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Rupert Vacation Rentals

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Rupert vacation homes in the setting of Vermont's natural beauty

Rupert occupies a beautiful spot in Bennington County, known for its rustic landscapes and fruit orchards. There are many vacation rentals in the area, such as farmhouses set in picturesque locations in the Green Mountains area. A stay at Rupert will give you opportunities to get closely acquainted with nature, taste some wonderful local cuisine, and enjoy activities like golfing and fishing.

Save up to 59%

Best Vacation Home Deals in Rupert

Sep 6 - Sep 13

-33%

~~$300~~

$200 per night

Cabin ∙ 7 guests ∙ 2 bedrooms

Entire Cabin in West Pawlet with Yard & Grill + Beautiful Views

4.9

"Excellent" (191 ratings)

Rupert, Bennington County, Vermont, United States

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Nov 25 - Dec 2

-59%

~~$955~~

$395 per night

House ∙ 8 guests ∙ 3 bedrooms

Vacation Home in Sunderland with Grill + Close-Up Views

5.0

"Excellent" (127 ratings)

Rupert, Bennington County, Vermont, United States

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Apr 1 - Apr 8

-33%

~~$343~~

$229 per night

House ∙ 8 guests ∙ 4 bedrooms

Vacation Home in Pawlet with Green Garden + Panoramic Views

5.0

"Excellent" (2 ratings)

Rupert, Bennington County, Vermont, United States

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Book the ideal vacation home for as little as $103 per night by searching among the 15 options available in Rupert. Every one of the vacation rentals from our partner websites are directly compared by the search engine , allowing you to save up to 58%.

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Top-Rated Rentals and Accommodations in Rupert

Nov 25 - Dec 2

$340 per night

House ∙ 4 guests ∙ 2 bedrooms

Entire House in Rupert with Grill & Yard

5.0

"Excellent" (194 ratings)

Rupert, Bennington County, Vermont, United States

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Jul 15 - Jul 22

$176 per night

Cabin ∙ 8 guests ∙ 4 bedrooms

Cabin in West Rupert with Yard & Grill

5.0

"Excellent" (84 ratings)

Rupert, Bennington County, Vermont, United States

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Apr 1 - Apr 8

-38%

~~$804~~

$502 per night

House ∙ 10 guests ∙ 4 bedrooms

Vacation Home in West Rupert with Grill & Yard

5.0

"Excellent" (43 ratings)

Rupert, Bennington County, Vermont, United States

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Recommended Vacation Rentals in Rupert

Find your perfect vacation rental in Rupert: from $103 per night

Apr 15 - Apr 22

$361 per night

House ∙ 9 guests ∙ 4 bedrooms

Family Friendly House in Manchester Center with Yard, Grill & Pool

5.0

"Excellent" (116 ratings)

Rupert, Bennington County, Vermont, United States

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Jun 10 - Jun 17

$173 per night

Cottage ∙ 4 guests ∙ 3 bedrooms

Cottage in Manchester Center with Yard

4.8

"Excellent" (85 ratings)

Rupert, Bennington County, Vermont, United States

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Apr 15 - Apr 22

$103 per night

Apartment ∙ 3 guests ∙ 2 bedrooms

Apartment in Salem with Yard & Grill

5.0

"Excellent" (10 ratings)

Rupert, Bennington County, Vermont, United States

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Apr 15 - Apr 22

-61%

~~$522~~

$206 per night

House ∙ 2 guests ∙ 1 bedroom

Vacation Home in Manchester Center with Outdoor Fireplace + Mountain Views

5.0

"Excellent" (52 ratings)

Rupert, Bennington County, Vermont, United States

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Apr 15 - Apr 22

$442 per night

House ∙ 14 guests ∙ 5 bedrooms

Vacation Home in Manchester Center with Yard & Grill + Mountain Views

4.9

"Excellent" (67 ratings)

Rupert, Bennington County, Vermont, United States

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May 20 - May 27

$251 per night

House ∙ 8 guests ∙ 3 bedrooms

House in Winhall

5.0

"Excellent" (18 ratings)

Rupert, Bennington County, Vermont, United States

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Dec 2 - Dec 9

-45%

~~$903~~

$513 per night

House ∙ 9 guests ∙ 4 bedrooms

Vacation Home in Dorset with Yard & Grill + Mountain Views

Rupert, Bennington County, Vermont, United States

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Apr 15 - Apr 22

$243 per night

Cabin ∙ 10 guests ∙ 5 bedrooms

Cabin in Sandgate with Grill, Yard & Pool

5.0

"Excellent" (39 ratings)

Rupert, Bennington County, Vermont, United States

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Nov 4 - Nov 11

-18%

~~$356~~

$293 per night

House ∙ 8 guests ∙ 4 bedrooms

House in Dorset with Yard & Grill

5.0

"Excellent" (48 ratings)

Rupert, Bennington County, Vermont, United States

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Find Fantastic yet Inexpensive Offers

