We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.
We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Vacation rentals in Monterey, MA and nearby

Use a credit card to book with our Peace of Mind Protection.
Learn more
Find a rental
Price per night
Min
to
Max
Bedrooms
Any
Amenities
Select
More filters
Find more rentals you can book on TripAdvisor!   We're showing you properties you can book on TripAdvisor first.
All 52 Rentals in the Monterey Area
loading...
From
$56
Per Night
Monterey
1 Bedroom, 1 Bathroom, Sleeps 1
6 photos Details Make Enquiry
From
$339
Per Night
Monterey
4 Bedrooms, 2 Bathrooms, Sleeps 6
29 photos Details Make Enquiry
From
$169
Per Night
Monterey
3 Bedrooms, 2 Bathrooms, Sleeps 7
13 photos Details Reviews (13) Make Enquiry

The following rentals are within 15 kilometres of Monterey, Massachusetts.

From
$395
Per Night
Lee
1 Bedroom, 1 Bathroom, Sleeps 2
Booking
17 photos Details Reviews (1) Make Enquiry
5 of 5 stars Reviewed 12 June 2014
I had several summer months here, it never disappoints. Full of nature's bounty, hospitable host, friendly vacationers. Very close to all the best of the Berkshires, Tanglewood...
See all reviews
From
$563
Per Night
Stockbridge
4 Bedrooms, 4 Bathrooms, Sleeps 12
Booking
32 photos Details Reviews (1) Make Enquiry
5 of 5 stars Reviewed 18 July 2014
Our family of 5 rented this home over July 4th weekend and we couldn't have been more pleased. The home has just been newly renovated, is very tastefully appointed and looks and...
See all reviews
From
$564
Per Night
Sheffield
4 Bedrooms, 3 Bathrooms, Sleeps 15
19 photos Details Reviews (8) Make Enquiry
5 of 5 stars Reviewed 6 August 2014
Casey's place was really lovely - just exactly as described! WONDERFUL central great room/dining room for our large group to gather and relax - and beautiful decks for reading...
5 of 5 stars Reviewed 23 February 2014
Racebrook Lodge is our "home away from home", and Casey and Dave (the owners) are so incredibly hospitable. This house, their most recent addition to the property, is the GEM of...
See all reviews
From
$226
Per Night
Lee
1 Bedroom, 1 Bathroom, Sleeps 2
Booking
8 photos Details Reviews (1) Make Enquiry
5 of 5 stars Reviewed 17 June 2014
We have taken the Writer's Room each Summer for about three years now. We find the Lodge to be authentic New England... our natural wood room to the rest of the house. It is...
See all reviews
From
$169
Per Night
Lee
1 Bedroom, 1 Bathroom, Sleeps 2
Booking
4 photos Details Reviews (1) Make Enquiry
5 of 5 stars Reviewed 17 June 2014
And I hope to stay here again in the future. I feel very comfortable here - good privacy, the house is huge, rustic charm, generally very quiet. The property is massive - and the...
See all reviews
Get the List
From
$339
Per Night
Lee
3 Bedrooms, 2 Bathrooms, Sleeps 5
25 photos Details Reviews (2) Make Enquiry
From
$423
Per Night
Lee
5 Bedrooms, 3 Bathrooms, Sleeps 11
Bookings
33 photos Details Reviews (8) Make Enquiry
4 of 5 stars Reviewed 27 September 2014
We went there for a golf buddy trip and it was the perfect place for us in the Berkshires. Place was very clean, and had all the comforts of home. Robin is super friendly and...
5 of 5 stars Reviewed 3 September 2014
This is a wonderful home! Robin has taken care with the furnishing and finishings, which are a nice blend of antique and modern. Her love of the home and region is apparent...
