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Monterey vacation rentals

We found 528 vacation rentals — enter your dates for availability

Discover a selection of 25 homes and other vacation rentals in Monterey that are perfect for your trip. Vacation homes provide the best amenities for you and your friends, family, or even pets, such as air conditioning and a pool. At the end of the day, you'll find a rental for everyone's needs, including accessible or non-smoking choices.

Vacation rentals with weekly discounts - Monterey

Showing deals for:Dec 26 - Jan 2

Image gallery for General Williams Estate House Lenox/Stockbridge

Front of house
9.8 out of 10, Exceptional, (110 reviews)
Exceptional
(110 reviews)

General Williams Estate House Lenox/Stockbridge

Stockbridge, MA

10% off
Price is CA $1,388
CA $12,047 total
includes taxes & fees
General Williams Estate House Lenox/Stockbridge

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Find out more about Monterey

Find out more about Monterey

Why people love visiting beautiful Monterey

The forests, wildlife and parks display a scene truly unique to Monterey. Well known for its hiking, fishing and boating, this scenic city won't disappoint. Whether you're planning a family holiday, romantic stay or friends trip, vacation rentals offer features like full kitchens and laundry facilities for a more convenient stay.

Activities and attractions in Monterey

Are you hoping to find attractions to visit in the city? Venture out of your vacation home and experience everything that makes Monterey a one-of-a-kind vacation spot. These are some of the most popular attractions to put on your list, all within 30 miles (48.2 km) of the city center:

  • Ski Butternut (5.6 mi / 8.9 km)
  • Wyndhurst Golf & Club (11.7 mi / 18.8 km)
  • Catamount Ski Area (13.7 mi / 22 km)
  • Bousquet Ski Area (16.7 mi / 26.8 km)
  • Furnace Brook Winery at Hilltop Orchards (17.3 mi / 27.9 km)
  • Les Trois Emme Winery (3.8 mi / 6.2 km)

Exploring the natural landscape of Monterey

Whether you're looking for exciting outdoor activities or just want to spend some time taking in the scenery, Monterey is a great place to get outside. Here are some of the area’s most enchanting natural features, all within 30 miles (48.2 km) of the city center:

  • Lake Buel (3.3 mi / 5.4 km)
  • Goose Pond Reservation (7.3 mi / 11.7 km)
  • Housatonic River (7.7 mi / 12.4 km)
  • Housatonic River Walk (7.7 mi / 12.4 km)
  • Pyramid Lake (7.8 mi / 12.6 km)
  • Lake Mansfield Park (8.1 mi / 13.1 km)

Transportation to and around Monterey

The nearest airport is in Pittsfield, MA (PSF-Pittsfield Municipal), located 17.5 mi (28.1 km) from the city center. If you can't find a flight that's convenient for your trip, you can also fly into Westfield, MA (BAF-Barnes Municipal), which is 25.3 mi (40.7 km) away.

Frequently asked questions

What is the best area to stay in Monterey when booking a vacation rental?
When considering a vacation rental in Monterey, Massachusetts, the best area to stay is close to the picturesque Lake Garfield. This serene neighbourhood not only offers stunning lake views but also provides easy access to various water activities and scenic walking trails. Visitors can enjoy leisurely strolls around the lake, superb for a relaxing afternoon, or partake in kayaking and fishing, making it a haven for nature enthusiasts.

Another appealing option is the vicinity of the town centre, where you can immerse yourself in the local charm. This area is home to quaint shops and delightful eateries, providing an authentic taste of New England hospitality. You'll find a range of vacation rentals here, from cosy cottages to spacious family homes, ensuring there's something to suit every traveller's needs.
How much does it cost to rent a vacation home in Monterey?
Prices for vacation rentals in Monterey vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Monterey to more spacious homes.
Are there any discounts for Monterey vacation house rentals?
You can find great discounts on house rentals in Monterey on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Where are the best areas for renting a beach house in Monterey?
For renting a beach house in Monterey, Massachusetts, visitors should focus on the picturesque coastal area near the town's beaches, particularly along the scenic coastline that offers a blend of natural beauty and charm. The region surrounding the beaches, such as Old Colony Beach and nearby White Horse Beach, features a variety of vacation rentals, including quaint cottages and larger family homes. Many of these properties come equipped with amenities such as outdoor decks, private patios, and fully functional kitchens, making them superb for self-catering during summer getaways.

