Holiday Rentals in Annapolis

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Holiday Rentals in Annapolis

Oceanfront - Hot Tub - Newly Remodeled Cottage
9.8 out of 10, Exceptional, 325 reviews
"We normally stay in Santa Cruz but I think we liked Bodega Bay better. The house was beautiful and right on the beach. Beautiful views and we were able to hear the ocean from our bedroom. Property was clean and beautiful."
Oceanfront - Hot Tub - Newly Remodeled Cottage
Spacious Yet Cozy Bodega Bay Experience!
8.8 out of 10, Excellent, 214 reviews
"Comfortable and clean, easy to find and short walk to Duncan's landing for excellent sunset viewing every night."
Spacious Yet Cozy Bodega Bay Experience!
Riverfront Cottage in Wine Country - Seasonal River Access - Dogs Stay for Free!
9.8 out of 10, Exceptional, 272 reviews
"We stayed for 3 nights in this comfortable, cozy cottage. We had everything we needed. The owner has thoughtfully provided all the comforts of home. The deck overlooks a lovely view of the river. We were able to walk to a few local restaurants. The public beach is nearby(walkable). We definitely would recommend this unit! We hope to return in the future."
Riverfront Cottage in Wine Country - Seasonal River Access - Dogs Stay for Free!
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Sunny Home. Hot Tub. Walk to 2 Beaches, Rec Center, Bluff Trail and the Lodge.
9.8 out of 10, Exceptional, 303 reviews
"Wonderful!"
Sunny Home. Hot Tub. Walk to 2 Beaches, Rec Center, Bluff Trail and the Lodge.
Gorgeous Esherick home with ocean views, hot tub, and trail to Black Point Beach
9.0 out of 10, Wonderful, 36 reviews
"The property is set on a picturesque spot in SeaRanch. Beautiful ocean views. The home itself has lots of nice and unexpected touches (amazing water pressure, oyster knife, dog blankets). It also had a few cost reducing pieces that ranked it down a notch for me (one ply toilet paper and paper towels, super thin cloth towels). We did have an issue with wet towels upon arrival and the property management remedied it within the first 24 hours of our stay. The outdoor space was very useful and...
Gorgeous Esherick home with ocean views, hot tub, and trail to Black Point Beach
Point Arena Lighthouse
3.0 star property
9.6 out of 10, Exceptional, 85 reviews
"Very well supplied and maintained "
The price is €234
per night
23 Jun - 24 Jun
Point Arena Lighthouse
Incredibly Beautiful, Private, Unique Home Perched On The Bluff At Ocean's Edge!
10.0 out of 10, Exceptional, 306 reviews
"This property is exactly as described. The views are beautiful and host is simple to communicate with."
Incredibly Beautiful, Private, Unique Home Perched On The Bluff At Ocean's Edge!
Wildwood Gardens Scenic Rustic Vacation Retreat on the River
9.6 out of 10, Exceptional, 168 reviews
"We had a great time in this lovely little house right on the river. The house is well appointed and close to the town center. The large property is so beautiful and peaceful. We will definitely stay here again!"
Wildwood Gardens Scenic Rustic Vacation Retreat on the River
Ocean view home with free WiFi, jetted tub and close beach access
9.0 out of 10, Wonderful, 105 reviews
"Well stocked great property with incredible views! Wish we could have stayed longer. Definitely hope to return."
Ocean view home with free WiFi, jetted tub and close beach access
Wagging Woods | 3 Gated Acres | Private Hot Tub | Dog-Friendly
8.6 out of 10, Excellent, 29 reviews
"Beautiful location. Very clean. Awesome if you had a dog!"
Wagging Woods | 3 Gated Acres | Private Hot Tub | Dog-Friendly
Secluded home with private saltwater pool, spa & amazing view - dog-friendly
8.6 out of 10, Excellent, 13 reviews
"This property was perfect for our writing retreat! It was spacious and comfortable, and set in a beautiful location. Would absolutely stay again!"
Secluded home with private saltwater pool, spa & amazing view - dog-friendly
Contemporary coastal home with private hot tub, shared pool, & ocean views
8.4 out of 10, Very good, 101 reviews
"overall quite nice. construction next door was minimal, BUT the closeness of the new structure really took away from the overall feel. i'm sure 5-6 established trees and a little time will soften this effect."
Contemporary coastal home with private hot tub, shared pool, & ocean views
Sunlit home near river with hot tub, washer/dryer, firepit - dogs OK
9.6 out of 10, Exceptional, 43 reviews
"Everything about this little cottage in the redwoods along the creek was perfect. It was very quiet and peaceful although we were here during the week. And while there are neighbors to the left and right. One was very quiet and the other neighbors were not there. a very nice place to retreat."