See all reviews
From
$282
Per Night
Great Barrington
2 Bedrooms, 1 Bathroom, Sleeps 5
Bookings
10 photos Details Reviews (2) Make Enquiry
5 of 5 stars Reviewed 20 May 2013
This was a perfect weekend for us. I am very picking when choosing a cabin rental because I want it to be "just right--" to fit into all of my ideal visions of the quintessential...
See all reviews
From
$220
Per Night
Great Barrington
1 Bedroom, 1 Bathroom, Sleeps 3
Bookings
10 photos Details Reviews (9) Make Enquiry
5 of 5 stars Reviewed 17 August 2014
We stayed at the cottage for three days, and it was just as lovely as advertised. The space is perfect for a couple, with a comfortable queen bed and well-equipped kitchen...
5 of 5 stars Reviewed 22 July 2014
My wife and I were extremely lucky to find Efrem and Frederica's cottage in The Berkshires. We really enjoyed the beautiful and relaxing view that their backyard had to offer! The...
See all reviews
From
$226
Per Night
Stockbridge
3 Bedrooms, 2 Bathrooms, Sleeps 7
Bookings
16 photos Details Reviews (4) Make Enquiry
4 of 5 stars Reviewed 24 October 2013
Some friends and I wanted to have a reunion as we are spread out along the east coast, and we were debating between camping or renting. I heard no end of the gratitude from my...
5 of 5 stars Reviewed 30 September 2013
We rented this cabin originally for 5: 2 adults and 3 children (6,11,13). At the last minute our older daughter (18) decided to join us. The cabin is very spacious and...
See all reviews
From
$367
Per Night
Great Barrington
5 Bedrooms, 4 Bathrooms, Sleeps 10
Bookings
27 photos Details Reviews (1) Make Enquiry
3 of 5 stars Reviewed 11 September 2014
This is a very large house, more than adequate in size for a group of ten people. It has a big yard and a spectacular view of the mountains, especially from an upstairs window...
See all reviews
From
$226
Per Night
Stockbridge
3 Bedrooms, 2 Bathrooms, Sleeps 8
Bookings
11 photos Details Reviews (1) Make Enquiry
3 of 5 stars Reviewed 30 July 2014
Nice house but tired bathrooms and kitchen. One great bedroom, two so so. Hot one nite and needed non existing a/c. Great screened porch with view of water. Canoe was a plus...
See all reviews
From
$5,079
Per Week
Great Barrington
6 Bedrooms, 6 Bathrooms, Sleeps 12
25 photos Details Make Enquiry
From
$339
Per Night
Norfolk, CT
3 Bedrooms, 3 Bathrooms, Sleeps 6
Booking
10 photos Details Make Enquiry
From
$395
Per Night
Great Barrington
5 Bedrooms, 3 Bathrooms, Sleeps 10
9 photos Details Make Enquiry
From
$113
Per Night
South Lee
1 Bedroom, 2 Bathrooms, Sleeps 4
12 photos Details Make Enquiry
From
$254
Per Night
Lee
4 Bedrooms, 3 Bathrooms, Sleeps 8
Booking
19 photos Details Make Enquiry
From
$242
Per Night
Stockbridge
3 Bedrooms, 2 Bathrooms, Sleeps 6
11 photos Details Make Enquiry
From
$649
Per Night
Stockbridge
3 Bedrooms, 3 Bathrooms, Sleeps 5
5 photos Details Make Enquiry
From
$564
Per Night
Stockbridge
3 Bedrooms, 3 Bathrooms, Sleeps 8
23 photos Details Make Enquiry
From
$226
Per Night
Lee
1 Bedroom, 1 Bathroom, Sleeps 4
12 photos Details Make Enquiry
From
$846
Per Night
Lee
5 Bedrooms, 5 Bathrooms, Sleeps 12
7 photos Details Make Enquiry
From
$226
Per Night
Great Barrington
2 Bedrooms, 1 Bathroom, Sleeps 4
Bookings
10 photos Details Make Enquiry
From
$677
Per Night
