Title: Bennington Vacation Rentals from CA $219: Short-Term Rentals for 2026 | Expedia.ca

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## Check prices for these dates

In two weeks

[Mar 27 - Mar 29](https://www.expedia.ca/Hotel-Search?regionId=553248635975849202&startDate=2026-03-27&endDate=2026-03-29&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[May 8 - May 10](https://www.expedia.ca/Hotel-Search?regionId=553248635975849202&startDate=2026-05-08&endDate=2026-05-10&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[Jun 5 - Jun 7](https://www.expedia.ca/Hotel-Search?regionId=553248635975849202&startDate=2026-06-05&endDate=2026-06-07&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[Jul 3 - Jul 5](https://www.expedia.ca/Hotel-Search?regionId=553248635975849202&startDate=2026-07-03&endDate=2026-07-05&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Our top choices for Bennington vacation rentals

![TV, fireplace, DVD player](https://images.trvl-media.com/lodging/96000000/95870000/95861300/95861216/d9cb2520.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/96000000/95870000/95861300/95861216/3ac611b2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, fireplace, DVD player](https://images.trvl-media.com/lodging/96000000/95870000/95861300/95861216/f1a355c8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/96000000/95870000/95861300/95861216/7e37ae4e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cabin in Madison

[](https://www.expedia.ca/Canaan-Hotels-A-Cozy.h95861216.Hotel-Information)

10/10

Exceptional

(16 reviews)

"Nice cabin"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Nathan M.

CA $145

CA $308 total

includes taxes & fees

Mar 15 - Mar 16

[](https://www.expedia.ca/Canaan-Hotels-A-Cozy.h95861216.Hotel-Information)

![TV, fireplace](https://images.trvl-media.com/lodging/96000000/95870000/95861300/95861214/8aa72f2d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, fireplace](https://images.trvl-media.com/lodging/96000000/95870000/95861300/95861214/c492298a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/96000000/95870000/95861300/95861214/a0c42af1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/96000000/95870000/95861300/95861214/fb1dc310.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cabin in Madison

[](https://www.expedia.ca/Canaan-Hotels-The-Areas-First-New-Construction-Short-Term-Rental-Tailored-For-You.h95861214.Hotel-Information)

10/10

Exceptional

(17 reviews)

"Our stay was amazing! Loved this cozy cabin in the woods! "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Alison F.

CA $145

CA $289 total

includes taxes & fees

Mar 15 - Mar 16

[](https://www.expedia.ca/Canaan-Hotels-The-Areas-First-New-Construction-Short-Term-Rental-Tailored-For-You.h95861214.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/118000000/117850000/117840100/117840020/2b777778.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, WiFi, bed sheets](https://images.trvl-media.com/lodging/118000000/117850000/117840100/117840020/4b03b8eb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/118000000/117850000/117840100/117840020/002145bf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/118000000/117850000/117840100/117840020/b1bd9da3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Madison Township

[](https://www.expedia.ca/Madison-Hotels-Maple-Cabin-At-Lost-Trails.h117840020.Hotel-Information)

10/10

Exceptional

(7 reviews)

"Very nice place definitely recommend "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Eric T.

CA $115

CA $212 total

includes taxes & fees

Mar 18 - Mar 19

[](https://www.expedia.ca/Madison-Hotels-Maple-Cabin-At-Lost-Trails.h117840020.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/101000000/100810000/100806000/100805995/24acbc04.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/101000000/100810000/100806000/100805995/e046bf1b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/101000000/100810000/100806000/100805995/3606019f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/101000000/100810000/100806000/100805995/30878268.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Sparta

[](https://www.expedia.ca/Warsaw-Hotels-Lake-House-With-Private-Dock-Ark-Encounter-Creation-Museum-Warsaw-Getaway.h100805995.Hotel-Information)

9.8/10

Exceptional

(10 reviews)

"Wonderful vacation home. Very clean, great host that was very helpful. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Ashley C.