Sunlit home near river with hot tub, washer/dryer, firepit - dogs OK
Oceanfront Studio with views of the Pacific Ocean & Direct Access to the Beach
9.8 out of 10, Exceptional, 13 reviews
"Location is the highlight of this Gualala studio. The stairs faded quickly into the spectacular views. This is a special retreat from the ordinary. Miren is a fantastic host, her knowledge of the area, attention to detail & warm hospitality all a highlight of our stay. We spent 3 nights & explored nearby, but the Anchor Bay beach below this studio makes this location a place of pure contentment, no need to roam. We hope to return."
Oceanfront Studio with views of the Pacific Ocean & Direct Access to the Beach
~ Riverfront 3 Bedroom + hot tub, private dock & kayaks. 3/4 mile from town ~
10.0 out of 10, Exceptional, 48 reviews
"The home is beautiful, comfortable and well stocked. We enjoyed the dock, the hot tub and the lovely kitchen and dining areas. It was quiet and serene. Hope to return soon."
~ Riverfront 3 Bedroom + hot tub, private dock & kayaks. 3/4 mile from town ~
Upscale Riverfront Magnificent Views & Hot Tub In Sonoma County Wine Country
10.0 out of 10, Exceptional, 91 reviews
"We went here with a group of friends and had the most amazing time! We will absolutely be going back. The house was really considered and had everything we needed. Also, can't beat being right on the water!"
Upscale Riverfront Magnificent Views & Hot Tub In Sonoma County Wine Country
SETTING PRIVATE 2 blk toTown/River/Beach-Lg Deck+SPA-Mini Golf+Tennis+Coast12 mi
9.8 out of 10, Exceptional, 259 reviews
"Girls trip to wine country. Perfect location and accommodations for 6 of us. Clare is super, we have stayed here twice."
SETTING PRIVATE 2 blk toTown/River/Beach-Lg Deck+SPA-Mini Golf+Tennis+Coast12 mi
Sunny Home w/ Private Hot Tub & Deck, Pools & Saunas - Two Dogs Welcome
9.0 out of 10, Wonderful, 51 reviews
"We spent four nights in this great home. It's in a nice location on a very quiet cul-de-sac. Close to day hiking trails and Gualala for restaurants. Home was very well equiped - we cooked several meals without finding any missing household items. Hot tub works great...which is sometimes a rarity in rental homes. We would definitely stay here again."
Sunny Home w/ Private Hot Tub & Deck, Pools & Saunas - Two Dogs Welcome
Riverfront Home, close to beach and restaurants
10.0 out of 10, Exceptional, 93 reviews
"We had a wonderful stay. The property was well taken care of (both lovely and clean) and the location was perfect! We look forward to revisiting as well as recommend this home to friends."
Riverfront Home, close to beach and restaurants
Your Oceanfront Experience - Hot Tub - Lovely Fenced Courtyard
9.8 out of 10, Exceptional, 375 reviews
"Our stay was wonderful! It was so relaxing and the ultimate renewal for us. The garden in the front was the first beautiful site and seeing the view of ocean as we walked up the driveway. We will be back again to make more memories. Thank you for opening your home to us."
Your Oceanfront Experience - Hot Tub - Lovely Fenced Courtyard
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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.

Other types of properties in Annapolis you may be interested in

Timber Cove Resort
3.5 star property
9.0 out of 10, Wonderful, 116 reviews
"An amazing property with a super friendly staff and great food! The views of the ocean are incredible. We wish we had been able to stay longer. Don’t hesitate - book this place if you can!!"
The price is €396
per night
20 Jun - 21 Jun
Timber Cove Resort
Gualala Country Inn
2.5 star property
8.8 out of 10, Excellent, 696 reviews
"Great cozy place to rest our heads for a night. Beautiful area surrounding the Hotel. Great customer service. "
The price is €176
per night
25 Jun - 26 Jun
Gualala Country Inn
Casa Secoya
2.5 star property
9.0 out of 10, Wonderful, 342 reviews
"Our family had a very nice stay and an excellent golfing experience."
The price is €155
per night
24 Jun - 25 Jun
Casa Secoya
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.

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, apart-hotels, 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 €234 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?

Sunny Home. Hot Tub. Walk to 2 Beaches, Rec Center, Bluff Trail and the Lodge.: This holiday home rental outside of Annapolis is located near the beach, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. It offers a garden, 1 hot tub and a selection of books so that you can immerse yourself in your holiday.

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 Walk On Beach.

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.

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