Best Vacation Homes in Rutland
Condo
10.0(34 Reviews)
2 Bedrooms
2 Baths
6 Guests
1950 ft²
Fireplace/Heating
Balcony/Terrace
Kitchen
Parking
US $276/Night
7 Nights - US $1,932
House
10.0(7 Reviews)
2 Bedrooms
2 Baths
6 Guests
1162.5 ft²
- Fireplace/Heating
- Parking
Internet
Child Friendly
US $320/Night
7 Nights - US $2,240
Bed & Breakfast
10.0(57 Reviews)
1 Bedroom
1 Bath
- Fireplace/Heating
- Balcony/Terrace
Breakfast- Parking
US $184/Night
7 Nights - US $1,291
Apartment
10.0(32 Reviews)
2 Bedrooms
1 Bath
4 Guests
1000 ft²
- Fireplace/Heating
Ocean View- Balcony/Terrace
View
US $299/Night
7 Nights - US $2,090
House
9.8(4 Reviews)
4 Bedrooms
2 Baths
8 Guests
129.17 ft²
- Fireplace/Heating
- View
- Parking
Air Conditioner
US $158/Night
7 Nights - US $1,103
Cottage
10.0(24 Reviews)
2 Bedrooms
2 Baths
4 Guests
1200 ft²
Hot Tub- Fireplace/Heating
Pool- Balcony/Terrace
US $328/Night
7 Nights - US $2,298
Apartment
10.0(14 Reviews)
1 Bedroom
1 Bath
4 Guests
- Fireplace/Heating
- Air Conditioner
- Internet
- Child Friendly
US $166/Night
7 Nights - US $1,165
Apartment
10.0(6 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
US $281/Night
7 Nights - US $1,970
Rutland Luxury Rentals
House
10.0(17 Reviews)
4 Bedrooms
4 Baths
8 Guests
4250 ft²
Private Pool- Hot Tub
- Fireplace/Heating
- Pool
US $2,072/Night
7 Nights - US $14,506
House
9.8(73 Reviews)
5 Bedrooms
5 Baths
13 Guests
9484 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $1,202/Night
7 Nights - US $8,416
House
4 Bedrooms
3 Baths
9 Guests
247.57 ft²
- Balcony/Terrace
- Parking
- Air Conditioner
- Internet
US $1,003/Night
7 Nights - US $7,021
House
9.0(2 Reviews)
4 Bedrooms
2 Baths
10 Guests
1732.99 ft²
- Fireplace/Heating
- View
- Parking
- Air Conditioner
US $884/Night
7 Nights - US $6,188
House
9.0(1 Review)
5 Bedrooms
4 Baths
10 Guests
150.69 ft²
- Fireplace/Heating
- Balcony/Terrace
- View
Pet Friendly
US $756/Night
7 Nights - US $5,292
House
10.0(34 Reviews)
4 Bedrooms
2 Baths
10 Guests
1728 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $699/Night
7 Nights - US $4,891
House
9.4(3 Reviews)
4 Bedrooms
2 Baths
14 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $678/Night
7 Nights - US $4,748
Cabin
10.0(28 Reviews)
3 Bedrooms
2 Baths
10 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $625/Night
7 Nights - US $4,377
Rutland Pet Friendly Vacation Rentals
House
9.6(4 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $372/Night
7 Nights - US $2,605
House
9.0(5 Reviews)
2 Bedrooms
2 Baths
4 Guests
1205.56 ft²
- Hot Tub
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $289/Night
7 Nights - US $2,023
Cottage
1 Bedroom
1 Bath
4 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $260/Night
7 Nights - US $1,818
Villa
8.0(34 Reviews)
3 Bedrooms
1 Bath
7 Guests
1420.84 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Parking
US $198/Night
7 Nights - US $1,386
House
10.0(37 Reviews)
5 Bedrooms
1 Bath
8 Guests
2000 ft²
Spa- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $622/Night
7 Nights - US $4,351
House
10.0(24 Reviews)
3 Bedrooms
2 Baths
6 Guests
- Hot Tub
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $443/Night
7 Nights - US $3,100
Cottage
10.0(21 Reviews)
3 Bedrooms
2 Baths
4 Guests
825 ft²
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
US $456/Night
7 Nights - US $3,192
House
10.0(15 Reviews)
5 Bedrooms
3 Baths
10 Guests
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
US $493/Night
7 Nights - US $3,453
Rutland Large Vacation Homes
Apartment
10.0(1 Review)
3 Bedrooms
1 Bath
13 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $448/Night
7 Nights - US $3,136
Villa
9.0(3 Reviews)
3 Bedrooms
3 Baths
6 Guests
2701.74 ft²
- Balcony/Terrace
- Breakfast
- Kitchen
- Parking
US $522/Night
7 Nights - US $3,654
House
9.8(94 Reviews)
4 Bedrooms
2 Baths
10 Guests
2500 ft²