Budget-friendly Vacation Rentals in Rupert

Mar 23 - Mar 30

-44%

~~$752~~

$420 per night

Villa ∙ 15 guests ∙ 6 bedrooms

Wonderful Villa in West Rupert with Wood-Burning Fireplace + Mountain Views

4.3

"Very good" (34 ratings)

Rupert, Bennington County, Vermont, United States

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Evolve

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Apr 15 - Apr 22

$241 per night

House ∙ 8 guests ∙ 4 bedrooms

House in West Rupert with Yard & Patio

Rupert, Bennington County, Vermont, United States

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FlipKey

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Apr 8 - Apr 15

-29%

~~$703~~

$500 per night

House ∙ 10 guests ∙ 4 bedrooms

Entire Vacation Home in West Rupert with Grill & Yard

4.9

"Excellent" (27 ratings)

Rupert, Bennington County, Vermont, United States

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Vacation Houses With Pools

Make a splash on your next vacation! Over 45% of in Rupert vacation rentals have a swimming pool.

Apr 8 - Apr 15

$360 per night

House ∙ 9 guests ∙ 4 bedrooms

Family Friendly House in Manchester Center with Yard, Grill & Pool

5.0

"Excellent" (116 ratings)

Rupert, Bennington County, Vermont, United States

Pool

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Apr 15 - Apr 22

$243 per night

Cabin ∙ 10 guests ∙ 5 bedrooms

Cabin in Sandgate with Grill, Yard & Pool

5.0

"Excellent" (39 ratings)

Rupert, Bennington County, Vermont, United States

Pool

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Mar 9 - Mar 16

$505 per night

Farmhouse ∙ 4 guests ∙ 5 bedrooms

Farm in Salem with Yard, Pool & Grill + Gorgeous Views

5.0

"Excellent" (69 ratings)

Rupert, Bennington County, Vermont, United States

Pool

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Dog-Friendly Vacation Rentals

Bring Fido on your next trip and book a stay in one of these pet-friendly rentals in Rupert!

Jun 10 - Jun 17

$300 per night

Cabin ∙ 8 guests ∙ 2 bedrooms

Cabin in North Hebron with Grill & Yard + Degree Views

5.0

"Excellent" (9 ratings)

Rupert, Bennington County, Vermont, United States

Pet-friendly

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Mar 26 - Apr 2

$495 per night

House ∙ 11 guests ∙ 5 bedrooms

Vacation Home in Dorset with Yard & Grill

5.0

"Excellent" (167 ratings)

Rupert, Bennington County, Vermont, United States

Pet-friendly

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Sep 6 - Sep 13

-33%

~~$301~~

$200 per night

Cabin ∙ 7 guests ∙ 2 bedrooms

Entire Cabin in West Pawlet with Yard & Grill + Beautiful Views

4.9

"Excellent" (191 ratings)

Rupert, Bennington County, Vermont, United States

Pet-friendly

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Best vacation rentals with a balcony

Looking for a home with a balcony? Check out these vacation homes in Rupert with their own private patios and balconies.

Apr 1 - Apr 8

-33%

~~$343~~

$229 per night

House ∙ 8 guests ∙ 4 bedrooms

Vacation Home in Pawlet with Green Garden + Panoramic Views

5.0

"Excellent" (2 ratings)

Rupert, Bennington County, Vermont, United States

Balcony

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Apr 8 - Apr 15

$442 per night

House ∙ 14 guests ∙ 5 bedrooms

Vacation Home in Manchester Center with Yard & Grill + Mountain Views

4.9

"Excellent" (67 ratings)

Rupert, Bennington County, Vermont, United States

Balcony

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Apr 15 - Apr 22

-20%

~~$613~~

$490 per night

House ∙ 11 guests ∙ 5 bedrooms

Vacation Home in Manchester Center with Grill & Yard + Mountain Views

5.0

"Excellent" (104 ratings)

Rupert, Bennington County, Vermont, United States

Balcony

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Popular Rental Amenities in Rupert

Grill (10)
Washer (10)
Fireplace (10)
Internet (10)
Kitchen (10)
TV (10)
Yard (10)
Microwave (10)
No smoking (8)
Pet allowed (7)
Air conditioning (7)
Dishwasher (6)

Use filters to search and find an offer matching your requirements among all of the properties in Rupert. In Rupert, 10 properties include "Grill". So, if you love to grill out, use the Grill filter to compare these rentals. Not as many accommodations in Rupert are available if you need a crib for your baby or if you want a rental providing a crib as "No pets allowed" and "Crib" are not often provided in Rupert.

The Weather in Rupert

- Rainy days

Check out our climate diagram to find the perfect month for your vacation. The highest average temperatures are in the month of July. Conversely, January is the coolest month in Rupert, with temperatures going under 12° The rainiest month is December while the driest month is August.

