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Top Holiday Rentals in Monterey

Rustic 3bd Lake Front Country Cottage

9.2 out of 10, Wonderful, (5)
"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, (123)
"A good place for vacation that you can enjoy and rest. Very nice and safe place."
The Ponds at Foxhollow

Spacious 5-bedroom house in charming Lee with WiFi

The price is £635
includes taxes & fees
11 Aug - 12 Aug
Spacious 5-bedroom house in charming Lee with WiFi

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

9.6 out of 10, Exceptional, (42)
"We had a wonderful stay. The cabin was clean and comfortable! "
Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns

Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets.

9.6 out of 10, Exceptional, (13)
"Very friendly hosts, great location. "
Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets.

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

9.8 out of 10, Exceptional, (146)
"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

Charming idyllic farmhouse minutes to Great Barrington MA and Salisbury CT

9.8 out of 10, Exceptional, (16)
"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

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, (45)
"We went as a family to get away from the city life for the weekend. We have no complaints except that it could’ve been a bit cleaner in the sense that there were many cobwebs. Nonetheless we rlly enjoyed our weekend in Great Barrington "
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!

Deluxe Queen Room with 2 Queen Beds

2.0 star property
2.0 out of 10, (2)
"The chemical smell in the room was overwhelming. There was no personal contact We called the number provided and was told We would get a full refund."
The price is £110
includes taxes & fees
14 Aug - 15 Aug
Deluxe Queen Room with 2 Queen Beds

Charming Cabin Lake Rights, Private Dock 3 bedroom, 2 bath. Sleeps 7.

9.6 out of 10, Exceptional, (60)
"Great"
Charming Cabin Lake Rights, Private Dock 3 bedroom, 2 bath. Sleeps 7.

Lakefront Bungalow

9.6 out of 10, Exceptional, (9)
"Nice location on water, clean, kitchen had all our needs--would stay there again."
Lakefront Bungalow

Big farmhouse in the foothills of the Berkshires

10.0 out of 10, Exceptional, (139)
"It is a quiet and beautiful home. The surrounding nature is peaceful and we saw many kinds of birds."
The price is £275
includes taxes & fees
5 Aug - 6 Aug
Big farmhouse in the foothills of the Berkshires

Quintessential 6-BR Berkshires Lodge

10.0 out of 10, Exceptional, (15)
"The house was perfect for our group of couples and young kids. Large bedrooms and beautiful property "
Quintessential 6-BR Berkshires Lodge

Peace and quiet on the lake

9.6 out of 10, Exceptional, (216)
"I love this place! It's been beautifully remodeled and is very comfortable. I would love to visit when it's warmer, but it's very cozy in the snow. I can't wait to come back with my kids. "
Peace and quiet on the lake

Amore Estate - beautiful room with many places to explore and relax in.

9.0 out of 10, Wonderful, (25)
"Beautiful, spacious house in a great location!"
Amore Estate - beautiful room with many places to explore and relax in.

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

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

10.0 out of 10, Exceptional, (8)
"Elise was an excellent host and super easy to work with. The property was even bigger, nicer, and cleaner than we expected. Plenty of room for a family getaway. "
Berkshires sanctuary with outdoor living area & firepit. 8minutes to Tanglewood!

Peaceful Retreat Compound 10 Minutes to Great Barrington!

10.0 out of 10, Exceptional, (26)
"Great property for the fire and pool. Highly recommend for multiple families/couples. Close to town."
Peaceful Retreat Compound 10 Minutes to Great Barrington!

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

10.0 out of 10, Exceptional, (122)
"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
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

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?

Spacious 5-bedroom house in charming Lee with WiFi: This holiday home rental outside of Monterey offers a fireplace, a BBQ and laundry facilities to help you feel perfectly comfortable in your new surroundings. Kitchen amenities such as a dishwasher and a microwave can make your holiday run smoothly.

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 Ashintully Gardens. In the wider area, you’ll find Lake Buel and Ski Butternut.

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.