Discover Your Perfect Rutland Vacation Homes

Rutland Luxury Rentals

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Rutland Pet Friendly Vacation Rentals

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8.4 (27 Reviews)
Villa
Indian Lake House
  • Air Conditioner
  • Parking
  • Pet Friendly
View Availability
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Rutland Large Vacation Homes

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9.3 (4 Reviews)
House
Our Pondside Cabin
  • Air Conditioner
  • Parking
  • Balcony/Terrace
View Availability
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Why Choose Rent By Owner for your Rutland Vacation Rental Homes?

What makes our Vacation Rentals special?

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Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
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Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
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Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.

Best Times to Visit Rutland

When should you plan your Vacation Rentals stay?

Timing your visit to this destination allows you to enjoy the region's best weather and local events, ensuring a memorable stay in your ideal vacation rental when the conditions align perfectly with your travel plans.

Peak Season Highlights

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Summer (June to August)

During the summer months, this destination experiences warm weather and longer daylight hours, making it ideal for enjoying outdoor activities and exploring the scenic region.

Average Temperature Daytime: 75°F to 85°F - Nighttime: 55°F to 65°F
autumn
Fall (September to November)

As the foliage turns vibrant shades, this time offers pleasant temperatures and a picturesque setting, perfect for sightseeing and outdoor adventures in the area.

Average Temperature Daytime: 65°F to 75°F - Nighttime: 45°F to 55°F

Off-Season Highlights

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Winter (December to February)

The winter season brings cooler temperatures and a quieter ambiance, providing a cozy atmosphere for those seeking peace and solitude here.

Average Temperature Daytime: 30°F to 40°F - Nighttime: 20°F to 30°F
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Spring (March to May)

Early spring offers mild weather and fewer visitors, allowing you to enjoy the natural beauty of the region at a more relaxed pace.

Average Temperature Daytime: 50°F to 60°F - Nighttime: 30°F to 40°F

Weekly Weather Forecast for Rutland

How to Book Your Rutland 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 Rutland

More Top-Rated Vacation Rentals in Rutland Area

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 a private outdoor space with a spacious yard perfect for relaxing or entertaining amidst the natural beauty of the region.
  • Take advantage of a well-maintained patio or deck area for outdoor dining and gatherings with scenic views of the surrounding landscape.
  • Benefit from a outdoor fire pit, ideal for cozy evenings and enjoying local tranquility here in the area.
  • Make use of a shared or private swimming pool to cool off during warmer months while soaking in the regional setting.
  • Explore the outdoors with access to walking trails or hiking paths directly from your rental property here.
  • Utilize outdoor sports facilities such as tennis courts or basketball half-courts if available at your stay in this destination.
  • Relax in a hammock or lounge chairs located in the garden or backyard, offering a peaceful retreat in the region's fresh air.

Top Attractions Around Rutland

What attractions are nearby?

Within this charming region, you can enjoy a variety of outdoor activities and local attractions that showcase the natural beauty and cultural heritage nearby your vacation rentals in Rutland, Massachusetts.

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Family Activities

  • Nature Trails and Hiking at Rutland State Forest: Explore scenic trails through the region's lush forests, perfect for family hikes and outdoor adventures.
  • Children’s Museum in Nearby Area: Discover interactive exhibits designed to engage young minds and foster learning during your stay here.
  • Fishing at Rutland Reservoir: Enjoy a relaxing day by the water, where your family can try fishing and appreciate the tranquil surroundings.
  • Local Parks and Picnic Areas: Spend quality time outdoors with family picnics and playground fun at well-maintained parks in this part of Massachusetts.
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Adult Activities

  • Hiking Trails: Explore the scenic hiking trails that wind through this area's natural landscape, offering stunning views and outdoor adventure right outside your vacation rental.
  • Local Wineries and Breweries: Visit the region’s renowned wineries and breweries to enjoy tastings and learn about local brewing and winemaking traditions during your stay.
  • Historical Sites Tour: Discover the area's rich history by touring local historical sites and landmarks that provide a glimpse into its cultural heritage.
  • Fishing and Boating: Engage in fishing or boating activities on nearby lakes and rivers, perfect for relaxing days immersed in nature during your trip here.

Rutland Travel Tips

How Can You Make the Most of Your Stay?

  • Explore local outdoor activities: Take advantage of the region's scenic parks and trails to enjoy hiking, biking, and other outdoor pursuits right from your vacation rental.
  • Discover regional dining options: Sample authentic cuisine at local eateries to get a taste of the area's culinary heritage during your stay.
  • Plan day trips to nearby attractions: Use your location as a base for visiting neighboring sites and landmarks that showcase the area's natural beauty and history.
  • Connect with the community: Engage with residents and attend local events or markets to gain a deeper appreciation of this destination’s culture and charm.

Transportation Options

  • Rutland Regional Transit: This local service offers convenient bus routes that connect you to key spots within the area, making it easy to explore your surroundings.
  • Private Car Services and Taxis: Available throughout the region, these options provide flexible and comfortable transportation for getting around during your stay.
  • Rental Cars: Several rental agencies operate near the destination, giving you the freedom to travel at your own pace while staying close to your vacation rentals here.
  • Amtrak Station in nearby Worcester: For longer journeys, this train station offers reliable rail connections to major cities across the country, ideal if you're planning to explore beyond this destination.

Local Customs Options

  • Community Events and Festivals: Embrace the local spirit by participating in seasonal festivals and community gatherings that highlight traditional New England customs here.
  • Local Hospitality: Experience the warm welcomes and friendly interactions characteristic of the region’s residents when you visit this area.
  • Historic Preservation: Appreciate the region’s commitment to maintaining its historical sites and structures, reflecting its rich heritage.
  • Farmers' Markets and Local Produce: Enjoy browsing vibrant farmers' markets where fresh, regional products are showcased, offering a taste of the area's agricultural roots.

Frequently Asked Questions About Rutland?

1. What are the top vacation rentals in Rutland?

There are a lot of options in Rutland. If you plan on staying in the Rutland area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Rutland:

2. Which vacation homes in Rutland are best for families?

If you are looking for a family-friendly vacation home in Rutland, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Rutland:

3. How many Rentbyowner vacation rentals are available in Rutland?

Currently, the total number of properties listed by Rent By Owner in 2025 is over 133 in the Rutland 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 Rutland. 

4. What is the cancellation policy for vacation rentals in Rutland, Massachusetts?

The cancellation policy varies by property, so it's best to review the specific listing details or contact the host directly to understand the terms and any applicable fees.

5. Are there any additional fees I should be aware of when booking a vacation rental in this area?

Additional fees such as cleaning fees, service charges, or taxes are often included in the listing description. Always check the detailed booking information or reach out to the owner for clarification.

6. How do I ensure the vacation rental meets my needs before booking?

You can review the property’s amenities, photos, and guest reviews on the listing page. If you have specific questions, contacting the host directly ensures your needs are fully understood before confirming your stay.

7. What is the process for checking in and out of a vacation rental in the region?

Check-in and check-out procedures are specified in each listing. Typically, hosts provide instructions closer to your arrival date—review these details carefully or contact the owner if you need further assistance.

8. Is there a minimum stay requirement for vacation rentals in this destination?

Minimum stay requirements vary depending on the property and season. You should verify this detail on the listing or inquire directly with the host to plan your visit accordingly.