A lake surrounded by autumn-colored trees reflecting on the water.

Monterey Holiday Rentals

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Check prices for these dates

In two weeks
25 Sept - 27 Sept
In two months
6 Nov - 8 Nov
In three months
4 Dec - 6 Dec
In four months
1 Jan - 3 Jan

Our top choices for Monterey holiday rentals

Lobby

1. Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (1,132 reviews)
"Clean & comfortable stay"
United States
Robert
The price is HK$624
HK$872 total
includes taxes & fees
1 Oct - 2 Oct
Berkshire Mountain Lodge
Private kitchen

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

Cozy 1-bedroom studio in serene Great Barrington with AC
Great Barrington
9.4 out of 10, Exceptional, (3 reviews)
"Great location, great property, great host"
United States
Shelly B.
The price is HK$882
HK$1,292 total
includes taxes & fees
14 Sept - 15 Sept
Cozy 1-bedroom studio in serene Great Barrington with AC
Interior

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

Real Estate: Therapy - Lake, Laundry, Love it
Sherwood Forest
8.0 out of 10, Very good, (1 review)
"Very good trip overall. Great location. Just a few things needed to make it over the top!"
United States
William C B.
The price is HK$455
HK$2,338 total
includes taxes & fees
13 Sept - 14 Sept
Real Estate: Therapy - Lake, Laundry, Love it
Interior

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

Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
Sherwood Forest
10.0 out of 10, Exceptional, (9 reviews)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
United States
Sharon K.
The price is HK$1,143
HK$2,941 total
includes taxes & fees
8 Sept - 9 Sept
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
Outdoor spa tub

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

Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
Sherwood Forest
9.8 out of 10, Exceptional, (16 reviews)
"Great place and welcoming stay!"
United States
Frank M.
The price is HK$1,256
HK$3,084 total
includes taxes & fees
8 Sept - 9 Sept
Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
Living area

6. Treetop Hideaway in Tyringham

Treetop Hideaway in Tyringham
Monterey
9.2 out of 10, Wonderful, (11 reviews)
"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!! "
United States
Samantha G.
The price is HK$2,211
HK$4,525 total
includes taxes & fees
21 Sept - 22 Sept
Treetop Hideaway in Tyringham
Outdoor dining

7. Cozy Camper tucked into the woods

Cozy Camper tucked into the woods
Sandisfield
The price is HK$1,425
HK$1,820 total
includes taxes & fees
14 Sept - 15 Sept
Cozy Camper tucked into the woods
Private kitchen

8. Home in Great Barrington

Home in Great Barrington
Great Barrington
9.8 out of 10, Exceptional, (38 reviews)
"Perfect location to walk into town - clean, light, airy and neat space. Enjoyable visit!"
United States
HEATHER G.
The price is HK$1,496
HK$2,416 total
includes taxes & fees
8 Sept - 9 Sept
Home in Great Barrington
Room

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

Quintessential Berkshire Escape - Artist Home, Tucked Away in Nature
Otis
The price is HK$1,722
HK$2,676 total
includes taxes & fees
8 Sept - 9 Sept
Quintessential Berkshire Escape - Artist Home, Tucked Away in Nature
Interior

10. Riverside Retreat in the Berkshires

Riverside Retreat in the Berkshires
Great Barrington
9.6 out of 10, Exceptional, (23 reviews)
"We had a great stay here with Study, shooting my college thesis film. I'd highly recommend this wonderfully decorated place with such a great host :)"
United States
Colin E.
The price is HK$1,588
HK$2,483 total
includes taxes & fees
8 Sept - 9 Sept
Riverside Retreat in the Berkshires
Beach

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

Hotel-like Balcony Suite—Private Wing&Entry—Ensuite Bath—View—Walk to Town, Lake
Great Barrington
10.0 out of 10, Exceptional, (3 reviews)
"We had a wonderful visit. They were so accommodating and great location to downtown. We’ll stay again!"
United States
Kristin O.
The price is HK$1,741
HK$2,750 total
includes taxes & fees
14 Sept - 15 Sept
Hotel-like Balcony Suite—Private Wing&Entry—Ensuite Bath—View—Walk to Town, Lake
Interior

