Annapolis Holiday Rentals from €80: Search Short-Term Rentals

Q: What are some of the best holiday rentals that Annapolis has to offer?

Relax by Russian River, spacious 6-bedroom retreat : This holiday home rental outside of Annapolis is located on a river, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 6 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Kick off your shoes and enjoy yourself with a selection of games and 1 hot tub.

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Our top choices for Annapolis holiday rentals

A rustic wooden house with a porch, wooden steps, and a sign that reads "QUILT".

1. Rendezvous Mendocino

Gualala

Tracey

includes taxes & fees

18 Nov - 19 Nov

A single-story cabin with a small porch, situated on a hillside overlooking a body of water and mountains.

2. The Ranch at Lake Sonoma

Geyserville

Epeli

includes taxes & fees

12 Dec - 13 Dec

A modern kitchen with a dining area, large windows, and a view of the beach.

3. Point Arena Lighthouse

Point Arena

Richard

includes taxes & fees

17 Nov - 18 Nov

Two wooden Adirondack chairs with striped cushions on a gravel surface, overlooking a lush green landscape with trees and a view of a distant field.

4. Enchanting Creekside Retreat: Your Downtown Oasis

Hopland

Allison R.

includes taxes & fees

12 Nov - 13 Nov

A bedroom with a bed, a chair, a table, and a view of the ocean through large sliding doors.

5. Serene Coastal Retreat Clark's Cove - Holiday Home

Jenner

A wooden interior with a dining area, a bench, and a mirror on the wall.

6. Cozy Riverfront Cabin - Beach Access & Wood Stove

Guerneville

Savannah M.

includes taxes & fees

15 Nov - 16 Nov

A beach with a large rock formation, a sandy shore, and a calm sea.

7. The Tiny Tipsy Turtle

Guerneville

ANTHONY B.

includes taxes & fees

12 Nov - 13 Nov

A wooden deck with a railing overlooking a grassy area and a body of water.

8. Ocean & River View EVC Hot & Cold Tubs Outdoor Shower Walk to Town Dog Friendly

Gualala

Lisa M.

A coastal landscape with large rocks and waves.

9. 2BR Estuary Views with Spa and Easy Ocean and River Access

Jenner

Dana H.

A spacious room with a high ceiling, large windows, a wooden floor, a rocking chair, a desk, and a bookshelf.

10. Secluded Ocean-view Retreat: Coastal Gualala Home

Gualala

Tracy

A modern house with a covered porch, outdoor seating, and a visible kitchen area.

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

Anchor Bay

Theodore

A modern building with a metal exterior, a wooden door, and a small window on the side.

12. Country Carriage House in Downtown Geyserville, Vineyard Views

Geyserville

Gina I.

includes taxes & fees

3 Dec - 4 Dec

A spacious room with a stone wall, a fireplace, wicker furniture, and large windows overlooking the sea.

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

Gualala

Michael M.

includes taxes & fees

15 Nov - 16 Nov

A hot tub on a wooden deck surrounded by tall trees.

14. Cozy Riverfront Cabin with Dock, Fire Pit & Dogs OK

Monte Rio

Samuel H.

A hot tub on a wooden deck with a view of a forested area.

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

Guerneville

Sherri

includes taxes & fees

21 Nov - 22 Nov

A wooden cabin with a front porch, a number '5' sign, and a fenced area.

16. Adorable 1-bedroom cabin in a peaceful retreat center in Philo

Philo

includes taxes & fees

18 Nov - 19 Nov

A modern interior with a kitchen, dining area, and living room.

17. Tranquil Redwood Retreat

Guerneville

Alex A.

A coastal house with a red roof, situated on a grassy cliff overlooking the ocean.

18. Point Arena Lighthouse - Keeper's Room

Point Arena

19. Enchanting Retreat in the heart of Redwoods

Guerneville

Josie B.

includes taxes & fees

12 Nov - 13 Nov

A kitchen with a stove, coffee maker, toaster, and utensils.

20. Darby’s Destination | Russian River Getaway

Monte rio

includes taxes & fees

12 Nov - 13 Nov

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Find holiday rentals that suit your style

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, 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 €80 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?

Relax by Russian River, spacious 6-bedroom retreat: This holiday home rental outside of Annapolis is located on a river, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 6 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Kick off your shoes and enjoy yourself with a selection of games and 1 hot tub.

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 Gualala Point Regional 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.

Holiday Rentals in Annapolis

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Annapolis holiday rentals

1. Rendezvous Mendocino

2. The Ranch at Lake Sonoma

3. Point Arena Lighthouse

4. Enchanting Creekside Retreat: Your Downtown Oasis

5. Serene Coastal Retreat Clark's Cove - Holiday Home

6. Cozy Riverfront Cabin - Beach Access & Wood Stove

7. The Tiny Tipsy Turtle

8. Ocean & River View EVC Hot & Cold Tubs Outdoor Shower Walk to Town Dog Friendly

9. 2BR Estuary Views with Spa and Easy Ocean and River Access

10. Secluded Ocean-view Retreat: Coastal Gualala Home

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

12. Country Carriage House in Downtown Geyserville, Vineyard Views

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

14. Cozy Riverfront Cabin with Dock, Fire Pit & Dogs OK

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

16. Adorable 1-bedroom cabin in a peaceful retreat center in Philo

17. Tranquil Redwood Retreat

18. Point Arena Lighthouse - Keeper's Room

19. Enchanting Retreat in the heart of Redwoods

20. Darby’s Destination | Russian River Getaway

Find holiday rentals that suit your style

Find out more about Annapolis

Annapolis holiday rentals: An excellent choice for every season

How to find incredible deals on Annapolis rentals

Frequently Asked Questions

Can I find holiday rentals in Annapolis?

What are some of the best holiday rentals that Annapolis has to offer?

What’s there to see and do in Annapolis?

What’s a holiday rental in Annapolis like?