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Our top choices for Monterey vacation homes
1. Treetop Hideaway in Tyringham
Treetop Hideaway in TyringhamMonterey
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!! "
Samantha G.
The price is AED 1,039
AED 1,999 total
includes taxes & fees
28 Oct - 29 Oct
2. Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, CanoeingSherwood Forest
9.8 out of 10, Exceptional, (17 reviews)
"Great place and welcoming stay!"
Frank M.
The price is AED 588
AED 1,359 total
includes taxes & fees
29 Sep - 30 Sep
3. 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, (9 reviews)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
Sharon K.
The price is AED 536
AED 1,296 total
includes taxes & fees
28 Sep - 29 Sep
4. Real Estate: Therapy - Lake, Laundry, Love it
Real Estate: Therapy - Lake, Laundry, Love itSherwood Forest
8.0 out of 10, Very good, (1 review)
"Very good trip overall. Great location. Just a few things needed to make it over the top!"
William C B.
The price is AED 356
AED 1,198 total
includes taxes & fees
5 Oct - 6 Oct
5. Home in Great Barrington
Home in Great BarringtonGreat Barrington
9.8 out of 10, Exceptional, (39 reviews)
"Perfect location to walk into town - clean, light, airy and neat space. Enjoyable visit!"
HEATHER G.
The price is AED 779
AED 1,157 total
includes taxes & fees
26 Oct - 27 Oct
6. Riverside Retreat in the Berkshires
Riverside Retreat in the BerkshiresGreat Barrington
9.6 out of 10, Exceptional, (27 reviews)
"If you like cuddly cats, book it! A quick night stay while in town for a wedding and Studly was a perfect host… and Marissa :)Easy location, was nice to watch the fish jump and bald eagle hunt for his breakfast as we enjoyed our coffee on the step."
Kelly B.
The price is AED 744
AED 1,102 total
includes taxes & fees
28 Sep - 29 Sep
7. Cheerful 3-bedroom cottage with woodstove
Cheerful 3-bedroom cottage with woodstoveSheffield
10.0 out of 10, Exceptional, (45 reviews)
"The property was centrally located for skiing, and was a comfortable stay."
Kelly R.
The price is AED 684
AED 1,519 total
includes taxes & fees
12 Oct - 13 Oct
8. Sweet Cozy Victorian in Housatonic. Close to everything.
Sweet Cozy Victorian in Housatonic. Close to everything.Housatonic
9.8 out of 10, Exceptional, (12 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!"
Peter S.
The price is AED 735
AED 1,210 total
includes taxes & fees
8 Oct - 9 Oct
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 Red Lion Inn
10/10 Excellent