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

Sweet Cozy Victorian in Housatonic. Close to everything.
Housatonic
9.8 out of 10, Exceptional, (10 reviews)
"The host did a great job of prepping the place and being welcoming to us. It was clean and thoughtfully designed. So happy we found this spot!"
United States
Peter S.
The price is HK$1,372
HK$2,505 total
includes taxes & fees
10 Sept - 11 Sept
Sweet Cozy Victorian in Housatonic. Close to everything.
Property grounds

13. Big farmhouse in the foothills of the Berkshires

Big farmhouse in the foothills of the Berkshires
Russell
10.0 out of 10, Exceptional, (150 reviews)
"Great location"
United States
Will G.
The price is HK$1,490
HK$2,760 total
includes taxes & fees
8 Sept - 9 Sept
Big farmhouse in the foothills of the Berkshires
Private kitchen

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

Bright, relaxing 2-story built in 1843, with WiFi & smart TVs in charming Dalton
Dalton
9.8 out of 10, Exceptional, (31 reviews)
"Excellent area for hiking the Berkshires! House is clean, comfortable, and perfect for cooking a quick dinner after showering off the mud and pine needles. Dog friendly. Right off the main street of a very nice neighborhood."
United States
Elizabeth G.
The price is HK$1,023
HK$2,535 total
includes taxes & fees
10 Sept - 11 Sept
Bright, relaxing 2-story built in 1843, with WiFi & smart TVs in charming Dalton
Property grounds

15. Cheerful 3-bedroom cottage with woodstove

Cheerful 3-bedroom cottage with woodstove
Sheffield
10.0 out of 10, Exceptional, (43 reviews)
"The property was centrally located for skiing, and was a comfortable stay."
United States
Kelly R.
The price is HK$1,937
HK$4,064 total
includes taxes & fees
22 Sept - 23 Sept
Cheerful 3-bedroom cottage with woodstove
Room

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

Cozy. Clean. Free bagel shop. 3 Fireplaces.
Great Barrington
10.0 out of 10, Exceptional, (2 reviews)
"The host was very responsive and friendly. The house was well equipped and very comfortable. We did get breakfast at the Great Barrington Bagel Company and had a great breakfast. Highly recommend!"
United States
Mary R.
The price is HK$2,487
HK$4,346 total
includes taxes & fees
14 Sept - 15 Sept
Cozy. Clean. Free bagel shop. 3 Fireplaces.
Terrace/patio

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

Ideal location for summer and winter activities with plenty of outdoor space.
Hillsdale
9.8 out of 10, Exceptional, (79 reviews)
"Excellent host!"
United States
Kenny
The price is HK$1,568
HK$2,977 total
includes taxes & fees
8 Sept - 9 Sept
Ideal location for summer and winter activities with plenty of outdoor space.
Private kitchen

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

NEW RENO - Chalet-style farm loft near Tanglewood
New Lebanon
8.6 out of 10, Excellent, (7 reviews)
"Awesome location went for a solo trip w the purpose of spending time alone in nature with myself and god got exactly that calm quiet beautiful scenic area great room and service would book again"
United States
Varun M.
The price is HK$549
HK$1,631 total
includes taxes & fees
10 Sept - 11 Sept
NEW RENO - Chalet-style farm loft near Tanglewood
Interior

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

Peaceful and cozy 1 bed 1 bath in quaint Winchester
Winchester
The price is HK$974
HK$1,743 total
includes taxes & fees
13 Sept - 14 Sept
Peaceful and cozy 1 bed 1 bath in quaint Winchester
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

Hotel On North

Hotel On North

10/10 Excellent
"This is a hidden gem in the Berkshires. The hotel is clean, rooms are gorgeous and the staff was really helpful."
Brian 1-night trip
Posted 10 hours ago
Hotel On North

Find out more about Monterey

Search for holiday rentals in Monterey on Expedia! You can easily find your home rentals, villas, holiday apartments in Monterey using one of the methods below:

  • View our selection of featured holiday rentals in Monterey
  • Use the map to find apartments and other holiday homes in the Monterey neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Monterey while they last

Look no further and take a look at our great range of rental properties in Monterey!

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.