Bennington Vacation Rentals

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Check prices for these dates

In two weeks
Jan 9 - Jan 11
In two months
Feb 20 - Feb 22
In three months
Mar 20 - Mar 22
In four months
Apr 17 - Apr 19

Our top choices for Bennington vacation rentals

Fridge, microwave, oven, stovetop
The Blue Door Place

The Blue Door Place

The Blue Door Place
Florence
9.6 out of 10, Exceptional, (19)
"Perfect spot "
United States
Damon G.
The price is ￥14,736
￥27,858 total
includes taxes & fees
Dec 27 - Dec 28
The Blue Door Place
Exterior detail
Cute Cottage/Pet Friendly/Clean/Trails/ Nature and Historic Madison

Cute Cottage/Pet Friendly/Clean/Trails/ Nature and Historic Madison

Cute Cottage/Pet Friendly/Clean/Trails/ Nature and Historic Madison
2.0 star property
Madison
The price is ￥12,350
￥24,962 total
includes taxes & fees
Dec 29 - Dec 30
Cute Cottage/Pet Friendly/Clean/Trails/ Nature and Historic Madison
Exterior
Lake House with Private Dock - Ark Encounter & Creation Museum Warsaw Getaway

Lake House with Private Dock - Ark Encounter & Creation Museum Warsaw Getaway

Lake House with Private Dock - Ark Encounter & Creation Museum Warsaw Getaway
Sparta
9.8 out of 10, Exceptional, (9)
"Wonderful vacation home. Very clean, great host that was very helpful. "
United States
Ashley C.
The price is ￥24,561
￥57,968 total
includes taxes & fees
Dec 27 - Dec 28
Lake House with Private Dock - Ark Encounter & Creation Museum Warsaw Getaway
TV, fireplace, DVD player
Cabin on the Ridge Su

Cabin on the Ridge Su

Cabin on the Ridge Su
Madison
10.0 out of 10, Exceptional, (15)
"Peaceful relaxing stay. Will go back."
United States
Wendy P.
The price is ￥18,557
￥37,660 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Cabin on the Ridge Su
Exterior
Cabin on the Ridge: The Sequel

Cabin on the Ridge: The Sequel

Cabin on the Ridge: The Sequel
Madison
10.0 out of 10, Exceptional, (17)
"Our stay was amazing! Loved this cozy cabin in the woods! "
United States
Alison F.
The price is ￥18,557
￥34,611 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Cabin on the Ridge: The Sequel
Fridge, microwave, oven, stovetop
Glenda’s Overlook..everything you need to make visiting Madison a great getaway!

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

Glenda’s Overlook..everything you need to make visiting Madison a great getaway!
Madison
9.8 out of 10, Exceptional, (53)
"It is a nice place. We were able to walk to the river and main street fairly easy. "
United States
Paul W.
The price is ￥16,374
￥34,970 total
includes taxes & fees
Dec 28 - Dec 29
Glenda’s Overlook..everything you need to make visiting Madison a great getaway!
Exterior
The Artist’s A-Frame

The Artist’s A-Frame

The Artist’s A-Frame
Madison
10.0 out of 10, Exceptional, (25)
"Wonderful place to stay "
United States
Susan H.
The price is ￥17,309
￥35,149 total
includes taxes & fees
Dec 28 - Dec 29
The Artist’s A-Frame
1 bedroom, WiFi
Charming new tiny house-Friendship IN

Charming new tiny house-Friendship IN

Charming new tiny house-Friendship IN
Versailles
The price is ￥13,723
￥30,215 total
includes taxes & fees
Dec 29 - Dec 30
Charming new tiny house-Friendship IN
Fridge, microwave, oven, stovetop
Peaceful Cozy Cabin 10 minutes from Historic downtown Madison

Peaceful Cozy Cabin 10 minutes from Historic downtown Madison

Peaceful Cozy Cabin 10 minutes from Historic downtown Madison
Madison
9.6 out of 10, Exceptional, (20)
"My wife and I enjoyed our stay here while checking out Madison. Great location, nicely decorated. "
United States
Justin L.
The price is ￥28,069
￥45,191 total
includes taxes & fees
Jan 7 - Jan 8, 2026
Peaceful Cozy Cabin 10 minutes from Historic downtown Madison
Property grounds
The Madison Inn, Hometown on Main Street, Suite 102, Charlottes corner overlook, Suite 102

