
Holiday Homes in Monterey
- Change your mindBook hotels with free cancellation
- Be pickySearch almost a million properties worldwide
Check prices for these dates
In two weeks
In two months
In three months
In four months
Our top choices for Monterey holiday homes

1. Real Estate: Therapy - Lake, Laundry, Love it
Real Estate: Therapy - Lake, Laundry, Love itSherwood Forest
9.6 out of 10, Exceptional, (4 reviews)
The price is AU$409
includes taxes & fees
17 Nov - 18 Nov

2. Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, CanoeingSherwood Forest
9.6 out of 10, Exceptional, (20 reviews)
The price is AU$532
includes taxes & fees
11 Nov - 12 Nov

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, (10 reviews)
The price is AU$507
includes taxes & fees
16 Nov - 17 Nov

4. Home in Great Barrington
Home in Great BarringtonGreat Barrington
9.8 out of 10, Exceptional, (42 reviews)
The price is AU$468
includes taxes & fees
15 Nov - 16 Nov

5. Leaf-Peeper Paradise in the Berkshires
Leaf-Peeper Paradise in the BerkshiresGreat Barrington
9.6 out of 10, Exceptional, (29 reviews)
The price is AU$415
includes taxes & fees
13 Nov - 14 Nov

6. 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 price is AU$420
includes taxes & fees
12 Nov - 13 Nov

7. Cheerful 3-bedroom cottage with woodstove
Cheerful 3-bedroom cottage with woodstoveSheffield
10.0 out of 10, Exceptional, (46 reviews)
The price is AU$580
includes taxes & fees
24 Nov - 25 Nov

8. Cozy. Clean. Free bagel shop. 3 Fireplaces.
Cozy. Clean. Free bagel shop. 3 Fireplaces.Great Barrington
10.0 out of 10, Exceptional, (5 reviews)
The price is AU$970
includes taxes & fees
16 Nov - 17 Nov

9. 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, (42 reviews)
The price is AU$1,159
includes taxes & fees
8 Dec - 9 Dec

10. Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness roomGreat Barrington
10.0 out of 10, Exceptional, (10 reviews)
The price is AU$1,745
includes taxes & fees
21 Nov - 22 Nov

11. Maya's Garden House: A Converted 3-Bedroom Barndominium on 32 Acres in Great Barrington
Maya's Garden House: A Converted 3-Bedroom Barndominium on 32 Acres in Great BarringtonGreat Barrington
The price is AU$1,963
includes taxes & fees
11 Nov - 12 Nov

12. Secluded Family Home in Serene Stockbridge Woods
Secluded Family Home in Serene Stockbridge WoodsStockbridge
10.0 out of 10, Exceptional, (30 reviews)
The price is AU$894
includes taxes & fees
11 Nov - 12 Nov

13. Sun Filled Lenox Retreat - Minutes to Tanglewood!
Sun Filled Lenox Retreat - Minutes to Tanglewood!Lee
10.0 out of 10, Exceptional, (12 reviews)
The price is AU$861
includes taxes & fees
11 Nov - 12 Nov

14. Beautiful and Private Home Centrally Located in the Berkshires
Beautiful and Private Home Centrally Located in the BerkshiresWest Stockbridge
The price is AU$1,809
includes taxes & fees
9 Dec - 10 Dec

15. Fantastic 2-bedroom house with AC in quaint Hillsdale.
Fantastic 2-bedroom house with AC in quaint Hillsdale.Hillsdale
The price is AU$879
includes taxes & fees
22 Nov - 23 Nov

16. Peaceful and cozy 1 bed 1 bath in quaint Winchester
Peaceful and cozy 1 bed 1 bath in quaint WinchesterWinchester
10.0 out of 10, Exceptional, (5 reviews)
The price is AU$276
includes taxes & fees
16 Nov - 17 Nov

17. NEW RENO - Chalet-style farm loft near Tanglewood
NEW RENO - Chalet-style farm loft near TanglewoodNew Lebanon
8.8 out of 10, Excellent, (8 reviews)
The price is AU$287
includes taxes & fees
11 Nov - 12 Nov

18. 1800s Carriage house in Berkshires / Hudson Valley
1800s Carriage house in Berkshires / Hudson ValleyNew Lebanon
7.0 out of 10, Good, (2 reviews)
The price is AU$312
includes taxes & fees
16 Nov - 17 Nov

19. Big farmhouse in the foothills of the Berkshires
Big farmhouse in the foothills of the BerkshiresRussell
10.0 out of 10, Exceptional, (156 reviews)
The price is AU$497
includes taxes & fees
16 Nov - 17 Nov

20. 1789 Shaker Farmhouse in Berkshires/Hudson Valley
1789 Shaker Farmhouse in Berkshires/Hudson ValleyCanaan
10.0 out of 10, Exceptional, (5 reviews)
The price is AU$588
includes taxes & fees
18 Nov - 19 Nov
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.
Find holiday rentals that suit your style
Aparthotels
Apartments
Save an average of 15% on thousands of hotels when you're signed in
Top Monterey Hotel Reviews

Berkshires Untold
8/10 Good
Find out more about Monterey
Monterey Holiday Homes information
Number of reviews | 235 |
|---|---|
Accommodation | 372 Holiday Homes |
Lowest Price | AU$276 |
Highest Price | AU$1,745 |
































































