Monterey Vacation Rentals from AED 470: Search Short-Term Rentals

Check prices for these dates

In two weeks

In two months

In three months

In four months

Our top choices for Monterey vacation rentals

Coffee/tea maker, fridge, microwave, oven

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

Great Barrington

bob i.

AED 605 total

includes taxes & fees

7 Sep - 8 Sep

2. Berkshire Mountain Lodge

Pittsfield

Robert

AED 470 total

includes taxes & fees

31 Aug - 1 Sep

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

Sherwood Forest

William C B.

AED 1,112 total

includes taxes & fees

13 Sep - 14 Sep

4. 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.

AED 2,139 total

includes taxes & fees

21 Sep - 22 Sep

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

Sherwood Forest

Frank M.

AED 1,457 total

includes taxes & fees

7 Sep - 8 Sep

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

Sherwood Forest

Sharon K.

AED 1,401 total

includes taxes & fees

9 Sep - 10 Sep

7. Cozy Riverside Berkshires Retreat

Great Barrington

Colin E.

AED 1,155 total

includes taxes & fees

8 Sep - 9 Sep

8. Home in Great Barrington

Great Barrington

HEATHER G.

AED 1,493 total

includes taxes & fees

3 Sep - 4 Sep

View all properties

Find vacation rentals that suit your style

Apartments

Aparthotels

Save an average of 15% on thousands of hotels when you're signed in

Sign in

Sign up, it's free

Top Monterey Hotel Reviews

The Cornell Inn, Lenox & The Berkshires

10/10 Excellent

"Room was"

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

10/10 Excellent

"Nice, well-maintained property, everything was very clean. The breakfast nook was not overly crazy crowded, which is really good traveling with young children. The staff even apologized for not having the waffle maker as a new one was being delivered. The hot tub was also a plus!"

The Black Swan Lee - Lenox, an Ascend Collection Hotel

8/10 Good

"I am not a person who usually writes a review but I loved the place. Room was great. Staff was great. I had never been to an Indian restaurant but everywhere I went people raved about I so we went and it was wonderful. Only a few small issues. The fan in our bathroom room needs attention. Very loud. Something is failing. The wifi was very weak in my room. Kept cutting out. and just one other suggestion. The balcony on the upper level should have privacy screens on the sides. Other wise I would absolutely go back."

The Little Lion

8/10 Good

"Clean and comfortable room for reasonable price. Central area/lobby is nice place to sit and read, relax, and/or eat breakfast (coffee provided). Also red Adirondack chairs up on hill behind rooms and small tables/chairs in front of some rooms. Can use the outdoor pool and whirl pool a few miles away at the Red Lion Inn, which is desirable feature on summer days. A few negatives. While the building and rooms are set back from the road, it’s located off a busy road that goes between Stockbridge and Great Barrington. You will hear the cars during the day. It’s also not what I would consider an “Inn” as it’s really a motel. It used to be the Briarcliff Motel before the Red Lion Inn purchased it. Any questions, requests, or comments need to contact them as the Little Lion didn’t have any full time staff and no one at front desk in the lobby when we stayed. We received text with code for room door."

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 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?

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

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.

Room 1

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Monterey vacation rentals

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

2. Berkshire Mountain Lodge

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

4. Treetop Hideaway in Tyringham

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

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

7. Cozy Riverside Berkshires Retreat

8. Home in Great Barrington

9. stylish Berkshires Retreat

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

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

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

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

14. The Brooks Motel: Exceptional Suite

15. Cheerful 3-bedroom cottage with woodstove

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

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

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

19. Stylish Mid-century Modern Berkshires Cape

20. Big farmhouse in the foothills of the Berkshires

Find vacation rentals that suit your style

Top Monterey Hotel Reviews

The Cornell Inn, Lenox & The Berkshires

Berkshires Untold

Holiday Inn Club Vacations Oak 'n Spruce Resort

Quality Inn Lee - Lenox South

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

The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Yankee Inn

The Red Lion Inn

The Little Lion

Frequently asked questions

Go further with the Expedia app