The Madison Inn, Hometown on Main Street, Suite 102, Charlottes corner overlook, Suite 102

The Madison Inn, Hometown on Main Street, Suite 102, Charlottes corner overlook, Suite 102
Madison
9.8 out of 10, Exceptional, (10)
"Super comfortable, clean little apartment in a quiet area off the main strip. We loved out stay!"
United States
Courtney G.
The price is ￥11,228
￥19,493 total
includes taxes & fees
Jan 4 - Jan 5, 2026
The Madison Inn, Hometown on Main Street, Suite 102, Charlottes corner overlook, Suite 102
Property grounds
Waterfront Cabin w/ A View! Large Family Retreat + Pet-Friendly

Waterfront Cabin w/ A View! Large Family Retreat + Pet-Friendly

Waterfront Cabin w/ A View! Large Family Retreat + Pet-Friendly
Warsaw
8.8 out of 10, Excellent, (8)
"The area is very quiet with plenty of space to stretch out. Quiet little town with friendly people. "
United States
Karen C.
The price is ￥30,494
￥72,813 total
includes taxes & fees
Dec 27 - Dec 28
Waterfront Cabin w/ A View! Large Family Retreat + Pet-Friendly
Smart TV
The Main St. Oasis - Heart of Downtown Madison - Steps from Shopping & Dining

The Main St. Oasis - Heart of Downtown Madison - Steps from Shopping & Dining

The Main St. Oasis - Heart of Downtown Madison - Steps from Shopping & Dining
Madison
10.0 out of 10, Exceptional, (21)
"Great downtown location in a peaceful little town. "
United States
Megan M.
The price is ￥18,557
￥35,687 total
includes taxes & fees
Jan 4 - Jan 5, 2026
The Main St. Oasis - Heart of Downtown Madison - Steps from Shopping & Dining
Outdoor dining
Riverside Storybook Cottage

Riverside Storybook Cottage

Riverside Storybook Cottage
Aurora
10.0 out of 10, Exceptional, (2)
"Great time and place!!!"
United States
Brad T.
The price is ￥32,100
￥68,312 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Riverside Storybook Cottage
Outdoor dining
Enchanting Historic Spa Loft. 3rd story private deck/jetted tub/Heart of Madison

Enchanting Historic Spa Loft. 3rd story private deck/jetted tub/Heart of Madison

Enchanting Historic Spa Loft. 3rd story private deck/jetted tub/Heart of Madison
2.0 star property
Madison
The price is ￥11,103
￥23,528 total
includes taxes & fees
Jan 18 - Jan 19, 2026
Enchanting Historic Spa Loft. 3rd story private deck/jetted tub/Heart of Madison
Terrace/patio
Riverview Home Near Creation Museum/Ark/Ski/Bikes/Cincinnati/Hot Tub-Sleeps 11

Riverview Home Near Creation Museum/Ark/Ski/Bikes/Cincinnati/Hot Tub-Sleeps 11

Riverview Home Near Creation Museum/Ark/Ski/Bikes/Cincinnati/Hot Tub-Sleeps 11
Aurora
10.0 out of 10, Exceptional, (52)
"We had a great visit— thank you!!!"
United States
Amy D.
The price is ￥29,858
￥77,103 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Riverview Home Near Creation Museum/Ark/Ski/Bikes/Cincinnati/Hot Tub-Sleeps 11
Interior
#207 King Suites, River Views, Deck, Downtown

#207 King Suites, River Views, Deck, Downtown

#207 King Suites, River Views, Deck, Downtown
Madison
10.0 out of 10, Exceptional, (37)
"Wonderful place. Been here a few times. Just perfect with a great balcony and view. "
United States
Patrick L.
The price is ￥29,473
￥65,132 total
includes taxes & fees
Dec 29 - Dec 30
#207 King Suites, River Views, Deck, Downtown
Fridge, microwave, oven, stovetop
"Madison Manor II" by The River: Hot Tub, Patio, FirePit, Grill

