Best Vacation Homes in Rupert
1700 ft²
7 Guests
2 Bedrooms
4 Bathrooms
Family Friendly
Cabin
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
CA $330/Night
For 7 Nights CA $2,312
4004.17 ft²
15 Guests
6 Bedrooms
4 Bathrooms
Free Cancellation
Villa
- Spa
- Fireplace/Heating
- Pool
CA $1,652/Night
For 7 Nights CA $11,561
1300 ft²
4 Guests
2 Bedrooms
2 Bathrooms
Ocean View
House
- Hot Tub
- Fireplace/Heating
- Ocean View
CA $698/Night
For 7 Nights CA $4,884
3595.15 ft²
11 Guests
1 Bedroom
3 Bathrooms
Free Cancellation
House
- Hot Tub
- Fireplace/Heating
- View
CA $754/Night
For 7 Nights CA $5,281
1320 ft²
6 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
CA $280/Night
For 7 Nights CA $1,960
1250 ft²
8 Guests
4 Bedrooms
2 Bathrooms
Family Friendly
Cabin
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
CA $322/Night
For 7 Nights CA $2,258
300 ft²
11 Guests
5 Bedrooms
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
CA $310/Night
For 7 Nights CA $2,171
3600 ft²
11 Guests
4 Bedrooms
2 Bathrooms
Family Friendly
House
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
CA $603/Night
For 7 Nights CA $4,219
Rupert Luxury Rentals
8 Guests
3 Bedrooms
2 Bathrooms
Ocean View
House
- Hot Tub
- Fireplace/Heating
- Ocean View
CA $1,711/Night
For 7 Nights CA $11,975
4000 ft²
15 Guests
6 Bedrooms
3 Bathrooms
Family Friendly
Villa
- Private Pool
- Fireplace/Heating
- Pool
CA $1,573/Night
For 7 Nights CA $11,014
2002.09 ft²
6 Guests
1 Bedroom
2 Bathrooms
Free Cancellation
House
- Fireplace/Heating
- Parking
- Internet
CA $907/Night
For 7 Nights CA $6,350
3000 ft²
10 Guests
4 Bedrooms
3 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
CA $853/Night
For 7 Nights CA $5,969
4000 ft²
10 Guests
4 Bedrooms
2 Bathrooms
Family Friendly
House
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
CA $660/Night
For 7 Nights CA $4,620
4 Guests
3 Bedrooms
3 Bathrooms
Ocean View
House
- Hot Tub
- Fireplace/Heating
- Ocean View
CA $589/Night
For 7 Nights CA $4,124
6 Guests
3 Bedrooms
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
CA $428/Night
For 7 Nights CA $2,996
6 Guests
3 Bedrooms
2 Bathrooms
House
- Fireplace/Heating
- Air Conditioner
- Internet
CA $413/Night
For 7 Nights CA $2,892
Rupert Pet Friendly Vacation Rentals
1610 ft²
8 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
CA $521/Night
For 7 Nights CA $3,646
2497.23 ft²
8 Guests
2 Bedrooms
2 Bathrooms
Free Cancellation
House
- Fireplace/Heating
- Pet Friendly
- Child Friendly
CA $362/Night
For 7 Nights CA $2,538
13 Guests
1 Bedroom
1 Bathroom
Family Friendly
Cabin
- Hot Tub
- Spa
- Fireplace/Heating
CA $547/Night
For 7 Nights CA $3,829
5143 ft²
8 Guests
5 Bedrooms
5 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
CA $985/Night
For 7 Nights CA $6,898
2600 ft²
8 Guests
3 Bedrooms
3 Bathrooms
Ocean View
House
- Oceanfront
- Pool
- Ocean View
CA $987/Night
For 7 Nights CA $6,909
5143 ft²
8 Guests
5 Bedrooms
6 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
CA $910/Night
For 7 Nights CA $6,374
6 Guests
3 Bedrooms
3 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
CA $830/Night
For 7 Nights CA $5,812
1000 ft²
4 Guests
2 Bedrooms
1 Bathroom
Family Friendly
House
- Hot Tub
- Spa
- Fireplace/Heating
CA $328/Night
For 7 Nights CA $2,295
Rupert Large Vacation Homes
10 Guests
4 Bedrooms
2 Bathrooms
Family Friendly
Other
- Fireplace/Heating
- Parking
- Air Conditioner
CA $264/Night
For 7 Nights CA $1,849
495.14 ft²
11 Guests
1 Bedroom
2 Bathrooms
House
- Fireplace/Heating
- Balcony/Terrace
- Child Friendly
CA $342/Night
For 7 Nights CA $2,394
Why Choose Rent By Owner for your Rupert Vacation Rental Homes?
