Holiday Rentals Annapolis from £67: Find Short-Term Rentals & Holiday Accommodations

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

3 Nov - 4 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

3 Nov - 4 Nov

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

3 Dec - 4 Dec

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

Chuck R.

includes taxes & fees

6 Nov - 7 Nov

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

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

Guerneville

Sherri

includes taxes & fees

3 Nov - 4 Nov

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

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

Jenner

includes taxes & fees

4 Nov - 5 Nov

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

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

Anchor Bay

Theodore

includes taxes & fees

4 Nov - 5 Nov

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

8. Cozy Riverfront Cabin - Beach Access & Wood Stove

Guerneville

Jehanne H.

includes taxes & fees

3 Nov - 4 Nov

A spacious living room with a fireplace, large windows offering ocean views, and a dining area with a view of the sea.

9. Pet-friendly Oceanfront Retreat w/King Beds & Hot Tub!

Gualala

Steve P.

includes taxes & fees

3 Nov - 4 Nov

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

includes taxes & fees

22 Nov - 23 Nov

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

11. Enchanting Retreat in the heart of Redwoods

Guerneville

Josie B.

includes taxes & fees

3 Nov - 4 Nov

12. Secluded Ocean-View Retreat: Coastal Gualala Home

Gualala

"Really beautiful property. The kitchen is incredible. The amenities are perfect. The views are absolutely stellar. Property manager Wendy is helpful, responsive and very nice. Only two suggestions. Upstairs analog/digital hybrid shower is complex and needs instructions. I figured it out eventually. And would have loved it if the outdoor hot tub was working. Still, minor blips in an otherwise perfect getaway. Will be back! "

Sixfinger G.

includes taxes & fees

22 Nov - 23 Nov

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

8 Nov - 9 Nov

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

14. Country Carriage House in Downtown Geyserville, Vineyard Views

Geyserville

Gina I.

includes taxes & fees

3 Dec - 4 Dec

15. Tranquil Redwood Retreat

Guerneville

Alex A.

includes taxes & fees

3 Nov - 4 Nov

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

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

Gualala

Lisa M.

includes taxes & fees

22 Nov - 23 Nov

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

17. The Tiny Tipsy Turtle

Guerneville

ANTHONY B.

includes taxes & fees

10 Nov - 11 Nov

A coastal landscape with large rocks and waves.

18. 2BR Estuary Views with Spa and Easy Ocean and River Access

Jenner

Dana H.

includes taxes & fees

11 Nov - 12 Nov

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

19. Point Arena Lighthouse - Keeper's Room

Point Arena

includes taxes & fees

3 Nov - 4 Nov

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

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

Monte Rio

Samuel H.

includes taxes & fees

3 Nov - 4 Nov

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Top Annapolis Hotel Reviews

Ocean Cove Lodge

10/10 Excellent

"We had a wonderful stay at this hotel! The room comfortable, and beautifully maintained. The staff was friendly, welcoming, and always ready to help. Everything was great, and we truly enjoyed our stay. We would definitely come back again and highly recommend this hotel!"

West Sonoma Inn & Spa

8/10 Good

"We chose this hotel because of the proximity to the Armstrong Redwoods State Natural Reserve, and it looked great from the pictures online. This hotel and spa was interesting. When we arrived, there was a sign at the front desk that said that if there wasn't anyone at the front desk to use the phone outside the office to call for someone. We got a hold of someone who came and helped us. Our rooms were not ready to we went to see the redwoods. (amazing) When we returned, no one again at the front desk. Made another phone call. Rooms were ready. The room and bathroom were bigger than expected. At 11:00 pm the smoke detector went off that was located outside of our room which would be outside, outside. Opened the door and it was pitch black. Couldn't see anything. We went to call the front desk and saw that there was a text saying that there was some road work happening on the main road and that we were going to be without power for several hours. Would expect more than a text about something like this) Tried to then call the front desk about the smoke detector and there is no one available at the front desk till the morning. Thank goodness there wasn't a real fire or an emergency because we wouldn't have been able to contact anyone. Tried to even use the phone outside the lobby but it was dead due to the lack of electricity. We all survived. I think we had a series of misfortunate events that night because its one of our favorite stories to tell everyone."

Timber Cove Resort

10/10 Excellent

"Lovely site with stunning views from all rooms, and an enjoyable Penisula walk throughout the property. Dinner at the Coast Kitchen was also very nice. Our complaints were that water bottles were not refilled in the rooms, nor were dirty cups & glasses replaced. We ended up going out & buying a jug of water and having to reuse drinkware. There was also no coffee available to make in the room, and it wasn’t readily available in the main lodge outside of the hours of 6AM - 8AM. Our dislikes seem minor but when you have such a nice facility with premium priced rooms, little inconveniences really stand out."

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 £67 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.

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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.

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

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

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

8. Cozy Riverfront Cabin - Beach Access & Wood Stove

9. Pet-friendly Oceanfront Retreat w/King Beds & Hot Tub!

10. Secluded Ocean-view Retreat: Coastal Gualala Home

11. Enchanting Retreat in the heart of Redwoods

12. Secluded Ocean-View Retreat: Coastal Gualala Home

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

14. Country Carriage House in Downtown Geyserville, Vineyard Views

15. Tranquil Redwood Retreat

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

17. The Tiny Tipsy Turtle

18. 2BR Estuary Views with Spa and Easy Ocean and River Access

19. Point Arena Lighthouse - Keeper's Room

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

Find holiday rentals that suit your style

Top Annapolis Hotel Reviews

Ocean Cove Lodge

Find out more about Annapolis

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