Discover a selection of 361 vacation rentals in Monterey, MA that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo vacation homes have the best amenities for hanging out with the people that matter most, including swimming pools and WiFi. Prices start at $165 per night, and houses and cabins are popular options for a stay in Monterey. Either way, you'll find a rental for everyone's needs.
Top rated rentals — Monterey
Destination guide

Beautiful Monterey will entice you

The forests, wildlife and parks display a scene truly unique to Monterey. This scenic city is known for its hiking, fishing and boating. Many rental homes come with outdoor spaces, separate dining areas and full kitchens, perfect if you want to enjoy some home-cooked meals.


Activities and attractions in Monterey

Do you want to find top things to see and do during your stay? Venture out of your cozy vacation rental and check out everything that makes Monterey a one-of-a-kind vacation spot. These are some of the top attractions to see, all within 30 miles (48.2 km) of the city center:

  • Dry Hill (3.6 mi / 5.7 km)
  • Les Trois Emme Winery (4.3 mi / 6.9 km)
  • Ski Butternut (5.2 mi / 8.3 km)
  • Questing (5.8 mi / 9.3 km)
  • Otis Ridge (6.2 mi / 10 km)
  • Greenock Country Club (7.4 mi / 12 km)
Natural features

Exploring the natural features in Monterey

Whether you're looking for fun outdoor activities or just want to appreciate the scenery, Monterey is a great spot to appreciate mother nature. Here are a few of the area's most stunning sights, all within 30 miles (48.2 km) of the city center:

  • Tyringham Cobble (3.8 mi / 6.2 km)
  • Beartown State Forest (3.9 mi / 6.2 km)
  • Goose Pond Reservation (6.1 mi / 9.8 km)
  • Lake Mansfield Park (7.5 mi / 12.1 km)
  • Umpachene Falls Park (7.6 mi / 12.2 km)
  • Berkshire Botanical Garden (9.3 mi / 14.9 km)
How to get there

Traveling to and around Monterey

Fly into Pittsfield, MA (PSF-Pittsfield Municipal), the closest airport, located 16.1 mi (25.9 km) from the city center. If you're unable to find a flight that fits your schedule, you could book a flight to Westfield, MA (BAF-Barnes Municipal), which is 25.8 mi (41.5 km) away.

How many vacation rentals are available around Monterey, MA?

Our 2021 property listings offer a large selection of 361 vacation rentals around Monterey. From 288 house rentals to 55 cabin rentals, find a unique house rental for you to enjoy a memorable holiday or a weekend with your family and friends.

Can I rent Houses in Monterey?

Yes, of course. Vrbo has 288 Houses in Monterey. Our other popular types of vacation rentals in Monterey include:

  • Cabins: 55 rentals available
  • Cottages: 49 rentals available
  • Condos/Apartments: 32 rentals available

But you can also enjoy a great stay in one of our other vacation rentals including Bungalows and more.

Can I find a vacation rental with pool in Monterey?

Yes, you can select your preferred vacation rental with pool among our 59 vacation rentals with pool available in Monterey. Please use our search bar to access the selection of vacation rentals available.