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Annapolis Holiday Rentals

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Our top choices for Annapolis holiday rentals

1. Rendezvous Mendocino

Rendezvous Mendocino
3.0 star property
Gualala
9.8 out of 10, Exceptional, (32 reviews)
"I had a fabulous stay here! The hosts were super attentive and helpful, the scones were to die for. The property was beautiful and well kept. I would definitely stay here again!"
United States
Ziv
The price is AU$353
includes taxes & fees
7 Oct - 8 Oct
Rendezvous Mendocino

2. The Ranch at Lake Sonoma

The Ranch at Lake Sonoma
1.0 star property
Geyserville
9.8 out of 10, Exceptional, (6 reviews)
"Nice camping spot "
United States
Evelyn
The price is AU$125
includes taxes & fees
8 Sept - 9 Sept
The Ranch at Lake Sonoma

3. Asian-themed Queen's Loft Apartment 10 mins to the beach and downtown!

Asian-themed Queen's Loft Apartment 10 mins to the beach and downtown!
GUALALA
10.0 out of 10, Exceptional, (1 review)
"Queen's Loft was a nice surprise! I expected a small second-story loft, but it was quite large with a kitchenette, nice roomy bathroom, dining area, living area and 2 king beds (and 2 twin bed that we didn't use), and lots of windows that we opened at night to let the cool, piney-scented air in. What I loved the most was how quiet it was there. Going to sleep breathing piney-scented cool air in complete silence was wonderful....best rest I've had in a long time!"
United States
Barbara
The price is AU$577
includes taxes & fees
5 Oct - 6 Oct
Asian-themed Queen's Loft Apartment 10 mins to the beach and downtown!

4. Ocean Bluff Home, Golf Privileges

Ocean Bluff Home, Golf Privileges
The Sea Ranch
10.0 out of 10, Exceptional, (80 reviews)
"We had such a lovely relaxing time at your beautiful home. Thank you so much. We hope to be back again."
United States
Jennifer T.
Ocean Bluff Home, Golf Privileges

5. Pet-Friendly Designer Oceanfront 3B House with King Beds & Hot Tub & Outdoor Kit

Pet-Friendly Designer Oceanfront 3B House with King Beds & Hot Tub & Outdoor Kit
Gualala
10.0 out of 10, Exceptional, (6 reviews)
"The panoramic ocean view was worth the price of admission. We had a glorious sunset every night of our stay. The house was very clean well equipped and we felt that special memories were made during our time there. We look forward to returning in the future. A big plus was “Seastone” is pet friendly and our miniature poodle Amber told us she had a great time."
United States
David D.
The price is AU$1,344
includes taxes & fees
8 Sept - 9 Sept
Pet-Friendly Designer Oceanfront 3B House with King Beds & Hot Tub & Outdoor Kit

6. Pet-friendly Oceanfront Retreat w/King Beds & Hot Tub!

Pet-friendly Oceanfront Retreat w/King Beds & Hot Tub!
Gualala
10.0 out of 10, Exceptional, (71 reviews)
"We enjoyed our stay, beautiful home with amazing views. Well appointed and very clean. Also, good location in walking distance to a couple of restaurants."
United States
Colin J.
The price is AU$1,218
includes taxes & fees
20 Sept - 21 Sept
Pet-friendly Oceanfront Retreat w/King Beds & Hot Tub!

7. Epic Mendocino Ocean Views, 5BR, Tesla Charger

Epic Mendocino Ocean Views, 5BR, Tesla Charger
Anchor Bay
7.0 out of 10, Good, (6 reviews)
"Nice place! Only 5 minutes from Gualala. The pool table was a lot of fun"
United States
Sean D.
The price is AU$1,255
includes taxes & fees
30 Sept - 1 Oct
Epic Mendocino Ocean Views, 5BR, Tesla Charger

8. Enchanting Creekside Retreat: Your Downtown Oasis

Enchanting Creekside Retreat: Your Downtown Oasis
Hopland
9.6 out of 10, Exceptional, (15 reviews)
"This is a handy location for Hopland "
United States
Chuck R.
The price is AU$362
includes taxes & fees
16 Sept - 17 Sept
Enchanting Creekside Retreat: Your Downtown Oasis

9. Vintage Shasta Camper with Relaxing Fire Pit Escape on Geyserville, California

Vintage Shasta Camper with Relaxing Fire Pit Escape on Geyserville, California
Geyserville
The price is AU$413
includes taxes & fees
8 Sept - 9 Sept
Vintage Shasta Camper with Relaxing Fire Pit Escape on Geyserville, California

