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Rupert Vacation Rentals

Find 15 available offers from 5 partners
Rupert
Anytime
Guests

Choose the perfect vacation rental

Price per night
Up to $100
$100 - $199
From $200
Accommodation types
Cabin
House
Farmhouse
Distance to center
1 km
2 km
5 km
Rating
4.5+
4+
3.5+

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.

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Best Vacation Home Deals in Rupert

Save up to 52%

Villa Rupert
Nov 25 - Dec 2
-34%
$734
$486 per night
Villa ∙ 15 guests ∙ 6 bedrooms
Villa in West Rupert with Wood-Burning Fireplace + Mountain Views
4.4
Very good (30 ratings)
Rupert, Bennington County, Vermont, United States
Details
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House Rupert
Dec 1 - Dec 8
-52%
$358
$172 per night
House ∙ 8 guests ∙ 4 bedrooms
House in Manchester Center with Wood-Burning Fireplace
5.0
Outstanding
Rupert, Bennington County, Vermont, United States
Details
Vacasa
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Cottage Rupert
Sep 26 - Oct 3
-40%
$175
$106 per night
Cottage ∙ 4 guests ∙ 2 bedrooms
Charming Cottage in Wells with Grill
4.7
Excellent (7 ratings)
Rupert, Bennington County, Vermont, United States
Details
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Book the ideal vacation home for as little as $176 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%.

Top-Rated Rentals and Accommodations in Rupert

Book Vacation Rental Offers with the Highest User Rating

House Rupert
Mar 30 - Apr 6
$340 per night
House ∙ 4 guests ∙ 2 bedrooms
Entire House in Rupert with Grill & Yard
5.0
Outstanding (204 ratings)
Rupert, Bennington County, Vermont, United States
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House Rupert
Apr 13 - Apr 20
$360 per night
House ∙ 10 guests ∙ 5 bedrooms
Vacation Home in Mount Tabor with Yard & Grill
5.0
Outstanding (33 ratings)
Rupert, Bennington County, Vermont, United States
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Apartment Rupert
Jul 6 - Jul 13
$140 per night
Apartment ∙ 3 guests ∙ 1 bedroom
Private Rental Apartment in Manchester Center with Perennial Garden + Open View
5.0
Outstanding (5 ratings)
Rupert, Bennington County, Vermont, United States
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Recommended Vacation Rentals in Rupert

Find your perfect vacation rental in Rupert: from $176 per night

Farmhouse Rupert
Nov 25 - Dec 2
$406 per night
Farmhouse ∙ 6 guests ∙ 3 bedrooms
Wonderful Farm in West Rupert with Grill & Yard
Rupert, Bennington County, Vermont, United States
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Villa Rupert
Dec 2 - Dec 9
-54%
$919
$420 per night
Villa ∙ 15 guests ∙ 6 bedrooms
Wonderful Villa in West Rupert with Wood-Burning Fireplace + Mountain Views
3.8
Good (5 ratings)
Rupert, Bennington County, Vermont, United States
Free cancellation
Details
Evolve
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Cottage Rupert
Oct 28 - Nov 4
-44%
$224
$125 per night
Cottage ∙ 4 guests ∙ 1 bedroom
Cottage in Wells with Grill
Rupert, Bennington County, Vermont, United States
Details
Expedia
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House Rupert
May 18 - May 25
$354 per night
House ∙ 12 guests ∙ 4 bedrooms
Vacation Home in Winhall with Grill + Amazing Views
4.9
Outstanding (31 ratings)
Rupert, Bennington County, Vermont, United States
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House Rupert
Mar 30 - Apr 6
$461 per night
House ∙ 14 guests ∙ 5 bedrooms
Vacation Home in Manchester Center with Yard & Grill + Mountain Views
4.9
Outstanding (63 ratings)
Rupert, Bennington County, Vermont, United States
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House Rupert
Nov 25 - Dec 2
$553 per night
House ∙ 8 guests ∙ 4 bedrooms
Beautiful Vacation Home in Manchester Center with Yard, Grill, Hot Tub + Great Views
5.0
Outstanding (48 ratings)
Rupert, Bennington County, Vermont, United States
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House Rupert
Nov 25 - Dec 2
$252 per night
House ∙ 8 guests ∙ 3 bedrooms
House in Winhall
5.0
Outstanding (20 ratings)
Rupert, Bennington County, Vermont, United States
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Farmhouse Rupert
Dec 9 - Dec 16
-23%
$650
$500 per night
Farmhouse ∙ 14 guests ∙ 5 bedrooms
Farm in Salem with Yard, Pool & Grill + Gorgeous Views
5.0
Outstanding (64 ratings)
Rupert, Bennington County, Vermont, United States
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House Rupert
Mar 30 - Apr 6
$325 per night
House ∙ 9 guests ∙ 4 bedrooms
Family Friendly House in Manchester Center with Yard, Grill & Pool
5.0
Outstanding (130 ratings)
Rupert, Bennington County, Vermont, United States
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Budget-friendly Vacation Rentals in Rupert

