Rupert Vacation Rentals

Compare 188 available properties from 17 providers
Rupert
Save up to 46%

Best vacation home deals in Rupert

$251
from $176
-30%
1000 ft² House
4 2
Dorset, Bennington County, Vermont, United States
Found on
VRBO
$204
from $147
-28%
1800 ft² House
10 4
Pawlet, Rutland County, Vermont, United States
Found on
VRBO
$341
from $185
-46%
1250 ft² House
8 4
Sandgate, Bennington County, Vermont, United States
Found on
VRBO

Book the ideal vacation home for as little as $85 per night by searching among the 188 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 46%.

Recommended vacation rentals in Rupert

Rent a vacation accommodation in Rupert: from $85 per night

from $243
2000 ft² House
6 3
Dorset, Bennington County, Vermont, United States
5.0
"Excellent" 5 reviews
Found on VRBO
$979
from $808
-18%
4000 ft² House
16 6
Dorset, Bennington County, Vermont, United States
5.0
"Excellent" 3 reviews
Found on VRBO
from $394
2400 ft² House
2 2
Manchester Center, Manchester, Vermont, United States
5.0
"Excellent" 5 reviews
Found on VRBO
$394
from $283
-28%
1800 ft² House
6 2
Manchester Center, Manchester, Vermont, United States
5.0
"Excellent" 44 reviews
Found on VRBO
from $836
4200 ft² House
12 5
Dorset, Bennington County, Vermont, United States
5.0
"Excellent" 4 reviews
Found on VRBO
from $370
3290 ft² House
10 4
Dorset, Bennington County, Vermont, United States
4.8
"Excellent" 4 reviews
Found on VRBO
from $290
The Dorset Inn
2 1
Dorset, Bennington County, Vermont, United States
4.6
"Excellent" 72 reviews
Found on Booking.com
from $269
Barrows House
2 1
Dorset, Bennington County, Vermont, United States
4.6
"Excellent" 25 reviews
Found on Booking.com
See all offers

  Vacation homes with fishing spots nearby

from $131
700 ft² House
3 2
Rupert, Bennington County, Vermont, United States
5.0
"Excellent" 22 reviews
Found on VRBO
$420
from $141
-66%
House
8 3
Dorset, Bennington County, Vermont, United States
4.1
"Very good" 19 reviews
Found on VRBO
from $392
2440 ft² House
9 4
Dorset, Bennington County, Vermont, United States
5.0
"Excellent" 24 reviews
Found on VRBO
$251
from $176
-30%
1000 ft² House
4 2
Dorset, Bennington County, Vermont, United States
4.7
"Excellent" 14 reviews
Found on VRBO
See all offers

  Vacation rentals with a fireplace

$491
from $327
-33%
4000 ft² House
14 4
Rupert, Bennington County, Vermont, United States
4.9
"Excellent" 26 reviews
Found on VRBO
from $580
House
6 4
Dorset, Bennington County, Vermont, United States
5.0
"Excellent" 3 reviews
Found on VRBO
from $591
5400 ft² House
11 4
Dorset, Bennington County, Vermont, United States
5.0
"Excellent" 12 reviews
Found on VRBO
$425
from $300
-29%
4000 ft² House
15 5
Rupert, Bennington County, Vermont, United States
4.5
"Outstanding" 7 reviews
Found on VRBO
See all offers

Popular rental amenities in Rupert

  • Internet (160)
  • TV (146)
  • No smoking (135)
  • Kitchen (134)
  • Parking (134)
  • Microwave (114)
  • AC (111)
  • Washer (111)
  • Fireplace (108)
  • Dishwasher (108)
  • Grill (103)
  • Fishing (102)
Use filters to search and find an offer matching your requirements among all of the properties in Rupert. In Rupert, 160 properties include "internet". So, if you need internet access during your vacation, use the internet filter to compare these rentals. Not as many accommodations in Rupert are available if you want a rental with a pool or if you enjoy soaking in the hot tub as "Jacuzzis" and "pools" are not often provided in Rupert.

Price and Availability Index Rupert

Vacation Rental Price Information in Rupert

The price graph will give you the nightly price average for the upcoming months of the year. The most expensive prices are in June (6/23 - 6/30). Prices reach an average of $456 per night. However, in November (11/3 - 11/10), prices decrease to an average of $368 per night.

Rental Availability Information in Rupert

Check how busy Rupert is with our availability graph. More people travel to Rupert a week in July (7/7 - 7/14). So far, 50% of the rentals are occupied this week. The week with the most available rentals is in October (10/27 - 11/3), with 93% of the vacation rentals available.

The weather in Rupert

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

Check out the climate diagram for Rupert. July is the warmest month in Rupert with average maximum temperatures of 82°. Conversely, January is the coolest month in Rupert, with temperatures going under 12° The rainiest month is December while the driest month is August.

134 among the 188 listed rentals in Rupert are house rentals. They account for many of the properties in this destination (64.73%). Interestingly, specific accommodation type, house rentals is $492 a night, with an average area of 2,940 ft². Furthermore, these accommodations are optimal for large groups, as most can accommodate 10 vacationers. If you are searching for another type of accommodation, you can find many other options, such as hotel rooms, which are the other very typical type of accommodation in Rupert. These accommodations cost $203 per night on average and have an average size of 340 ft².

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.

Show all 188 properties
Food & Drinks

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.

Art & Culture

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.

Local Attractions

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.

We compare more than 250 providers, including:

Booking.com Vacation Rentals in Rupert VRBO Vacation Rentals in Rupert HomeAway Vacation Rentals in Rupert TripAdvisor Vacation Rentals in Rupert VacationRentals.com Vacation Rentals in Rupert HouseTrip Vacation Rentals in Rupert FlipKey Vacation Rentals in Rupert Wimdu Vacation Rentals in Rupert 9flats.com Vacation Rentals in Rupert VaycayHero Vacation Rentals in Rupert PerfectPlaces.com Vacation Rentals in Rupert Homestay.com Vacation Rentals in Rupert only-apartments Vacation Rentals in Rupert Interhome Vacation Rentals in Rupert Bedycasa Vacation Rentals in Rupert Novasol Vacation Rentals in Rupert HomeEscape Vacation Rentals in Rupert

Vacation destinations near Rupert