CA $214

CA $509 total

includes taxes & fees

Mar 12 - Mar 13

[](https://www.expedia.ca/Warsaw-Hotels-Lake-House-With-Private-Dock-Ark-Encounter-Creation-Museum-Warsaw-Getaway.h100805995.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/118000000/117850000/117840100/117840018/e447409f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/118000000/117850000/117840100/117840018/3e20fda9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/118000000/117850000/117840100/117840018/8fc00cc3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/118000000/117850000/117840100/117840018/583df61d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cabin in Madison Township

[](https://www.expedia.ca/Madison-Hotels-Walnut-Cabin-At-Lost-Trails.h117840018.Hotel-Information)

10/10

Exceptional

(2 reviews)

"Was a great space! Clean, modern and very cute! Would highly recommend "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Anna M.

CA $130

CA $229 total

includes taxes & fees

Mar 16 - Mar 17

[](https://www.expedia.ca/Madison-Hotels-Walnut-Cabin-At-Lost-Trails.h117840018.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/118000000/117850000/117840100/117840022/592d0290.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/118000000/117850000/117840100/117840022/5d7b2d62.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/118000000/117850000/117840100/117840022/fde45310.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/118000000/117850000/117840100/117840022/d2dbaec7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Madison Township

[](https://www.expedia.ca/Madison-Hotels-Sassafras-Cabin-At-Lost-Trails.h117840022.Hotel-Information)

9.8/10

Exceptional

(7 reviews)

"The amenities were in excellent condition and great layout of the property. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Ed S.

CA $120

CA $216 total

includes taxes & fees

Mar 16 - Mar 17

[](https://www.expedia.ca/Madison-Hotels-Sassafras-Cabin-At-Lost-Trails.h117840022.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/96000000/95870000/95861300/95861212/eb3ac305.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, fireplace, DVD player](https://images.trvl-media.com/lodging/96000000/95870000/95861300/95861212/a895cd40.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, fireplace, DVD player](https://images.trvl-media.com/lodging/96000000/95870000/95861300/95861212/1044ee11.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/96000000/95870000/95861300/95861212/ca6519f7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Madison

[](https://www.expedia.ca/Madison-Hotels-5-Minutes-From-Downtown-Madison.h95861212.Hotel-Information)

10/10

Exceptional

(28 reviews)

"This is a fantastic property with attentive hosts! Super easy from start to finish. Clean and homey accommodations. We would definitely choose to stay here again!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Laura P.

CA $136

CA $295 total

includes taxes & fees

Mar 15 - Mar 16

[](https://www.expedia.ca/Madison-Hotels-5-Minutes-From-Downtown-Madison.h95861212.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/123000000/122760000/122751500/122751483/11029ec6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/123000000/122760000/122751500/122751483/6d22fd76.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/123000000/122760000/122751500/122751483/w1018h1009x34y0-6c638f7e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Miscellaneous](https://images.trvl-media.com/lodging/123000000/122760000/122751500/122751483/f3088b94.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cottage in Madison

[](https://www.expedia.ca/Madison-Hotels-Cute-CottagePet-FriendlyCleanTrails-Nature-And-Historic-Madison.h122751483.Hotel-Information)

8.8/10

Excellent

(3 reviews)

"The host was communicative! The space was clean:) Our pups were cozy! The host sent recommendations as well! Thanks, Laurel! "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Meghan B.

CA $121

CA $233 total

includes taxes & fees

Mar 15 - Mar 16

[](https://www.expedia.ca/Madison-Hotels-Cute-CottagePet-FriendlyCleanTrails-Nature-And-Historic-Madison.h122751483.Hotel-Information)

![Private kitchen](https://images.trvl-media.com/lodging/120000000/119720000/119711700/119711645/f4faebb0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, WiFi](https://images.trvl-media.com/lodging/120000000/119720000/119711700/119711645/c63e60d8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/120000000/119720000/119711700/119711645/141012ba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/120000000/119720000/119711700/119711645/w2096h1179x230y0-667550a6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Versailles

[](https://www.expedia.ca/Versailles-Hotels-Charming-New-Tiny-House-Friendship-IN.h119711645.Hotel-Information)

CA $120

CA $263 total

includes taxes & fees

Mar 23 - Mar 24

[](https://www.expedia.ca/Versailles-Hotels-Charming-New-Tiny-House-Friendship-IN.h119711645.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/118000000/117850000/117840100/117840024/897874f5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/118000000/117850000/117840100/117840024/374ba0ee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/118000000/117850000/117840100/117840024/c52282e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/118000000/117850000/117840100/117840024/4daae9ad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cabin in Madison Township

[](https://www.expedia.ca/Madison-Hotels-Mulberry-Cabin-At-Lost-Trails.h117840024.Hotel-Information)

10/10

Exceptional

(1 review)

"Mulberry Cabin at Lost Trails was great! The cabin was cozy and felt pretty private (even though the other cabins are within view). The bed was super comfy, and they did a great job making sure the cabin had everything one might need on a trip away from home. It was also very close to all things Madison, so it felt very convenient. We would definitely stay there again!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Emily I.

