Photo by Fun Travelog

Monterey Vacation Rentals

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
Jan 4 - Jan 5
Tomorrow
Jan 5 - Jan 6
Next weekend
Jan 9 - Jan 11
In two weeks
Jan 16 - Jan 18

Our top choices for Monterey vacation rentals

Fridge, microwave, oven, stovetop
Hupi House: A Peaceful, Wooded, Lakeside Sanctuary

Hupi House: A Peaceful, Wooded, Lakeside Sanctuary

Hupi House: A Peaceful, Wooded, Lakeside Sanctuary
Monterey
10.0 out of 10, Exceptional, (1)
"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.
The price is ￥133,000
￥274,217 total
includes taxes & fees
Jan 18 - Jan 19
Hupi House: A Peaceful, Wooded, Lakeside Sanctuary
Outdoor dining
Wintery Cabin-Berkshires! Dog-friendly. Hike/Ski Appalachian Tr. Walk to lake!

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)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
United States
Sharon K.
The price is ￥22,867
￥58,653 total
includes taxes & fees
Jan 6 - Jan 7
Wintery Cabin-Berkshires! Dog-friendly. Hike/Ski Appalachian Tr. Walk to lake!
Exterior
Wintery Cottage in the Berkshires! Dog friendly, Hot Tub, Hiking, Shopping, Dine

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)
"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 ￥25,126
￥61,527 total
includes taxes & fees
Jan 6 - Jan 7
Wintery Cottage in the Berkshires! Dog friendly, Hot Tub, Hiking, Shopping, Dine
Property grounds
Big farmhouse in the foothills of the Berkshires

Big farmhouse in the foothills of the Berkshires

Big farmhouse in the foothills of the Berkshires
Russell
10.0 out of 10, Exceptional, (143)
"Perfect spot for a family celebration!"
United States
Kerry P.
The price is ￥25,879
￥50,564 total
includes taxes & fees
Jan 6 - Jan 7
Big farmhouse in the foothills of the Berkshires
Fridge, microwave, oven, stovetop
Near Tanglewood: Historic Summer Retreat

Near Tanglewood: Historic Summer Retreat

Near Tanglewood: Historic Summer Retreat
New Lebanon
9.6 out of 10, Exceptional, (24)
"Perfect cosy home to stay at for a Berkshire vacation. Easy to get to everything."
United States
Paul S.
The price is ￥22,114
￥58,143 total
includes taxes & fees
Feb 2 - Feb 3
Near Tanglewood: Historic Summer Retreat
Fridge, microwave, oven, stovetop
Home in Great Barrington

Home in Great Barrington

Home in Great Barrington
Great Barrington
9.8 out of 10, Exceptional, (26)
"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 ￥23,714
￥40,328 total
includes taxes & fees
Jan 6 - Jan 7
Home in Great Barrington
Exterior
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere

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)
"Great cottage - well appointed and very clean. No air conditioning so a bit warm when it’s hot out, but all in all a great stay"
United States
Lindsey E.
The price is ￥25,408
￥65,697 total
includes taxes & fees
Jan 7 - Jan 8
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
Terrace/patio
Historic Berkshires Home Near Tanglewood, Trails & Wineries

Historic Berkshires Home Near Tanglewood, Trails & Wineries

Historic Berkshires Home Near Tanglewood, Trails & Wineries
Lebanon Springs
8.8 out of 10, Excellent, (20)
"Great stay in the Berkshires for a wedding. Amanda was very accommodating and communicative. "
United States
Wendy D.
The price is ￥23,526
￥60,252 total
includes taxes & fees
Feb 1 - Feb 2
Historic Berkshires Home Near Tanglewood, Trails & Wineries
Fridge, microwave, oven, stovetop
Sun Filled Lenox Retreat - Minutes to Tanglewood!

Sun Filled Lenox Retreat - Minutes to Tanglewood!

Sun Filled Lenox Retreat - Minutes to Tanglewood!
Lee
9.4 out of 10, Exceptional, (3)
"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 ￥28,231
￥72,178 total
includes taxes & fees
Jan 6 - Jan 7
Sun Filled Lenox Retreat - Minutes to Tanglewood!
Dining
Guesthouse Cabin vacation rentals in Berkshire County

Guesthouse Cabin vacation rentals in Berkshire County

Guesthouse Cabin vacation rentals in Berkshire County
Sheffield
10.0 out of 10, Exceptional, (9)
"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 ￥61,638
￥108,794 total
includes taxes & fees
Jan 6 - Jan 7
Guesthouse Cabin vacation rentals in Berkshire County
TV, offices
The Brooks Motel: Exceptional Suite

The Brooks Motel: Exceptional Suite

The Brooks Motel: Exceptional Suite
Hillsdale
9.2 out of 10, Wonderful, (5)
"Clean, industrial, very comfy bed, easy to book and to check in and out. Would stay again."
United States
Deidre H.
The price is ￥24,938
￥31,444 total
includes taxes & fees
Jan 6 - Jan 7
The Brooks Motel: Exceptional Suite
Fridge, microwave, oven, stovetop
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!