Find Fantastic yet Inexpensive Offers

Villa Rupert
Oct 21 - Oct 28
$578 per night
Villa ∙ 15 guests ∙ 6 bedrooms
Villa in West Rupert with Grill, Yard & Pool
Rupert, Bennington County, Vermont, United States
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Cottage Rupert
Oct 21 - Oct 28
-58%
$301
$127 per night
Cottage ∙ 6 guests ∙ 3 bedrooms
Rustic Cottage in Salem with Yard
4.9
Outstanding (24 ratings)
Rupert, Bennington County, Vermont, United States
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House Rupert
Dec 9 - Dec 16
-37%
$455
$287 per night
House ∙ 8 guests ∙ 4 bedrooms
Vacation Home in Pawlet with Green Garden + Panoramic Views
5.0
Outstanding (5 ratings)
Rupert, Bennington County, Vermont, United States
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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!

Cottage  Rupert
Mar 30 - Apr 6
$227 per night
Cottage ∙ 4 guests ∙ 1 bedroom
Cottage in Manchester Center with Private Parking + Mountain View
5.0
Outstanding (165 ratings)
Rupert, Bennington County, Vermont, United States
Pet-friendly
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House  Rupert
Jun 1 - Jun 8
$495 per night
House ∙ 11 guests ∙ 5 bedrooms
Vacation Home in Dorset with Yard & Grill
5.0
Outstanding (173 ratings)
Rupert, Bennington County, Vermont, United States
Pet-friendly
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House  Rupert
Jun 15 - Jun 22
$226 per night
House ∙ 4 guests ∙ 2 bedrooms
Vacation Home in Wells with Grill & Yard + Breath-Taking Views
4.4
Very good (47 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.

Chalet  Rupert
Jun 15 - Jun 22
$232 per night
Chalet ∙ 12 guests ∙ 4 bedrooms
Chalet in Granville with Yard & Grill
4.7
Excellent (34 ratings)
Rupert, Bennington County, Vermont, United States
Balcony
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Cabin  Rupert
Dec 23 - Dec 30
$175 per night
Cabin ∙ 7 guests ∙ 4 bedrooms
Cabin in Hartford with Grill & Yard + Beautiful Views
5.0
Outstanding (1 rating)
Rupert, Bennington County, Vermont, United States
Balcony
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House  Rupert
Feb 3 - Feb 10
-32%
$437
$297 per night
House ∙ 12 guests ∙ 3 bedrooms
House in Wells with Yard & Grill + Lake Views
4.9
Outstanding (83 ratings)
Rupert, Bennington County, Vermont, United States
Balcony
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Apartments With Balconies or Patios