Particularly appealing is the proximity to local attractions like the charming downtown area, where visitors can find delightful shops, restaurants, and cafés serving fresh seafood. For those interested in outdoor activities, the nearby coastal trails provide stunning views and opportunities for hiking and birdwatching. Many rentals in this area also offer easy access to the sandy shores, allowing guests to enjoy swimming, sunbathing, and beachcombing.
What is the most popular type of vacation rental accomodation in Monterey?
In Monterey, vacation houses are the most popular type of accommodation, with around 23 available throughout the area. These houses often feature multiple bedrooms, spacious living areas, and fully equipped kitchens, making them ideal for families or groups looking for a home away from home. Many properties also include outdoor spaces such as decks or gardens, superb for enjoying the picturesque surroundings after a day of exploring the nearby beaches or the scenic coastline. Additionally, there are several cottages, cabins, and chalets available, each offering a unique charm and comfort, allowing visitors to choose the style that best suits their needs.
Are there any family house rentals in Monterey?
In Monterey, Massachusetts, families will find a variety of vacation rentals—approximately 26 options available throughout the area. This charming coastal town offers a mix of properties that cater to families, many situated near attractions such as the picturesque beaches and the scenic coastline.

Visitors can expect homes with spacious living areas, fully equipped kitchens ideal for preparing family meals, and outdoor spaces superb for children to play. Many accommodations also feature amenities like Wi-Fi and laundry facilities, ensuring a comfortable stay for all ages.
Can I rent a vacation home with a pool or hot tub in Monterey?
In Monterey, there are several vacation homes available for rent that feature pools and hot tubs, making it a delightful destination for those seeking relaxation. The area offers a variety of charming neighbourhoods, including the scenic Cannery Row, known for its beautiful waterfront views and proximity to local attractions, as well as the tranquil Carmel-by-the-Sea, which boasts stunning beaches and upscale dining options.
Can I find long-stay vacation rentals in Monterey?
A long-stay vacation rental in Monterey is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Are there pet-friendly house rentals in Monterey?
In Monterey, there are several pet-friendly house rentals available, offering a range of amenities to ensure a comfortable stay for both you and your furry friend. Many of these properties feature spacious living areas, fully equipped kitchens, and outdoor spaces where pets can enjoy the fresh air.

The seaside location of Monterey provides easy access to beautiful parks and beaches where pets are welcome. For example, the scenic Cannery Row area is not only famous for its shops and restaurants but also offers nearby access to the stunning coastline. Additionally, the area around the Monterey State Beach allows pets on a leash, making it a great spot for long walks and enjoying the ocean views.
Are there any remote work vacation rentals in Monterey?
In Monterey, Massachusetts, there are numerous vacation rentals suitable for remote work, with around 34 options available. These properties cater to professionals seeking a conducive work environment, often featuring amenities such as high-speed Wi-Fi, dedicated workspaces with desks and ergonomic chairs, and even additional equipment like computer monitors. Many rentals come with comfortable living areas that allow for relaxation after a productive day. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Monterey vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Monterey with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
What are popular rental amenities in Monterey?
In Monterey, popular vacation rentals typically feature essential amenities that cater to the needs of travellers. Most rooms come equipped with a kitchen, allowing guests to prepare their own meals, along with a refrigerator and stovetop for convenience. Additionally, many rentals include a dishwasher, which adds to the ease of maintaining a clean and tidy space during a stay.
When is the best time to visit Monterey for a vacation rental?
The best time to visit Monterey for a vacation rental is during the peak season from June to August, particularly in July, when the area is vibrant and bustling with activity. This summer period draws in travellers eager to explore the stunning coastal scenery, indulge in outdoor adventures, and partake in local festivals and events. With temperatures typically ranging from 15 to 25 degrees Celsius, it's an ideal climate for enjoying the beaches, hiking along scenic trails, or visiting the famous Monterey Bay Aquarium.

During these months, you'll find a lot of activities to keep you engaged, from kayaking in the bay to exploring the charming Cannery Row. The lively atmosphere makes it easy to connect with fellow visitors and immerse yourself in the community's spirit.

If you're looking to save a bit while still enjoying the beauty of Monterey, consider planning your visit in December. While the weather is cooler, with temperatures averaging around 5 to 15 degrees Celsius, the winter months bring a quieter charm to the area. This peaceful time is superb for those who enjoy a more relaxed pace, offering opportunities for serene walks along the coast and enjoying the beautiful vacation decorations throughout the town.
How early should I book a Monterey vacation rental?
Book your Monterey vacation rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Monterey?
In Monterey, Massachusetts, visitors can enjoy a tranquil getaway surrounded by natural beauty. The town is known for its picturesque landscapes and proximity to the stunning Lake Garfield, where guests can enjoy activities such as swimming, kayaking, and picnicking. The nearby Beartown State Forest offers hiking trails and opportunities for wildlife viewing, making it ideal for nature enthusiasts.
Can I change or cancel my Monterey home rental booking on Vrbo?
To find Monterey vacation rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cosy flat or a countryside retreat, you can turn your space into a standout destination—become a host and let Vrbo handle the heavy lifting to help you thrive.
Are all fees included in the Monterey vacation rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.

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