A lake surrounded by autumn-colored trees reflecting on the water.

Monterey Vacation Rentals

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Check prices for these dates

In two weeks
Sep 4 - Sep 6
In two months
Oct 16 - Oct 18
In three months
Nov 13 - Nov 15
In four months
Dec 11 - Dec 13

Our top choices for Monterey vacation rentals

A spacious cabin with large windows, a gray sofa, and a wooden ceiling.

1. 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 ￥44,824
￥92,573 total
includes taxes & fees
Sep 21 - Sep 22
Treetop Hideaway in Tyringham
A spacious lobby with a fireplace, multiple seating areas, and a chandelier.

2. Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (1,086 reviews)
"A nice place to stay in the Berkshires."
United States
Robert
The price is ￥15,036
￥20,346 total
includes taxes & fees
Aug 31 - Sep 1
Berkshire Mountain Lodge
A modern kitchen with a central island, wooden beams, and a view to the outdoors.

3. Home in Great Barrington

Home in Great Barrington
Great Barrington
9.8 out of 10, Exceptional, (38 reviews)
"Perfect location to walk into town - clean, light, airy and neat space. Enjoyable visit!"
United States
HEATHER G.
The price is ￥42,917
￥64,628 total
includes taxes & fees
Aug 25 - Aug 26
Home in Great Barrington
A two-story house with a front porch, surrounded by a garden with various plants and rocks.

4. 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)
"The house was lovely - my sisters and I had a wonderful time. Everything was warm and welcoming - it felt like home! We hope to make it an annual visit :)"
United States
Anonymous traveler
The price is ￥84,244
￥150,205 total
includes taxes & fees
Sep 20 - Sep 21
Walk into town, soak up sun on enclosed porch & steps away from nature trails!
A staircase leading to a second floor, a living room with a sofa, and a kitchen area.

5. Cozy Riverside Berkshires Retreat

Cozy Riverside Berkshires Retreat
Great Barrington
9.6 out of 10, Exceptional, (23 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 ￥30,399
￥47,273 total
includes taxes & fees
Sep 21 - Sep 22
Cozy Riverside Berkshires Retreat
A spacious living room with a sectional sofa, a coffee table, and a dining area with a table and chairs. There is a large window providing a view of the outdoors.

6. 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, (7 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 ￥89,982
￥211,123 total
includes taxes & fees
Aug 25 - Aug 26
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
A compact kitchen with a refrigerator, oven, microwave, and coffee maker.

7. Cozy 1-bedroom studio in serene Great Barrington with AC

Cozy 1-bedroom studio in serene Great Barrington with AC
Great Barrington
9.0 out of 10, Wonderful, (2 reviews)
"great location , berkshires are awesome . very clean , host is excellent ."
United States
bob i.
The price is ￥16,451
￥24,589 total
includes taxes & fees
Aug 31 - Sep 1
Cozy 1-bedroom studio in serene Great Barrington with AC
A bedroom with a brick fireplace, wooden beams, a bed with white bedding, and a wall-mounted picture.

8. Cozy. Clean. Free bagel shop. 3 Fireplaces.

Cozy. Clean. Free bagel shop. 3 Fireplaces.
Great Barrington
10.0 out of 10, Exceptional, (2 reviews)
"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 ￥50,665
￥88,552 total
includes taxes & fees
Sep 1 - Sep 2
Cozy. Clean. Free bagel shop. 3 Fireplaces.
A modern kitchen with a central island, bar stools, a stove, and a sink.

9. Renovated Downtown Great Barrington House

Renovated Downtown Great Barrington House
Great Barrington
8.0 out of 10, Very Good, (2 reviews)
"This is a very nice place to stay. My wife and I both remarked on how comfortable we felt there. A proper home away from home. It was well stocked on all fronts, including the kitchen. And I think what put the finishing touch on was the attention to detail... The towels were large, the bathroom rolls were Charmin Ultrasoft, and there were tissue boxes everywhere you're likely to need them. The hosts seem to work with a service, so you can reach someone with questions immediately, and the hosts...
United States
Anonymous traveler
The price is ￥142,674
￥243,037 total
includes taxes & fees
Aug 23 - Aug 24
Renovated Downtown Great Barrington House
A hot tub with a string of lights above it, set against a dark night sky.

10. 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, (16 reviews)
"Great place and welcoming stay!"
United States
Frank M.
The price is ￥25,464
￥63,065 total
includes taxes & fees
Aug 25 - Aug 26
Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
A spacious bedroom with a four-poster bed, a large window, and a view of the outdoors.

11. Stylish Mid-century Modern Berkshires Cape

Stylish Mid-century Modern Berkshires Cape
Lee
10.0 out of 10, Exceptional, (6 reviews)
"Besides, it being in a great location, the home is absolutely lovely!"
United States
H B.
The price is ￥80,826
￥138,754 total
includes taxes & fees
Sep 2 - Sep 3
Stylish Mid-century Modern Berkshires Cape
An outdoor seating area with wicker furniture and a glass table, surrounded by lush greenery.

