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Annapolis Holiday Rentals

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Our top choices for Annapolis holiday rentals

1. Rendezvous Mendocino

Rendezvous Mendocino
3.0 star property
Gualala
9.8 out of 10, Exceptional, (46 reviews)
"Privacy, amazing breakfast, attentive staff, EV charging available"
United States
Tracey
The price is NZ$398
includes taxes & fees
1 Nov - 2 Nov
Rendezvous Mendocino

2. The Ranch at Lake Sonoma

The Ranch at Lake Sonoma
1.0 star property
Geyserville
9.0 out of 10, Wonderful, (10 reviews)
"Enjoyed my stay"
United States
Epeli
The price is NZ$161
includes taxes & fees
30 Oct - 31 Oct
The Ranch at Lake Sonoma

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

Serene Coastal Retreat Clark's Cove - Holiday Home
Jenner
The price is NZ$1,249
includes taxes & fees
4 Nov - 5 Nov
Serene Coastal Retreat Clark's Cove - Holiday Home

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

Pet-Friendly Designer Oceanfront 3B House with King Beds & Hot Tub & Outdoor Kit
Gualala
10.0 out of 10, Exceptional, (9 reviews)
"The property was great, exactly as advertised, view is spectacular. And thank goodness for the wind-sheltered back patio with bbq, because I'm guessing our 3-day stay was one of the windier stretches of the summer. (as luck would have it, not a wind-wave on the ocean this morning when we left). All in all, we had a great time, thank you!"
United States
Michael M.
The price is NZ$1,883
includes taxes & fees
8 Nov - 9 Nov
Pet-Friendly Designer Oceanfront 3B House with King Beds & Hot Tub & Outdoor Kit

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

Ocean & River View EVC Hot & Cold Tubs Outdoor Shower Walk to Town Dog Friendly
Gualala
10.0 out of 10, Exceptional, (75 reviews)
"Great stay, wonderful house "
United States
Tracy H.
The price is NZ$2,329
includes taxes & fees
22 Nov - 23 Nov
Ocean & River View EVC Hot & Cold Tubs Outdoor Shower Walk to Town Dog Friendly

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

Pet-friendly Oceanfront Retreat w/King Beds & Hot Tub!
Gualala
10.0 out of 10, Exceptional, (76 reviews)
"Beautiful setting - well appointed - fit all our needs - grandparents, parents, 3 year old and dog."
United States
Steve P.
The price is NZ$1,724
includes taxes & fees
30 Oct - 31 Oct
Pet-friendly Oceanfront Retreat w/King Beds & Hot Tub!

7. Russian River RV Campground

Russian River RV Campground
1.5 star property
Cloverdale
10.0 out of 10, Exceptional, (2 reviews)
"We had a great time in the cabin. It was well stocked, had a nice layout, and was bigger than expected. The bunk bed are creatively placed and reminiscent of a cubby hole. The property is undergoing upgrades to the public restrooms so it will be even better soon. "
United States
Samantha
Russian River RV Campground

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

Epic Mendocino Ocean Views, 5BR, Tesla Charger
Anchor Bay
8.0 out of 10, Very good, (11 reviews)
"Outstanding view with large deck. The kitchen was perfect for our needs."
United States
Theodore
The price is NZ$1,575
includes taxes & fees
1 Nov - 2 Nov
Epic Mendocino Ocean Views, 5BR, Tesla Charger

9. Point Arena Lighthouse

Point Arena Lighthouse
3.0 star property
Point Arena
9.6 out of 10, Exceptional, (127 reviews)
"Very nice and picturesque location. "
United States
Richard
The price is NZ$396
includes taxes & fees
29 Nov - 30 Nov
Point Arena Lighthouse

10. Enchanting Creekside Retreat: Your Downtown Oasis

Enchanting Creekside Retreat: Your Downtown Oasis
Hopland
9.8 out of 10, Exceptional, (18 reviews)
"This is a handy location for Hopland "
United States
Chuck R.
The price is NZ$452
includes taxes & fees
6 Nov - 7 Nov
Enchanting Creekside Retreat: Your Downtown Oasis

