoyable.Gonna book it for next year in just a few minutes."
Riverfront Cottage in Wine Country - Seasonal River Access - Dogs Stay for Free!
Oceanfront - Hot Tub - Newly Remodeled Cottage
Outdoor spa tub

Oceanfront - Hot Tub - Newly Remodeled Cottage

9.8 out of 10, Exceptional, (391)
"Our third stay and first time booking three nights which seems to be the sweet spot for an extended weekend since you get two full days to relax along the coast. Already can't wait to book our next visit to this charming property!"
Oceanfront - Hot Tub - Newly Remodeled Cottage
Oceanfront Room with Direct Beach Access CYG
Terrace/patio

Oceanfront Room with Direct Beach Access CYG

8.8 out of 10, Excellent, (3)
"Helpful staff."
The price is ￥22,077
￥27,596 total
includes taxes & fees
Sep 11 - Sep 12
Oceanfront Room with Direct Beach Access CYG
Dog-friendly home with private hot tub, ocean/meadow views & shared pools
Fridge, microwave, oven, stovetop

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

9.6 out of 10, Exceptional, (119)
"I’ve stayed at sea ranch many times and was impressed by all aspects of this home. It’s modern, has a great location close to the walk-on beach, and the kitchen is equipped with everything you need for a gourmet meal. Five stars!"
Dog-friendly home with private hot tub, ocean/meadow views & shared pools
Your Oceanfront Experience - Hot Tub - Lovely Fenced Courtyard
Interior

Your Oceanfront Experience - Hot Tub - Lovely Fenced Courtyard

9.8 out of 10, Exceptional, (449)
"The house is lovely and perfecty located for us with our dog to enjoy walks on the beach! We especially loved the view (of course) and the garden area in the front. It was the perfect getaway location. We plan on making this a yearly stay. "
Your Oceanfront Experience - Hot Tub - Lovely Fenced Courtyard
Luxurious Large Home, Beautiful Pool, Extensive Gardens
Beach towels

Luxurious Large Home, Beautiful Pool, Extensive Gardens

9.8 out of 10, Exceptional, (153)
"We absolutely loved this spot for our engagement celebration. It housed us comfortably, provided all the necessities, and made it as fun as could be. Top notch"
Luxurious Large Home, Beautiful Pool, Extensive Gardens
Oceanfront Studio with views of the Pacific Ocean & Direct Access to the Beach S
Property grounds

Oceanfront Studio with views of the Pacific Ocean & Direct Access to the Beach S

9.6 out of 10, Exceptional, (57)
"Loved having a large room with a kitchen and a balcony overlooking the ocean. Our host was very pleasant and helpful."
Oceanfront Studio with views of the Pacific Ocean & Direct Access to the Beach S
Oceanfront home with panoramic ocean views, pool, & private hot tub
Pool

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

8.8 out of 10, Excellent, (176)
"Fabulous, comfortable, warm home to welcome friends and family. "
Oceanfront home with panoramic ocean views, pool, & private hot tub
Wildwood Gardens Scenic Rustic Vacation Retreat on the River
Property grounds

Wildwood Gardens Scenic Rustic Vacation Retreat on the River

9.6 out of 10, Exceptional, (189)
"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
Oceanfront home with private hot tub, views, & close beach access
Interior

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

9.2 out of 10, Wonderful, (97)
"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
RIGHT ON THE OCEAN BLUFF with Romance and Luxury: When ONLY THE BEST Will Do..
On the beach, sun loungers, beach towels

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

10.0 out of 10, Exceptional, (250)
"Beautiful home and surroundings. Well-appointed kitchen. Great communication with owner. Will return in June along with some warmer weather."
RIGHT ON THE OCEAN BLUFF with Romance and Luxury: When ONLY THE BEST Will Do..
Gorgeous Esherick home with ocean views, hot tub, and trail to Black Point Beach
Dining

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
Asti Estate Enchanting Wine Country Farm
Private kitchen

Asti Estate Enchanting Wine Country Farm

10.0 out of 10, Exceptional, (1)
"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
Rendezvous Mendocino
Outdoor spa tub

Rendezvous Mendocino

3.0 star property
9.0 out of 10, Wonderful, (6)
"Cute quaint property conveniently located. Very clean great owners very accommodating. Definitely staying again"
The price is ￥39,775
￥44,151 total
includes taxes & fees
Sep 11 - Sep 12
Rendezvous Mendocino
Dog-Friendly Home with WiFi, Ocean Views, Shared Pool, & Prime Location
TV, fireplace, DVD player, books

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

8.8 out of 10, Excellent, (109)
"The property had beautiful views. I’m sending suggestions to the property manager owner that could make the stay better."
Dog-Friendly Home with WiFi, Ocean Views, Shared Pool, & Prime Location
Stairway to Heaven with EV Charger
Fridge, microwave, oven, stovetop

Stairway to Heaven with EV Charger

9.4 out of 10, Exceptional, (14)
"Beautiful location and property! Just know you are 10-15 minutes from anything really (stores, restaurants, beach). Apartment was clean and well stocked. Owner was responsive and shared farm fresh eggs. We loved the EV charging availability. "
The price is ￥21,527
￥40,827 total
includes taxes & fees
Sep 8 - Sep 9
Stairway to Heaven with EV Charger
Dog-friendly beach house with private hot tub, indoor pool, WiFi & ocean views
Fridge, microwave, oven, stovetop

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
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

Search for holiday rentals in Annapolis on Expedia! You can easily find your home rentals, villas, holiday apartments in Annapolis using one of the methods below:

  • View our selection of featured holiday rentals in Annapolis
  • Use the map to find apartments and other holiday homes in the Annapolis neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Annapolis while they last

Look no further and take a look at our great range of rental properties in Annapolis!

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Frequently asked questions

Can I find vacation rentals in Annapolis?

Yes, you can find vacation rentals near popular local attractions in Annapolis, or you can select a more remote option if you'd like a relaxing place to stay.

What are some of the best vacation home rentals in Annapolis?

Point Arena Lighthouse: You might like this vacation home rental near Annapolis. It is located by the ocean and has a private yard, a selection of games, and free WiFi to put you at ease in your new surroundings. Kitchen amenities include a fridge, a microwave, and a coffee maker.

What’s there to see and do in Annapolis?

While you're exploring the area, Gualala River and Pebble Beach are a couple of picturesque spots to get outside and enjoy nature. In the larger area, you’ll find Black Point Beach and Sea Ranch Golf Links.

What’s a vacation rental in Annapolis like?

Vacation rentals are privately owned properties you can book for a long or short time in Annapolis. Vacation rentals offer amenities such as hot tubs, fire pits, and patios so you'll feel just like you're staying in your own home. If you're concerned about a clean environment, vacation rentals can offer a sense of privacy away from shared hotel elevators and lobbies bustling with people while still allowing you a great travel experience. You'll also find more space in a vacation rental than in a standard hotel, which makes a vacation rental a great choice for small groups.