Holiday Rentals in Annapolis

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Holiday Rentals in Annapolis

Terre Haute Casino Resort

4.0 star property
9.4 out of 10, Exceptional, (553)
"Great place to stay"
The price is €130
includes taxes & fees
22 Sept - 23 Sept
Terre Haute Casino Resort

Drury Inn & Suites Terre Haute

3.0 star property
9.6 out of 10, Exceptional, (1009)
"Very friendly staff and the rooms are so clean! I also enjoy the free evening dining "
The price is €99
includes taxes & fees
23 Sept - 24 Sept
Drury Inn & Suites Terre Haute

La Quinta Inn & Suites by Wyndham Terre Haute

3.0 star property
9.0 out of 10, Wonderful, (1007)
"A great place to stay!"
The price is €113
includes taxes & fees
25 Sept - 26 Sept
La Quinta Inn & Suites by Wyndham Terre Haute

Quality Inn Terre Haute University Area

2.5 star property
7.0 out of 10, Good, (1003)
"I like its area of front area and pool . "
The price is €53
includes taxes & fees
29 Sept - 30 Sept
Quality Inn Terre Haute University Area

Best Western Plus Covered Bridge Inn

2.5 star property
8.6 out of 10, Excellent, (916)
"Great breakfast."
The price is €91
includes taxes & fees
21 Sept - 22 Sept
Best Western Plus Covered Bridge Inn

Hampton Inn & Suites Crawfordsville

2.5 star property
9.2 out of 10, Wonderful, (772)
"A very nice property and staff were very welcoming and helpful. Well appointed rooms and a great breakfast and eating area. A very comfortable place to stay."
The price is €102
includes taxes & fees
6 Oct - 7 Oct
Hampton Inn & Suites Crawfordsville

Sleep Inn And Suites Danville

2.5 star property
8.0 out of 10, Very good, (692)
"Love this place"
The price is €90
includes taxes & fees
6 Oct - 7 Oct
Sleep Inn And Suites Danville

Days Inn & Suites by Wyndham Terre Haute

2.0 star property
5.2 out of 10, (1009)
"Personal touches made the place seem more like someone's guest room than a motel."
The price is €51
includes taxes & fees
21 Sept - 22 Sept
Days Inn & Suites by Wyndham Terre Haute

Comfort Inn

2.5 star property
8.6 out of 10, Excellent, (748)
"The breakfast was good. "
The price is €102
includes taxes & fees
6 Oct - 7 Oct
Comfort Inn

Best Western Riverside Inn

2.5 star property
8.0 out of 10, Very good, (783)
"Great location for my trip."
The price is €86
includes taxes & fees
1 Oct - 2 Oct
Best Western Riverside Inn

Sleep Inn Terre Haute University Area

2.5 star property
7.8 out of 10, Good, (1006)
"The staff was very nice and polite, the breakfast was very nice. "
The price is €61
includes taxes & fees
22 Sept - 23 Sept
Sleep Inn Terre Haute University Area

Super 8 by Wyndham Terre Haute

2.0 star property
6.8 out of 10, (1003)
"Nice place to stay"
The price is €58
includes taxes & fees
25 Sept - 26 Sept
Super 8 by Wyndham Terre Haute

Days Hotel & Conference Center by Wyndham Danville

2.0 star property
6.4 out of 10, (610)
"Would stay again. "
The price is €52
includes taxes & fees
12 Oct - 13 Oct
Days Hotel & Conference Center by Wyndham Danville

Best Western Plus Crawfordsville Hotel

2.5 star property
8.6 out of 10, Excellent, (1007)
"Absolutely loved it!!! It was so clean and nice. We will be staying here every time we come to a Green Bay game. "
The price is €86
includes taxes & fees
9 Oct - 10 Oct
Best Western Plus Crawfordsville Hotel

Baymont by Wyndham Danville IL

2.5 star property
7.2 out of 10, Good, (575)
"It was great I had a fun time"
The price is €67
includes taxes & fees
28 Sept - 29 Sept
Baymont by Wyndham Danville IL

Holiday Inn Terre Haute by IHG

3.0 star property
8.4 out of 10, Very good, (854)
"This property was very clean, breakfasts were very good and staff was nice! Enjoyed my stay for a 8U Softball tournament & would stay again!"
The price is €108
includes taxes & fees
28 Sept - 29 Sept
Holiday Inn Terre Haute by IHG

Holiday Inn Express Hotel & Suites Crawfordsville by IHG

2.5 star property
9.2 out of 10, Wonderful, (895)
"Hotel was easy to find, clean, quiet and excellent breakfast. "
The price is €118
includes taxes & fees
21 Sept - 22 Sept
Holiday Inn Express Hotel & Suites Crawfordsville by IHG

Hampton Inn Terre Haute

2.5 star property
8.2 out of 10, Very good, (980)
"Property is ok for an overnight stay. "
The price is €90
includes taxes & fees
28 Sept - 29 Sept
Hampton Inn Terre Haute

Candlewood Suites Terre Haute by IHG

2.5 star property
9.2 out of 10, Wonderful, (838)
"Friendly staff!"
The price is €107
includes taxes & fees
29 Sept - 30 Sept
Candlewood Suites Terre Haute by IHG

Motel 6 Crawfordsville, IN

2.0 star property
5.6 out of 10, (586)
"Great staffing and quiet place to stay"
The price is €65
includes taxes & fees
6 Oct - 7 Oct
Motel 6 Crawfordsville, IN
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

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 €158 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?

Cute, pet-friendly home in quiet neighborhood. Close to state parks & downtown.: This holiday home rental outside of Annapolis offers a patio, a selection of games and air conditioning to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

What’s there to see and do in Annapolis?

While you're exploring the area, Lake Waveland and Rockville Lake Park are a couple of picturesque spots to get outside and enjoy nature. In the wider area, you’ll find Turkey Run State Park and Billie Creek Village.

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 offer amenities such as kitchens and laundry facilities so you'll have everything you want. If you're concerned about a clean environment, holiday rentals can offer a sense of security away from public hotel lifts and lobbies bustling with people while still allowing you to travel. You'll also get more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a popular option for a small group gathering.