What makes our Vacation Rentals special?
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.
Best Times to Visit Rupert
When should you plan your Vacation Rentals stay?
To make the most of your stay, consider visiting during the region’s shoulder seasons when the weather is mild, and the area offers a peaceful retreat away from the peak crowd levels.
Peak Season Highlights
Summer (June to August)
During the warm summer months, you can enjoy the region's lush landscapes and pleasant weather, ideal for outdoor activities and exploring scenic nature.
Average Temperature Daytime: 75°F to 85°F - Nighttime: 55°F to 65°F
Fall (September to November)
Experience the vibrant foliage and crisp air as the area transforms into a stunning display of colors, attracting visitors seeking picturesque views and outdoor adventures.
Average Temperature Daytime: 60°F to 70°F - Nighttime: 40°F to 50°F
Off-Season Highlights
Winter (December to February)
The quieter winter season offers serene snowy landscapes and opportunities for cozy stays, perfect for those looking to escape the crowds and enjoy peaceful scenery.
Average Temperature Daytime: 20°F to 35°F - Nighttime: 10°F to 20°F
Spring (March to May)
As the region awakens from winter, spring showcases blooming flowers and milder temperatures, providing a tranquil setting for relaxed getaways before the busy summer season.
Average Temperature Daytime: 45°F to 60°F - Nighttime: 30°F to 40°F
Weekly Weather Forecast for Rupert
How to Book Your Rupert Vacation Rental Home
What's our booking process?
Our platform allows you to browse a curated selection of vacation rentals. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.
Booking Steps
01
Search Properties
Use our filters to find the right property that fits your needs.
02
Select a Rental
Click on your preferred listing to view details, amenities, and pricing.
03
Book Online
Follow the link to finalize your reservation directly on the partner’s website.
Explore and book the perfect rental in Rupert
Common Vacation Rentals Amenities
What amenities can you expect?
Our Vacation Rentals are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:
Indoor Features
- Fully-equipped kitchens with modern appliances
- Comfortable living areas with flat-screen TVs
- Free Wi-Fi for staying connected
- Air conditioning and heating for year-round comfort
- In-unit washers and dryers for convenience
- Luxurious bedrooms with premium bedding
- Spa-like bathrooms with soaking tubs or walk-in showers
Outdoor Amenities
- Enjoy outdoor gatherings with a spacious patio or deck area, perfect for relaxing and socializing amidst the scenic surroundings.
- Take advantage of nearby hiking trails and outdoor pathways that showcase the natural beauty of the region.
- Benefit from private or shared access to picturesque gardens or landscaped yards to enhance your outdoor experience.
- Make use of outdoor fire pits or fire rings for cozy evenings under the stars in this peaceful destination.
- Explore the area’s open spaces through opportunities for birdwatching or wildlife viewing right from your rental.
- Utilize outdoor sports amenities such as volleyball courts, horseshoe pits, or badminton setups often found at properties here.
- Access outdoor parking facilities conveniently located near your vacation rental to streamline your arrival and departures.
Top Attractions Around Rupert
What attractions are nearby?
Here, you can explore a variety of outdoor activities and scenic attractions that showcase the natural beauty of the region, making your stay memorable and engaging.
Family Activities
- Hiking at Mount Equinox: Explore scenic trails nearby that offer stunning vistas and family-friendly walking paths, perfect for outdoor adventures with the kids.
- Visit to the Vermont Heritage Museum: Discover local history and culture through interactive exhibits, engaging all family members in understanding the area's roots.
- Lake Adventure Activities: Enjoy swimming, fishing, or paddleboarding at a nearby lake, providing fun-filled water experiences for families seeking relaxation and recreation.
- Farm Tours in the Region: Experience farm life firsthand with guided tours where children can meet farm animals and learn about sustainable agriculture practices.
Adult Activities
- Hiking the Green Mountain Trail: Explore scenic pathways that wind through lush forests and offer breathtaking views, perfect for outdoor enthusiasts staying in this region.
- Visiting Local Art Galleries: Discover the area's vibrant arts scene by exploring galleries featuring regional artists and unique Vermont-inspired works.
- Shopping at Farmers Markets: Experience the local flavors and artisanal crafts at nearby farmers markets, a great way to immerse yourself in the area's culture.