CA $147

CA $247 total

includes taxes & fees

Mar 16 - Mar 17

[](https://www.expedia.ca/Madison-Hotels-Mulberry-Cabin-At-Lost-Trails.h117840024.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/110000000/109530000/109527800/109527752/0aff7c9c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, video games, foosball, books](https://images.trvl-media.com/lodging/110000000/109530000/109527800/109527752/b773dc60.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/110000000/109530000/109527800/109527752/39687320.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/110000000/109530000/109527800/109527752/43e11a3d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Warsaw

[](https://www.expedia.ca/Warsaw-Hotels-Waterfront-Cabin-W-A-View-Large-Family-Retreat-Pet-Friendly.h109527752.Hotel-Information)

8.8/10

Excellent

(8 reviews)

"The area is very quiet with plenty of space to stretch out. Quiet little town with friendly people. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Karen C.

CA $168

CA $518 total

includes taxes & fees

Mar 12 - Mar 13

[](https://www.expedia.ca/Warsaw-Hotels-Waterfront-Cabin-W-A-View-Large-Family-Retreat-Pet-Friendly.h109527752.Hotel-Information)

![Dining](https://images.trvl-media.com/lodging/89000000/88260000/88253400/88253382/8164c41b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/89000000/88260000/88253400/88253382/7e07383d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![4 bedrooms, iron/ironing board, travel crib, free WiFi](https://images.trvl-media.com/lodging/89000000/88260000/88253400/88253382/14b5564f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/89000000/88260000/88253400/88253382/b33016a0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Aurora

[](https://www.expedia.ca/Aurora-Hotels-Riverview-Retreat-Riverviews-Near-Ski-SlopesCreation-MuseumArkZooCincinnati.h88253382.Hotel-Information)

10/10

Exceptional

(55 reviews)

"We had a great visit— thank you!!!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Amy D.

CA $280

CA $703 total

includes taxes & fees

Mar 23 - Mar 24

[](https://www.expedia.ca/Aurora-Hotels-Riverview-Retreat-Riverviews-Near-Ski-SlopesCreation-MuseumArkZooCincinnati.h88253382.Hotel-Information)

![Smart TV](https://images.trvl-media.com/lodging/106000000/105110000/105105600/105105513/bf33beba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/106000000/105110000/105105600/105105513/aab5f477.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/106000000/105110000/105105600/105105513/c7ba1628.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/106000000/105110000/105105600/105105513/720ba05a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Madison

[](https://www.expedia.ca/Madison-Hotels-Glendas-Overlookeverything-You-Need-To-Make-Visiting-Madison-A-Great-Getaway.h105105513.Hotel-Information)

9.8/10

Exceptional

(56 reviews)

"Nice friendly town and eating places"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Paul P.

CA $170

CA $339 total

includes taxes & fees

Mar 25 - Mar 26

[](https://www.expedia.ca/Madison-Hotels-Glendas-Overlookeverything-You-Need-To-Make-Visiting-Madison-A-Great-Getaway.h105105513.Hotel-Information)

![Exterior detail](https://images.trvl-media.com/lodging/108000000/107290000/107288400/107288400/c0e5dad1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, WiFi, bed sheets](https://images.trvl-media.com/lodging/108000000/107290000/107288400/107288400/c549b2c4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/108000000/107290000/107288400/107288400/b2b9faaa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/108000000/107290000/107288400/107288400/e5cb0ab4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Madison

[](https://www.expedia.ca/Madison-Hotels-Charolottes-Corner-Overlook.h107288400.Hotel-Information)

8.8/10

Excellent

(10 reviews)

"Very easy check in and nice location. Very comfortable stay. "

![United Kingdom](https://a.travel-assets.com/egds/marks/flags/uk.svg)

Michael S.

