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
7 Aug - 9 Aug
In two months
18 Sept - 20 Sept
In three months
16 Oct - 18 Oct
In four months
13 Nov - 15 Nov

Our top choices for Monterey holiday rentals

Outdoor dining

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

Berkshires Mountain Retreat w Panoramic Views, 5 Decks, Hot Tub, near Tanglewood
New Lebanon
The price is HK$3,726
HK$6,412 total
includes taxes & fees
22 Jul - 23 Jul
Berkshires Mountain Retreat w Panoramic Views, 5 Decks, Hot Tub, near Tanglewood
Coffee/tea maker, fridge, microwave, oven

Cozy 1-bedroom studio in serene Great Barrington with AC

Cozy 1-bedroom studio in serene Great Barrington with AC
Great Barrington
8.0 out of 10, Very good, (1 review)
"Though small, the apartment was efficient, clean, and well stocked in paper type supplies. The kitchen was also efficient though lacking in some basic utensils. They say location, location, location. And, yes, the location is excellent. An easy, short, and nice walk into town . 8"
United States
Deborah S.
The price is HK$811
HK$1,213 total
includes taxes & fees
9 Aug - 10 Aug
Cozy 1-bedroom studio in serene Great Barrington with AC
Lobby

Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (1,015 reviews)
"Clean room, friendly staff, nice property"
United States
Joseph
The price is HK$1,048
HK$1,345 total
includes taxes & fees
19 Aug - 20 Aug
Berkshire Mountain Lodge
Outdoor spa tub

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, (15 reviews)
"Great place and welcoming stay!"
United States
Frank M.
The price is HK$1,503
HK$3,387 total
includes taxes & fees
28 Jul - 29 Jul
Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
Interior

Real Estate: Therapy - Lake, Laundry, Love it

Real Estate: Therapy - Lake, Laundry, Love it
Sherwood Forest
The price is HK$737
HK$2,671 total
includes taxes & fees
23 Jul - 24 Jul
Real Estate: Therapy - Lake, Laundry, Love it
TV

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$2,909
HK$5,412 total
includes taxes & fees
22 Jul - 23 Jul
Treetop Hideaway in Tyringham
Interior

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, (5 reviews)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
United States
Sharon K.
The price is HK$1,517
HK$3,402 total
includes taxes & fees
27 Jul - 28 Jul
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
Coffee/tea maker, fridge, microwave, oven

Home in Great Barrington

Home in Great Barrington
Great Barrington
9.6 out of 10, Exceptional, (34 reviews)
"Adorable guest home in Great Barrington! Light and bright. Perfect space for our family of 4. Well equipped kitchen and easy walk to downtown and groceries at the co-op. Would definitely stay here again!"
United States
Julie J.
The price is HK$2,117
HK$3,170 total
includes taxes & fees
29 Jul - 30 Jul
Home in Great Barrington
Interior

Cozy Riverside Berkshires Retreat

Cozy Riverside Berkshires Retreat
Great Barrington
9.4 out of 10, Exceptional, (19 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$1,905
HK$2,864 total
includes taxes & fees
12 Aug - 13 Aug
Cozy Riverside Berkshires Retreat
Smart TV

stylish Berkshires Retreat

stylish Berkshires Retreat
Lee
9.0 out of 10, Wonderful, (2 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$1,602
HK$3,348 total
includes taxes & fees
28 Jul - 29 Jul
stylish Berkshires Retreat
Desk, iron/ironing board, WiFi, bed sheets

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$1,176
HK$1,493 total
includes taxes & fees
22 Jul - 23 Jul
The Brooks Motel: Exceptional Suite
Property grounds

Big farmhouse in the foothills of the Berkshires

Big farmhouse in the foothills of the Berkshires
Russell
10.0 out of 10, Exceptional, (148 reviews)
"Great location"
United States
Will G.
The price is HK$1,490
HK$2,776 total
includes taxes & fees
2 Aug - 3 Aug
Big farmhouse in the foothills of the Berkshires
2 bedrooms, free WiFi, bed sheets

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$847
HK$1,581 total
includes taxes & fees
26 Jul - 27 Jul
Peaceful and cozy 1 bed 1 bath in quaint Winchester
Interior

Guesthouse Cabin vacation rentals in Berkshire County

Guesthouse Cabin vacation rentals in Berkshire County
Sheffield
10.0 out of 10, Exceptional, (12 reviews)
"Really enjoyed the cabin. The pictures don’t do the view justice as it’s an amazing vista overlooking the Berkshires. "
United States
Tom S.
The price is HK$3,136
HK$5,438 total
includes taxes & fees
3 Aug - 4 Aug
Guesthouse Cabin vacation rentals in Berkshire County
Beach nearby

Beachwood Cottage

Beachwood Cottage
Stockbridge
9.8 out of 10, Exceptional, (6 reviews)
"We had a great week at this cottage and Daryl was a responsive and helpful host. Our kids are already asking to return next year."
United States
Christine P.
The price is HK$2,744
HK$5,001 total
includes taxes & fees
6 Aug - 7 Aug
Beachwood Cottage
Property grounds

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

Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
Hinsdale
9.8 out of 10, Exceptional, (38 reviews)
"Gorgeous place.Great stay.Will diff be backG"
United States
Gerard C.
The price is HK$1,947
HK$3,997 total
includes taxes & fees
23 Jul - 24 Jul
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
Interior

Sweet Cozy Victorian in Housatonic. Close to everything.

Sweet Cozy Victorian in Housatonic. Close to everything.
Housatonic
9.8 out of 10, Exceptional, (7 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$2,548
HK$3,985 total
includes taxes & fees
2 Aug - 3 Aug
Sweet Cozy Victorian in Housatonic. Close to everything.
Exterior

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

Walk into town, soak up sun on enclosed porch & steps away from nature trails!
Stockbridge
10.0 out of 10, Exceptional, (39 reviews)
"Charming house in a wonderful setting in the Berkshires. "
United States
Mark Cristen J.
The price is HK$5,088
HK$8,582 total
includes taxes & fees
22 Jul - 23 Jul
Walk into town, soak up sun on enclosed porch & steps away from nature trails!
TV, fireplace, printers

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, (6 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$4,438
HK$10,413 total
includes taxes & fees
23 Jul - 24 Jul
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
Desk, iron/ironing board, WiFi, bed sheets

The Brooks Motel: Exceptional Suite

The Brooks Motel: Exceptional Suite
Hillsdale
8.4 out of 10, Very good, (6 reviews)
"Clean, industrial, very comfy bed, easy to book and to check in and out. Would stay again."
United States
Deidre H.
The price is HK$1,239
HK$1,572 total
includes taxes & fees
27 Jul - 28 Jul
The Brooks Motel: Exceptional Suite
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

The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel

10/10 Excellent
"As of late we have been traveling with our small dog. Most hotels that accept pets you end up in the most dinghy room and not kept well. Not here the room was clean well kept and no odor. "
Robert 1-night trip
Posted less than an hour ago
The Black Swan Lee - Lenox, an Ascend Collection Hotel

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.