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Monterey holiday rentals

We found 542 holiday rentals — enter your dates for availability
Discover a selection of 26 homes and other holiday rentals in Monterey that are perfect for your trip. Holiday homes provide the amenities that you need and want for your family, friends or furry companion, such as air conditioning and cable TV. At the end of the day, you'll be able to choose a property to rent that has what everyone needs, including accessible or non-smoking choices.

Holiday rentals with weekly discounts – Monterey

Showing deals for:6 Nov - 13 Nov

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Why visit Monterey

  • Scenic Landscapes: Experience the tranquil beauty of Monterey's picturesque settings, perfect for leisurely walks and family outings.
  • Outdoor Activities: Engage in various water activities on pristine lakes and explore nature reserves ideal for hiking and picnicking.
  • Rich History: Discover historic houses and cultural landmarks that reflect the area's heritage and charm.
  • Family-Friendly Atmosphere: Enjoy a welcoming environment that caters to families, making it an excellent destination for all ages.
  • Charming Accommodations: Choose from a variety of holiday rentals, including cosy cottages and private homes, to enhance your stay.

Popular types of accommodation in Monterey

Welcome to Monterey, Massachusetts, a charming city nestled along the scenic coastline. Known for its tranquil beauty, Monterey offers a delightful selection of holiday rentals, including private homes, condos, and cosy cottages. Explore the stunning natural landscapes, enjoy water activities on the pristine lakes, and immerse yourself in the rich local culture. With a variety of accommodation options available, your perfect getaway in Monterey awaits.

  • Private Holiday Homes: The most sought-after option for visitors, offering a home-like atmosphere and ample space for families or groups.
  • Condos: A popular choice for those seeking modern amenities and communal facilities in a vibrant setting.
  • Cottages: Charming and quaint, these are ideal for a cosy retreat, often nestled in picturesque surroundings.
  • Cabins: Perfect for those wanting a rustic experience, combining comfort with nature right at your doorstep.
  • Apartments: Convenient and often centrally located, these spaces offer a practical base for exploring Monterey.**

Top attractions near Monterey

Monterey, Massachusetts is a charming city perfect for those seeking outdoor adventures, romantic escapes, and scenic beauty. The local attractions include historic houses, nature reserves, and lakes, offering a blend of culture and adventure suitable for day trips. Visitors can enjoy the rich history of the area and immerse themselves in its picturesque settings, making for an unforgettable holiday experience.

  • National Shrine of the Divine Mercy: A serene shrine exuding cultural ambience, located 14km from Monterey, ideal for spiritual reflection and cultural immersion.
  • Norman Rockwell Museum: An art museum steeped in cultural heritage, situated 16km from Monterey, offering a glimpse into timeless artistic expressions.
  • Lake Buel: A picturesque lake with charming beaches, scenic views and outdoor romance, positioned 5km from Monterey, perfect for a leisurely retreat.

Things to do recommended for couples

Monterey offers enchanting experiences for couples. Enjoy a romantic stroll along the scenic coastline, followed by a candlelit dinner at a charming local restaurant. Don’t miss the breathtaking sunset views from the beach, creating the perfect backdrop for a memorable evening together.

Things to do recommended for families

Families can explore the serene beauty of Lake Garfield, perfect for swimming and picnicking, or discover the scenic hiking trails at the nearby Beartown State Forest, offering stunning views and opportunities for wildlife spotting. A delightful day awaits in the charming surroundings of Monterey.

Things to do recommended for groups

Discover an exhilarating day out at Lime Rock Park, a motor racing venue 31km from Monterey, perfect for those with a taste for sports and adventure. Alternatively, zip through the trees at Catamount Aerial Adventure Park, a zipline and ropes course 23km away, offering a thrilling outdoor escapade.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

What do I need to keep in mind when booking a vacation in Monterey

Whether you're travelling with a group, as a family, with your pets, or seeking extended stays, be sure to refine your search using the appropriate criteria. Here are some Stayz booking tips to help you make the right choices.

  • Traveling to Monterey with a group: Consider how many bedrooms you might require, along with features like a fully-equipped kitchen or an outdoor area for group gatherings. Fortunately, Stayz allows you to filter for these criteria and many more.
  • Traveling to Monterey with young kids: Traveling with young children can present its challenges. It's essential to prioritise their comfort and safety, as well as access to age-appropriate facilities, such as a private swimming pool. It is also wise to consider how close you are to attractions that are family-friendly.
  • Taking your pets with you to Monterey: For many, a family holiday wouldn't be the same without their furry companion by their side. If this resonates with you, take a look at Stayz properties that welcome pets. Many of these pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Monterey: If you're searching for holiday lets offering discounts for monthly stays, you've come to the right place. With the appropriate filter, you can effortlessly locate and save on long-term rentals. Don't forget to include additional amenities like a parking space, a well-equipped kitchen, or a private pool in your search.

