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Monterey Luxury Rentals

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Why Choose Rent By Owner for your Monterey 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 Monterey

When should you plan your Vacation Rentals stay?

Choosing the ideal time to visit here can enhance your experience, as this destination offers different charms depending on the season, making your stay in Monterey, Massachusetts, USA, truly memorable.

Peak Season Highlights

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Summer (June to August)

During the peak summer months, you can enjoy warm weather and longer daylight hours, making it ideal for outdoor activities and exploring the scenic surroundings of this destination.

Average Temperature Daytime: 75-85°F - Nighttime: 60-65°F
autumn
Fall (September to October)

Autumn is a popular time to visit when the region is painted with vibrant fall foliage, offering a picturesque backdrop for your stay and outdoor adventures.

Average Temperature Daytime: 65-75°F - Nighttime: 50-55°F

Off-Season Highlights

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Winter (November to February)

The winter months bring cooler temperatures and quieter streets, providing a peaceful retreat for those seeking tranquility and cozy accommodations.

Average Temperature Daytime: 40-50°F - Nighttime: 30-35°F
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Spring (March to May)

Early spring offers mild weather and fewer crowds, allowing you to enjoy the area’s natural beauty as it awakens from winter dormancy.

Average Temperature Daytime: 55-65°F - Nighttime: 40-45°F

Weekly Weather Forecast for Monterey

How to Book Your Monterey 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 Monterey

More Top-Rated Vacation Rentals in Monterey 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 outdoor dining areas or picnic spaces to take in the scenic views of the region.
  • Take advantage of private or shared gardens to relax amidst lush greenery.
  • Make use of spacious decks or patios perfect for lounging or entertaining guests.
  • Benefit from access to outdoor fireplaces or fire pits for cozy evenings outdoors.
  • Explore well-maintained pathways or hiking trails that wind through the natural landscape.
  • Utilize outdoor swimming pools or hot tubs for a refreshing dip after exploring the area.
  • Enjoy recreational amenities such as tennis courts, volleyball courts, or outdoor game areas available on select properties.

Top Attractions Around Monterey

What attractions are nearby?

In this charming destination, you can explore a variety of outdoor activities and local attractions that showcase the natural beauty and rich history of the area.

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Family Activities

  • Monterey Bay Kayaking Tour: Embark on a family-friendly kayaking adventure to explore the scenic waters and diverse wildlife in this coastal region.
  • Discovering Local History at Monterey Historical Society Museum: Dive into the area's rich heritage with engaging exhibits that showcase its unique past, perfect for curious young minds.
  • Family Picnic at Lake Garfield: Enjoy a relaxing day outdoors with picturesque views, swimming, and picnic facilities at this popular local spot.
  • Hiking Trails in Pittsfield State Forest: Adventure through well-maintained trails suitable for all ages, offering breathtaking scenery and an opportunity to connect with nature here in the region.
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Adult Activities

  • Exploring the scenic trails of the region: Discover breathtaking views and tranquil nature walks that showcase the natural beauty of this destination.
  • Visiting local art galleries and cultural spots: Immerse yourself in the vibrant arts scene that highlights the region’s creative spirit and history.
  • Enjoying wine tasting at nearby vineyards: Savor the flavors of regional wines as you take advantage of guided tours and tastings offered throughout the area.
  • Participating in outdoor recreational activities: Engage in kayaking, biking, or horseback riding adventures that let you experience the region's diverse landscapes firsthand.

Other Places to Stay in Monterey, MA

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Bidwell House Museum Vacation Rentals
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Monterey Travel Tips

How Can You Make the Most of Your Stay?

  • Plan Your Visit During Off-Peak Seasons: Visiting during the quieter months allows you to enjoy a more relaxed atmosphere and better access to local attractions in this region.
  • Explore Local Flavors and Dining Options: Take advantage of the area's renowned eateries to savor authentic regional cuisine that enhances your overall experience here.
  • Discover Hidden Gems and Scenic Spots: Use your rental as a base to explore lesser-known scenic areas and peaceful retreats within this destination.
  • Prepare for Outdoor Activities: Pack suitable gear for outdoor adventures often available nearby, from hiking trails to water-based pursuits, making the most of your stay in the region.

Transportation Options

  • Rental Car Services: Local rental agencies provide flexible transportation options for exploring the surrounding area at your own pace.
  • Public Transportation: Bus services connect you to nearby towns and attractions, offering an economical way to navigate here without the need for a personal vehicle.
  • Taxi and Rideshare: Taxis and rideshare apps offer convenient point-to-point transportation within this region, ideal for quick trips or arriving from nearby airports.
  • Bike Rentals: For a scenic and eco-friendly experience, bike rentals are available to enjoy the natural beauty of the area at your leisure.

Local Customs Options

  • Greeting Customs: Locals in this region often greet visitors with warm, friendly smiles and a relaxed attitude, reflecting the welcoming spirit of Monterey's community.
  • Local Dining Etiquette: When enjoying meals here, it’s customary to appreciate farm-to-table cuisine and engage in conversations about regional produce and culinary traditions.
  • Celebration of Arts and Festivals: Participating in or observing local arts festivals and craft fairs is a cherished tradition, highlighting the area's appreciation for creative expression.
  • Respect for Natural Surroundings: Visitors are encouraged to honor the scenic landscapes by practicing eco-friendly habits and respecting outdoor spaces during your stay.

Monterey Vacation Rental Frequently Asked Questions

1. What are the top vacation rentals in Monterey?

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

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

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

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

Currently, the total number of properties listed by Rent By Owner in 2026 is over 47 in the Monterey 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 Monterey. 

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

The cancellation policy varies by property. To understand the specific terms, including potential refunds or penalties, please review the listing details or contact the property owner directly before booking.

5. How do I check the availability of vacation rentals in this destination?

Availability depends on the dates you select. You can easily view available properties by entering your preferred travel dates on the booking site and filtering results accordingly.

6. Are there any additional fees I should expect when booking a vacation rental here?

Additional fees such as cleaning fees, service charges, or security deposits are often specified within each listing. Be sure to review the fee details during the booking process or contact the owner for clarification.

7. Can I communicate directly with the property owner before booking?

Yes, most listings provide a messaging feature that allows you to ask questions directly to the owner. This helps ensure all your inquiries about the property and stay are addressed beforehand.

8. What amenities are typically included in vacation rentals in this area?

Amenities vary by property but commonly include essentials like Wi-Fi, parking, and kitchen facilities. For specific amenities, review the property listing details or reach out to the owner to confirm what’s available during your stay.