Monterey Holiday Rentals

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Check prices for these dates

In two weeks
13 Mar - 15 Mar
In two months
24 Apr - 26 Apr
In three months
22 May - 24 May
In four months
19 Jun - 21 Jun

Our top choices for Monterey holiday rentals

Interior

Guesthouse Cabin vacation rentals in Berkshire County

Guesthouse Cabin vacation rentals in Berkshire County
Sheffield
10.0 out of 10, Exceptional, (10 reviews)
"Great place. I highly recommend for a group or family. Amazing views! Beautiful property very private and quiet. Cabin was also very well stocked and had great outdoor space. "
United States
deborah d.
The price is HK$3,129
HK$5,479 total
includes taxes & fees
2 Mar - 3 Mar
Guesthouse Cabin vacation rentals in Berkshire County
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, (34 reviews)
"A college friends' retreat was fantastic, in part due to the location, cleanliness and amenities in this 3 bedroom house. Furniture was comfortable and kitchen was stocked with everything we needed. "
United States
cathy c.
The price is HK$2,339
HK$5,086 total
includes taxes & fees
2 Mar - 3 Mar
Walk into town, soak up sun on enclosed porch & steps away from nature trails!
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, (36 reviews)
"Amazing, peaceful, immaculately clean property. "
United States
Cec C.
The price is HK$2,011
HK$4,195 total
includes taxes & fees
30 Mar - 31 Mar
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
Exterior

Dugway Hideaway Walking Distance to Lime Rock Park

Dugway Hideaway Walking Distance to Lime Rock Park
Salisbury
9.2 out of 10, Wonderful, (15 reviews)
"Super clean, great communication and Super location if you are going to the track. Love my stay there, will definitely do it again and definitely recommend."
United States
Brig
The price is HK$1,565
HK$2,417 total
includes taxes & fees
2 Mar - 3 Mar
Dugway Hideaway Walking Distance to Lime Rock Park
TV

Treetop Hideaway in Tyringham

Treetop Hideaway in Tyringham
Monterey
9.0 out of 10, Wonderful, (10 reviews)
"This was the perfect location for our mom and daughters weekend! Spacious comfortable. Our only regret was that we didn’t stay longer!"
United States
Sarah B.
The price is HK$2,026
HK$4,325 total
includes taxes & fees
2 Mar - 3 Mar
Treetop Hideaway in Tyringham
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, (143 reviews)
"Perfect spot for a family celebration!"
United States
Kerry P.
The price is HK$1,565
HK$2,845 total
includes taxes & fees
2 Mar - 3 Mar
Big farmhouse in the foothills of the Berkshires
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, (3 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$4,450
HK$10,423 total
includes taxes & fees
2 Mar - 3 Mar
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
Interior

Secluded Sophistication in the Berkshires - 49 Acres of Quiet Luxury in Becket.

Secluded Sophistication in the Berkshires - 49 Acres of Quiet Luxury in Becket.
Becket
10.0 out of 10, Exceptional, (1 review)
"Beautiful home, attentive host. Location is as peaceful as can be. "
United States
Rick M.
The price is HK$2,691
HK$4,911 total
includes taxes & fees
2 Mar - 3 Mar
Secluded Sophistication in the Berkshires - 49 Acres of Quiet Luxury in Becket.
Exterior detail

3-bedroom house in beautiful Berkshires, close to amenities!

3-bedroom house in beautiful Berkshires, close to amenities!
Pittsfield
The price is HK$1,408
HK$2,403 total
includes taxes & fees
2 Mar - 3 Mar
3-bedroom house in beautiful Berkshires, close to amenities!
Smart TV, books

Berkshires Cottage! Dog friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing

Berkshires Cottage! Dog friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
Sherwood Forest
9.8 out of 10, Exceptional, (14 reviews)
"Nicole was very attentive and very quick to respond to any question we had. Her cottage was perfect for a quiet getaway, just what everybody needs!"
United States
Matthew F.
The price is HK$1,253
HK$3,086 total
includes taxes & fees
12 Mar - 13 Mar
Berkshires Cottage! Dog friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
Property grounds

Cheerful 3-bedroom cottage with woodstove

Cheerful 3-bedroom cottage with woodstove
Sheffield
10.0 out of 10, Exceptional, (42 reviews)
"The property was centrally located for skiing, and was a comfortable stay."
United States
Kelly R.
The price is HK$1,854
HK$3,950 total
includes taxes & fees
8 Mar - 9 Mar
Cheerful 3-bedroom cottage with woodstove
Interior

Family Ski Getaway in the Berkshires

Family Ski Getaway in the Berkshires
Great Barrington
9.0 out of 10, Wonderful, (11 reviews)
"Close to a great bakery and near to a farm market and shopping mall. "
United States
Cristine C.
The price is HK$1,510
HK$2,368 total
includes taxes & fees
14 Mar - 15 Mar
Family Ski Getaway in the Berkshires
Fridge, microwave, oven, stovetop

