Photo by Elizabeth Massa Peroulakis

Holiday Rentals in Monterey

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Holiday Rentals in Monterey

Rustic 3bd Lake Front Country Cottage

9.4 out of 10, Exceptional, (3)
"Enjoy our hikes and lake front view as well as kayaking around lake. Pretty area."
Rustic 3bd Lake Front Country Cottage

The Ponds at Foxhollow

3.0 star property
8.6 out of 10, Excellent, (121)
"A good place for vacation that you can enjoy and rest. Very nice and safe place."
The price is €221
includes taxes & fees
13 Jul - 14 Jul
The Ponds at Foxhollow

Charming idyllic farmhouse minutes to Great Barrington MA and Salisbury CT

10.0 out of 10, Exceptional, (12)
"Host was extremely accommodating and house was as-advertised. Great spot to explore great Barrington and surrounding towns! Wood burning stove and fireplaces are a real highlight! Fire pit is not advertised on listing but there is one. Would recommend highly"
Charming idyllic farmhouse minutes to Great Barrington MA and Salisbury CT

Berkshires sanctuary with outdoor living area & firepit. 8minutes to Tanglewood!

10.0 out of 10, Exceptional, (7)
"Delightful property, worked well for our needs"
Berkshires sanctuary with outdoor living area & firepit. 8minutes to Tanglewood!

Deluxe Queen Room with 2 Queen Beds

2.0 star property
2.0 out of 10, (1)
"Wrote to them asking for early check in around 1pm for 3pm check in, no reply. Not a problem, early check in isn’t a guarantee. Get to the property 10 mins before check in and no one is there, wait around for 30 mins, no one there, no one answering in the app, no one picking up the phone. By 340 called Vrbo who canceled my reservation around 4pm the property called asked if I left, I said I did and booked somewhere else, no apology, no reasoning, just “ok” and hung up. Thankfully there was...
The price is €136
includes taxes & fees
6 Jul - 7 Jul
Deluxe Queen Room with 2 Queen Beds

Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns

9.6 out of 10, Exceptional, (41)
"We had a wonderful stay. The cabin was clean and comfortable! "
Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns

The Kemble- Built by a US Secretary of State in Lenox

10.0 out of 10, Exceptional, (17)
"Loved the property. Perfect for our gathering."
The Kemble- Built by a US Secretary of State in Lenox

Lakefront Berkshires Retreat w/ Deck, Dock & Boat!

7.2 out of 10, Good, (44)
"The property was great overall. I was not impressed with finding cobwebs around furniture, or with the hair in the shower and the toothpaste on the sink, mirror mirrorandbehind behind"
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!

Spacious 5-bedroom house in charming Lee with WiFi

The price is €754
includes taxes & fees
16 Jul - 17 Jul
Spacious 5-bedroom house in charming Lee with WiFi

Cozy Modern 4 Bedroom Log Cabin on 45 Secluded Acres in the Berkshires

Cozy Modern 4 Bedroom Log Cabin on 45 Secluded Acres in the Berkshires

Big farmhouse in the foothills of the Berkshires

10.0 out of 10, Exceptional, (136)
"This was the perfect place to stay while we visited family in Massachusetts. The place was kept beautifully and had all of the amenities to make our visit comfortable. We will definitely book this place in the future."
The price is €316
includes taxes & fees
30 Jun - 1 Jul
Big farmhouse in the foothills of the Berkshires

Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table

9.8 out of 10, Exceptional, (144)
"Plenty of space to stay with friends but have your own space. Lots of outdoors activities in the area which was perfect. Clean, comfortable and pool table and hot tub were a plus! "
Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table

A Beautiful Log Cabin In The Woods, On Pontoosuc Lake, Yet Near Everything

10.0 out of 10, Exceptional, (119)
"Had an amazing weekend in this beautiful cabin! Highly recommend staying here! Great host, amazing views, beautiful property!"
A Beautiful Log Cabin In The Woods, On Pontoosuc Lake, Yet Near Everything

Peace and quiet on the lake

9.6 out of 10, Exceptional, (216)
"This property was in an incredible location with a nice cozy feel. It was perfect for my family of 6. I highly recommend this place!"
Peace and quiet on the lake

Imagine Being Lakeside This Summer! Book Now!

10.0 out of 10, Exceptional, (16)
"Had a great trip. House was perfect for our group. Comfy beds, great fireplace and nice location near lots of local attractions."
Imagine Being Lakeside This Summer! Book Now!

Exclusive Estate, Heated Yearround Outdoor Pool

9.6 out of 10, Exceptional, (19)
"Lovely horse farm in the woods but not too far from useful shops. We had a great experience."
Exclusive Estate, Heated Yearround Outdoor Pool

Spacious Berkshire Summer Rental, Private Dock on Lake 3 BR/2b

9.6 out of 10, Exceptional, (98)
"Great place!"
Spacious Berkshire Summer Rental, Private Dock on Lake 3 BR/2b

Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets.

9.8 out of 10, Exceptional, (11)
"Very friendly hosts, great location. "
Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets.

Lakefront Retreat on Robinson Pond - Stunning Sunrise

10.0 out of 10, Exceptional, (22)
"The house is in a great location with easy access to great food and activities. The house is extremely clean and the decor is charming and modern. Vincent was extremely communicative. All in, it was a wonderful stay and we look forward to returning!"
Lakefront Retreat on Robinson Pond - Stunning Sunrise

Quintessential 6-BR Berkshires Lodge

10.0 out of 10, Exceptional, (13)
"The house was perfect for our group of couples and young kids. Large bedrooms and beautiful property "
Quintessential 6-BR Berkshires Lodge
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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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?

Deluxe Queen Room with 2 Queen Beds: This holiday home rental outside of Monterey is equipped with an outdoor pool, air conditioning and WiFi to help you feel comfortable during your stay.

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?

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 Ski Butternut and Umpachene Falls Park.

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.