Monterey Vacation Rentals from $173: Search Short-Term Rentals

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Our top choices for Monterey vacation rentals

Berkshires Mountain Retreat w Panoramic Views, 5 Decks, Hot Tub, near Tanglewood

New Lebanon

$730 nightly

Jul 21 - Jul 22

Total with taxes and fees

Coffee/tea maker, fridge, microwave, oven

Cozy 1-bedroom studio in serene Great Barrington with AC

Great Barrington

Deborah S.

$139 nightly

Jul 27 - Jul 28

Total with taxes and fees

Berkshire Mountain Lodge

Pittsfield

Joseph

$155 nightly

Aug 19 - Aug 20

Total with taxes and fees

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

Sherwood Forest

Frank M.

$387 nightly

Jul 28 - Jul 29

Total with taxes and fees

Real Estate: Therapy - Lake, Laundry, Love it

Sherwood Forest

$305 nightly

Jul 23 - Jul 24

Total with taxes and fees

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.

$653 nightly

Jul 22 - Jul 23

Total with taxes and fees

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

Sherwood Forest

Sharon K.

$403 nightly

Aug 3 - Aug 4

Total with taxes and fees

Home in Great Barrington

Great Barrington

Julie J.

$362 nightly

Jul 29 - Jul 30

Total with taxes and fees

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Top Monterey Hotel Reviews

The Little Lion

10/10 Excellent

"Always love to stay here! Thanks"

Berkshires Untold

8/10 Good

"Its an interesting experience in that we thought we were staying at a hotel/ inn. The pictures and the website lead one to believe that but when we got there, we saw a motel. Nothing wrong with that but we felt we had been misinformed. They push the pcitures of the Club room which looks like an inn/ restaurant but that is the front of the building but attached to it is the motel where you stay. Again, once we knew that, we were fine but honestly, we were looking for more of an Inn or a hotel/ inn. It comes over as a glorified motel. The staff is wonderful and the Club room is a nice addition but I really thought the advertising was duplicitous. We were talking to a friend about it and she agreed that she also felt misled. I'm not sure that they have to do this but I guess if you put motel, you wouldn't get as much interest nor could you charge the same? Other than that, no comment."

The Yankee Inn

10/10 Excellent

"The room was neat and had access to outside to enjoy sitting. The fridge in the room was a convenient size for cold and frozen foods. The staff was responsive to issues, even when I told them they could wait to fix it until after we left (it was fixed quickly. The breakfast was excellent and offered a nice variety. Would happily stay here again."

The Red Lion Inn

8/10 Good

"Dinner in the main dining room was amazing! Food delicious and staff attentive. We stayed in the Stephen’s House and arrived in the dark. It was not well lighted and 184 was up a huge flight of stairs. We had to haul up too many bags! We would have done a sm. 1 night bag If we had known this was a second floor. Beds were very uncomfortable soft and towels with stains. The kitchen area was without a refrigerator turned on and no ice. The front desk attendant was very efficient and ran some ice over! We love Red Lion Inn and found some things a bit off this time."

FairBridge Inn Express

8/10 Good

"Room was clean and in excellent condition - apparently they have totally renovated since earlier reviews that mentioned severe problems. The exterior could use some paint, but the room was perfectly clean and fairly spacious. All the little things, like good A/C, shower temp/pressure, a working mini-fridge, etc., were completely fine. Complaints: I couldn't get the WiFi to work. Also: it's not in the most scenic part of Pittsfield, but it's just minutes from the nicer areas, and a short walk to fast food or decent chain restaurants like Friendlys, Applebees, and Starbucks."

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 $173 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

Berkshires Mountain Retreat w Panoramic Views, 5 Decks, Hot Tub, near Tanglewood

Cozy 1-bedroom studio in serene Great Barrington with AC

Berkshire Mountain Lodge

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

Real Estate: Therapy - Lake, Laundry, Love it

Treetop Hideaway in Tyringham

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

Home in Great Barrington

Cozy Riverside Berkshires Retreat

stylish Berkshires Retreat

The Brooks Motel: Exceptional Suite

Big farmhouse in the foothills of the Berkshires

Peaceful and cozy 1 bed 1 bath in quaint Winchester

Guesthouse Cabin vacation rentals in Berkshire County

Beachwood Cottage

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

Sweet Cozy Victorian in Housatonic. Close to everything.

Walk into town, soak up sun on enclosed porch & steps away from nature trails!

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

The Brooks Motel: Exceptional Suite

Find vacation rentals that suit your style

Top Monterey Hotel Reviews

The Little Lion

Find out more about Monterey

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