Home in Great Barrington

Home in Great Barrington
Great Barrington
9.8 out of 10, Exceptional, (27 reviews)
"Great stay in a cool, new space, totally walkable to Railroad St. I would definitely go back to GB and would try to stay here again. "
United States
Cameron M.
The price is HK$1,260
HK$2,107 total
includes taxes & fees
2 Mar - 3 Mar
Home in Great Barrington
Outdoor dining

3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
Pittsfield
7.8 out of 10, Good, (7 reviews)
"The space was well situated to our plans, food,lake and hiking and very clean but smelled sooo strongly of dogs that we limited our time inside."
United States
Liz V.
The price is HK$2,105
HK$3,811 total
includes taxes & fees
2 Mar - 3 Mar
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
Interior

Luxury Barn Retreat — All-Season Escape Awaits!

Luxury Barn Retreat — All-Season Escape Awaits!
East Chatham
10.0 out of 10, Exceptional, (2 reviews)
"Accommodations were even better than we expected. The rooms were very clean, and there are unique (and sometimes whimsical, other times thought-provoking) decorations/pictures throughout the barn. The kitchen was basically a chef’s kitchen- all appliances were top notch. The backyard was spacious, and even contained a (non-working) pay phone booth! My wife loved the swinging two-seat chair on the porch! "
United States
Timothy S.
The price is HK$2,621
HK$4,872 total
includes taxes & fees
2 Mar - 3 Mar
Luxury Barn Retreat — All-Season Escape Awaits!

The Brooks Motel: Exceptional Suite

The Brooks Motel: Exceptional Suite
Hillsdale
7.0 out of 10, Good, (4 reviews)
"Location was good for what we wanted. The people involved responded quickly. The bed was very comfortable. Reasonably clean, the coffee pot had leftover coffee in it and a dirty spoon on the counter. The biggest issue was the musty odor."
United States
John P.
The price is HK$1,244
HK$1,568 total
includes taxes & fees
2 Mar - 3 Mar
The Brooks Motel: Exceptional Suite
3 bedrooms, iron/ironing board, WiFi, bed sheets

Cozy. Clean. Free bagel shop. 3 Fireplaces.

Cozy. Clean. Free bagel shop. 3 Fireplaces.
Great Barrington
10.0 out of 10, Exceptional, (1 review)
"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$2,660
HK$4,597 total
includes taxes & fees
2 Mar - 3 Mar
Cozy. Clean. Free bagel shop. 3 Fireplaces.
Fridge, microwave, oven, stovetop

Spacious 5-bedroom house in charming Lee with WiFi

Spacious 5-bedroom house in charming Lee with WiFi
Lee
8.8 out of 10, Excellent, (3 reviews)
"House was clean and made our Thanksgiving great with it's size and amenities. "
United States
Khalil S.
The price is HK$3,716
HK$6,738 total
includes taxes & fees
16 Mar - 17 Mar
Spacious 5-bedroom house in charming Lee with WiFi
Smart TV, books

Sun Filled Lenox Retreat - Minutes to Tanglewood!

Sun Filled Lenox Retreat - Minutes to Tanglewood!
Lee
9.6 out of 10, Exceptional, (4 reviews)
"Very charming, comfortable, and clean. It was in a great location and only minutes away from a lot of sightseeing locations. House management was very accommodating and friendly. I would stay here again."
United States
Paulo I.
The price is HK$1,408
HK$3,574 total
includes taxes & fees
2 Mar - 3 Mar
Sun Filled Lenox Retreat - Minutes to Tanglewood!
TV, fireplace, DVD player, books

Berkshires farm, 30+ guests, 50 acres

Berkshires farm, 30+ guests, 50 acres
New Lebanon
10.0 out of 10, Exceptional, (1 review)
The price is HK$7,776
HK$14,423 total
includes taxes & fees
3 Mar - 4 Mar
Berkshires farm, 30+ guests, 50 acres
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 Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

10/10 Excellent
"Clean room, breakfast was good👍"
Antonina 1-night trip
Posted 5 days ago
The Yankee, Trademark Collection by Wyndham

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!

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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?

Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country: This holiday home rental outside of Monterey is located near skiing, and has a fireplace, a patio 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. You can relax into your holiday with a garden and a selection of games.

How many holiday rentals are there in Monterey?

With 22 Expedia holiday rentals, you're guaranteed to find just the right place for your Monterey stay.

What can I see and do in Monterey?

Enjoy the area's cultural attractions such as Bidwell House Museum, or get outdoors into nature at a spot like Lake Buel. In the wider area, you’ll find Tyringham Cobble 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.