12. Cheerful 3-bedroom cottage with woodstove

Cheerful 3-bedroom cottage with woodstove
Sheffield
10.0 out of 10, Exceptional, (43 reviews)
"The property was centrally located for skiing, and was a comfortable stay."
United States
Kelly R.
The price is ￥39,261
￥82,561 total
includes taxes & fees
Sep 22 - Sep 23
Cheerful 3-bedroom cottage with woodstove
An outdoor deck with a grill, seating area, and a view of the surrounding greenery.

13. Stockbridge In-town Escape

Stockbridge In-town Escape
Stockbridge
The price is ￥63,977
￥101,001 total
includes taxes & fees
Aug 30 - Aug 31
Stockbridge In-town Escape
A sandy beach with a lake and forest in the background.

14. Hotel-like Balcony Suite—Private Wing&Entry—Ensuite Bath—View—Walk to Town, Lake

Hotel-like Balcony Suite—Private Wing&Entry—Ensuite Bath—View—Walk to Town, Lake
Great Barrington
10.0 out of 10, Exceptional, (3 reviews)
"We had a wonderful visit. They were so accommodating and great location to downtown. We’ll stay again!"
United States
Kristin O.
The price is ￥34,190
￥53,638 total
includes taxes & fees
Sep 21 - Sep 22
Hotel-like Balcony Suite—Private Wing&Entry—Ensuite Bath—View—Walk to Town, Lake
A house with a porch, a garden with pink flowers, and a stone wall along the road.

15. Big farmhouse in the foothills of the Berkshires

Big farmhouse in the foothills of the Berkshires
Russell
10.0 out of 10, Exceptional, (149 reviews)
"Great location"
United States
Will G.
The price is ￥30,201
￥56,620 total
includes taxes & fees
Aug 23 - Aug 24
Big farmhouse in the foothills of the Berkshires
A kitchen with white shelves containing various kitchenware, a kettle, and a window with a view of trees and a building outside.

16. Sweet Cozy Victorian in Housatonic. Close to everything.

Sweet Cozy Victorian in Housatonic. Close to everything.
Housatonic
9.8 out of 10, Exceptional, (10 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 ￥27,816
￥50,601 total
includes taxes & fees
Sep 1 - Sep 2
Sweet Cozy Victorian in Housatonic. Close to everything.
A cozy attic bedroom with a sloped ceiling, wooden beams, a large window with a view of trees, a bed, a desk, and a kitchenette.

17. 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, (7 reviews)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
United States
Sharon K.
The price is ￥26,227
￥63,919 total
includes taxes & fees
Sep 9 - Sep 10
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
A living room with a brown leather sofa, two grey armchairs, a glass coffee table, and a wooden side table with a lamp.

18. stylish Berkshires Retreat

stylish Berkshires Retreat
Lee
9.0 out of 10, Wonderful, (4 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 ￥25,750
￥61,253 total
includes taxes & fees
Sep 20 - Sep 21
stylish Berkshires Retreat
A modern interior with a loft-style ceiling, a grey sofa, a wooden coffee table, and a kitchen area with a large TV.

19. Fantastic 2-bedroom house with AC in quaint Hillsdale.

Fantastic 2-bedroom house with AC in quaint Hillsdale.
Hillsdale
The price is ￥64,176
￥107,660 total
includes taxes & fees
Aug 23 - Aug 24
Fantastic 2-bedroom house with AC in quaint Hillsdale.
A spacious living area with a large sofa, a kitchen island with bar stools, a wooden staircase, and a television displaying a movie.

20. Real Estate: Therapy - Lake, Laundry, Love it

Real Estate: Therapy - Lake, Laundry, Love it
Sherwood Forest
The price is ￥8,424
￥45,985 total
includes taxes & fees
Sep 13 - Sep 14
Real Estate: Therapy - Lake, Laundry, Love it
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 Whitlock

The Whitlock

8/10 Good
"The Whitlock is a lovely old inn, located right in the heart of Lenox and walkable to everything in town. The staff is also lovely. Our room was spacious and well layed out. [but for an ADA compliant walk in shower, you need more than grab bars - a rubber matt in the shower is a necessity!!] However, for a hotel that calls itself hi-end, it fell far short of that mark. First and foremost, the email communications with both Hotels.com and the The Whitlock were like a Marx Brothers skit: We were first told the check in would be at the Constance down the street, not at the Whitlock. When I asked the off-shore "team" about that, I was told that the Whitlock was under new management and no longer had off-site check-in. The additional info we received with attached links also did not work - the response: it will work the day of check in!!?? [ps - they were not "live" links, just a series of numbers and letters] It's great to try and streamline operations, but those operations MUST work, and the responses from the team must make sense!!!"
Paula M. 2-night trip
Posted less than an hour ago
The Whitlock

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
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  • 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?

Lakefront Retreat with Stunning Views | Forget-Me-Not by AvantStay: This highly rated vacation home rental in Monterey is located on a lake and has a fireplace, a balcony, and a barbecue grill 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 you can cook with friends or family. It offers a garden, a selection of games, and a hot tub so you can immerse yourself in your vacation.

How many vacation rentals are there in Monterey?

With 25 Expedia vacation rentals, you're sure 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 larger area, you’ll find Mount Wilcox and Lake Buel.

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.