Annapolis Holiday Rentals

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Annapolis holiday rentals

The Ranch at Lake Sonoma

The Ranch at Lake Sonoma
1.0 star property
Geyserville
10.0 out of 10, Exceptional, (2 reviews)
"Nice camping spot "
United States
Evelyn
The price is AU$101
includes taxes & fees
2 Feb - 3 Feb
The Ranch at Lake Sonoma

Point Arena Lighthouse

Point Arena Lighthouse
3.0 star property
Point Arena
9.6 out of 10, Exceptional, (117 reviews)
"Great location with a view"
United States
Shalini
The price is AU$339
includes taxes & fees
29 Jan - 30 Jan
Point Arena Lighthouse

Enchanting Creekside Retreat: Your Downtown Oasis

Enchanting Creekside Retreat: Your Downtown Oasis
Hopland
9.4 out of 10, Exceptional, (10 reviews)
"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 AU$395
includes taxes & fees
25 Jan - 26 Jan
Enchanting Creekside Retreat: Your Downtown Oasis

Rendezvous Mendocino

Rendezvous Mendocino
3.0 star property
Gualala
9.6 out of 10, Exceptional, (14 reviews)
"We loved staying here! Clean, cozy, and close to great coffee and Thai food. Diane and Damian were very friendly and welcoming. They heated up our room for us on a cold evening. We had to leave early but Diane brought over granola for us the night before so we could enjoy it for breakfast. Lovely hosts! "
Canada
Daniel
The price is AU$365
includes taxes & fees
18 Feb - 19 Feb
Rendezvous Mendocino

The Tiny Tipsy Turtle

The Tiny Tipsy Turtle
2.0 star property
Guerneville
10.0 out of 10, Exceptional, (46 reviews)
"Great location to walk to town!"
United States
Brenda R.
The price is AU$293
includes taxes & fees
1 Feb - 2 Feb
The Tiny Tipsy Turtle

Russian River Retreat! Woodsy Guerneville Bungalow

Russian River Retreat! Woodsy Guerneville Bungalow
3.0 star property
Guerneville
The price is AU$643
includes taxes & fees
2 Feb - 3 Feb
Russian River Retreat! Woodsy Guerneville Bungalow

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

Redwood Cabin w/ Hot Tub | Canyon View | Dogs OK
Guerneville
10.0 out of 10, Exceptional, (1 review)
"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$704
includes taxes & fees
25 Jan - 26 Jan
Redwood Cabin w/ Hot Tub | Canyon View | Dogs OK

Cozy Riverfront Cabin - Beach Access & Wood Stove

Cozy Riverfront Cabin - Beach Access & Wood Stove
Guerneville
9.8 out of 10, Exceptional, (13 reviews)
"Wonderful location and had everything we needed! "
United States
Maryrose H.
The price is AU$733
includes taxes & fees
21 Jan - 22 Jan
Cozy Riverfront Cabin - Beach Access & Wood Stove

Stairway to Heaven with EV Charger

Stairway to Heaven with EV Charger
Gualala
9.6 out of 10, Exceptional, (17 reviews)
"What a great place to stay. We loved our stay at this get away!!!"
United States
Karen S.
The price is AU$388
includes taxes & fees
9 Feb - 10 Feb
Stairway to Heaven with EV Charger

Adventure Alexander Valley Lodge With Pool & Hot Tub 6 Bedroom Villa

Adventure Alexander Valley Lodge With Pool & Hot Tub 6 Bedroom Villa
3.5 star property
Geyserville
The price is AU$1,821
includes taxes & fees
2 Feb - 3 Feb
Adventure Alexander Valley Lodge With Pool & Hot Tub 6 Bedroom Villa

Cozy cabin deep in the redwoods / WiFi & Hot Tub

Cozy cabin deep in the redwoods / WiFi & Hot Tub
Guerneville
10.0 out of 10, Exceptional, (1 review)
"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 AU$385
includes taxes & fees
19 Feb - 20 Feb
Cozy cabin deep in the redwoods / WiFi & Hot Tub

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!
2.0 star property
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$609
includes taxes & fees
21 Jan - 22 Jan
Asian-themed Queen's Loft Apartment 10 mins to the beach and downtown!

Oceanfront Room with Direct Beach Access CYG

Oceanfront Room with Direct Beach Access CYG
Gualala
9.4 out of 10, Exceptional, (10 reviews)
"Wonderful place! We will definitely be back."
United States
Matt K.
The price is AU$281
includes taxes & fees
20 Feb - 21 Feb
Oceanfront Room with Direct Beach Access CYG

Norcal Hideaway

Norcal Hideaway
Guerneville
10.0 out of 10, Exceptional, (12 reviews)
"Beautiful setting "
United States
LouAnn O.
The price is AU$647
includes taxes & fees
21 Jan - 22 Jan
Norcal Hideaway

Ocean View, Cozy 2-bedroom cabin in tranquil Gualala with WiFi and huge firepit

Ocean View, Cozy 2-bedroom cabin in tranquil Gualala with WiFi and huge firepit
2.0 star property
gualala
The price is AU$498
includes taxes & fees
23 Jan - 24 Jan
Ocean View, Cozy 2-bedroom cabin in tranquil Gualala with WiFi and huge firepit

Alexander Valley Lodge w/ Pool, Hot tub, Waterfall, Pool table and Tiki Bar

Alexander Valley Lodge w/ Pool, Hot tub, Waterfall, Pool table and Tiki Bar
2.5 star property
Geyserville
9.2 out of 10, Wonderful, (15 reviews)
"Fabulous property perfect for our needs. Family was able to stay together eat meals together in the big kitchen enjoy fantastic outdoor time together - really nice ambience and breathtaking views."
United States
Margo R.
The price is AU$1,698
includes taxes & fees
26 Jan - 27 Jan
Alexander Valley Lodge w/ Pool, Hot tub, Waterfall, Pool table and Tiki Bar

Octagon Luxury Retreat• Hot Tub• Redwood Views• Forest Getaway

Octagon Luxury Retreat• Hot Tub• Redwood Views• Forest Getaway
2.0 star property
Cazadero
The price is AU$1,143
includes taxes & fees
2 Feb - 3 Feb
Octagon Luxury Retreat• Hot Tub• Redwood Views• Forest Getaway

Russian River Retreat! Woodsy Guerneville Bungalow

Russian River Retreat! Woodsy Guerneville Bungalow
2.0 star property
Guerneville
10.0 out of 10, Exceptional, (1 review)
"Owner communication timely and professional "
United States
Mike H.
The price is AU$633
includes taxes & fees
2 Feb - 3 Feb
Russian River Retreat! Woodsy Guerneville Bungalow

Enchanting Retreat in the heart of Redwoods

Enchanting Retreat in the heart of Redwoods
Guerneville
8.8 out of 10, Excellent, (12 reviews)
"Beautiful, clean house nestled in the woods. Loved the hot tub and the fire pit in the AM. Super comfortable mattresses."
United States
Jennifer H.
The price is AU$451
includes taxes & fees
2 Feb - 3 Feb
Enchanting Retreat in the heart of Redwoods

Point Arena Lighthouse - Keeper's Room

Point Arena Lighthouse - Keeper's Room
Point Arena
The price is AU$426
includes taxes & fees
22 Jan - 23 Jan
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.
Save an average of 15% on thousands of hotels when you're signed in

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$101 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 Sea Ranch Golf Links and Gualala Arts Center.

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.