10. Redwood Cabin w/ Hot Tub | Canyon View | Dogs OK

Redwood Cabin w/ Hot Tub | Canyon View | Dogs OK
Guerneville
9.0 out of 10, Wonderful, (6 reviews)
"Our stay was fantastic! The cabin was everything we needed for a few days; cozy, and quiet. The outdoor spaces were great and the hot tub was perfect at the end of the day. The host was super helpful and responded to my questions almost immediately. "
United States
Rosa N.
The price is AU$600
includes taxes & fees
8 Sept - 9 Sept
Redwood Cabin w/ Hot Tub | Canyon View | Dogs OK

11. The Tiny Tipsy Turtle

The Tiny Tipsy Turtle
Guerneville
10.0 out of 10, Exceptional, (66 reviews)
"Great little place to stay / perfect location in town close to everything / wonderful front patio "
United States
ANTHONY B.
The price is AU$295
includes taxes & fees
23 Sept - 24 Sept
The Tiny Tipsy Turtle

12. Octagon•Retreat•Hot tub•5 min to River

Octagon•Retreat•Hot tub•5 min to River
Cazadero
10.0 out of 10, Exceptional, (3 reviews)
"Everything was wonderful. We enjoyed our stay! So beautiful and relaxing!!"
United States
Cary Z.
The price is AU$1,215
includes taxes & fees
9 Sept - 10 Sept
Octagon•Retreat•Hot tub•5 min to River

13. River View Tree House, Entire House W Hot tub

River View Tree House, Entire House W Hot tub
Monte Rio
10.0 out of 10, Exceptional, (1 review)
"Gorgeous, unique cabin treehouse! Great, hot cedar hot tub. Clean rooms. Truly homey vibe. Host was very responsive and accommodating. "
United States
Alondra
The price is AU$428
includes taxes & fees
14 Sept - 15 Sept
River View Tree House, Entire House W Hot tub

14. Cozy Cabin in Redwoods | Hot Tub

Cozy Cabin in Redwoods | Hot Tub
Guerneville
10.0 out of 10, Exceptional, (2 reviews)
"Very cute clean property just as advertised."
United States
Craig S.
Cozy Cabin in Redwoods | Hot Tub

15. Point Arena Lighthouse - Keeper's Room

Point Arena Lighthouse - Keeper's Room
Point Arena
10.0 out of 10, Exceptional, (1 review)
The price is AU$399
includes taxes & fees
29 Sept - 30 Sept
Point Arena Lighthouse - Keeper's Room

16. Tranquil Redwood Retreat

Tranquil Redwood Retreat
Guerneville
8.8 out of 10, Excellent, (13 reviews)
"Perfect hun for enjoying downtown guernville "
United States
Alex A.
The price is AU$481
includes taxes & fees
10 Sept - 11 Sept
Tranquil Redwood Retreat

17. Creekside Under the Redwoods

Creekside Under the Redwoods
Guerneville
9.8 out of 10, Exceptional, (21 reviews)
"Very cute and comfortable place! We enjoyed our stay!"
United States
Kathy M.
The price is AU$481
includes taxes & fees
9 Sept - 10 Sept
Creekside Under the Redwoods

18. Cozy Riverfront Cabin - Beach Access & Wood Stove

Cozy Riverfront Cabin - Beach Access & Wood Stove
Guerneville
9.8 out of 10, Exceptional, (23 reviews)
"It was wonderful, we'll be back!"
United States
Jehanne H.
The price is AU$782
includes taxes & fees
20 Sept - 21 Sept
Cozy Riverfront Cabin - Beach Access & Wood Stove

19. Artsy Retreat - Woodstove, Grill, and Patio

Artsy Retreat - Woodstove, Grill, and Patio
Guerneville
10.0 out of 10, Exceptional, (4 reviews)
"Loved this cute place. Clean and exactly as described. Thanks again"
United States
Tamora P.
The price is AU$693
includes taxes & fees
8 Sept - 9 Sept
Artsy Retreat - Woodstove, Grill, and Patio

20. Hillside Retreat in the Redwoods | Hot Tub

Hillside Retreat in the Redwoods | Hot Tub
Guerneville
10.0 out of 10, Exceptional, (5 reviews)
"Great place! Nice and cozy!"
United States
John B.
The price is AU$865
includes taxes & fees
10 Sept - 11 Sept
Hillside Retreat in the Redwoods | Hot Tub
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

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$125 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?

Upscale, Spectacular Oceanfront, Inside State Beach Park, 3 Mins Drive To Beach!: This holiday home rental outside of Annapolis is located on the beach, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Make the most of games in this rental home to help you unwind.

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 Gualala Point Regional Park and Salt Point State Park.

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.