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Monterey Vacation Rentals

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    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
Oct 17 - Oct 19
In two months
Nov 28 - Nov 30
In three months
Dec 26 - Dec 28
In four months
Jan 23 - Jan 25

Vacation Rentals in Monterey

The Ponds at Foxhollow
Indoor pool, outdoor pool, pool umbrellas, sun loungers

The Ponds at Foxhollow

3.0 star property
8.6 out of 10, Excellent, (131)
"We were 4 adult friends sharing a 2-bedroom and enjoyed the size of the space and the location of the condo was under a 10 min drive to all the sights"
The Ponds at Foxhollow
Spacious 5-bedroom house in charming Lee with WiFi
5 bedrooms, iron/ironing board, WiFi, bed sheets

Spacious 5-bedroom house in charming Lee with WiFi

$707 nightly
The price is $790
Oct 7 - Oct 8
Total with taxes and fees
Spacious 5-bedroom house in charming Lee with WiFi
Amore Estate - beautiful room with many places to explore and relax in.
Fridge, microwave, oven, stovetop

Amore Estate - beautiful room with many places to explore and relax in.

9.0 out of 10, Wonderful, (28)
"Beautiful, spacious house in a great location!"
Amore Estate - beautiful room with many places to explore and relax in.
Bright, relaxing 2-story built in 1843, with WiFi & smart TVs in charming Dalton
Fridge, microwave, oven, stovetop

Bright, relaxing 2-story built in 1843, with WiFi & smart TVs in charming Dalton

2.0 star property
10.0 out of 10, Exceptional, (12)
"My husband and I and our little dog had an amazing stay in Dalton. The space was clean, perfectly decorated and comfortable! We only stayed a few days and wanted to stay so much longer! Coffee for the humans and frog toys and treats for Sully! Very convenient to all the Berkshires has to offer. Communication with the owner was prompt and always helpful!! Highly recommend and hope to return. "
Bright, relaxing 2-story built in 1843, with WiFi & smart TVs in charming Dalton
Peace and quiet on the lake
Interior

Peace and quiet on the lake

9.6 out of 10, Exceptional, (222)
"Comfortable home with amazing view. Enjoyed taking a walk around the lake (1 hour approx). Had an amazing dinner at Dream Away lodge which is 15 minutes away. "
Peace and quiet on the lake
Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating
Exterior

Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating

9.6 out of 10, Exceptional, (224)
"Great place to get away from it all. Very quiet. Short drive to trailheads and restaurants and all the other hustle and bustle of the Berkshires."
Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating
The Kemble- Built by a US Secretary of State in Lenox
Exterior detail

The Kemble- Built by a US Secretary of State in Lenox

10.0 out of 10, Exceptional, (17)
"Loved the property. Perfect for our gathering."
The Kemble- Built by a US Secretary of State in Lenox
The Blue Elm - A Historic Berkshire Cottage
Exterior

The Blue Elm - A Historic Berkshire Cottage

10.0 out of 10, Exceptional, (10)
"Everything was great...and beautiful!"
$362 nightly
The price is $404
Oct 5 - Oct 6
Total with taxes and fees
The Blue Elm - A Historic Berkshire Cottage
Charming Cabin Lake Rights, Private Dock 3 bedroom, 2 bath. Sleeps 7.
Terrace/patio

Charming Cabin Lake Rights, Private Dock 3 bedroom, 2 bath. Sleeps 7.

9.6 out of 10, Exceptional, (62)
"This cottage never disappoints! Great place to relax, refresh and spend time with friends and family. Decor is perfect and the view and dock are off the charts. "
Charming Cabin Lake Rights, Private Dock 3 bedroom, 2 bath. Sleeps 7.
Enjoy comfortable elegance in this secluded grand home located in town
Exterior

Enjoy comfortable elegance in this secluded grand home located in town

10.0 out of 10, Exceptional, (73)
"Great location for access to both Tanglewood and Lenox center. "
Enjoy comfortable elegance in this secluded grand home located in town
Premiere Berkshire Country Estate w/ Private Pool & Tennis Court - 5 mins to GB!
Fridge, microwave, oven, stovetop

Premiere Berkshire Country Estate w/ Private Pool & Tennis Court - 5 mins to GB!

10.0 out of 10, Exceptional, (55)
"We loved Manor Lane! It had every amenity you could ask for. The house is fun and charming and there are thoughtful touches everywhere you look! We had fun watching movies in the living room, playing games in the lounge, cooking family meals in the spectacular kitchen and playing tennis in the sunshine. A perfect 10!"
Premiere Berkshire Country Estate w/ Private Pool & Tennis Court - 5 mins to GB!
Guesthouse Cabin vacation rentals in Berkshire County
Dining

Guesthouse Cabin vacation rentals in Berkshire County

10.0 out of 10, Exceptional, (9)
"Really enjoyed the cabin. The pictures don’t do the view justice as it’s an amazing vista overlooking the Berkshires. "
$622 nightly
The price is $695
Oct 1 - Oct 2
Total with taxes and fees
Guesthouse Cabin vacation rentals in Berkshire County
Berkshires Family Inn – For Getaways & Big Groups! Walkable to Butternut!
Smart TV, fireplace, DVD player

Berkshires Family Inn – For Getaways & Big Groups! Walkable to Butternut!