Where to stay near Monterey

Discover scenic Monterey, Massachusetts, where the charm of coastal vistas meets a friendly, family-oriented ambiance. Enjoy romantic strolls and outdoor adventures amidst beautiful landscapes and inviting neighbourhoods, perfect for a leisurely family getaway. Experience the relaxed atmosphere and natural splendour that define this lovely destination, offering a truly memorable escape.

  • Lenox: Nestled 21km from Monterey, Lenox is a charming city celebrated for its blend of entertainment, romance, and cultural allure. The region offers a diverse range of experiences, from attending live music concerts and theatrical performances to enjoying winter sports such as skiing. Visitors can also explore the scenic beauty of nearby lakes and mountains, and even participate in events at local conference venues. The city’s unique geographic setting enhances every travel experience, making it a delightful destination for culture enthusiasts and those seeking a romantic retreat alike.
  • The Berkshires: A mere 5km from Monterey, The Berkshires invites travellers with its emphasis on outdoor activities and adventure. Known for its breathtaking scenery, the area is ideal for those keen to embrace nature and the great outdoors. Whether you’re keen on skiing at expansive ski fields and resorts or simply soaking in the picturesque landscapes of lakes and mountains, The Berkshires promises an invigorating experience. The local event conference venues add a touch of cultural sophistication to this adventure-filled region.
  • Great Barrington: Located 13km from Monterey, Great Barrington offers a dynamic blend of adventure and sports with a focus on skiing. This vibrant city caters to enthusiasts of winter sports, providing access to ski fields, resorts, and a variety of related activities. Beyond the slopes, visitors can explore the nearby natural attractions including lakes, mountains, and a national state park, all contributing to a well-rounded travel experience that balances adrenaline with nature’s tranquillity.

Best time to go to Monterey

If you're planning a trip to Monterey, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs from June to August, while off-peak times, like October to December tend to have fewer bookings and better deals.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
January23.2°F (-4.9°C)Light RainMostly CloudyAverageAverage
February24.8°F (-4.0°C)Light RainMostly CloudyAverageAverage
March32.5°F (0.3°C)Light RainMostly CloudyAverageSlightly Low
April44.2°F (6.8°C)Light RainMostly CloudyAverageSlightly Low
May55.9°F (13.3°C)Light RainMostly SunnyAverageAverage
June63.7°F (17.6°C)Light RainMostly SunnySlightly HighAverage
July69.8°F (21.0°C)Light RainMostly SunnySlightly HighSlightly High
August67.8°F (19.9°C)Light RainMostly SunnySlightly HighSlightly High
September60.8°F (16.0°C)Light RainMostly SunnyAverageAverage
October49.8°F (9.9°C)Light RainMostly SunnySlightly LowSlightly Low
November37.8°F (3.2°C)Light RainMostly SunnySlightly LowAverage
December29.7°F (-1.3°C)Light RainMostly CloudySlightly LowSlightly High

Booking with Stayz is a breeze

Are you aiming to save on your upcoming holiday? Being flexible with your travel dates can be beneficial, as prices are subject to change. Moreover, booking a longer stay could unlock substantial savings. To find a Stayz property that suits your budget, simply use our filters to sort by price, location, and type of holiday rental.

Stayz Trips: Planning as easy as it gets

Trip Boards from Stayz offer a user-friendly space where you can create new journeys, continue planning from where you last stopped, or review and organise your itineraries. Your saved or booked properties are neatly grouped into Potential, Upcoming, or Current Trips. To begin using Trip Boards, please visit: https://www.stayz.com.au/trips.

**Based on Vrbo properties bookings.

Why people love visiting scenic 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 trip with friends, holiday rentals offer features like full kitchens and laundry facilities for a more convenient stay.

