A coastal town with clear turquoise waters, rocky shores, and white buildings.

Holiday Homes in Anna

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Check prices for these dates

In two weeks
6 Nov - 8 Nov
In two months
18 Dec - 20 Dec
In three months
15 Jan - 17 Jan
In four months
12 Feb - 14 Feb

Our top choices for Anna holiday homes

A room with a clear glass display unit holding wine bottles and glasses.

1. Cozy and Updated Farmhouse with King Suite

Cozy and Updated Farmhouse with King Suite
Anna
10.0 out of 10, Exceptional, (28 reviews)
"Comfortable bed which is what we needed. We weren’t there long but is was everything we needed."
United States
Kathy H.
The price is NZ$301
includes taxes & fees
27 Oct - 28 Oct
Cozy and Updated Farmhouse with King Suite
A spacious living room with a brown leather sofa, a dining area with a wooden table and chairs, a kitchen with white cabinets and a central island, and large windows with blinds.

2. Pa’s House is an enjoyable, entirely remodeled, 2-bedroom farmhouse near Anna.

Pa’s House is an enjoyable, entirely remodeled, 2-bedroom farmhouse near Anna.
Anna
10.0 out of 10, Exceptional, (12 reviews)
"We enjoyed our stay here. The beds were very comfortable and it was close to all of the wineries along the wine trail."
United States
Kristi H.
The price is NZ$465
includes taxes & fees
26 Oct - 27 Oct
Pa’s House is an enjoyable, entirely remodeled, 2-bedroom farmhouse near Anna.
A large, two-story house with a wrap-around porch, surrounded by a well-maintained garden with various flowering plants.

3. Magical Victorian near hiking / wine trail

Magical Victorian near hiking / wine trail
Anna
9.8 out of 10, Exceptional, (20 reviews)
"Everything was beautiful, and although we weren’t there for a long time, enjoyed an Incredible sleep in the most comfortable beds!"
United States
Rachel H.
The price is NZ$605
includes taxes & fees
25 Oct - 26 Oct
Magical Victorian near hiking / wine trail
A brick building with a sign reading "1898 Guesthouse".

4. Stunning 2 bedroom in town, close to Shawnee National Forest

Stunning 2 bedroom in town, close to Shawnee National Forest
Jonesboro
10.0 out of 10, Exceptional, (15 reviews)
"Cool renovated property that keeps that old fashioned charm. Spacious living with all the amenities you need for a vacation stay."
United States
Dylan
The price is NZ$561
includes taxes & fees
10 Nov - 11 Nov
Stunning 2 bedroom in town, close to Shawnee National Forest
A spacious living area with a kitchen, a dining table, and comfortable seating.

5. Peach Tree Inn, downtown Cobden

Peach Tree Inn, downtown Cobden
Cobden
10.0 out of 10, Exceptional, (3 reviews)
"Amazing place to stay. Excellent location, beautiful rooms and accommodation and the host was so responsive. We will definitely be back!"
United States
Rebecca L.
The price is NZ$407
includes taxes & fees
26 Oct - 27 Oct
Peach Tree Inn, downtown Cobden
A kitchen with wooden cabinets, a countertop, and a window with blinds.

6. Crossview Cottage - Direct view of Bald Knob Cross

Crossview Cottage - Direct view of Bald Knob Cross
Alto Pass
10.0 out of 10, Exceptional, (1 review)
"Quiet, private, and perfect for one or two adults!"
United States
Anthony R.
The price is NZ$262
includes taxes & fees
26 Oct - 27 Oct
Crossview Cottage - Direct view of Bald Knob Cross
A cabin with a wooden deck and a 'WELCOME' sign, surrounded by trees.

7. Secluded treehouse with indoor fireplace

Secluded treehouse with indoor fireplace
Makanda
10.0 out of 10, Exceptional, (30 reviews)
"Very nice place. We enjoyed it."
United States
Gregory M.
The price is NZ$335
includes taxes & fees
2 Nov - 3 Nov
Secluded treehouse with indoor fireplace
A wooden deck with two white Adirondack chairs and a small round table.

8. Walk to Weddings-Wineries-Trails, Family Friendly Home in Downtown Alto Pass

Walk to Weddings-Wineries-Trails, Family Friendly Home in Downtown Alto Pass
Alto Pass
10.0 out of 10, Exceptional, (5 reviews)
"The house was very welcoming and clean. Very inviting for our short stay. "
United States
brian O.
The price is NZ$457
includes taxes & fees
26 Oct - 27 Oct
Walk to Weddings-Wineries-Trails, Family Friendly Home in Downtown Alto Pass
A red barn-style building with a sign reading "Farm Market" and a stage with chairs and a table.

9. Farm Fresh Eggs, Golf Cart, Telescope

Farm Fresh Eggs, Golf Cart, Telescope
Alto Pass
9.8 out of 10, Exceptional, (15 reviews)
"It’s a very cute old farm house nestled in a peach orchard! Rolling hills with a porch swing that overlooks the orchards and a pond. The hosts provide all of the essential's for a comfortable stay! Communication is wonderful from beginning to the end! Would stay here again and again!"
United States
Gary A.
The price is NZ$452
includes taxes & fees
23 Nov - 24 Nov
Farm Fresh Eggs, Golf Cart, Telescope
Interior

10. Convenient, Cozy and Pet Friendly 2-bedroom home in Beautiful Makanda

Convenient, Cozy and Pet Friendly 2-bedroom home in Beautiful Makanda
Makanda
10.0 out of 10, Exceptional, (1 review)
"We will definitely book our next stay with this home as it was very very clean and had everything we needed for our stay. The host is very easy to communicate with, even though we didn't need to contact her about anything during our stay because everything was perfect. Having a garage to park in was definitely a plus. The king beds were comfy and the kitchen was stock with everything that we needed. Thanks again."
United States
Rosa R.
The price is NZ$271
includes taxes & fees
27 Oct - 28 Oct
Convenient, Cozy and Pet Friendly 2-bedroom home in Beautiful Makanda
A covered porch with a wooden railing, a table with chairs, and a sofa.

