Annapolis Holiday Rentals

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Holiday Rentals in Annapolis

Incredibly Beautiful, Private, Unique Home Perched On The Bluff At Ocean's Edge!
10.0 out of 10, Exceptional, (403)
"Wonderful adventure,"
United States
Susan K.
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, (348)
"Little paradise as soon as you walk down the path you see beauty. It was perfect my husband and dogs. "
United States
Kim B.
Riverfront Cottage in Wine Country - Seasonal River Access - Dogs Stay for Free!
Your Oceanfront Experience - Hot Tub - Lovely Fenced Courtyard
9.8 out of 10, Exceptional, (460)
"Perfect beach getaway for a couple of nights. The view was amazing and the home was cozy. We enjoyed the hot tub!"
United States
Megan H.
Your Oceanfront Experience - Hot Tub - Lovely Fenced Courtyard
Ocean View Home near Shell Beach w/ Hot Tub, Fireplace, Shared Pool - Dogs OK
8.0 out of 10, Very good, (46)
"The patio was nice and the view from the main (second) level is special. The house was very clean but could use some more upkeep on the outside."
United States
Kevin P.
Ocean View Home near Shell Beach w/ Hot Tub, Fireplace, Shared Pool - Dogs OK
Oceanfront Studio with views of the Pacific Ocean & Direct Access to the Beach S
9.6 out of 10, Exceptional, (62)
"We had a wonderful stay! The room had everything we could have hoped for, and the view was absolutely amazing. Miren was a fantastic host; knowledgeable about the area and full of great recommendations. We would definitely come back!"
United States
Jennifer R.
Oceanfront Studio with views of the Pacific Ocean & Direct Access to the Beach S
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 !"
United States
Tamara
The price is NZ$158
includes taxes & fees
3 Nov - 4 Nov
The Ranch at Lake Sonoma
~ Home w/Gas Fireplace + 3 Cottages w/Baths + Hot Tub ~ Pool ~ Pet Friendly ~
9.8 out of 10, Exceptional, (44)
"Overall was a nice stay. Great for private getaway "
United States
Monica L.
~ Home w/Gas Fireplace + 3 Cottages w/Baths + Hot Tub ~ Pool ~ Pet Friendly ~
Oceanfront - Hot Tub - Newly Remodeled Cottage
9.8 out of 10, Exceptional, (396)
"Perfect getaway and the hot tub was a hit. "
United States
Jennifer T.
Oceanfront - Hot Tub - Newly Remodeled Cottage
Alexander Valley Lodge w/ Pool, Hot tub, Waterfall, Pool table and Tiki Bar
2.5 star property
9.0 out of 10, Wonderful, (12)
"Great property, spacious & unique space for large groups! The house, while a bit dated, was comfortable for all our guests. The pool table was fun to have and although the pool is on the smaller side, it still worked out fine with our large group to mingle in & around. As another guest commented, the kitchen is a bit small for the size of the house but still worked out fine for us. The house features impressive, high ceilings throughout that add to its spacious, lodge like charm. We did notice...
United States
Joe V.
The price is NZ$1,632
includes taxes & fees
10 Nov - 11 Nov
Alexander Valley Lodge w/ Pool, Hot tub, Waterfall, Pool table and Tiki Bar
Rendezvous Mendocino
3.0 star property
9.4 out of 10, Exceptional, (11)
"Beautiful rooms & property. Very comfortable beds. Our room had a gorgeous view of the ocean. And we highly recommend the homemade biscuits & scones. They were amazing!"
United States
Colette
The price is NZ$446
includes taxes & fees
4 Nov - 5 Nov
Rendezvous Mendocino
Oceanfront Room with Direct Beach Access CYG
9.2 out of 10, Wonderful, (7)
"Helpful staff."
United States
james
The price is NZ$329
includes taxes & fees
3 Nov - 4 Nov
Oceanfront Room with Direct Beach Access CYG
Sunny Home w/ Private Hot Tub & Deck, Pools & Saunas - Two Dogs Welcome
9.0 out of 10, Wonderful, (71)
"We had a great time with our family here!"
United States
Bernadette U.
Sunny Home w/ Private Hot Tub & Deck, Pools & Saunas - Two Dogs Welcome
RIGHT ON THE OCEAN BLUFF with Romance and Luxury: When ONLY THE BEST Will Do..
10.0 out of 10, Exceptional, (257)
"Excellent with sunny skies and superb views."
Canada
Albert H.
RIGHT ON THE OCEAN BLUFF with Romance and Luxury: When ONLY THE BEST Will Do..
Luxurious Large Home, Beautiful Pool, Extensive Gardens
9.8 out of 10, Exceptional, (156)
"We had a great time hanging out at the pool with the family,"
United States
Jeanette H.
Luxurious Large Home, Beautiful Pool, Extensive Gardens
Point Arena Lighthouse
3.0 star property
9.6 out of 10, Exceptional, (110)
"Was very quaint and quiet"
United States
Jim
The price is NZ$396
includes taxes & fees
3 Nov - 4 Nov
Point Arena Lighthouse
Dog-friendly beach house with private hot tub, indoor pool, WiFi & ocean views
9.0 out of 10, Wonderful, (53)
"Great place to stay! It felt like home away from home."
United States
Teryn O.
Dog-friendly beach house with private hot tub, indoor pool, WiFi & ocean views
Come take in the ocean, gaze at the starry skies, commune with nature.
10.0 out of 10, Exceptional, (253)
"What a relaxing retreat! We enjoyed our stay, and only wish it had been a much longer one!"
United States
Michael
Come take in the ocean, gaze at the starry skies, commune with nature.
Wildwood Gardens Scenic Rustic Vacation Retreat on the River
9.6 out of 10, Exceptional, (193)
"Bliss on the Russian River. Great location to access the river and spend time enjoying the beautiful views. We saw lots of birds our favorite was the Great Blue Heron. We enjoyed the hot tub as well. Bed was comfortable and kitchen had everything we needed to feel at home. Also dog friendly we will book again! "
United States
Zane F.
Wildwood Gardens Scenic Rustic Vacation Retreat on the River
Private Courtyard with Hot Tub... Ocean View...2 min. walk to bluff
10.0 out of 10, Exceptional, (163)
"Great location, great hiking, views. "
United States
Brenda G.
Private Courtyard with Hot Tub... Ocean View...2 min. walk to bluff
Pet-friendly Oceanfront Retreat w/King Beds & Hot Tub!
10.0 out of 10, Exceptional, (49)
"Truly beautiful house. We had such a relaxing stay and really enjoyed the area!"
United States
Rebekka V.
The price is NZ$1,571
includes taxes & fees
6 Nov - 7 Nov
Pet-friendly Oceanfront Retreat w/King Beds & 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 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$158 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.