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)
"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 ￥42,206
￥77,277 total
includes taxes & fees
Jan 6 - Jan 7
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
Exterior
Berkshires farm, 30+ guests, 50 acres

Berkshires farm, 30+ guests, 50 acres

Berkshires farm, 30+ guests, 50 acres
2.0 star property
New Lebanon
The price is ￥155,272
￥288,523 total
includes taxes & fees
Jan 12 - Jan 13
Berkshires farm, 30+ guests, 50 acres
Fridge, microwave, oven, stovetop
The Birdsong Apt. | Game Room & Fire Pit

The Birdsong Apt. | Game Room & Fire Pit

The Birdsong Apt. | Game Room & Fire Pit
2.0 star property
Winchester
The price is ￥28,231
￥60,775 total
includes taxes & fees
Jan 18 - Jan 19
The Birdsong Apt. | Game Room & Fire Pit
Property grounds
Cheerful 3-bedroom cottage with woodstove

Cheerful 3-bedroom cottage with woodstove

Cheerful 3-bedroom cottage with woodstove
Sheffield
10.0 out of 10, Exceptional, (41)
"The property was centrally located for skiing, and was a comfortable stay."
United States
Kelly R.
The price is ￥37,171
￥78,660 total
includes taxes & fees
Jan 6 - Jan 7
Cheerful 3-bedroom cottage with woodstove
Interior
Suite 4 - Quiet and private accommodations in a country setting.

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)
"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 ￥34,348
￥44,091 total
includes taxes & fees
Jan 19 - Jan 20
Suite 4 - Quiet and private accommodations in a country setting.
Game room
Family Ski Getaway in the Berkshires

Family Ski Getaway in the Berkshires

Family Ski Getaway in the Berkshires
Great Barrington
9.4 out of 10, Exceptional, (6)
"The host was exceptional and so kind. The location was in close proximity to 3 quaint New England small towns whose downtowns had many restaurants and local shops to enjoy-Great Barrington (GB Eats for breakfast), Stockbridge (best shopping) and Lenox (exceptional dinner at Frankie’s Italian). The house looked updated on the outside but inside looked like early 1900s with a hint of Victorian influence. My only caution is for anyone with mobility issues as all 3 bedrooms and the only (very small)...
United States
Kathy C.
The price is ￥31,760
￥46,688 total
includes taxes & fees
Jan 6 - Jan 7
Family Ski Getaway in the Berkshires
Fridge, microwave, oven, stovetop
Great Barrington Get Away

Great Barrington Get Away

Great Barrington Get Away
Great Barrington
9.4 out of 10, Exceptional, (26)
"We stayed here for Memorial Day weekend and had a wonderful trip. Close to the downtown shops, and all the supplies a family needs staying in a home. Thanks for the great stay!"
United States
Elizabeth G.
The price is ￥48,620
￥86,194 total
includes taxes & fees
Jan 6 - Jan 7
Great Barrington Get Away
Property grounds
3-bedroom house in beautiful Berkshires, close to amenities!

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

3-bedroom house in beautiful Berkshires, close to amenities!
Pittsfield
The price is ￥31,195
￥51,838 total
includes taxes & fees
Jan 10 - Jan 11
3-bedroom house in beautiful Berkshires, close to amenities!
Outdoor dining
Sweet Cozy Victorian in Housatonic. Close to everything.

Sweet Cozy Victorian in Housatonic. Close to everything.

Sweet Cozy Victorian in Housatonic. Close to everything.
Housatonic
10.0 out of 10, Exceptional, (3)
"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 ￥21,173
￥37,840 total
includes taxes & fees
Feb 1 - Feb 2
Sweet Cozy Victorian in Housatonic. Close to everything.
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Monterey Hotel Reviews

The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

10/10 Excellent
"Room was cozy and clean. Loved the fireplace & view. Great price too. Cameron at the front desk was pleasant and working hard the several times we saw him. Pool was warm & hot tub was nice! Overall, great stay! Will definitely stay again! "
Kimberly 1-night trip
Posted 2 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!

Frequently asked questions

Can I find vacation rentals in Monterey?

Yes, we give you a choice of vacation rentals close to the most popular attractions in Monterey, or you can select a secluded option if you'd like a relaxing place to stay. Monterey is known for its forests.

What are some of the best vacation home rentals that Monterey has to offer?

Cozy lake house with hot tub. Enjoy everything the Berkshires have to offer!: This vacation home rental near Monterey offers a fireplace, a patio, and a barbecue grill 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 you can cook with friends or family. You can relax into your vacation with a selection of games and a hot tub.

How many vacation rentals are there in Monterey?

With 22 Expedia vacation rentals, you're sure 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 larger area, you’ll find Questing and Ski Butternut.

What are vacation rentals like in Monterey?

Vacation rentals are privately owned properties you can reserve for several days or more in Monterey. Vacation rentals provide amenities such as hot tubs, fire pits, and patios so you'll have a home away from home. If you're concerned about a sanitized environment, vacation rentals can provide a sense of security away from shared hotel elevators and busy reception areas while still allowing you the enjoyment of travel. You'll also have more space in a vacation rental than in a hotel, which makes a vacation rental an attractive option for families.