Monterey Holiday Rentals from NZ$189: Search Short-Term Rentals

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Our top choices for Monterey holiday rentals

A spacious lobby with a fireplace, multiple seating areas, and a chandelier.

1. Berkshire Mountain Lodge

Pittsfield

Robert

includes taxes & fees

1 Oct - 2 Oct

A compact kitchen with a refrigerator, oven, microwave, and coffee maker.

2. Cozy 1-bedroom studio in serene Great Barrington with AC

Great Barrington

Shelly B.

includes taxes & fees

11 Sept - 12 Sept

A spacious living area with a large sofa, a kitchen island with bar stools, a wooden staircase, and a television displaying a movie.

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

Sherwood Forest

William C B.

includes taxes & fees

13 Sept - 14 Sept

A cozy attic bedroom with a sloped ceiling, wooden beams, a large window with a view of trees, a bed, a desk, and a kitchenette.

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

Sherwood Forest

Sharon K.

includes taxes & fees

7 Sept - 8 Sept

A hot tub with a string of lights above it, set against a dark night sky.

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

Sherwood Forest

Frank M.

includes taxes & fees

7 Sept - 8 Sept

A spacious cabin with large windows, a gray sofa, and a wooden ceiling.

6. 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.

includes taxes & fees

21 Sept - 22 Sept

A garden area with potted plants, a wooden fence, and outdoor furniture.

7. Cozy Camper tucked into the woods

Sandisfield

includes taxes & fees

16 Sept - 17 Sept

A modern kitchen with a central island, wooden beams, and a view to the outdoors.

8. Home in Great Barrington

Great Barrington

HEATHER G.

includes taxes & fees

8 Sept - 9 Sept

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Top Monterey Hotel Reviews

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

10/10 Excellent

"Clean, great location and affordable."

Quality Inn Great Barrington

10/10 Excellent

"Staff at the front desk were welcoming, friendly, and helpful throughout my stay. The room was very clean. The bed was comfortable. The shower had good water pressure and plenty of hot water. The room was equipped with a refrigerator, microwave, and coffeemaker, as well as a TV, and the WiFi worked fine. The breakfast area in the office building had several tables, and included a "make-your-own-waffles" station (love that!), buffet-style scrambled eggs and sausage, as well pre-packaged muffins. Yogurt and other items were available in a refrigerator. Parking was in a a space right outside the room entrance on the first floor, which was ground level. The location is on Main Street (Route 7) in Great Barrington, but set back from the road so there's less traffic noise. There are restaurants and shops in easy walking distance of this motel, and it is an easy drive of 15 mins. or so to the nearby towns of Lenox, Lee (location of Mass. Turnpike exit/entrance), West Stockbridge, and Stockbridge that have their own shops, restaurants, sites, and venues of interest. I highly recommend this motel."

Lakefront Retreat with Stunning Views | Forget-Me-Not by AvantStay

8/10 Good

"The house & location are wonderful. We were there for a week & we totally enjoyed ourselves. The difference between a good house & an excellent house is that everything works in an excellent house. There are a few items that do need attention. (1) The lock on the back door to the patio was broken when we arrived. We were all surprised it was not fixed before our arrival. I reported it the first day but it never was fixed. A temporary solution was offered the day before we left. (2) The water pressure is poor. A plumber was sent out the first day to try to fix it. An air lock was the problem and venting that was only a temporary solution. We were a total of 6 adults & only one person could take a shower at a time. If two people showered, one shower would just trickle. If the sink in the kitchen was on at the same time, one of the showers would stop for a minute. An air lock in the pipes would ensue. For a house that is supposed to sleep 10, that is just not acceptable. (3) Hot water. The last person to shower never had enough. (4) No dressers. 3 couples with clothes for a week. The limited shelving in the closets were not enough. (5) No full length mirrors. (6) The internet kicks you off randomly. (7) The pool table would be great if there weren’t an obvious slant that gathered the balls on one side of the table. The surface of the table has a tear & there was no chalk for the cue sticks. (8) The dock has no cleats. There are poles at each end of the dock that be used."

Find out more about Monterey

Everything you need to know about Monterey holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Monterey holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Monterey holiday 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 months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Monterey holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Monterey holiday rentals we have selected for you start as low as NZ$189 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Monterey rentals

At Expedia, we put the best Monterey holiday 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 holiday.

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.

Frequently asked questions

Can I find holiday rentals in Monterey?

Yes, there are holiday rentals close to the most popular sights in Monterey, or you can select a more secluded option if you're looking for a relaxing stay. Monterey is known for its forests.

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

Lakefront Retreat with Stunning Views | Forget-Me-Not by AvantStay: This highly rated holiday home rental in Monterey is located on a lake, and has a fireplace, a balcony and a BBQ 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 that you can cook with friends or family. It offers a garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday.

How many holiday rentals are there in Monterey?

With 25 Expedia holiday rentals, you're guaranteed 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 wider area, you’ll find Mount Wilcox and Lake Buel.

What are holiday rentals like in Monterey?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Monterey. Holiday rentals feature extras like laundry facilities and kitchens so you'll be comfy for your stay. If you're concerned about a clean environment, a holiday rental can offer a sense of privacy away from shared hotel lifts and bustling concierge desks while still allowing you the excitement and enjoyment of travel. You'll also have more space in a holiday rental than in a traditional hotel, which makes a holiday rental an attractive choice for family trips.

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Check prices for these dates

Our top choices for Monterey holiday rentals

1. Berkshire Mountain Lodge

2. Cozy 1-bedroom studio in serene Great Barrington with AC

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

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

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

6. Treetop Hideaway in Tyringham

7. Cozy Camper tucked into the woods

8. Home in Great Barrington

9. Quintessential Berkshire Escape - Artist Home, Tucked Away in Nature

10. Cozy Riverside Berkshires Retreat

11. Hotel-like Balcony Suite—Private Wing&Entry—Ensuite Bath—View—Walk to Town, Lake

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

13. Big farmhouse in the foothills of the Berkshires

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

15. Cheerful 3-bedroom cottage with woodstove

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

17. The Brooks Motel: Exceptional Suite

18. Ideal location for summer and winter activities with plenty of outdoor space.

19. NEW RENO - Chalet-style farm loft near Tanglewood

20. Peaceful and cozy 1 bed 1 bath in quaint Winchester

Find holiday rentals that suit your style

Top Monterey Hotel Reviews

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

Berkshire Mountain Lodge

The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Red Lion Inn

Holiday Inn Express Hotel & Suites Great Barrington by IHG

FairBridge Inn Express

Quality Inn Great Barrington

Hotel On North

Lakefront Retreat with Stunning Views | Forget-Me-Not by AvantStay

Find out more about Monterey

Frequently asked questions

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