11. Secluded Ocean-view Retreat: Coastal Gualala Home

Secluded Ocean-view Retreat: Coastal Gualala Home
3.0 star property
Gualala
10.0 out of 10, Exceptional, (1 review)
"Gorgeous views, spacious home, clean and comfortable."
United States
Tracy
The price is NZ$864
includes taxes & fees
22 Nov - 23 Nov
Secluded Ocean-view Retreat: Coastal Gualala Home

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

Redwood Cabin w/ Hot Tub | Canyon View | Dogs OK
Guerneville
9.4 out of 10, Exceptional, (10 reviews)
"Very unique and charming property. Definitely felt like being in a tree house in the redwoods. We spent most of our time when there sitting on the deck. It was conveniently located to everything we wanted to do - drive to the coast, hike at the state park, and visit nearby restaurants and wineries."
United States
Sherri
Redwood Cabin w/ Hot Tub | Canyon View | Dogs OK

13. Cozy Riverfront Cabin - Beach Access & Wood Stove

Cozy Riverfront Cabin - Beach Access & Wood Stove
Guerneville
9.8 out of 10, Exceptional, (29 reviews)
"It was wonderful, we'll be back!"
United States
Jehanne H.
The price is NZ$859
includes taxes & fees
1 Nov - 2 Nov
Cozy Riverfront Cabin - Beach Access & Wood Stove

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

Cozy Riverfront Cabin with Dock, Fire Pit & Dogs OK
Monte Rio
9.8 out of 10, Exceptional, (9 reviews)
"Great place and stay"
United States
Samuel H.
The price is NZ$918
includes taxes & fees
3 Nov - 4 Nov
Cozy Riverfront Cabin with Dock, Fire Pit & Dogs OK

15. 2BR Estuary Views with Spa and Easy Ocean and River Access

2BR Estuary Views with Spa and Easy Ocean and River Access
Jenner
9.4 out of 10, Exceptional, (12 reviews)
"What a great place to experience Jenner. Definitely will come back!"
United States
Dana H.
The price is NZ$1,111
includes taxes & fees
8 Nov - 9 Nov
2BR Estuary Views with Spa and Easy Ocean and River Access

16. Vintage Shasta Camper with Relaxing Fire Pit Escape on Geyserville, California

Vintage Shasta Camper with Relaxing Fire Pit Escape on Geyserville, California
Geyserville
The price is NZ$556
includes taxes & fees
2 Nov - 3 Nov
Vintage Shasta Camper with Relaxing Fire Pit Escape on Geyserville, California

17. Country Carriage House in Downtown Geyserville, Vineyard Views

Country Carriage House in Downtown Geyserville, Vineyard Views
Geyserville
10.0 out of 10, Exceptional, (5 reviews)
"Cozy, rustic, and with all great amenities."
United States
Gina I.
The price is NZ$709
includes taxes & fees
3 Nov - 4 Nov
Country Carriage House in Downtown Geyserville, Vineyard Views

18. The Tiny Tipsy Turtle

The Tiny Tipsy Turtle
Guerneville
10.0 out of 10, Exceptional, (67 reviews)
"Great little place to stay / perfect location in town close to everything / wonderful front patio "
United States
ANTHONY B.
The price is NZ$379
includes taxes & fees
11 Nov - 12 Nov
The Tiny Tipsy Turtle

19. Point Arena Lighthouse - Keeper's Room

Point Arena Lighthouse - Keeper's Room
Point Arena
10.0 out of 10, Exceptional, (1 review)
The price is NZ$505
includes taxes & fees
3 Nov - 4 Nov
Point Arena Lighthouse - Keeper's Room

20. Pumpkin House Summary

Pumpkin House Summary
Guerneville
10.0 out of 10, Exceptional, (13 reviews)
"Nice place, quiet. Loved the hot tub. "
United States
Nathan B.
The price is NZ$647
includes taxes & fees
1 Nov - 2 Nov
Pumpkin House Summary
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

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Annapolis holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Annapolis. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Annapolis. Seeing all the best attractions is bound to make you fall in love with Annapolis. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Annapolis short-term rentals, that won’t be hard to do.

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.