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

House  Rupert
Nov 25 - Dec 2
$330 per night
House ∙ 10 guests ∙ 4 bedrooms
Wonderful House in Manchester with Yard & Grill
5.0
Outstanding (31 ratings)
Rupert, Bennington County, Vermont, United States
Balcony/Patio
Details
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House  Rupert
Nov 25 - Dec 2
$447 per night
House ∙ 8 guests ∙ 3 bedrooms
Charming Vacation Home in Manchester Center + Mountain Views
5.0
Outstanding (33 ratings)
Rupert, Bennington County, Vermont, United States
Balcony/Patio
Details
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Cottage  Rupert
Nov 3 - Nov 10
$284 per night
Cottage ∙ 6 guests ∙ 3 bedrooms
Cottage in East Dorset with Yard
5.0
Outstanding (92 ratings)
Rupert, Bennington County, Vermont, United States
Balcony/Patio
Details
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Popular Rental Amenities in Rupert

  • Pet-friendly (5)
  • Pool (5)
  • Fireplace (10)
  • WiFi (11)
  • Kitchen (10)
  • TV (9)
  • Fishing (3)
  • Air conditioning (10)
  • Grill (10)
  • Washing machine (9)
  • No smoking (9)
  • Microwave (10)

Use filters to search and find an offer matching your requirements among all of the properties in Rupert. In Rupert, 5 properties include "Pets allowed". So, if you are looking for a pet-friendly rental, use the Pets allowed filter to compare these rentals. Not as many accommodations in Rupert are available if you dislike handwashing dishes or if you don't have a dog as "No pets allowed" and "Dishwasher" are not often provided in Rupert.

The Weather in Rupert

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32°
12°
15 days 15
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34°
12°
13 days 13
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43°
21°
13 days 13
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57°
34°
12 days 12
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72°
48°
14 days 14
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77°
54°
15 days 15
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82°
59°
14 days 14
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81°
57°
11 days 11
max.
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73°
48°
11 days 11
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61°
39°
14 days 14
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48°
28°
11 days 11
max.
Min.
37°
23°
19 days 19
Jan.
Feb.
Mar.
Apr.
May
June
July
Aug.
Sep.
Oct.
Nov.
Dec.
- 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

Sun, 24 Sep
68°
46°

15%

6 h

4 mi/h

Mon, 25 Sep
66°
46°

5%

11 h

5 mi/h

Tue, 26 Sep
59°
50°

15%

2 h

4 mi/h

Wed, 27 Sep
55°
44°

0%

0 h

4 mi/h

Thu, 28 Sep
51°
44°

15%

0 h

2 mi/h

Fri, 29 Sep
60°
48°

10%

1 h

2 mi/h

Sat, 30 Sep
62°
51°

15%

1 h

3 mi/h

Accommodations for your vacation in Rupert

3 among the 15 listed rentals in Rupert are house rental. They account for nearly half of the properties in this destination (42.86%). Interestingly, specific accommodation type, house rental is $706 a night, with an average area of 257 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 $1,002 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 $176
⭐ Popular amenities Pets allowed, Pool and Fireplace
🐾 Pet friendly homes 4 homes
🏊 Vacation rentals with pools 4 homes

Frequently Asked Questions

What is the average price per night for a vacation home in Rupert?

The nightly price of accommodations in Rupert starts at $176. If you’re interested in a house rental, the average price is $706 per night. A villa Rupert will cost $1,002 per night on average.

How many vacation rentals are available for booking in Rupert?

There are currently 15 vacation rentals available for booking for your next trip.

What are the most popular amenities for vacation rentals in Rupert?

Three most popular amenities for vacation rentals in Rupert include accommodations with: Pets allowed, Pool, and Fireplace.

How many vacation homes with pools are there in Rupert?

There are 4 vacation rentals from 5 providers in Rupert.

Are dogs allowed in vacation rentals in Rupert?

If you are traveling with a pet in Rupert - 44% of rentals allow pets.

What's the best time of year to travel to Rupert?

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

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