CA $125

CA $205 total

includes taxes & fees

Mar 12 - Mar 13

[](https://www.expedia.ca/Madison-Hotels-Charolottes-Corner-Overlook.h107288400.Hotel-Information)

![Exterior detail](https://images.trvl-media.com/lodging/112000000/111160000/111151300/111151245/cf725d26.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/112000000/111160000/111151300/111151245/a2f1e9b1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/112000000/111160000/111151300/111151245/681d3bc1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, fireplace](https://images.trvl-media.com/lodging/112000000/111160000/111151300/111151245/368b6b52.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cabin in Madison

[](https://www.expedia.ca/Madison-Hotels-Rustic-Cabin-At-Lost-Trails.h111151245.Hotel-Information)

10/10

Exceptional

(21 reviews)

"The Rustic Cabin was perfect for our quick visit to the Madison area. The place was comfortable and inviting and tucked away ensuring a quiet and relaxing stay."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Rachel L.

CA $122

CA $219 total

includes taxes & fees

Mar 17 - Mar 18

[](https://www.expedia.ca/Madison-Hotels-Rustic-Cabin-At-Lost-Trails.h111151245.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/92000000/91880000/91872200/91872159/c68fa647.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/92000000/91880000/91872200/91872159/562e1144.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/92000000/91880000/91872200/91872159/ea021f0f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/92000000/91880000/91872200/91872159/00284b98.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cabin in Madison

[](https://www.expedia.ca/Madison-Hotels-Peaceful-Cozy-Cabin-10-Minutes-From-Historic-Downtown-Madison.h91872159.Hotel-Information)

9.6/10

Exceptional

(21 reviews)

"My wife and I enjoyed our stay here while checking out Madison. Great location, nicely decorated. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Justin L.

CA $244

CA $394 total

includes taxes & fees

Mar 22 - Mar 23

[](https://www.expedia.ca/Madison-Hotels-Peaceful-Cozy-Cabin-10-Minutes-From-Historic-Downtown-Madison.h91872159.Hotel-Information)

![Smart TV](https://images.trvl-media.com/lodging/114000000/113730000/113727100/113727046/ad5d5be4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/114000000/113730000/113727100/113727046/7af63ee5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/114000000/113730000/113727100/113727046/20c83a91.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/114000000/113730000/113727100/113727046/a175c776.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Madison

[](https://www.expedia.ca/Madison-Hotels-The-Main-St-Oasis-Heart-Of-Downtown-Madison-Steps-From-Shopping-Dining.h113727046.Hotel-Information)

10/10

Exceptional

(25 reviews)

"Always a wonderful place to stay!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Leann L.

CA $145

CA $289 total

includes taxes & fees

Mar 15 - Mar 16

[](https://www.expedia.ca/Madison-Hotels-The-Main-St-Oasis-Heart-Of-Downtown-Madison-Steps-From-Shopping-Dining.h113727046.Hotel-Information)

![Pool](https://images.trvl-media.com/lodging/67000000/66450000/66446500/66446465/7c0a4c35.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/67000000/66450000/66446500/66446465/67835d54.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/67000000/66450000/66446500/66446465/865c66bf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/67000000/66450000/66446500/66446465/b2235b91.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Madison

[](https://www.expedia.ca/Madison-Hotels-209-Kings.h66446465.Hotel-Information)

10/10

Exceptional

(63 reviews)

"Great house, great location and the host was very responsive! I would definitely recommend this place. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Lisa C.

CA $273

CA $596 total

includes taxes & fees

Mar 15 - Mar 16

[](https://www.expedia.ca/Madison-Hotels-209-Kings.h66446465.Hotel-Information)

![Pool](https://images.trvl-media.com/lodging/82000000/81010000/81001800/81001761/1b2d2f92.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/82000000/81010000/81001800/81001761/758cfbb8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/82000000/81010000/81001800/81001761/590dcf14.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/82000000/81010000/81001800/81001761/007e0a65.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Madison

[](https://www.expedia.ca/Madison-Hotels-Generals-Quarters.h81001761.Hotel-Information)

10/10

Exceptional

(38 reviews)

"Great Amenities! The layout was perfect and the house was well stocked. Kitchen and bathrooms had everything we needed. Great location. Minutes away from restaurants and shops. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Michele D.

