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

Lobby

1. Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (1,078 reviews)
"A nice place to stay in the Berkshires."
United States
Robert
$125 nightly
The price is $139
Aug 31 - Sep 1
Total with taxes and fees
Berkshire Mountain Lodge
Coffee/tea maker, fridge, microwave, oven

2. 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.
$139 nightly
The price is $155
Aug 31 - Sep 1
Total with taxes and fees
Cozy 1-bedroom studio in serene Great Barrington with AC
Interior

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

Real Estate: Therapy - Lake, Laundry, Love it
Sherwood Forest
$269 nightly
The price is $300
Sep 13 - Sep 14
Total with taxes and fees
Real Estate: Therapy - Lake, Laundry, Love it
TV

4. 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.
$549 nightly
The price is $580
Sep 16 - Sep 17
Total with taxes and fees
Treetop Hideaway in Tyringham
Outdoor spa tub

5. 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.
$362 nightly
The price is $404
Aug 25 - Aug 26
Total with taxes and fees
Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
Interior

6. 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.
$364 nightly
The price is $407
Aug 25 - Aug 26
Total with taxes and fees
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
Interior

7. 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.
$269 nightly
The price is $301
Sep 1 - Sep 2
Total with taxes and fees
Cozy Riverside Berkshires Retreat
Beach nearby, sun loungers, beach towels

8. 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.
$285 nightly
The price is $318
Sep 15 - Sep 16
Total with taxes and fees
Hotel-like Balcony Suite—Private Wing&Entry—Ensuite Bath—View—Walk to Town, Lake
Coffee/tea maker, fridge, microwave, oven

9. 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.
$366 nightly
The price is $409
Aug 24 - Aug 25
Total with taxes and fees
Home in Great Barrington
Smart TV

10. 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.
$344 nightly
The price is $384
Sep 15 - Sep 16
Total with taxes and fees
stylish Berkshires Retreat
Interior

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

Sweet Cozy Victorian in Housatonic. Close to everything.
Housatonic
9.8 out of 10, Exceptional, (9 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.
$285 nightly
The price is $318
Sep 1 - Sep 2
Total with taxes and fees
Sweet Cozy Victorian in Housatonic. Close to everything.
Terrace/patio

12. Enjoy a restful stay with fast internet, smart TV and the company of your pet.

Enjoy a restful stay with fast internet, smart TV and the company of your pet.
winsted
9.4 out of 10, Exceptional, (51 reviews)
"Fantastic hosts and great facilities would highly recommend"
United States
Steve
$213 nightly
The price is $241
Aug 31 - Sep 1
Total with taxes and fees
Enjoy a restful stay with fast internet, smart TV and the company of your pet.
Desk, iron/ironing board, WiFi, bed sheets

13. The Brooks Motel: Exceptional Suite

The Brooks Motel: Exceptional Suite
Hillsdale
7.2 out of 10, Good, (5 reviews)
"Close to the competition I was in"
United States
Joan
$172 nightly
The price is $193
Aug 20 - Aug 21
Total with taxes and fees
The Brooks Motel: Exceptional Suite
Coffee/tea maker, fridge, microwave, oven

14. NEW RENO - Chalet-style farm loft near Tanglewood

NEW RENO - Chalet-style farm loft near Tanglewood
New Lebanon
8.6 out of 10, Excellent, (7 reviews)
"We enjoyed our stay and the location. This rustic, spacious loft was great for our brief visit to the Berkshires. "
United States
Joanna P.
$200 nightly
The price is $202
Aug 20 - Aug 21
Total with taxes and fees
NEW RENO - Chalet-style farm loft near Tanglewood
Property grounds

15. 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.
$465 nightly
The price is $519
Sep 7 - Sep 8
Total with taxes and fees
Cheerful 3-bedroom cottage with woodstove
Coffee/tea maker, fridge, microwave, oven

16. Bright, relaxing 2-story built in 1843, with WiFi & smart TVs in charming Dalton

Bright, relaxing 2-story built in 1843, with WiFi & smart TVs in charming Dalton
Dalton
9.8 out of 10, Exceptional, (31 reviews)
"This was a wonderful place to stay. We especially loved the easy access to the toys so the kids could start playing while we unloaded the car. It was perfect and just what we needed."
United States
Megan A.
$293 nightly
The price is $327
Aug 31 - Sep 1
Total with taxes and fees
Bright, relaxing 2-story built in 1843, with WiFi & smart TVs in charming Dalton
3 bedrooms, iron/ironing board, WiFi, bed sheets

17. 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.
$503 nightly
The price is $561
Sep 1 - Sep 2
Total with taxes and fees
Cozy. Clean. Free bagel shop. 3 Fireplaces.
Property grounds

18. 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.
$316 nightly
The price is $334
Aug 25 - Aug 26
Total with taxes and fees
Big farmhouse in the foothills of the Berkshires
4 bedrooms, travel crib, WiFi, bed sheets

19. 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.
$782 nightly
The price is $873
Sep 2 - Sep 3
Total with taxes and fees
Stylish Mid-century Modern Berkshires Cape
Outdoor dining

20. Stockbridge In-town Escape

Stockbridge In-town Escape
Stockbridge
$603 nightly
The price is $635
Aug 30 - Aug 31
Total with taxes and fees
Stockbridge In-town Escape
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

Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox

8/10 Good
"The motel is in a great location. You could walk to everything. The room was clean and comfortable although the air conditioning in the room didn't work very well. The fan ran but it didn't cool the room."
Jen 1-night trip
Posted 5 hours ago
Howard Johnson by Wyndham Lenox

Find out more about Monterey

Everything you need to know about Monterey vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Monterey vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Monterey vacation 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 low season months. For more hustle and bustle, you may prefer to visit Monterey in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $139 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Monterey rentals

At Expedia, we put the best Monterey vacation 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 vacation.

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.

Explore a world of travel with Expedia

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.