Activities and attractions in Monterey

Do you want to find top things to see and do while you're in the area? Venture out of your cosy holiday rental and experience everything that Monterey has to offer. These are some of the major attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • Ski Butternut (5.6 mi / 8.9 km)
  • Umpachene Falls Park (6.6 mi / 10.7 km)
  • Wyndhurst Golf & Club (11.7 mi / 18.8 km)
  • Catamount Ski Area (13.7 mi / 22 km)
  • Kennedy Park (14.3 mi / 22.9 km)
  • Bousquet Ski Area (16.7 mi / 26.8 km)

Exploring the natural landscape of Monterey

Whether you're looking for fun outdoor activities or just want to take in the scenery, Monterey is a great place to spend some time outside. Here are a few of the area's most eye-catching features, all within 30 miles (48.2 km) of the city centre:

  • Lake Buel (3.3 mi / 5.4 km)
  • Umpachene Falls Park (6.6 mi / 10.7 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)
  • Lake Mansfield Park (8.1 mi / 13.1 km)

Transport to and around Monterey

The nearest airport is in Pittsfield, MA (PSF-Pittsfield Municipal), located 17.5 mi (28.1 km) from the city centre. 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 most popular type of holiday home accommodation in Monterey?
Houses are the most popular kind of holiday home in Monterey, according to our data. Even if you've got something bigger or smaller in mind, Stayz has holiday homes in loads of sizes and shapes. Look through our options to find your ideal match.
How much does it cost to rent a holiday home in Monterey?
The average price for a holiday home in Monterey is determined by a number of factors, including season, length of stay and property type. Whether you're searching for a sprawling villa with room to move around or a quaint cabin ideal for just you and the kids, just add your dates of travel to find stays with fantastic value.
How much does it cost to rent a beach house in Monterey?
Prices for beach houses in Monterey may vary depending on the style and size of the property and when you're travelling. All you have to do is enter your travel dates into Stayz and how many guests to view available options and prices. From there you can use our filter tool to refine your search results by ratings, nearby activities and more.
Are there pet-friendly holiday homes in Monterey?
With 26 properties that welcome four-legged guests, your furry friend can also come along on your Monterey holiday. Use the filter tool to search our pet-friendly holiday homes and find a stay that'll set tails wagging on Stayz.
Can I rent a house with a pool in Monterey?
Mark the "pool" box in our filter tool and you'll find two houses with private pools in Monterey on Stayz. Morning soak, afternoon splash or midnight swim? Downtime is up to you when your holiday home boasts its own swimming pool.
What are popular home amenities in Monterey?
The most popular home amenities people look for in Monterey are a fireplace, a firepit and tennis. Whether you're going on holiday with friends, family or even pets, Stayz holiday properties include the best amenities for hanging out with the people that matter most.
Are there large group holiday homes in Monterey?
Monterey has six holiday homes that can fit 10 or more guests. These stays come with plenty of space to enjoy good times with your favourite people.
Are there holiday homes in Monterey that welcome kids?
Monterey has 26 family-friendly holiday homes to choose from. And booking a stay that welcomes little ones is easy with our "Properties good for families" filter. Besides having the whole place to yourselves, you'll also get access to conveniences and perks like living rooms, full kitchens and private pools.
What are the top attractions for families in Monterey?
You'll find loads of wonderful things to see and do with the family in Monterey, such as:

  • Umpachene Falls Park
  • County Beach
  • Housatonic River Walk

Are there one-bedroom holiday homes in Monterey?
Yes, Monterey has two one-bedroom homes available. Usually situated in desirable areas because of their smaller size, a one-bedroom property is great if you're getting away with a friend or your partner. And with home comforts like wireless internet and more privacy than a standard hotel, you'll be able to kick back and relax while exploring this terrific destination.
Can I find two-bedroom holiday homes in Monterey?
Gather your loved ones and experience complete comfort and privacy in one of the five two-bedroom holiday properties Monterey has to offer.
Are there holiday homes with WiFi in Monterey?
Whether you'd like to stay in touch with the news, reply to emails or surf social media, there are 11 holiday homes with WiFi in Monterey. Check the "WiFi" box when searching on Stayz and stay connected on your holiday.
How can I find holiday homes with air conditioning in Monterey?
Monterey has 20 holiday homes where you can chill out in air-conditioned comfort. To find a stay on Stayz with this perk, enter your dates of travel and use the convenient filters to select the "air conditioning" box.
How old do you have to be to rent a holiday home in Monterey?
The minimum required age is generally 16, 18 or 21. It can differ between properties on Stayz, so look at the rules of your preferred Monterey stay before booking.
How long can I rent a holiday home in Monterey for?
The length of time you can rent a holiday home in Monterey is up to the property. Simply enter your preferred dates to see a list of options offering extended stays. With loads of creature comforts such as washing machines and air conditioning, as well as some offering discounted weekly or monthly prices, you're sure to find somewhere just right to call your home away from home in Monterey.