"Madison Manor II" by The River: Hot Tub, Patio, FirePit, Grill

"Madison Manor II" by The River: Hot Tub, Patio, FirePit, Grill
Madison
10.0 out of 10, Exceptional, (14)
"Madison Manor II was perfect for our annual girls trip. We were comfortable, location was great, the home was very clean."
United States
Carissa N.
The price is ￥23,703
￥56,131 total
includes taxes & fees
Jan 4 - Jan 5, 2026
"Madison Manor II" by The River: Hot Tub, Patio, FirePit, Grill
Microwave, oven, stovetop, dishwasher
The Main Stay - Steps from Ohio River, Shopping, & Dining on Main St

The Main Stay - Steps from Ohio River, Shopping, & Dining on Main St

The Main Stay - Steps from Ohio River, Shopping, & Dining on Main St
2.0 star property
Madison
The price is ￥18,588
￥65,492 total
includes taxes & fees
Dec 30 - Dec 31
The Main Stay - Steps from Ohio River, Shopping, & Dining on Main St
Fridge, microwave, oven, stovetop
#209 Kings, River View, Deck, Bicentennial Park

#209 Kings, River View, Deck, Bicentennial Park

#209 Kings, River View, Deck, Bicentennial Park
Madison
10.0 out of 10, Exceptional, (62)
"Great house, great location and the host was very responsive! I would definitely recommend this place. "
United States
Lisa C.
The price is ￥33,839
￥71,180 total
includes taxes & fees
Dec 28 - Dec 29
#209 Kings, River View, Deck, Bicentennial Park
Outdoor dining
"Madison Manor I" By the River - Special Dec 6 - Tickets to Christmas Homes Tour

"Madison Manor I" By the River - Special Dec 6 - Tickets to Christmas Homes Tour

"Madison Manor I" By the River - Special Dec 6 - Tickets to Christmas Homes Tour
Madison
9.6 out of 10, Exceptional, (12)
"We thoroughly enjoyed our time! Great place! We would definitely stay there again!"
United States
Howard B.
The price is ￥24,015
￥56,669 total
includes taxes & fees
Jan 4 - Jan 5, 2026
"Madison Manor I" By the River - Special Dec 6 - Tickets to Christmas Homes Tour
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 Bennington Hotel Reviews

Holiday Inn Express Hotel & Suites Madison by IHG

Holiday Inn Express Hotel & Suites Madison by IHG

10/10 Excellent
"Food was hot and enjoyable "
Mark 5-night trip
Posted 5 days ago
Holiday Inn Express Hotel & Suites Madison by IHG

Find out more about Bennington

Search for holiday rentals in Bennington on Expedia! You can easily find your home rentals, villas, holiday apartments in Bennington using one of the methods below:

  • View our selection of featured holiday rentals in Bennington
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Look no further and take a look at our great range of rental properties in Bennington!

Frequently asked questions

Can I find vacation rentals in Bennington?

Yes, we have vacation rentals close to popular local attractions in Bennington, or you can choose a more remote option if you're looking for a relaxing stay.

What are some of the best vacation home rentals in Bennington?

Riverview Home Near Creation Museum/Ark/Ski/Bikes/Cincinnati/Hot Tub-Sleeps 11: Visitors like this Bennington vacation home rental. It is located on a river and has a balcony, a garden, and a barbecue grill to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Kick off your shoes and enjoy yourself with a selection of games and a hot tub.

What’s there to see and do in Bennington?

Explore the area and family-friendly sights such as Madison Railroad Station Museum, or get out into nature at a spot like General Butler State Resort Park. Belterra Casino and Versailles State Park are a couple of places you'll find in the larger area.

What’s a vacation rental in Bennington like?

A vacation rental is a private property you can book for short or long periods in Bennington. Vacation rentals feature extras such as kitchens and laundry facilities to help you enjoy your stay. If you're concerned about a clean environment, vacation rentals can provide a sense of privacy away from public hotel elevators and bustling concierge desks while still allowing you the enjoyment of travel. You'll also get more space in a vacation rental than in a hotel, which is another reason why a vacation rental is a great option for family trips or small group gatherings.