- Fireplace/Heating
- Balcony/Terrace
- View
- Kitchen
US $482/Night
7 Nights - US $3,372
House
8.7(4 Reviews)
4 Bedrooms
2 Baths
10 Guests
2497.23 ft²
Oceanfront- Spa
- Fireplace/Heating
- Ocean View
US $488/Night
7 Nights - US $3,418
House
9.8(27 Reviews)
5 Bedrooms
2 Baths
12 Guests
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
US $561/Night
7 Nights - US $3,929
House
10.0(15 Reviews)
5 Bedrooms
3 Baths
12 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $600/Night
7 Nights - US $4,200
House
10.0(4 Reviews)
4 Bedrooms
2 Baths
10 Guests
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $663/Night
7 Nights - US $4,643
House
9.6(5 Reviews)
5 Bedrooms
3 Baths
12 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $640/Night
7 Nights - US $4,480
Why Choose Rent By Owner for your Rutland 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 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
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
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
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
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
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.
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.
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.
Rutland Vacation Rental Frequently Asked Questions
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:
- Convenient, clean and cozy 3 bedroom, 2 bath overlooking idyllic lake whittemore
- The Inn Crowd Bed and Breakfast
- Upscale 4 Bedroom Condo w King Bed Suite
- ❤️Upscale, Zen Pool Retreat for Non-Smokers
- Lakefront; view of ski mountain, firepit, dock, kayaks, laundry, outdoor shower
- Leicester Lake Front Home, Come Relax!
- Bright and Spacious 2BR/2BATH Condo with Parking- Highly recommended by guests
- Waterfront Retreat: 2BR with Huge Deck on Lake Lashaway Views in E. Brookfield!
- Cottage on Partridge Pond
- Our pondside cabin - a charming retreat with modern amenities near Wachusett Mtn
2. How many vacation rentals have private pools in Rutland?
There are 3 vacation rentals with private pools near Rutland. Top-rated RBO homes that have access to a swimming pool include:
3. 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:
4. How many Rentbyowner vacation rentals are available in Rutland?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 156 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.
5. 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.
6. 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.
7. 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.
8. 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.
9. 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.
Rutland Top Rated Vacation Rentals
House
10.0(45 Reviews)
3 Bedrooms
1 Bath
6 Guests
1300 ft²
- Private Pool
- Hot Tub
- Fireplace/Heating
- Pool
US $279/Night
7 Nights - US $1,955
House
10.0(1 Review)
3 Bedrooms
2 Baths
8 Guests
1500 ft²
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
US $407/Night
7 Nights - US $2,850
Hotel
9.0(1001 Reviews)
1 Bath
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Breakfast
US $203/Night
7 Nights - US $1,423
Hotel
8.6(570 Reviews)
1 Bath
374.94 ft²
- Private Pool
- Oceanfront
- Fireplace/Heating
- Pool
US $194/Night
7 Nights - US $1,357
Hotel
8.4(1006 Reviews)
1 Bath
- Fireplace/Heating
- Pool
- Breakfast
- Kitchen
US $216/Night
7 Nights - US $1,514
Hotel
8.2(210 Reviews)
8 Baths
305.43 ft²
- Private Pool
- Oceanfront
- Fireplace/Heating
- Pool
US $231/Night
7 Nights - US $1,615
New
House
2 Bedrooms
2 Baths
4 Guests
1700.7 ft²
- Hot Tub
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $403/Night
7 Nights - US $2,822
Apartment
8.0(6 Reviews)
1 Bedroom
1 Bath
4 Guests
- Hot Tub
- Spa
- Fireplace/Heating
- Pool
US $199/Night
7 Nights - US $1,393
