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Holiday homes in Monterey You’ll Love

Top-Rated Monterey Holiday homes for Every Budget and Style!

Looking for a holiday home in Monterey (Massachusetts)? Browse a wide range of vacation rentals – from cozy retreats to spacious family homes – starting at just $51.00 per night. Whether you are planning a weekend getaway or a longer stay, you will find the perfect home away from home in the heart of Monterey.

We found 10 Holiday-homes in Monterey and the surrounding area (within 40 miles)

The Mill River Cabin with Fireplace and River View! in Mill River, USA

The Mill River Cabin with Fireplace and...

Holiday home in Mill River near Monterey, Massachusetts
The Mill River Cabin with Fireplace and River View! is located in Mill River, just 8 miles from Great Falls and 8.2 miles from Canaan Village Historic...
  • Parking
  • Pets allowed

Exceptional 6 Reviews 10.0

from $283.34 Show details »

Cabin with 3 Acres, Tennis Courts By 4 Ski Mtns in Sandisfield, USA

Cabin with 3 Acres, Tennis Courts By 4 S...

Holiday home in Sandisfield near Monterey, Massachusetts
Cabin with 3 Acres, Tennis Courts By 4 Ski Mtns offers accommodations in Sandisfield, 17 miles from Norman Rockwell Museum and 18 miles from Tanglewoo...
  • Parking
  • Pets allowed
  • Spa and wellness centre

Very good 1 Reviews 8.0

from $311.16 Show details »

Berkshire Vacation Rentals: Peaceful Post and Beam Loft Sleeps 9 in New Marlborough, USA

Berkshire Vacation Rentals: Peaceful Pos...

Holiday home in New Marlborough near Monterey, Massachusetts , Hartsville Mill River Road 1089
Berkshire Vacation Rentals: Peaceful Post and Beam Loft Sleeps 9 offers accommodations in New Marlborough, 15 miles from Norman Rockwell Museum and 17...
  • Parking
  • Pets allowed

Exceptional 2 Reviews 9.5

from $261.02 Show details »

Half Moon by AvantStay 4BR Cabin w Large Deck Yard w Patio Outdoor Dining in Great Barrington, USA

Half Moon by AvantStay 4BR Cabin w Large...

Holiday home in Great Barrington near Monterey, Massachusetts
Half Moon by AvantStay 4BR Cabin w Large Deck Yard w Patio Outdoor Dining offers accommodations in Great Barrington, 11 miles from Norman Rockwell Mus...
  • Pets allowed

Good 1 Reviews 7.0

from $299.28 Show details »

Cozy Great Barrington Home about 1 Mi to Ski Resort! in Great Barrington, USA

Cozy Great Barrington Home about 1 Mi to...

Holiday home in Great Barrington near Monterey, Massachusetts
Cozy Great Barrington Home about 1 Mi to Ski Resort! is located in Great Barrington, just 14 miles from Cranwell Spa & Golf Club and 14 miles from Tan...
  • Parking

Good 1 Reviews 7.0

from $487.09 Show details »

Monterey Haven Less Than half Mi to Lake Garfield with Kayaks in Monterey, USA

Monterey Haven Less Than half Mi to Lake...

Holiday home in Monterey, Massachusetts
Monterey Haven Less Than half Mi to Lake Garfield with Kayaks offers accommodations in Monterey, 17 miles from Norman Rockwell Museum and 18 miles fro...
  • Parking

no reviews

from $336.06 Show details »

Lake Haven in Monterey, USA

Lake Haven

Holiday home in Monterey, Massachusetts , 33 Lime Rock Lane
Lake Haven is located in Monterey, just 13 miles from Cranwell Spa & Golf Club and 15 miles from Norman Rockwell Museum.
  • Parking
  • Pets allowed
  • Family rooms

no reviews

from $90.00 Show details »

Cozy Monterey Home with Porch Walk to Lake Garfield in Monterey, USA

Cozy Monterey Home with Porch Walk to La...

Holiday home in Monterey, Massachusetts
Cozy Monterey Home with Porch Walk to Lake Garfield is located in Monterey, just 14 miles from Norman Rockwell Museum and 15 miles from Tanglewood.
  • Parking

Fabulous 1 Reviews 9.0

from $339.73 Show details »

Monterey Home with Hot Tub, Pool and Game Room! in Monterey, USA

Monterey Home with Hot Tub, Pool and Gam...

Holiday home in Monterey, Massachusetts
Monterey Home with Hot Tub, Pool and Game Room! offers accommodations in Monterey, 14 miles from Norman Rockwell Museum and 15 miles from Tanglewood.
  • Parking
  • Outdoor pool
  • Swimming Pool

no reviews

from $1.157.96 Show details »

Berkshires Cabin 2 Mi to Appalachian Trail! in Otis, USA

Berkshires Cabin 2 Mi to Appalachian Tra...

Holiday home in Otis near Monterey, Massachusetts
Berkshires Cabin 2 Mi to Appalachian Trail! offers accommodations in Otis, 16 miles from Tanglewood and 16 miles from Tanglewood Musical Center.
  • Parking
  • Spa and wellness centre

Fabulous 1 Reviews 9.0

from $331.11 Show details »

Number of Holiday homes in Monterey 10
Number of guest ratings 2
Average price per night $352.00
Lowest price per night $51,00
Highest price per night $4.626,94

Top 10 Cheapest Holiday-homes in Monterey

Discover the Cheapest Holiday-homes in Monterey – Ranked by Lowest Nightly Rates.

Top 10 Most Booked Holiday-homes in Monterey

Check out the Most Booked Holiday-homes in Monterey – Based on Guest Popularity.

Holiday homes in Monterey (Massachusetts), comfortable and familiar

Staying in a holiday or vacation home in Monterey can be a great alternative to a hotel or resort. They can range from small cottages to luxurious villas, and are often located in popular tourist destinations such as beaches or mountains. One of the main benefits is the privacy and flexibility that comes with having your own space. Unlike a hotel room, a holiday home provides you with a living area, kitchen, and sometimes even outdoor space, allowing you to cook your own meals, relax in comfort, and enjoy the company of your friends or family without the interruptions of other guests.

Holiday homes often offer more space than a hotel room. This can be particularly useful for families or groups of friends traveling together, who may need more than one room or want to avoid the cramped feeling of a single hotel room. They can also provide a more authentic travel experience, allowing guests to immerse themselves in the local culture and lifestyle. This can be particularly appealing for those who prefer to stay in quieter, residential areas away from the hustle and bustle of tourist hotspots.

Find the best Holiday home in Monterey for your needs

Holiday homes should offer a comfortable and enjoyable stay, providing all the necessary amenities and conveniences to make your vacation experience memorable. At a minimum, your holiday home in Monterey should offer a clean and well-maintained living space with comfortable furnishings, adequate lighting, and climate control.

In addition to basic amenities such as a fully equipped kitchen, comfortable bedding, and clean linens and towels, holiday homes should also offer modern conveniences such as Wi-Fi, cable or streaming TV, and laundry facilities. A private outdoor space, such as a balcony or terrace, can also add to the overall enjoyment. They can also offer additional features such as a swimming pool, hot tub, or outdoor grill. Location is also important, for example, close to popular tourist attractions, restaurants and shopping areas.

Accommodation data and pictures provided by Booking.com