CA $257

CA $567 total

includes taxes & fees

Mar 16 - Mar 17

[](https://www.expedia.ca/Madison-Hotels-Generals-Quarters.h81001761.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/102000000/101980000/101970300/101970271/4653afac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/102000000/101980000/101970300/101970271/f45754fe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, books](https://images.trvl-media.com/lodging/102000000/101980000/101970300/101970271/f2aa2ca5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, books](https://images.trvl-media.com/lodging/102000000/101980000/101970300/101970271/7516ac33.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Madison

[](https://www.expedia.ca/Madison-Hotels-Madison-Manor-II-HotTub-Walk-To-Downtown.h101970271.Hotel-Information)

10/10

Exceptional

(15 reviews)

"Great location and the host thought of everything to stock the house with."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Kinni L.

CA $211

CA $546 total

includes taxes & fees

Mar 30 - Mar 31

[](https://www.expedia.ca/Madison-Hotels-Madison-Manor-II-HotTub-Walk-To-Downtown.h101970271.Hotel-Information)

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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## Find vacation rentals that suit your style

Apartments

[](https://www.expedia.ca/Hotel-Search?destination=Bennington%2C+Indiana%2C+United+States+of+America&regionId=553248635975849202&latLong=38.858948%2C-85.140509&adults=2&startDate=2026-06-09&d1=2026-06-09&endDate=2026-06-12&d2=2026-06-12&lodging=APARTMENT)

Cabins

[](https://www.expedia.ca/Hotel-Search?destination=Bennington%2C+Indiana%2C+United+States+of+America&regionId=553248635975849202&latLong=38.858948%2C-85.140509&adults=2&startDate=2026-06-09&d1=2026-06-09&endDate=2026-06-12&d2=2026-06-12&lodging=CABIN)

Private vacation homes

[](https://www.expedia.ca/Hotel-Search?destination=Bennington%2C+Indiana%2C+United+States+of+America&regionId=553248635975849202&latLong=38.858948%2C-85.140509&adults=2&startDate=2026-06-09&d1=2026-06-09&endDate=2026-06-12&d2=2026-06-12&lodging=VACATION_HOME)

Cottages

[](https://www.expedia.ca/Hotel-Search?destination=Bennington%2C+Indiana%2C+United+States+of+America&regionId=553248635975849202&latLong=38.858948%2C-85.140509&adults=2&startDate=2026-06-09&d1=2026-06-09&endDate=2026-06-12&d2=2026-06-12&lodging=COTTAGE)

Chalets

[](https://www.expedia.ca/Hotel-Search?destination=Bennington%2C+Indiana%2C+United+States+of+America&regionId=553248635975849202&latLong=38.858948%2C-85.140509&adults=2&startDate=2026-06-09&d1=2026-06-09&endDate=2026-06-12&d2=2026-06-12&lodging=CHALET)

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## Top Bennington Hotel Reviews

![Best Way Inn Madison](https://images.trvl-media.com/lodging/1000000/10000/8000/7911/30741410_y.jpg)

### Best Way Inn Madison

10/10 Excellent

"Great stay, great staff and very helpful. I stayed there after a surgery so i could be close to my husband's work for the first few days and the staff at bestway were amazing!! "

[](https://expedia.ca/Madison-Hotels-Best-Way-Inn-Madison.h7911.Hotel-Information)

![Belterra Casino Resort](https://images.trvl-media.com/lodging/2000000/1160000/1152900/1152807/04047b8f_y.jpg)

### Belterra Casino Resort

10/10 Excellent

"The room (as always), clean and COMFY. Pleasant front desk @ arrival, maintenance (not needed),and all staff. NEVER an issue whenever we stay ⭐⭐⭐⭐⭐"

[](https://expedia.ca/Madison-Hotels-Belterra-Casino-Resort.h1152807.Hotel-Information)

![Quality Inn Carrollton](https://images.trvl-media.com/lodging/1000000/20000/12100/12064/f2f43231_y.jpg)

### Quality Inn Carrollton

10/10 Excellent

"Great."

