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
28 Aug - 30 Aug
In two months
9 Oct - 11 Oct
In three months
6 Nov - 8 Nov
In four months
4 Dec - 6 Dec

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, (1,059 reviews)
"Clean room, friendly staff, nice property"
United States
Joseph
The price is HK$742
HK$1,004 total
includes taxes & fees
31 Aug - 1 Sept
Berkshire Mountain Lodge
Interior

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

Real Estate: Therapy - Lake, Laundry, Love it
Sherwood Forest
The price is HK$839
HK$2,804 total
includes taxes & fees
26 Aug - 27 Aug
Real Estate: Therapy - Lake, Laundry, Love it
TV

3. 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$2,612
HK$5,050 total
includes taxes & fees
1 Sept - 2 Sept
Treetop Hideaway in Tyringham
Outdoor spa tub

4. 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$1,396
HK$3,260 total
includes taxes & fees
9 Sept - 10 Sept
Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
Interior

5. 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$2,353
HK$3,356 total
includes taxes & fees
31 Aug - 1 Sept
Home in Great Barrington
Interior

6. Cozy Riverside Berkshires Retreat

Cozy Riverside Berkshires Retreat
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$1,666
HK$2,580 total
includes taxes & fees
19 Aug - 20 Aug
Cozy Riverside Berkshires Retreat
Beach nearby, sun-loungers, beach towels

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

Hotel-like Balcony Suite—View—Private Wing&Entry—Ensuite Bath—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$1,569
HK$2,252 total
includes taxes & fees
8 Sept - 9 Sept
Hotel-like Balcony Suite—View—Private Wing&Entry—Ensuite Bath—Walk to Town, Lake
Interior

8. 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, (6 reviews)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
United States
Sharon K.
The price is HK$1,334
HK$3,181 total
includes taxes & fees
9 Sept - 10 Sept
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
Smart TV

9. stylish Berkshires Retreat

stylish Berkshires Retreat
Lee
8.8 out of 10, Excellent, (3 reviews)
"Property was just as described, clean and well equipped. Had excellent communication with the host. Would highly recommend staying here."
United States
Donna K.
The price is HK$1,638
HK$3,486 total
includes taxes & fees
19 Aug - 20 Aug
stylish Berkshires Retreat
Interior

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

Sweet Cozy Victorian in Housatonic. Close to everything.
Housatonic
9.8 out of 10, Exceptional, (9 reviews)
The price is HK$1,373
HK$2,497 total
includes taxes & fees
1 Sept - 2 Sept
Sweet Cozy Victorian in Housatonic. Close to everything.
Desk, iron/ironing board, WiFi, bed sheets

11. The Brooks Motel: Exceptional Suite

The Brooks Motel: Exceptional Suite
Hillsdale
7.2 out of 10, Good, (5 reviews)
"Close to the competition I was in"
United States
Joan
The price is HK$1,177
HK$1,494 total
includes taxes & fees
11 Aug - 12 Aug
The Brooks Motel: Exceptional Suite
3 bedrooms, iron/ironing board, WiFi, bed sheets

12. 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$3,248
HK$5,345 total
includes taxes & fees
8 Sept - 9 Sept
Cozy. Clean. Free bagel shop. 3 Fireplaces.
Coffee/tea maker, fridge, microwave, oven

13. 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, (30 reviews)
"This was a wonderful place to stay. We especially loved the easy access to the toys so the kids could start playing while we unloaded the car. It was perfect and just what we needed."
United States
Megan A.
The price is HK$1,094
HK$2,633 total
includes taxes & fees
12 Aug - 13 Aug
Bright, relaxing 2-story built in 1843, with WiFi & smart TVs in charming Dalton
Terrace/patio

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

Enjoy a restful stay with fast internet, smart TV and the company of your pet.
winsted
9.4 out of 10, Exceptional, (50 reviews)
"Fantastic hosts and great facilities would highly recommend"
United States
Steve
The price is HK$988
HK$1,670 total
includes taxes & fees
11 Aug - 12 Aug
Enjoy a restful stay with fast internet, smart TV and the company of your pet.
4 bedrooms, travel cot, WiFi, bed sheets

15. Stylish Mid-century Modern Berkshires Cape

Stylish Mid-century Modern Berkshires Cape
Lee
10.0 out of 10, Exceptional, (6 reviews)
"Besides, it being in a great location, the home is absolutely lovely!"
United States
H B.
The price is HK$3,989
HK$6,848 total
includes taxes & fees
2 Sept - 3 Sept
Stylish Mid-century Modern Berkshires Cape
Smart TV, books

16. Spacious Central Berkshires Home for Groups

Spacious Central Berkshires Home for Groups
Lee
8.0 out of 10, Very good, (1 review)
"This older home was beautifully renovated and was able to easily accommodate our large group."
United States
Beth S.
The price is HK$2,408
HK$4,775 total
includes taxes & fees
19 Aug - 20 Aug
Spacious Central Berkshires Home for Groups
TV, fireplace, printers

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

Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
Great Barrington
10.0 out of 10, Exceptional, (7 reviews)
"Everything was well taken care of, the hosts were extremely nice, and the area is perfect! The city is also different and really cute! Will come back for sure!"
United States
Roberta
The price is HK$4,462
HK$10,452 total
includes taxes & fees
13 Aug - 14 Aug
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
Outdoor dining

18. Stockbridge In-town Escape

Stockbridge In-town Escape
Stockbridge
The price is HK$3,158
HK$4,985 total
includes taxes & fees
30 Aug - 31 Aug
Stockbridge In-town Escape
Coffee/tea maker, fridge, microwave, oven

19. 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)
"We enjoyed our stay and the location. This rustic, spacious loft was great for our brief visit to the Berkshires. "
United States
Joanna P.
The price is HK$596
HK$1,688 total
includes taxes & fees
13 Aug - 14 Aug
NEW RENO - Chalet-style farm loft near Tanglewood
Coffee/tea maker, fridge, microwave, stovetop

20. Berkshire House Stay: 5BR/5BA

Berkshire House Stay: 5BR/5BA
Lee
10.0 out of 10, Exceptional, (22 reviews)
"Wonderful stay, beautiful, well equipped and clean property. Highly recommend for an adult famiky getaway "
United States
jennifer r.
Berkshire House Stay: 5BR/5BA
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

Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South

8/10 Good
"No frills, no thrills. Just fine for a quick stay."
Ann 3-night trip
Posted less than an hour ago
Quality Inn Lee - Lenox South

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 26 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 Lake Buel and Ski Butternut.

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.