Annapolis Holiday Rentals

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Check prices for these dates

In two weeks
2 Jan - 4 Jan
In two months
13 Feb - 15 Feb
In three months
13 Mar - 15 Mar
In four months
10 Apr - 12 Apr

Our top choices for Annapolis holiday rentals

Front of property
The Ranch at Lake Sonoma

The Ranch at Lake Sonoma

The Ranch at Lake Sonoma
1.0 star property
Geyserville
10.0 out of 10, Exceptional, (2)
"Nice camping spot "
United States
Evelyn
The price is S$87
includes taxes & fees
19 Dec - 20 Dec
The Ranch at Lake Sonoma
Beach/ocean view
Point Arena Lighthouse

Point Arena Lighthouse

Point Arena Lighthouse
3.0 star property
Point Arena
9.6 out of 10, Exceptional, (113)
"Great location with a view"
United States
Shalini
The price is S$243
includes taxes & fees
21 Dec - 22 Dec
Point Arena Lighthouse
Premium bedding, individually decorated, individually furnished
Rendezvous Mendocino

Rendezvous Mendocino

Rendezvous Mendocino
3.0 star property
Gualala
9.4 out of 10, Exceptional, (13)
"I loved everything about the property. The breakfast was out of this world! It was nice and quiet, a very relaxed atmosphere. Excellent wi-fi. We could hear the sea lions and we could also see the ocean. We had a wonderful stay!"
United States
Leoni
The price is S$315
includes taxes & fees
4 Jan - 5 Jan, 2026
Rendezvous Mendocino
Interior
Russian River Retreat! Woodsy Guerneville Bungalow

Russian River Retreat! Woodsy Guerneville Bungalow

Russian River Retreat! Woodsy Guerneville Bungalow
3.0 star property
Guerneville
The price is S$574
includes taxes & fees
23 Dec - 24 Dec
Russian River Retreat! Woodsy Guerneville Bungalow
Exterior
Adventure Alexander Valley Lodge With Pool & Hot Tub 6 Bedroom Villa

Adventure Alexander Valley Lodge With Pool & Hot Tub 6 Bedroom Villa

Adventure Alexander Valley Lodge With Pool & Hot Tub 6 Bedroom Villa
3.5 star property
Geyserville
The price is S$1,515
includes taxes & fees
13 Jan - 14 Jan, 2026
Adventure Alexander Valley Lodge With Pool & Hot Tub 6 Bedroom Villa
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

Timber Cove Resort

Timber Cove Resort

10/10 Excellent
"great location and excellent accommodation's to unplug and celebrate my birthday. . "
Karen 2-night trip
Posted 12 hours ago
Timber Cove Resort

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.