Annapolis Holiday Rentals

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Our top choices for Annapolis holiday rentals

Camping in Geyserville

The Ranch at Lake Sonoma
1.0 star property
10.0 out of 10, Exceptional, (2)
"Nice camping spot "
United States
Evelyn
The price is NZ$117
includes taxes & fees
19 Dec - 20 Dec
The Ranch at Lake Sonoma

Holiday Home in Point Arena

Point Arena Lighthouse
3.0 star property
9.6 out of 10, Exceptional, (113)
"Great location with a view"
United States
Shalini
The price is NZ$323
includes taxes & fees
22 Dec - 23 Dec
Point Arena Lighthouse

Aparthotel in Gualala

Rendezvous Mendocino
3.0 star property
9.4 out of 10, Exceptional, (13)
"I loved everything about the property. The breakfast was out of this world! It was nice and quiet, a very relaxed atmosphere. Excellent wi-fi. We could hear the sea lions and we could also see the ocean. We had a wonderful stay!"
United States
Leoni
The price is NZ$423
includes taxes & fees
21 Dec - 22 Dec
Rendezvous Mendocino
9.4 out of 10, Exceptional, (9)
"We loved this little house. It was set back from the street all on its own but walkable to all of the restaurants, etc. The owner was so communicative and had the air conditioner running before we got there which was a bonus! We would definitely stay here again. "
United States
J C.
The price is NZ$450
includes taxes & fees
19 Dec - 20 Dec
Enchanting Creekside Retreat: Your Downtown Oasis

Cabin in Guerneville

The Tiny Tipsy Turtle
2.0 star property
10.0 out of 10, Exceptional, (41)
"Great location to walk to town!"
United States
Brenda R.
The price is NZ$337
includes taxes & fees
22 Dec - 23 Dec
The Tiny Tipsy Turtle
10.0 out of 10, Exceptional, (1)
"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 NZ$855
includes taxes & fees
22 Dec - 23 Dec
Redwood Cabin w/ Hot Tub | Canyon View | Dogs OK
3.0 star property
The price is NZ$770
includes taxes & fees
19 Dec - 20 Dec
Russian River Retreat! Woodsy Guerneville Bungalow
2.0 star property
The price is NZ$847
includes taxes & fees
21 Dec - 22 Dec
Cozy Riverfront Cabin w/ Dock, Fire Pit & Dogs OK
10.0 out of 10, Exceptional, (1)
"We stayed the weekend with friends at this beautiful hideaway in the woods and had a wonderful time. The house was spotless, the jacuzzi was perfect, the lighting was fun and ethereal, the fireplace was cozy, tv was easy to operate and had Netflix (thanks!). The beds are on the soft side, and curtains are sheer, which didn’t bother us, but that might be hard for some folks. We had a great time! Thank you so much!!!"
United States
Laine & Guy H.
The price is NZ$422
includes taxes & fees
14 Jan - 15 Jan 2026
Cozy cabin deep in the redwoods / WiFi & Hot Tub
6.0 out of 10, (3)
"This rental unit is part of a large older home in downtown Cloverdale. It is very basic, simple and clean with no frills. The canopy bed was interesting..."
United States
JoAnne S.
The price is NZ$308
includes taxes & fees
27 Dec - 28 Dec
Wine Country 1-bedroom retreat with WiFi, AC in charming Cloverdale
9.8 out of 10, Exceptional, (13)
"Wonderful location and had everything we needed! "
United States
Maryrose H.
The price is NZ$859
includes taxes & fees
22 Dec - 23 Dec
Cozy Riverfront Cabin - Beach Access & Wood Stove
10.0 out of 10, Exceptional, (1)
"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 NZ$705
includes taxes & fees
19 Dec - 20 Dec
Asian-themed Queen's Loft Apartment 10 mins to the beach and downtown!

Holiday Home in Guerneville

Norcal Hideaway
10.0 out of 10, Exceptional, (12)
"Beautiful setting "
United States
LouAnn O.
The price is NZ$834
includes taxes & fees
19 Dec - 20 Dec
Norcal Hideaway
The price is NZ$2,085
includes taxes & fees
13 Jan - 14 Jan 2026
Adventure Alexander Valley Lodge With Pool & Hot Tub 6 Bedroom Villa

Holiday Home in Guerneville

Redwoods getaway w/ decks & fenced yard
9.0 out of 10, Wonderful, (2)
"The cabin is thoughtfully and beautifully appointed. Perfectly cozy for our group of three (two adults, one tween) and a dog. We really enjoyed our stay. Very close to a lot of fun activities and peaceful. Host Mike was awesome and communicative."
United States
Beth G.
The price is NZ$719
includes taxes & fees
19 Dec - 20 Dec
Redwoods getaway w/ decks & fenced yard
8.8 out of 10, Excellent, (12)
"The property/rental itself is vety nice and well appointed. However, the location leaves a little to be desired. It's essentially a trailer park and not the "nestled in the redwoods" place we were thinking it would be. Property owner/manager was very responsive throughout the rental process."
United States
Tim L.
The price is NZ$534
includes taxes & fees
22 Dec - 23 Dec
Enchanting Retreat in the heart of Redwoods
2.0 star property
9.6 out of 10, Exceptional, (4)
"Cute place. Great location. Property manager was helpful and responsive. Can't wait to return!"
United States
Shannon A.
The price is NZ$801
includes taxes & fees
19 Dec - 20 Dec
Cozy Redwood 2BR • Walk to Monte Rio Beach
9.6 out of 10, Exceptional, (17)
"What a great place to stay. We loved our stay at this get away!!!"
United States
Karen S.
The price is NZ$484
includes taxes & fees
21 Dec - 22 Dec
Stairway to Heaven with EV Charger
10.0 out of 10, Exceptional, (1)
The price is NZ$1,280
includes taxes & fees
4 Jan - 5 Jan 2026
Sequoia Sisters - pvt yard, hot tub, family fun
The price is NZ$404
includes taxes & fees
21 Dec - 22 Dec
Point Arena Lighthouse - Keeper's Room
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 favorite 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 depends 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 NZ$117 per night. Entering your travel dates in the search wizard you might find 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.