Tyringham
4 Bedrooms, 3 Bathrooms, Sleeps 8
15 photos Details Make Enquiry
From
$203
Per Night
Sandisfield
3 Bedrooms, 3 Bathrooms, Sleeps 6
15 photos Details Make Enquiry
From
$536
Per Night
Great Barrington
4 Bedrooms, 6 Bathrooms, Sleeps 12
22 photos Details Make Enquiry
From
$339
Per Night
Great Barrington
4 Bedrooms, 2 Bathrooms, Sleeps 9
Bookings
11 photos Details Make Enquiry
From
$147
Per Night
Stockbridge
1 Bedroom, 1 Bathroom, Sleeps 4
16 photos Details Make Enquiry
From
$226
Per Night
Great Barrington
2 Bedrooms, 2 Bathrooms, Sleeps 4
10 photos Details Make Enquiry
From
$423
Per Night
Lee
2 Bedrooms, 2 Bathrooms, Sleeps 6
5 photos Details Make Enquiry
From
$141
Per Night
Lee
1 Bedroom, 1 Bathroom, Sleeps 2
Bookings
10 photos Details Make Enquiry
From
$226
Per Night
Lee
1 Bedroom, 1 Bathroom, Sleeps 6
Booking
7 photos Details Make Enquiry
From
$198
Per Night
Lee
1 Bedroom, 1 Bathroom, Sleeps 2
2 photos Details Make Enquiry
From
$254
Per Night
Tyringham
1 Bedroom, 1 Bathroom, Sleeps 2
Booking
10 photos Details Make Enquiry
From
$282
Per Night
Tyringham
1 Bedroom, 1 Bathroom, Sleeps 4
9 photos Details Make Enquiry
From
$226
Per Night
Great Barrington
4 Bedrooms, 3 Bathrooms, Sleeps 10
15 photos Details Make Enquiry
From
$339
Per Night
Great Barrington
3 Bedrooms, 2 Bathrooms, Sleeps 6
Booking
23 photos Details Make Enquiry
From
$226
Per Night
Stockbridge
2 Bedrooms, 2 Bathrooms, Sleeps 6
24 photos Details Make Enquiry
From
$282
Per Night
Lee
3 Bedrooms, 2 Bathrooms, Sleeps 8
11 photos Details Reviews (2) Make Enquiry
4 of 5 stars Reviewed 18 June 2013
This property was a great home base for our brief visit to the Berkshires. Plenty of space and well equipped. We especially enjoyed the beautiful property, whether sitting on the...
See all reviews
From
$649
Per Night
Great Barrington
4 Bedrooms, 3 Bathrooms, Sleeps 10
33 photos Details Reviews (3) Make Enquiry
From
$112
Per Night
Stockbridge
3 Bedrooms, 2 Bathrooms, Sleeps 6
19 photos Details Reviews (21) Make Enquiry
5 of 5 stars Reviewed 20 July 2014
Stayed one night for weekend to Tanglewood festival. At first, it was a bit hard to find the house number accessing from north, but very close to the campus. Followed Carole's...
5 of 5 stars Reviewed 19 July 2014
We have been to the Berkshires numerous times, and the Cottage B&B provides a genuine Berkshire experience, both because of the great location and gracious, knowledgeable owner...
See all reviews
From
$282
Per Night
Great Barrington
3 Bedrooms, 2 Bathrooms, Sleeps 8
19 photos Details Make Enquiry
From
$282
Per Night
Stockbridge
3 Bedrooms, 2 Bathrooms, Sleeps 8
13 photos Details Make Enquiry
From
$339
Per Night
Housatonic
4 Bedrooms, 3 Bathrooms, Sleeps 10
9 photos Details Make Enquiry
From
$282
Per Night
Lee
3 Bedrooms, 2 Bathrooms, Sleeps 6
Booking
10 photos Details Make Enquiry
Go to map view
Book Online(43)
Use filters to find the best results!

Suitability

  • Wheelchair access (4)
  • Elder access (25)
  • Suitable for children (32)
  • Pet friendly (20)
  • Smoking allowed (0)

Amenities

  • Internet (42)
  • Other outdoor space (40)
  • Grill (36)
  • Parking (35)
  • Washer/Dryer (32)
  • View all amenities
List your property for free!
List your accommodation
for free on our website.
Reach millions worldwide.
Add a Listing


In partnership with
Get the List
Nearby cities