Monterey Vacation Rentals from $155: Search Short-Term Rentals

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Our top choices for Monterey vacation rentals

1. Treetop Hideaway in Tyringham

Monterey

"We had coordinated an early check-in, but when we arrived, the house hadn’t been cleaned yet which was a miscommunication. I reached out to Catherine and she promptly responded and got the cleaners RIGHT over. The house was spotless and in wonderful condition for the rest of our stay, and it was dealt with very quickly and wonderfully. Would definitely stay again. The house was great for our girls trip. Also the beds are very comfortable!! "

Samantha G.

$606 nightly

Sep 2 - Sep 3

Total with taxes and fees

2. Cozy Riverside Berkshires Retreat

Great Barrington

Colin E.

$286 nightly

Aug 25 - Aug 26

Total with taxes and fees

3. Berkshire Mountain Lodge

Pittsfield

Joseph

$138 nightly

Aug 30 - Aug 31

Total with taxes and fees

Coffee/tea maker, fridge, microwave, oven

4. Home in Great Barrington

Great Barrington

HEATHER G.

$366 nightly

Aug 12 - Aug 13

Total with taxes and fees

5. Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing

Sherwood Forest

Frank M.

$385 nightly

Sep 7 - Sep 8

Total with taxes and fees

3 bedrooms, iron/ironing board, WiFi, bed sheets

6. Cozy. Clean. Free bagel shop. 3 Fireplaces.

Great Barrington

Mary R.

$637 nightly

Sep 1 - Sep 2

Total with taxes and fees

7. Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room

Great Barrington

Roberta

$1,189 nightly

Aug 13 - Aug 14

Total with taxes and fees

8. Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!

Sherwood Forest

Sharon K.

$389 nightly

Sep 7 - Sep 8

Total with taxes and fees

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Top Monterey Hotel Reviews

Berkshire Mountain Lodge

8/10 Good

"Very nice space with a full kitchen. You can definitely stay here for a week comfortably. Personally, I didn’t think the bed or the pillows were that comfortable but other than that, it was great."

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

8/10 Good

"Stayed for two nights in a 2 bedroom villa. The place was very clean, beds and bedding were comfortable. The place could stand a refresh - more so the kitchen and bathrooms but not terribly awful by any means. The area of the property where we stayed was quiet and peaceful."

The Red Lion Inn

10/10 Excellent

"Escaped into another world on each floor's hallway-the memorabilia and artwork spoke of an honest, New England history. The atmosphere was perfect for a genuine, original immersion into New England's past and LOVED going up and down the 150yr old elevator! Meals delicious w/excellent service. Only one issue we had: the AC in the room was difficult to adjust and were quite chilled even w/turning the thermostat up to 80 deg!!!!!!!!! as suggested by the front desk. Shall make this a yearly visit!"

Quality Inn Great Barrington

10/10 Excellent

"Very nice front desk staff-courteous, upbeat, helpful. Room was clean but leftover trash in bin and no ice tray in refrigerator. VERY comfortable bed. Train in middle of the night was a throwback experience to a different age-i liked it but some would be frightened of the noise. Excellent location."

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 $155 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.

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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?

Lakefront Retreat with Stunning Views | Forget-Me-Not by AvantStay: This highly rated vacation home rental in Monterey is located on a lake and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a garden, a selection of games, and a hot tub so you can immerse yourself in your vacation.

How many vacation rentals are there in Monterey?

With 26 Expedia vacation rentals, you're sure to find just the right place for your Monterey stay.

What can I see and do in Monterey?

Cultural attractions include Bidwell House Museum, whereas Lake Garfield is a spot to enjoy nature. In the larger area, you’ll find Lake Buel and Ski Butternut.

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.

Monterey Vacation Rentals

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Check prices for these dates

Our top choices for Monterey vacation rentals

1. Treetop Hideaway in Tyringham

2. Cozy Riverside Berkshires Retreat

3. Berkshire Mountain Lodge

4. Home in Great Barrington

5. Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing

6. Cozy. Clean. Free bagel shop. 3 Fireplaces.

7. Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room

8. Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!

9. Guesthouse Cabin vacation rentals in Berkshire County

10. stylish Berkshires Retreat

11. Stylish Mid-century Modern Berkshires Cape

12. Sweet Cozy Victorian in Housatonic. Close to everything.

13. Big farmhouse in the foothills of the Berkshires

14. Spacious Central Berkshires Home for Groups

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

16. Real Estate: Therapy - Lake, Laundry, Love it

17. Enjoy a restful stay with fast internet, smart TV and the company of your pet.

18. The Brooks Motel: Exceptional Suite

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

20. Gorgeous Mountain Views Retreat: Family & Nature

Find vacation rentals that suit your style

Top Monterey Hotel Reviews

Berkshire Mountain Lodge

Find out more about Monterey

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