11. Beautiful location in the secluded woods

Beautiful location in the secluded woods
Pomona
9.8 out of 10, Exceptional, (83 reviews)
"This rental was very clean, pet friendly, and definitely secluded. We enjoyed our stay here."
United States
Candi M.
The price is NZ$308
includes taxes & fees
27 Oct - 28 Oct
Beautiful location in the secluded woods
A living room with a TV, a fireplace, a sofa, and wall art.

12. Little Blue Cottage on Spanish

Little Blue Cottage on Spanish
Cape Girardeau
8.4 out of 10, Very good, (59 reviews)
"Great cute place. "
United States
Jeremy W.
The price is NZ$190
includes taxes & fees
26 Oct - 27 Oct
Little Blue Cottage on Spanish
Ground floor of the Euro

13. The Little Château | Woodland Escape

The Little Château | Woodland Escape
Cape Girardeau
The price is NZ$389
includes taxes & fees
29 Oct - 30 Oct
The Little Château | Woodland Escape
A bathroom with a toilet, sink, mirror, and shower curtain.

14. The Lux Collective- Private Hot Tub, Dry Bar, 1-Acre Yard & Fire Pit

The Lux Collective- Private Hot Tub, Dry Bar, 1-Acre Yard & Fire Pit
Murphysboro
The price is NZ$399
includes taxes & fees
26 Oct - 27 Oct
The Lux Collective- Private Hot Tub, Dry Bar, 1-Acre Yard & Fire Pit
A two-story house with a front porch, a small garden, and a white picket fence.

15. 3+ acre Home: Pool Table, Putt-Putt, 4 miles to Downtown and SEMO, Summer Pool

3+ acre Home: Pool Table, Putt-Putt, 4 miles to Downtown and SEMO, Summer Pool
Cape Girardeau
8.8 out of 10, Excellent, (46 reviews)
"Will definitely book again! Great location, comfortable stay."
United States
Pynktoria !.
The price is NZ$552
includes taxes & fees
26 Oct - 27 Oct
3+ acre Home: Pool Table, Putt-Putt, 4 miles to Downtown and SEMO, Summer Pool
A spacious living area with a kitchen, a dining table, and comfortable seating.

16. Heart of Wine country in Cobden

Heart of Wine country in Cobden
Cobden
10.0 out of 10, Exceptional, (1 review)
"We throughly enjoyed the accommodations and plan I. Returning! Checking in was easy, and they worked with us on an earlier check in. Checking out process was very smooth and easy. We can’t wait to book our next trip."
United States
CHEA M.
The price is NZ$407
includes taxes & fees
25 Oct - 26 Oct
Heart of Wine country in Cobden
A spacious living area with a kitchen, a dining table, and comfortable seating.

17. King Suite, Hot Tub, walk to Iron Whisk

King Suite, Hot Tub, walk to Iron Whisk
Cobden
The price is NZ$407
includes taxes & fees
25 Oct - 26 Oct
King Suite, Hot Tub, walk to Iron Whisk
Exterior

18. Romantic Creekside Retreat | Fireplace | Deck | Pet Friendly

Romantic Creekside Retreat | Fireplace | Deck | Pet Friendly
Cape Girardeau
10.0 out of 10, Exceptional, (3 reviews)
"The house was very clean and Will kept and the whole property was well maintained. It was very comfortable and nicely decorated. The host was very responsive and helpful! Would definitely stay again and recommend."
United States
Sara C.
The price is NZ$392
includes taxes & fees
4 Nov - 5 Nov
Romantic Creekside Retreat | Fireplace | Deck | Pet Friendly
A cozy living room with leather sofas, a stone fireplace, and large windows.

19. 3BR Ridge Home · Hot Tub, Firepit & Valley Views

3BR Ridge Home · Hot Tub, Firepit & Valley Views
Carbondale
9.6 out of 10, Exceptional, (36 reviews)
"Great place to stay in the Carbondale area! Secluded location but close enough to town for dining and entertainment. Would definitely stay again! "
United States
Scott A. B.
The price is NZ$765
includes taxes & fees
25 Oct - 26 Oct
3BR Ridge Home · Hot Tub, Firepit & Valley Views
A large, two-story house with a well-lit porch and a fire pit in the yard.

20. Owl's Nest is a perfect getaway in the woods with lakes nearby. Pet friendly!

Owl's Nest is a perfect getaway in the woods with lakes nearby. Pet friendly!
Carbondale
10.0 out of 10, Exceptional, (22 reviews)
"Planning to stay here again in the Fall - everything we needed and more. Very clean, and beautiful home."
United States
Jenna S.
Owl's Nest is a perfect getaway in the woods with lakes nearby. Pet friendly!
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 Anna Hotel Reviews

Drury Inn & Suites Marion

Drury Inn & Suites Marion

10/10 Excellent
"Excellent very good High quality"
laurie 2-night trip
Posted 4 hours ago
Drury Inn & Suites Marion

Find out more about Anna

Anna Holiday Homes information

Number of reviews
380
Accommodation
196 Holiday Homes
Lowest Price
NZ$190
Highest Price
NZ$765