[](https://expedia.ca/Carrollton-Hotels-Quality-Inn-Carrollton.h12064.Hotel-Information)

![Glenda’s Overlook..everything you need to make visiting Madison a great getaway!](https://images.trvl-media.com/lodging/106000000/105110000/105105600/105105513/bf33beba_y.jpg)

### Glenda’s Overlook..everything you need to make visiting Madison a great getaway!

10/10 Excellent

"Loved the House! Very clean and well decorated. Host was very nice and very easy to communicate with. Definitely recommend! "

[](https://expedia.ca/Madison-Hotels-Glendas-Overlookeverything-You-Need-To-Make-Visiting-Madison-A-Great-Getaway.h105105513.Hotel-Information)

![Rising Star Casino Resort](https://images.trvl-media.com/lodging/1000000/160000/151200/151163/8fd638a0_y.jpg)

### Rising Star Casino Resort

2/10 Terrible

"Terrible "

[](https://expedia.ca/Lawrenceburg-Hotels-Rising-Star-Casino-Resort.h151163.Hotel-Information)

![The Chandler Hotel](https://images.trvl-media.com/lodging/94000000/93090000/93082900/93082881/baa85c95_y.jpg)

### The Chandler Hotel

10/10 Excellent

"Room was beautiful. "

[](https://expedia.ca/Madison-Hotels-The-Chandler-Hotel.h93082881.Hotel-Information)

![Ramada by Wyndham Sparta/At Speedway](https://images.trvl-media.com/lodging/1000000/980000/972800/972772/3310105f_y.jpg)

### Ramada by Wyndham Sparta/At Speedway

4/10 Poor

"I was suppose to had a hot tub it didnt"

[](https://expedia.ca/Carrollton-Hotels-Ramada-By-Wyndham-SpartaAt-Speedway.h972772.Hotel-Information)

![Fairway Inn Florence](https://images.trvl-media.com/lodging/106000000/105640000/105639100/105639028/d947c4ca_y.jpg)

### Fairway Inn Florence

10/10 Excellent

"Good flights "

[](https://expedia.ca/Florence-Hotels-Fairway-Inn-Florence.h105639028.Hotel-Information)

![Rustic cabin just outside of Madison!](https://images.trvl-media.com/lodging/91000000/90910000/90904900/90904820/cfc50150_y.jpg)

### Rustic cabin just outside of Madison!

10/10 Excellent

"Our crew of 10 loved staying in this cozy cabin for the weekend. The listing doesn't do justice to the beautiful creek that sits just in front of the house. We were concerned about having to cross the creek, but it ended up being mostly a very wet driveway at that point fortunately. So many little amenities to make it feel like home! We are hoping to stay here again in the future."

[](https://expedia.ca/Madison-Hotels-Rustic-Cabin-Across-The-Creek.h90904820.Hotel-Information)

## Find out more about Bennington

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation 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 or room. 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 vacation just got upgraded.  
  
As much as you love your short-term rental, it’s always good to get out and explore to soak up . 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 . Seeing all the best attractions is bound to make you fall in love with Bennington. Who knows, you may even be tempted to extend your vacation rental 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 vacation 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 short-term rentals, that won’t be hard to do.   

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- [Vacation Homes in Bennington ](https://expedia.ca/Bennington-Private-Vacation-Homes.d553248635975849202-aaPrivateVacationHomes.Travel-Guide-Accommodation)
- [Apartments in Bennington ](https://expedia.ca/Bennington-Apartments.d553248635975849202-aaApartments.Travel-Guide-Accommodation)
- [Cabin Rentals in Bennington ](https://expedia.ca/Bennington-Cabins.d553248635975849202-aaCabins.Travel-Guide-Accommodation)
- [Cottages in Bennington ](https://expedia.ca/Bennington-Cottages.d553248635975849202-aaCottages.Travel-Guide-Accommodation)
- [Motels in Bennington ](https://expedia.ca/Bennington-Motels.d553248635975849202-aaMotels.Travel-Guide-Accommodation)
- [Guest Houses in Bennington ](https://expedia.ca/Bennington-Guest-Houses.d553248635975849202-aaGuestHouses.Travel-Guide-Accommodation)
- [Chalets in Bennington ](https://expedia.ca/Bennington-Chalets.d553248635975849202-aaChalets.Travel-Guide-Accommodation)
- [Inns in Bennington ](https://expedia.ca/Bennington-Inns.d553248635975849202-aaInns.Travel-Guide-Accommodation)
- [B&B in Bennington ](https://expedia.ca/Bennington-Bed-And-Breakfast.d553248635975849202-aaBedAndBreakfast.Travel-Guide-Accommodation)

## Frequently asked questions

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