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Monterey holiday rentals

We found 545 holiday rentals — enter your dates for availability

Discover a selection of 22 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:29 May - 5 Jun

Image gallery for Waterfront Cottage 10 Min From Great Barrington

Property grounds
10 out of 10, Exceptional, (100 reviews)
Exceptional
(100 reviews)

Waterfront Cottage 10 Min From Great Barrington

New Marlborough

8% off
Price is S$3,150
for 7 nights, 1 cottage
S$450 per night
includes taxes & fees
Waterfront Cottage 10 Min From Great Barrington

Find spaces that suit your style

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  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

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)
  • Otis Ridge (5.8 mi / 9.3 km)
  • Wyndhurst Golf & Club (11.7 mi / 18.8 km)
  • Maple Corner Farm Cross Country Ski Area (13.5 mi / 21.8 km)
  • Catamount Ski Area (13.7 mi / 22 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)
  • Tyringham Cobble (5.2 mi / 8.3 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 rental accommodation in Monterey?
Houses are the most popular kind of holiday rental in Monterey, according to our data. Even if you've got something bigger or smaller in mind, Vrbo 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 rental 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 Vrbo 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 rentals 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 rentals and find a stay that'll set tails wagging on Vrbo.
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 Vrbo. Morning soak, afternoon splash or midnight swim? Downtime is up to you when your holiday home boasts its own swimming pool.
What are popular rental amenities in Monterey?
The most popular rental 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, Vrbo holiday properties include the best amenities for hanging out with the people that matter most.
Are there large group holiday rentals 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 rentals in Monterey that welcome kids?
Monterey has 26 family-friendly holiday rentals 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 rentals in Monterey?
Yes, Monterey has two one-bedroom rentals 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 rentals 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 rentals 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 Vrbo and stay connected on your holiday.
How can I find holiday rentals with air conditioning in Monterey?
Monterey has 20 holiday rentals where you can chill out in air-conditioned comfort. To find a stay on Vrbo 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 rental in Monterey?
The minimum required age is generally 16, 18 or 21. It can differ between properties on Vrbo, so look at the rules of your preferred Monterey stay before booking.
How long can I rent a holiday rental in Monterey for?
The length of time you can rent a holiday rental 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.

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