10.0 out of 10, Exceptional, (27)
"Spacious, welcoming, so well stocked, we felt lucky to find the property."
Berkshires Family Inn – For Getaways & Big Groups! Walkable to Butternut!
Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table
Outdoor dining

Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table

9.8 out of 10, Exceptional, (148)
"We had a fabulous stay at this lovely home in the Berkshires! The house was well equipped with everything needed to make our stay with our family so enjoyable. Great communication with the host in helping to resolve a small issue with loss of power on 2nd floor but was easily resolved."
Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table
Charming idyllic farmhouse minutes to Great Barrington MA and Salisbury CT
Exterior

Charming idyllic farmhouse minutes to Great Barrington MA and Salisbury CT

9.8 out of 10, Exceptional, (21)
"We had a wonderful time, the property is lovely and the house is delightful."
Charming idyllic farmhouse minutes to Great Barrington MA and Salisbury CT
Elegant 19th Century New England Newly Renovated 1BR Vacation Rental
Terrace/patio

Elegant 19th Century New England Newly Renovated 1BR Vacation Rental

9.4 out of 10, Exceptional, (68)
"Location cannot be outdone. This rental was spacious, well stocked, extremely clean, and a very responsive kind owner. Highly recommended:)"
Elegant 19th Century New England Newly Renovated 1BR Vacation Rental
Antique Farmhouse Totally Restored
Exterior

Antique Farmhouse Totally Restored

10.0 out of 10, Exceptional, (91)
"Enjoyed the property, location and charming house that was well stocked with everything we needed."
Antique Farmhouse Totally Restored
Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets.
Property grounds

Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets.

9.8 out of 10, Exceptional, (19)
"Very friendly hosts, great location. "
Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets.
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
Exterior

Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere

9.8 out of 10, Exceptional, (30)
"Hindsale-perfect little hideaway, minutes from where we needed to be. Harrison’s little home was equipped with amenities/tasteful luxuries, and cozy nooks. We all loved the loft-could not believe how large the space was! Hot tub nights-perfect ending:) Thank you, Harrison."
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
Private Island - Largest Fresh Water Reservoir in Mass
Interior

Private Island - Largest Fresh Water Reservoir in Mass

8.8 out of 10, Excellent, (8)
"We had a great time. The owner Bill was a great host."
Private Island - Largest Fresh Water Reservoir in Mass
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Monterey Hotel Reviews

Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites

10/10 Excellent
"Staff is friendly and accommodating "
Karol 1-night trip
Posted 5 days ago
Best Western Plus Berkshire Hills Inn & Suites

Find out more about Monterey

Find out more about Monterey

Everything you need to know about Monterey vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Monterey vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Monterey vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Monterey vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Monterey. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Monterey in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $404 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Monterey rentals

At Expedia, we put the best Monterey vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Monterey rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Monterey vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Monterey. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

Explore a world of travel with Expedia

Frequently asked questions

Can I find vacation rentals in Monterey?

Yes, we give you a choice of vacation rentals close to the most popular attractions in Monterey, or you can select a secluded option if you'd like a relaxing place to stay. Monterey is known for its forests.

What are some of the best vacation home rentals that Monterey has to offer?

Spacious 5-bedroom house in charming Lee with WiFi: This vacation home near Monterey offers a fireplace, a barbecue grill, and laundry facilities to help you feel perfectly comfortable in your new surroundings. Kitchen amenities like a dishwasher and a microwave can make your vacation run smoothly.

How many vacation rentals are there in Monterey?

With 25 Expedia vacation rentals, you're sure to find just the right place for your Monterey stay.

What can I see and do in Monterey?

Enjoy the area's cultural attractions such as Bidwell House Museum, or get outdoors into nature at a spot like Lake Buel. In the larger area, you’ll find Ski Butternut and Goose Pond Reservation.

What are vacation rentals like in Monterey?

Vacation rentals are privately owned properties you can reserve for several days or more in Monterey. Vacation rentals provide amenities such as hot tubs, fire pits, and patios so you'll have a home away from home. If you're concerned about a sanitized environment, vacation rentals can provide a sense of security away from shared hotel elevators and busy reception areas while still allowing you the enjoyment of travel. You'll also have more space in a vacation rental than in a hotel, which makes a vacation rental an attractive option for families.