Annapolis Holiday Rentals

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Holiday Rentals in Annapolis

Our top choices for Annapolis holiday rentals

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 AU$104
includes taxes & fees
1 Oct - 2 Oct
The Ranch at Lake Sonoma

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 AU$344
includes taxes & fees
16 Sept - 17 Sept
Point Arena Lighthouse

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!

9.8 out of 10, Exceptional, (337)
"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

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

8.8 out of 10, Excellent, (3)
"Helpful staff."
The price is AU$292
includes taxes & fees
26 Sept - 27 Sept
Oceanfront Room with Direct Beach Access CYG

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

9.8 out of 10, Exceptional, (451)
"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

9.8 out of 10, Exceptional, (154)
"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

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

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

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

9.2 out of 10, Wonderful, (97)
"A slice of heaven. An amazing place. A top notch property from check in to check out. Reluctantly sharing the review because we would love to keep it a secret. "
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..

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

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

10.0 out of 10, Exceptional, (2)
"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

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 AU$459
includes taxes & fees
9 Sept - 10 Sept
Rendezvous Mendocino

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

9.4 out of 10, Exceptional, (14)
"Beautiful location, deep in the redwoods. Loved the peace and quiet of the unit (save for the early rising roosters!) The unit was clean and cozy, and we enjoyed ourselves immensely. Would definitely stay again. "
The price is AU$404
includes taxes & fees
7 Sept - 8 Sept
Stairway to Heaven with EV Charger

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

Everything you need to know about Annapolis holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Annapolis holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Annapolis holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Annapolis holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Annapolis. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Annapolis holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Annapolis holiday rentals we have selected for you start as low as AU$104 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Annapolis rentals

At Expedia, we put the best Annapolis holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Annapolis rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Annapolis holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Annapolis. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Can I find holiday rentals in Annapolis?

Yes, there are holiday rentals close to the most popular sights in Annapolis, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Annapolis has to offer?

Point Arena Lighthouse: This holiday home rental outside of Annapolis is located by the ocean, and has a private garden, 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 wider area, you’ll find Black Point Beach and Sea Ranch Golf Links.

What’s a holiday rental in Annapolis like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Annapolis. Holiday rentals provide amenities such as hot tubs, fire pits and patios so you'll have a home away from home. If you're concerned about a clean environment, a holiday rental can provide a sense of privacy away from public hotel lifts and bustling concierge desks while still allowing you to travel. You'll also find more space in a holiday rental than in a hotel, which is another reason why a holiday rental is an attractive option for families.