7-Day Weather Forecast in Rupert

Wed, 22 Mar

44°

30°

Thu, 23 Mar

42°

37°

Fri, 24 Mar

39°

30°

Sat, 25 Mar

30°

Sun, 26 Mar

35°

30°

Mon, 27 Mar

41°

28°

Tue, 28 Mar

32°

30°

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Accommodations for your vacation in Rupert

5 among the 15 listed rentals in Rupert are house rental. They account for more than half of the properties in this destination (50%). Interestingly, specific accommodation type, house rental is $740 a night, with an average area of 234 m². Furthermore, these accommodations are optimal for large groups, as most can accommodate 8 vacationers. If you are searching for another type of accommodation, you can find many other options, such as villa, which are the other very typical type of accommodation in Rupert. These accommodations cost $872 per night on average and have an average size of 371 m².

Where to find the best food in Rupert?

Apple pies and cider

If you are in Vermont, you cannot leave until you have tasted the apples and the dishes made from locally grown apples. Your vacation at Rupert will familiarize you with apple cider, apple pie, as well as baked items made from apples. The Dutton Berry Farmstands in Manchester is a good place to visit if you love orchards and apples. Throughout the area, you will come across farms selling dishes made from local produce such as corn, strawberries and squash.

What are the best places to discover the arts and culture of Rupert?

Explore the museums in and around Rupert

The Bennington Museum displays works of craft such as glassware, pottery, and woodcrafts. The museum is located inside a decommissioned train station, and close to the downtown city area.

Another attraction is the Bennington Center for the Arts, with exhibitions of paintings by local and American artists, as well as a historical museum of covered bridges, a typical architectural feature of the area.

One of the notable attractions of the city lies in nearby Manchester where you can visit the home of the Abraham Lincoln's family.

Where are the unique attractions in Rupert?

Golf courses in Rupert

Rupert and surrounding areas have plenty of golf courses. You can play a round at the public golf courses or choose memberships at the private facilities.

The Mount Snow Country Club has been helping golfers perfect their skills and enjoy the game since the 1970s. You might also like to try your hand at the sport in the Ekwanok Country Club.

Information about vacation rentals in Rupert

💳 Possible discounts	up to 58%
🌙 Nightly prices starting at	$103
⭐ Popular amenities	Grill, Washing machine and Fireplace
🐾 Pet friendly accommodations	8 properties
🏊 Vacation rentals with pools	5 properties

Frequently Asked Questions

What is the average nightly price for a vacation rental in Rupert?

The nightly price of accommodations in Rupert starts at $103. If you would like to stay in a house rental, the average price is $740 per night. A villa Rupert will cost on average $872 per night.

How many vacation rentals are available to book in Rupert?

There are 15 vacation homes from 5 providers in Rupert.

What amenities are most popular for vacation rentals in Rupert?

Three most popular amenities for vacation home rentals in Rupert include accommodations with: Grill, Washing machine, and Fireplace.

How many vacation homes with a pool are in Rupert?

Browse 5 vacation rentals available in Rupert for renting.

Are pets allowed in vacation homes in Rupert?

Finding a rental in Rupert that allows pets is definitely possible, with 8 pet-friendly available.

When is it better to travel to Rupert?

If booking a vacation rental in Rupert, consider that rainy season is typically in December or January, with August often being the driest.

We list offers from thousands of providers, including:

max. Min. 32° 12° 15 days 15	max. Min. 34° 12° 13 days 13	max. Min. 43° 21° 13 days 13	max. Min. 57° 34° 12 days 12	max. Min. 72° 48° 14 days 14	max. Min. 77° 54° 15 days 15	max. Min. 82° 59° 14 days 14	max. Min. 81° 57° 11 days 11	max. Min. 73° 48° 11 days 11	max. Min. 61° 39° 14 days 14	max. Min. 48° 28° 11 days 11	max. Min. 37° 23° 19 days 19
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Rupert Vacation Rentals

Choose the perfect vacation rental

Rupert vacation homes in the setting of Vermont's natural beauty

Best Vacation Home Deals in Rupert

Top-Rated Rentals and Accommodations in Rupert

Recommended Vacation Rentals in Rupert

Budget-friendly Vacation Rentals in Rupert

Vacation Houses With Pools

Dog-Friendly Vacation Rentals

Best vacation rentals with a balcony

Popular Rental Amenities in Rupert

The Weather in Rupert

7-Day Weather Forecast in Rupert

Accommodations for your vacation in Rupert

Apple pies and cider

Explore the museums in and around Rupert

Golf courses in Rupert

Information about vacation rentals in Rupert

Frequently Asked Questions

What is the average nightly price for a vacation rental in Rupert?

How many vacation rentals are available to book in Rupert?

What amenities are most popular for vacation rentals in Rupert?

How many vacation homes with a pool are in Rupert?

Are pets allowed in vacation homes in Rupert?

When is it better to travel to Rupert?

Vacation Destinations Near Rupert

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