Monterey Holiday Rentals

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Our top choices for Monterey holiday rentals

Hupi House: A Peaceful, Wooded, Lakeside Sanctuary

Hupi House: A Peaceful, Wooded, Lakeside Sanctuary
Monterey
10.0 out of 10, Exceptional, (1 review)
"Hupi House was the perfect location for our girls reunion weekend. It was a great mix of a quiet retreat in nature and good meals/shopping in town. The property and house are beautiful and updated. Beds and linens are top notch! Highly recommend."
United States
Kim H.
Hupi House: A Peaceful, Wooded, Lakeside Sanctuary

Wintery Cabin-Berkshires! Dog-friendly. Hike/Ski Appalachian Tr. Walk to lake!

Wintery Cabin-Berkshires! Dog-friendly. Hike/Ski Appalachian Tr. Walk to lake!
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.
Wintery Cabin-Berkshires! Dog-friendly. Hike/Ski Appalachian Tr. Walk to lake!

Wintery Cottage in the Berkshires! Dog friendly, Hot Tub, Hiking, Shopping, Dine

Wintery Cottage in the Berkshires! Dog friendly, Hot Tub, Hiking, Shopping, Dine
Sherwood Forest
9.6 out of 10, Exceptional, (10 reviews)
"Very nice location with tons of privacy, yet not too far from things to do. Very easy for our dog to navigate the property as well."
United States
James D.
The price is NZ$673
includes taxes & fees
29 Jan - 30 Jan
Wintery Cottage in the Berkshires! Dog friendly, Hot Tub, Hiking, Shopping, Dine

Home in Great Barrington

Home in Great Barrington
Great Barrington
9.8 out of 10, Exceptional, (26 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 NZ$429
includes taxes & fees
26 Jan - 27 Jan
Home in Great Barrington

Near Tanglewood: Historic Summer Retreat

Near Tanglewood: Historic Summer Retreat
New Lebanon
9.2 out of 10, Wonderful, (25 reviews)
"Perfect cosy home to stay at for a Berkshire vacation. Easy to get to everything."
United States
Paul S.
The price is NZ$587
includes taxes & fees
21 Jan - 22 Jan
Near Tanglewood: Historic Summer Retreat

The Brooks Motel: Exceptional Suite

The Brooks Motel: Exceptional Suite
Hillsdale
9.2 out of 10, Wonderful, (5 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 NZ$346
includes taxes & fees
3 Feb - 4 Feb
The Brooks Motel: Exceptional Suite

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, (35 reviews)
"Amazing, peaceful, immaculately clean property. "
United States
Cec C.
The price is NZ$738
includes taxes & fees
21 Jan - 22 Jan
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere

Historic Berkshires Home Near Tanglewood, Trails & Wineries

Historic Berkshires Home Near Tanglewood, Trails & Wineries
Lebanon Springs
9.0 out of 10, Wonderful, (21 reviews)
"Great stay in the Berkshires for a wedding. Amanda was very accommodating and communicative. "
United States
Wendy D.
The price is NZ$640
includes taxes & fees
21 Jan - 22 Jan
Historic Berkshires Home Near Tanglewood, Trails & Wineries

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 NZ$542
includes taxes & fees
26 Jan - 27 Jan
Big farmhouse in the foothills of the Berkshires

Sun Filled Lenox Retreat - Minutes to Tanglewood!

Sun Filled Lenox Retreat - Minutes to Tanglewood!
Lee
9.6 out of 10, Exceptional, (4 reviews)
"The house is in a great location and is very user friendly and well equipped. The only suggestion I would make is to put an air conditioner in the third bedroom. Overall, a lovely stay."
United States
Sarah D.
The price is NZ$779
includes taxes & fees
21 Jan - 22 Jan
Sun Filled Lenox Retreat - Minutes to Tanglewood!

Sweet Cozy Victorian in Housatonic. Close to everything.

Sweet Cozy Victorian in Housatonic. Close to everything.
Housatonic
10.0 out of 10, Exceptional, (3 reviews)
"Emma's property is adorable! Clean, well appointed with fresh flowers on the table to great us. Smooth and easy communication from start to finish. Really close to Tanglewood and all the activities Western Massachusetts has to offer."
United States
Cheryl F.
The price is NZ$458
includes taxes & fees
1 Feb - 2 Feb
Sweet Cozy Victorian in Housatonic. Close to everything.

Guesthouse Cabin vacation rentals in Berkshire County

Guesthouse Cabin vacation rentals in Berkshire County
Sheffield
10.0 out of 10, Exceptional, (9 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 NZ$1,172
includes taxes & fees
3 Feb - 4 Feb
Guesthouse Cabin vacation rentals in Berkshire County

Berkshires farm, 30+ guests, 50 acres

Berkshires farm, 30+ guests, 50 acres
2.0 star property
New Lebanon
10.0 out of 10, Exceptional, (1 review)
The price is NZ$2,749
includes taxes & fees
27 Jan - 28 Jan
Berkshires farm, 30+ guests, 50 acres

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!
2.0 star property
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 NZ$845
includes taxes & fees
21 Jan - 22 Jan
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

Family Ski Getaway in the Berkshires

Family Ski Getaway in the Berkshires
Great Barrington
9.2 out of 10, Wonderful, (7 reviews)
"Close to a great bakery and near to a farm market and shopping mall. "
United States
Cristine C.
The price is NZ$504
includes taxes & fees
21 Jan - 22 Jan
Family Ski Getaway in the Berkshires

Suite 4 - Quiet and private accommodations in a country setting.

Suite 4 - Quiet and private accommodations in a country setting.
Spencertown
10.0 out of 10, Exceptional, (3 reviews)
"Happy to have found this lovely place, which is convenient to Tanglewood, pin-drop quiet, and super comfortable. Next time I will avoid VRBO, though, because of its extortionary fees, and book directly with the inn."
United States
jwnyc3
The price is NZ$627
includes taxes & fees
30 Jan - 31 Jan
Suite 4 - Quiet and private accommodations in a country setting.

Suite 3 - Quiet and private accommodations in a country setting.

Suite 3 - Quiet and private accommodations in a country setting.
Spencertown
10.0 out of 10, Exceptional, (1 review)
"Fantastic place to stay!"
United States
James
The price is NZ$467
includes taxes & fees
25 Jan - 26 Jan
Suite 3 - Quiet and private accommodations in a country setting.

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

3-bedroom house in beautiful Berkshires, close to amenities!
Pittsfield
The price is NZ$594
includes taxes & fees
17 Feb - 18 Feb
3-bedroom house in beautiful Berkshires, close to amenities!

Renovated house. Built in 1890s. No neighbors in sight.

Renovated house. Built in 1890s. No neighbors in sight.
2.0 star property
Chatham
The price is NZ$522
includes taxes & fees
25 Jan - 26 Jan
Renovated house. Built in 1890s. No neighbors in sight.
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

Find out more about Monterey

Everything you need to know about Monterey holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Monterey holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Monterey holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Monterey holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Monterey. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Monterey holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Monterey holiday rentals we have selected for you start as low as NZ$429 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Monterey rentals

At Expedia, we put the best Monterey holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Monterey rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Monterey holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Monterey. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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?

Cozy lake house with hot tub. Enjoy everything the Berkshires have to offer!: This holiday home rental outside of Monterey offers a fireplace, a patio and a BBQ to help you feel perfectly comfortable 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 selection of games and 1 hot tub.

How many holiday rentals are there in Monterey?

With 21 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 Otis Ridge.

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.