- Enjoying Scenic Drives: Take a leisurely drive along picturesque routes that showcase the natural beauty and tranquil landscapes of here’s countryside.
Other Places to Stay in Rupert, VT
West Rupert
Merck Forest Farmland Center
Rupert Travel Tips
How Can You Make the Most of Your Stay?
- Explore Local Outdoor Activities: Take advantage of the region’s beautiful natural scenery by engaging in outdoor pursuits such as hiking, biking, or fishing, which are easily accessible from your vacation rental.
- Visit Seasonal Events and Markets: Check out local markets and seasonal festivals that showcase the area’s vibrant community and offer authentic regional products during your stay.
- Plan Cultural and Historical Tours: Discover the area's rich history and cultural heritage through guided tours or educational sites nearby, enriching your overall experience.
- Choose Conveniently Located Rental Properties: Select a vacation rental close to key attractions and amenities to maximize your leisure time and minimize travel hassle throughout your visit.
Transportation Options
- Vermont Transit Bus Service: This affordable option provides reliable transportation across the region, making it easy for you to explore Rupert and its surroundings.
- Local Taxi Services: Convenient for quick trips within the area, taxis offer flexible and direct transportation options during your stay here.
- Car Rentals: Renting a vehicle gives you the freedom to discover the region at your own pace, with many rental agencies available nearby.
- Regional Shuttle Services: These scheduled shuttle options connect you to larger cities and key attractions in this part of Vermont, ideal for day trips or airport transfers.
Local Customs Options
- Southern Vermont Hospitality: Embrace the warm greeting and welcoming attitude characteristic of this region’s friendly community when you arrive at your vacation rental in Rupert, Vermont.
- Local Agricultural Traditions: Participate in or observe seasonal farm activities that reflect the area's rich agricultural heritage, offering an authentic experience during your stay here.
- Seasonal Festivals: Enjoy the vibrant local festivals that celebrate the region’s history and natural beauty, creating memorable cultural experiences during your visit.
- Respect for Nature: Practice environmentally conscious habits by respecting the scenic landscapes and natural resources, which are integral to the identity of this destination in Vermont.
Frequently Asked Questions About Rupert?
1. What are the top vacation rentals in Rupert?
There are a lot of options in Rupert. If you plan on staying in the Rupert area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Rupert:
- Private and Artistic cabin, Pet friendly, no cleaning fee
- Creekside Camp. NO CLEANING FEE. Relax in the Hot Tub Creekside - Vermont Style
- Log Cabin In The Woods
- Vermont Treehouse compound: no cleaning fee. Spend a few days In the Trees
- Restored Vermont Home & 'Cook's Country' TV Set
- Beautifully restored 1806 Vermont farmhouse & “Cook’s Country” TV set
- Rustic farmhouse w/gorgeous views, a hot tub, no cleaning fees, & many updates
- Charming Farmhouse, upstate NY.
- Skiing house n Serene 3-bedroom house with AC in charming Dorset
- adirondack style all season lodge/resort on a natural glacier pond
2. Which vacation homes in Rupert are best for families?
If you are looking for a family-friendly vacation home in Rupert, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Rupert:
3. How many Rentbyowner vacation rentals are available in Rupert?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 31 in the Rupert area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Rupert.
4. What is the cancellation policy for vacation rentals in this region?
Cancellation policies vary by property, so it is important to review the specific rental listing for detailed terms. Some properties may offer flexible or free cancellations, while others have stricter policies. Contact the property owner directly if you need clarification.
5. Are there any specific check-in and check-out times I should be aware of when booking here?
Check-in and check-out times are set by each vacation rental host and can differ from property to property. Be sure to read the listing details carefully or communicate with the property owner to confirm your arrival and departure schedule.
6. How do I find out about amenities available at the vacation rentals in this area?
Amenities are listed on each property’s page, including details like Wi-Fi, kitchen facilities, parking, and more. If specific amenities are important to your stay, reach out to the host to confirm availability before booking.
7. What should I know about local regulations or restrictions when staying in a vacation rental here?
Local regulations regarding short-term rentals can vary; some areas may require registration or impose certain restrictions. Check the property listing or contact the host for guidance on rules that may affect your stay.
8. Is there a recommended way to handle cancellations or changes to my reservation?
It is best to review the property's cancellation policy at the time of booking. For any changes or cancellations, communicate directly with the property owner as soon as possible to understand your options and avoid potential fees.
